Practical ideas for what’s next.

 Designed for independent insurance agency owners and leaders, IA Evolve brings together perspectives from across the independent agency ecosystem. Explore strategies, tools and insights you can put to work in your agency now, with sessions covering growth, technology, AI, market opportunities, agency operations and more.

Choose the topics most relevant to you and build your own IA Evolve experience.

Conference Program

11:00 AM

Conference Opens: Innovation Lab & Networking

Arrive early to explore the Innovation Lab, connect in the networking lounge, visit the resource area, stop by the photo...

Conference Opens: Innovation Lab & Networking

Arrive early to explore the Innovation Lab, connect in the networking lounge, visit the resource area, stop by the photo booth, and get started on the event scavenger hunt before the main stage program begins.

Learn More
11:30 AM

Opening Main Stage: Reimagining Agency Growth - What's Next is Now

Kick off IA Evolve with opening remarks from Matt Masiello, CEO of SIAA, followed by a main stage conversation with indu...

Opening Main Stage: Reimagining Agency Growth - What's Next is Now

Kick off IA Evolve with opening remarks from Matt Masiello, CEO of SIAA, followed by a main stage conversation with industry leaders from across the independent agency ecosystem. This session will explore how agency growth, carrier relationships, technology, market access, and client expectations are evolving—and what those changes mean for independent agency owners, producers, future owners, carriers, technology partners, and others across the P&C industry.

Session Speakers

 

speaker headshot
Matt Masiello CEO SIAA
Biography

As CEO of SIAA, Matt Masiello has responsibility for executive management of the largest alliance of independent insurance agencies in the United States and its related companies, providing leadership to senior executives of SIAA and Master Agencies across the country.

His more than 30 years of industry experience have instilled in him the skills, knowledge, and expertise to lead SIAA. Matt has responsibility for the organization's overall success,including providing strategic vision for its future and piloting the organization in the execution of that vision. SIAA includes the following strategic business units:

• The Agent Alliance has 49 regional Master Agencies covering all 50 states with over 5,200 independent insurance agencies as Members, which write over $17 billion in P&C premium.

• Sequel Insurance Agencies is a Top 100 retail agency.

• Xchange – Powered by SIAA is a wholesale and MGA platform dedicated to providing member agencies with faster, easier, and frictionless processes in conjunction with non-standard submissions.

• Portfolio IQ is a data driven platform utilizing AI to provide business intelligence that improves growth quality and operational efficiencies for members and partners. In his tenure with SIAA and the insurance industry, Matt has:

• Developed SIAA's internal operations and executed its strategic direction as COO for over 10 years.

• Provided leadership and operational management beginning in 1993 for SAN Group (SIAA's founding and largest Master Agency), as President and CEO.

• Published Insurance Agency 4.0 (Nov 2020), a book depicting how IAs can prepare their agency for the future, develop a digital road map, and increase profit, scalability and time.

• Received the IBA Hot 100 Award in 2017, as a leader shaping the future of the insurance industry.

• Led SIAA, its Member Agencies, Master Agencies and Strategic Partners in raising hundreds of thousands of dollars for Dana-Farber Cancer Institute & The Jimmy Fund, Wounded Warriors Project, Veterans Count, and a number of other philanthropic organizations.

In the last 30 years, Matt has become a subject-matter expert in the field of insurance distribution and agency development. He is a frequent contributor to many industry publications, including Insurance Journal, Property Casualty 360, National Underwriter Magazine, PIA Magazine, Independent Agent, Best's Review and The Standard. Matt is also a frequent presenter and speaker at a variety of insurance conferences, meetings and events.

He has served on regional and national advisory councils for numerous insurance companies and serves on the Board of Trustees of Tilton School. Matt resides on the seacoast of New Hampshire with his wife and three sons. When not working, you can find him and his family boating, fishing, hiking, traveling, or skiing.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Karen Eckert SVP, Personal Insurance Agent Distribution Travelers
Biography

Karen Eckert is Senior Vice President of Personal Insurance Agent Distribution at Travelers. She oversees the Agent Distribution organization for Personal Insurance, which includes seven regional sales teams, inside sales, a national partners sales team, an agency enablement circle and a home office field sales operations group. Her team is comprised of 260 sales professionals who support over $14 billion in premium across more than 20,000 independent agency locations in the U.S. With over 35 years of agency experience in both Business and Personal Insurance, Karen joined Travelers in 2009 in the Select business unit, leading several regions before moving to Personal Insurance and assuming her current role leading the Personal Insurance Agent Distribution Team in 2023.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Hunter Moss CEO SIAA Xchange
Biography

Hunter Moss is Chief Executive Officer of Xchange, SIAA's embedded wholesale and MGA platform, built to simplify E&S placement for members. He sets the strategic vision, owns the platform and program roadmap, and secures the carrier and Lloyd's capacity behind new programs. Hunter has spent his career building MGAs, launching carrier relationships, structuring reinsurance programs, and navigating the Lloyd's of London market. He has also led M&A transactions, raised capital from strategic investors, and created underwriting platforms from the ground up.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Graham Blackwell CEO, President and Incoming CEO Applied Systems
Biography
Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Tim deRosa President Sequel Insurance Agencies
Biography
Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Matt Masiello CEO SIAA
Biography

As CEO of SIAA, Matt Masiello has responsibility for executive management of the largest alliance of independent insurance agencies in the United States and its related companies, providing leadership to senior executives of SIAA and Master Agencies across the country.

His more than 30 years of industry experience have instilled in him the skills, knowledge, and expertise to lead SIAA. Matt has responsibility for the organization's overall success,including providing strategic vision for its future and piloting the organization in the execution of that vision. SIAA includes the following strategic business units:

• The Agent Alliance has 49 regional Master Agencies covering all 50 states with over 5,200 independent insurance agencies as Members, which write over $17 billion in P&C premium.

• Sequel Insurance Agencies is a Top 100 retail agency.

• Xchange – Powered by SIAA is a wholesale and MGA platform dedicated to providing member agencies with faster, easier, and frictionless processes in conjunction with non-standard submissions.

• Portfolio IQ is a data driven platform utilizing AI to provide business intelligence that improves growth quality and operational efficiencies for members and partners. In his tenure with SIAA and the insurance industry, Matt has:

• Developed SIAA's internal operations and executed its strategic direction as COO for over 10 years.

• Provided leadership and operational management beginning in 1993 for SAN Group (SIAA's founding and largest Master Agency), as President and CEO.

• Published Insurance Agency 4.0 (Nov 2020), a book depicting how IAs can prepare their agency for the future, develop a digital road map, and increase profit, scalability and time.

• Received the IBA Hot 100 Award in 2017, as a leader shaping the future of the insurance industry.

• Led SIAA, its Member Agencies, Master Agencies and Strategic Partners in raising hundreds of thousands of dollars for Dana-Farber Cancer Institute & The Jimmy Fund, Wounded Warriors Project, Veterans Count, and a number of other philanthropic organizations.

In the last 30 years, Matt has become a subject-matter expert in the field of insurance distribution and agency development. He is a frequent contributor to many industry publications, including Insurance Journal, Property Casualty 360, National Underwriter Magazine, PIA Magazine, Independent Agent, Best's Review and The Standard. Matt is also a frequent presenter and speaker at a variety of insurance conferences, meetings and events.

He has served on regional and national advisory councils for numerous insurance companies and serves on the Board of Trustees of Tilton School. Matt resides on the seacoast of New Hampshire with his wife and three sons. When not working, you can find him and his family boating, fishing, hiking, traveling, or skiing.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Karen Eckert SVP, Personal Insurance Agent Distribution Travelers
Biography

Karen Eckert is Senior Vice President of Personal Insurance Agent Distribution at Travelers. She oversees the Agent Distribution organization for Personal Insurance, which includes seven regional sales teams, inside sales, a national partners sales team, an agency enablement circle and a home office field sales operations group. Her team is comprised of 260 sales professionals who support over $14 billion in premium across more than 20,000 independent agency locations in the U.S. With over 35 years of agency experience in both Business and Personal Insurance, Karen joined Travelers in 2009 in the Select business unit, leading several regions before moving to Personal Insurance and assuming her current role leading the Personal Insurance Agent Distribution Team in 2023.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Hunter Moss CEO SIAA Xchange
Biography

Hunter Moss is Chief Executive Officer of Xchange, SIAA's embedded wholesale and MGA platform, built to simplify E&S placement for members. He sets the strategic vision, owns the platform and program roadmap, and secures the carrier and Lloyd's capacity behind new programs. Hunter has spent his career building MGAs, launching carrier relationships, structuring reinsurance programs, and navigating the Lloyd's of London market. He has also led M&A transactions, raised capital from strategic investors, and created underwriting platforms from the ground up.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Graham Blackwell CEO, President and Incoming CEO Applied Systems
Biography
Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Tim deRosa President Sequel Insurance Agencies
Biography
Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM
Learn More
12:30 PM

Break / Innovation Lab & Transition

Take a short break, visit the Innovation Lab, connect in the networking lounge, explore resources, or continue the scave...

Break / Innovation Lab & Transition

Take a short break, visit the Innovation Lab, connect in the networking lounge, explore resources, or continue the scavenger hunt before making your way to the first set of concurrent sessions.

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12:40 PM

Innovation, Underwriting Discipline, and Growth in the Independent Agency Channel

Explore how carrier priorities, product strategy, underwriting discipline, and market trends are shaping growth opportun...

Innovation, Underwriting Discipline, and Growth in the Independent Agency Channel

Explore how carrier priorities, product strategy, underwriting discipline, and market trends are shaping growth opportunities across the independent agency channel. This session will help agency principals, producers, carrier partners, and industry professionals better understand how alignment can support profitable, sustainable growth.

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Putting Data and AI-Supported Insights to Work

See how agencies can use better intelligence to identify opportunities, prioritize growth conversations, focus producer ...

Putting Data and AI-Supported Insights to Work

See how agencies can use better intelligence to identify opportunities, prioritize growth conversations, focus producer effort, and make more confident business decisions. This practical session connects data and AI-supported insights to everyday agency planning, client engagement, and growth execution.

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01:15 PM

Commercial Lines Innovation and Smarter Agency Growth

Gain perspective on commercial lines trends, product evolution, underwriting expectations, and small business opportunit...

Commercial Lines Innovation and Smarter Agency Growth

Gain perspective on commercial lines trends, product evolution, underwriting expectations, and small business opportunities that matter to independent agencies and their partners. This session is designed to help attendees understand where the market is moving and how agencies and carriers can support stronger client value and growth.

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How to Access More Opportunity, Support, and Scale

Learn how independent agencies can expand market access, strengthen operations, use smarter intelligence, tap specialty ...

How to Access More Opportunity, Support, and Scale

Learn how independent agencies can expand market access, strengthen operations, use smarter intelligence, tap specialty resources, and connect with growth support designed around real agency needs. This session is useful for current members looking to maximize available capabilities, producers and future owners exploring what growth can look like, and prospective members evaluating the value of joining a larger independent agency network.

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01:50 PM

Modern Retail Agency Operations: Tools, Technology, and AI at Work

Hear directly from agency owners in a main stage panel discussion focused on how retail agencies are modernizing day-to-...

Modern Retail Agency Operations: Tools, Technology, and AI at Work

Hear directly from agency owners in a main stage panel discussion focused on how retail agencies are modernizing day-to-day operations. This session explores practical approaches to workflows, automation, agency management systems, data, and AI-supported processes, with real-world perspective on what is working, what is challenging, and how agencies can improve efficiency, execution, productivity, and client experience without losing the human connection that defines independent agencies.

Session Speakers

 

speaker headshot
Frank Sentner Sentwood Consulting
Biography

Frank Sentner has been providing technology solutions to the insurance industry for 50 years. His consulting practice is focused on improving the business processes of insurers, insurance brokerage firms, and insurance technology solution providers. He has managed major policy, billing, and claims system replacement projects for insurers and has provided strategic technology consulting for large insurance brokerage firms. Frank led the development of the first ACORD Forms-based agency management system while working for Insurnet in 1976. He started his consulting firm in 1982, then merged it with two other founders in 1984 to form Creative Information Systems (CISCo) where he designed and developed Sagitta, the first ACORD AL3-based agency system, which is still used today by some of the largest insurance brokers in the world. For the last decade, Frank has focused on mentoring Startup InsurTech firms and is currently on the board or advisory board for eight startups. His only remaining corporate consulting client is ACORD.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Evan Silverio Silverio Insurance Agency
Biography

Evan Silverio is President & CEO of Silverio Insurance Group consisting of Silverio Insurance, Woodcome Insurance and Secky Insurance; independent P&C agencies operating across Massachusetts, New Hampshire, and Rhode Island. Building on a family business founded in 1986, he has grown the group into a multi-agency platform serving a diverse, multilingual client base built through organic growth, agency acquisitions and talent development. He is also a real estate investor and an active civic leader in the Merrimack Valley of Massachusetts.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Chris Paradiso Paradiso Finacial and Insurance Services
Biography

Chris Paradiso stands as one of the most influential and forward-thinking agency owners in the insurance industry today. With over 25 years of experience as a licensed insurance agent, Chris’s relentless commitment to exceptional customer service has propelled his agency, Paradiso Insurance, into a thriving operation of 50+ employees. Founded in 2006, the agency has achieved remarkable milestones, including winning Safeco and Liberty Mutual’s prestigious National Agent for the Future Award in 2019. Currently licensed in 44 states, Paradiso Insurance is on track to achieve nationwide licensing in all 50 states. Chris’s visionary leadership extends beyond his agency. Through his coaching platform, Paradiso Presents, he has inspired and guided hundreds of insurance agencies to innovate and achieve success. His influence is further amplified by his roles on the advisory boards of Rough Notes, a leading insurance publication, 101 Weston Labs, Phase 4 Veterans Wall, and the Flagpole Committee. In 2010, Chris was recognized for his work within his local community and throughout Connecticut when he received the Community Service Award from Rough Notes spotlighting the various ways, he gives back including the Bikes for Reading program, Reverse Trick-or-Treat and Annual Flag Day Event. In 2011, Chris launched “Paradiso Presents,” a groundbreaking program focused on social media marketing, data utilization, and process optimization. This initiative equips insurance agencies with the tools to thrive in today’s complex, technology-driven landscape. His innovative marketing strategies have been widely adopted across the industry, earning him a reputation as a digital trailblazer in a field often slow to embrace technological advancements. Chris’s work with Aureus Analytics exemplifies his commitment to leveraging data for enhanced customer insights and service. By championing the use of cutting-edge analytics, he is helping agencies nationwide improve their customer relationships and financial performance. At his core, Chris Paradiso is a family man who leads with the belief that family is everything and that passion for one’s work transforms it into a lifelong joy. His dedication to innovation, community, and mentorship continues to shape the future of the insurance industry.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Anurag Shah Chief Data Officer SIAA
Biography

As SIAA’s Chief Data Officer, Anurag is responsible for developing and executing the overall Data, Analytics and AI Strategy across the organization. This includes deploying data platforms across members as well as Master agencies and strategic carrier partners. He is also responsible for developing the analytics and AI roadmap that will help the organization achieve its vision. Anurag has over 25 years of experience of building and scaling technology products and services. Before joining SIAA, Anurag was the CEO and Co-Founder of DONNA.ai (Aureus Analytics) where he led the organization's overall growth, product roadmap and execution strategy and the eventual sale to SIAA. At DONNA ai he worked closely with a large number of independent insurance agencies across the US and helped them grow their businesses using AI and Data. Anurag started his first technology venture – ESI, at the age of 24, which was later acquired by Omnitech, where he served as the COO & Head of Global Operations. Prior to ESI, he worked for IBM & CBay systems. Anurag's strengths lie at the intersection of business and technology, focusing on artificial intelligence and machine learning. He is a co-author of two patents: Network Analysis and SentiMeter®. Anurag is an engineering graduate from the University of Mumbai and has studied management at NMIMS in Mumbai and executive management from the ISB, Hyderabad. He has also studied Machine Learning from Stanford. As a technology entrepreneur and artificial intelligence subject matter expert, Anurag is continuously thinking of disruptive ways to connect the evolution of AI and its application to various industries, including insurance. Anurag lives in Connecticut with his wife and two sons.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Brandon Hill Stockton-Hill Insurance
Biography
Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Frank Sentner Sentwood Consulting
Biography

Frank Sentner has been providing technology solutions to the insurance industry for 50 years. His consulting practice is focused on improving the business processes of insurers, insurance brokerage firms, and insurance technology solution providers. He has managed major policy, billing, and claims system replacement projects for insurers and has provided strategic technology consulting for large insurance brokerage firms. Frank led the development of the first ACORD Forms-based agency management system while working for Insurnet in 1976. He started his consulting firm in 1982, then merged it with two other founders in 1984 to form Creative Information Systems (CISCo) where he designed and developed Sagitta, the first ACORD AL3-based agency system, which is still used today by some of the largest insurance brokers in the world. For the last decade, Frank has focused on mentoring Startup InsurTech firms and is currently on the board or advisory board for eight startups. His only remaining corporate consulting client is ACORD.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Evan Silverio Silverio Insurance Agency
Biography

Evan Silverio is President & CEO of Silverio Insurance Group consisting of Silverio Insurance, Woodcome Insurance and Secky Insurance; independent P&C agencies operating across Massachusetts, New Hampshire, and Rhode Island. Building on a family business founded in 1986, he has grown the group into a multi-agency platform serving a diverse, multilingual client base built through organic growth, agency acquisitions and talent development. He is also a real estate investor and an active civic leader in the Merrimack Valley of Massachusetts.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Chris Paradiso Paradiso Finacial and Insurance Services
Biography

Chris Paradiso stands as one of the most influential and forward-thinking agency owners in the insurance industry today. With over 25 years of experience as a licensed insurance agent, Chris’s relentless commitment to exceptional customer service has propelled his agency, Paradiso Insurance, into a thriving operation of 50+ employees. Founded in 2006, the agency has achieved remarkable milestones, including winning Safeco and Liberty Mutual’s prestigious National Agent for the Future Award in 2019. Currently licensed in 44 states, Paradiso Insurance is on track to achieve nationwide licensing in all 50 states. Chris’s visionary leadership extends beyond his agency. Through his coaching platform, Paradiso Presents, he has inspired and guided hundreds of insurance agencies to innovate and achieve success. His influence is further amplified by his roles on the advisory boards of Rough Notes, a leading insurance publication, 101 Weston Labs, Phase 4 Veterans Wall, and the Flagpole Committee. In 2010, Chris was recognized for his work within his local community and throughout Connecticut when he received the Community Service Award from Rough Notes spotlighting the various ways, he gives back including the Bikes for Reading program, Reverse Trick-or-Treat and Annual Flag Day Event. In 2011, Chris launched “Paradiso Presents,” a groundbreaking program focused on social media marketing, data utilization, and process optimization. This initiative equips insurance agencies with the tools to thrive in today’s complex, technology-driven landscape. His innovative marketing strategies have been widely adopted across the industry, earning him a reputation as a digital trailblazer in a field often slow to embrace technological advancements. Chris’s work with Aureus Analytics exemplifies his commitment to leveraging data for enhanced customer insights and service. By championing the use of cutting-edge analytics, he is helping agencies nationwide improve their customer relationships and financial performance. At his core, Chris Paradiso is a family man who leads with the belief that family is everything and that passion for one’s work transforms it into a lifelong joy. His dedication to innovation, community, and mentorship continues to shape the future of the insurance industry.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Anurag Shah Chief Data Officer SIAA
Biography

As SIAA’s Chief Data Officer, Anurag is responsible for developing and executing the overall Data, Analytics and AI Strategy across the organization. This includes deploying data platforms across members as well as Master agencies and strategic carrier partners. He is also responsible for developing the analytics and AI roadmap that will help the organization achieve its vision. Anurag has over 25 years of experience of building and scaling technology products and services. Before joining SIAA, Anurag was the CEO and Co-Founder of DONNA.ai (Aureus Analytics) where he led the organization's overall growth, product roadmap and execution strategy and the eventual sale to SIAA. At DONNA ai he worked closely with a large number of independent insurance agencies across the US and helped them grow their businesses using AI and Data. Anurag started his first technology venture – ESI, at the age of 24, which was later acquired by Omnitech, where he served as the COO & Head of Global Operations. Prior to ESI, he worked for IBM & CBay systems. Anurag's strengths lie at the intersection of business and technology, focusing on artificial intelligence and machine learning. He is a co-author of two patents: Network Analysis and SentiMeter®. Anurag is an engineering graduate from the University of Mumbai and has studied management at NMIMS in Mumbai and executive management from the ISB, Hyderabad. He has also studied Machine Learning from Stanford. As a technology entrepreneur and artificial intelligence subject matter expert, Anurag is continuously thinking of disruptive ways to connect the evolution of AI and its application to various industries, including insurance. Anurag lives in Connecticut with his wife and two sons.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Brandon Hill Stockton-Hill Insurance
Biography
Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM
Learn More
02:40 PM

Practical AI for Everyday Agency Work

Move beyond broad AI trends and focus on realistic, high-value use cases for independent agencies and the partners who s...

Practical AI for Everyday Agency Work

Move beyond broad AI trends and focus on realistic, high-value use cases for independent agencies and the partners who support them. This session highlights practical ways AI can support client communications, renewal preparation, account summaries, follow-up, internal handoffs, first drafts of marketing content, and administrative efficiency—while keeping privacy, accuracy review, and human judgment at the center.

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03:15 PM

Risk Management, Underwriting Insight, and Agency Value Creation

Learn how risk management trends, underwriting insight, customer education, and carrier expertise can strengthen client ...

Risk Management, Underwriting Insight, and Agency Value Creation

Learn how risk management trends, underwriting insight, customer education, and carrier expertise can strengthen client relationships and improve outcomes across the independent agency channel. This session is designed to help agencies and carrier partners deepen advisory value, improve collaboration, and identify opportunities to support better decisions for clients.

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Smarter Specialty Placement: Taking the Pain Out of E&S

Improve confidence in placing complex risks by focusing on submission quality, underwriting expectations, wholesale coll...

Smarter Specialty Placement: Taking the Pain Out of E&S

Improve confidence in placing complex risks by focusing on submission quality, underwriting expectations, wholesale collaboration, and practical market access. This session helps agency owners understand when to seek specialty support, how to package risk details clearly, and how to improve placement outcomes for hard-to-place accounts.

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03:50 PM

Producer Productivity and Sales Execution

Focus on practical tactics agencies can use to improve producer productivity, sales follow-up, pipeline visibility, rene...

Producer Productivity and Sales Execution

Focus on practical tactics agencies can use to improve producer productivity, sales follow-up, pipeline visibility, renewal preparation, cross-sell opportunities, and account prioritization. This session gives agency owners, leaders, producers, and future owners actionable ideas for strengthening business development discipline and helping teams focus time on the right opportunities

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The Modern Agency Tech Stack

Understand the core systems, integrations, and workflow decisions that shape how an agency operates day to day. This ses...

The Modern Agency Tech Stack

Understand the core systems, integrations, and workflow decisions that shape how an agency operates day to day. This session helps agency owners evaluate technology more clearly, avoid unnecessary complexity, and identify where tools can create immediate operational efficiency.

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04:25 PM

From Quote to Bind: Reducing Friction in the Agency Workflow

Take a tactical look at the pain points that slow agency teams down—from intake, quoting, submissions, remarketing, co...

From Quote to Bind: Reducing Friction in the Agency Workflow

Take a tactical look at the pain points that slow agency teams down—from intake, quoting, submissions, remarketing, comparative rating, and document management to handoffs and follow-up. This session helps agency owners identify workflow improvements that can save time, reduce friction, and support better execution.

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Marketing, Retention, and Client Experience

Explore how communication, marketing automation, client segmentation, retention strategies, and digital engagement can s...

Marketing, Retention, and Client Experience

Explore how communication, marketing automation, client segmentation, retention strategies, and digital engagement can strengthen relationships and create more consistent client touchpoints. This session helps agency owners think more intentionally about client experience as a driver of retention and growth.

Learn More
11:30 AM

Opening Main Stage: Reimagining Agency Growth - What's Next is Now

Kick off IA Evolve with opening remarks from Matt Masiello, CEO of SIAA, followed by a main stage conversation with indu...

Opening Main Stage: Reimagining Agency Growth - What's Next is Now

Kick off IA Evolve with opening remarks from Matt Masiello, CEO of SIAA, followed by a main stage conversation with industry leaders from across the independent agency ecosystem. This session will explore how agency growth, carrier relationships, technology, market access, and client expectations are evolving—and what those changes mean for independent agency owners, producers, future owners, carriers, technology partners, and others across the P&C industry.

Session Speakers

 

speaker headshot
Matt Masiello CEO SIAA
Biography

As CEO of SIAA, Matt Masiello has responsibility for executive management of the largest alliance of independent insurance agencies in the United States and its related companies, providing leadership to senior executives of SIAA and Master Agencies across the country.

His more than 30 years of industry experience have instilled in him the skills, knowledge, and expertise to lead SIAA. Matt has responsibility for the organization's overall success,including providing strategic vision for its future and piloting the organization in the execution of that vision. SIAA includes the following strategic business units:

• The Agent Alliance has 49 regional Master Agencies covering all 50 states with over 5,200 independent insurance agencies as Members, which write over $17 billion in P&C premium.

• Sequel Insurance Agencies is a Top 100 retail agency.

• Xchange – Powered by SIAA is a wholesale and MGA platform dedicated to providing member agencies with faster, easier, and frictionless processes in conjunction with non-standard submissions.

• Portfolio IQ is a data driven platform utilizing AI to provide business intelligence that improves growth quality and operational efficiencies for members and partners. In his tenure with SIAA and the insurance industry, Matt has:

• Developed SIAA's internal operations and executed its strategic direction as COO for over 10 years.

• Provided leadership and operational management beginning in 1993 for SAN Group (SIAA's founding and largest Master Agency), as President and CEO.

• Published Insurance Agency 4.0 (Nov 2020), a book depicting how IAs can prepare their agency for the future, develop a digital road map, and increase profit, scalability and time.

• Received the IBA Hot 100 Award in 2017, as a leader shaping the future of the insurance industry.

• Led SIAA, its Member Agencies, Master Agencies and Strategic Partners in raising hundreds of thousands of dollars for Dana-Farber Cancer Institute & The Jimmy Fund, Wounded Warriors Project, Veterans Count, and a number of other philanthropic organizations.

In the last 30 years, Matt has become a subject-matter expert in the field of insurance distribution and agency development. He is a frequent contributor to many industry publications, including Insurance Journal, Property Casualty 360, National Underwriter Magazine, PIA Magazine, Independent Agent, Best's Review and The Standard. Matt is also a frequent presenter and speaker at a variety of insurance conferences, meetings and events.

He has served on regional and national advisory councils for numerous insurance companies and serves on the Board of Trustees of Tilton School. Matt resides on the seacoast of New Hampshire with his wife and three sons. When not working, you can find him and his family boating, fishing, hiking, traveling, or skiing.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Karen Eckert SVP, Personal Insurance Agent Distribution Travelers
Biography

Karen Eckert is Senior Vice President of Personal Insurance Agent Distribution at Travelers. She oversees the Agent Distribution organization for Personal Insurance, which includes seven regional sales teams, inside sales, a national partners sales team, an agency enablement circle and a home office field sales operations group. Her team is comprised of 260 sales professionals who support over $14 billion in premium across more than 20,000 independent agency locations in the U.S. With over 35 years of agency experience in both Business and Personal Insurance, Karen joined Travelers in 2009 in the Select business unit, leading several regions before moving to Personal Insurance and assuming her current role leading the Personal Insurance Agent Distribution Team in 2023.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Hunter Moss CEO SIAA Xchange
Biography

Hunter Moss is Chief Executive Officer of Xchange, SIAA's embedded wholesale and MGA platform, built to simplify E&S placement for members. He sets the strategic vision, owns the platform and program roadmap, and secures the carrier and Lloyd's capacity behind new programs. Hunter has spent his career building MGAs, launching carrier relationships, structuring reinsurance programs, and navigating the Lloyd's of London market. He has also led M&A transactions, raised capital from strategic investors, and created underwriting platforms from the ground up.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Graham Blackwell CEO, President and Incoming CEO Applied Systems
Biography
Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Tim deRosa President Sequel Insurance Agencies
Biography
Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Matt Masiello CEO SIAA
Biography

As CEO of SIAA, Matt Masiello has responsibility for executive management of the largest alliance of independent insurance agencies in the United States and its related companies, providing leadership to senior executives of SIAA and Master Agencies across the country.

His more than 30 years of industry experience have instilled in him the skills, knowledge, and expertise to lead SIAA. Matt has responsibility for the organization's overall success,including providing strategic vision for its future and piloting the organization in the execution of that vision. SIAA includes the following strategic business units:

• The Agent Alliance has 49 regional Master Agencies covering all 50 states with over 5,200 independent insurance agencies as Members, which write over $17 billion in P&C premium.

• Sequel Insurance Agencies is a Top 100 retail agency.

• Xchange – Powered by SIAA is a wholesale and MGA platform dedicated to providing member agencies with faster, easier, and frictionless processes in conjunction with non-standard submissions.

• Portfolio IQ is a data driven platform utilizing AI to provide business intelligence that improves growth quality and operational efficiencies for members and partners. In his tenure with SIAA and the insurance industry, Matt has:

• Developed SIAA's internal operations and executed its strategic direction as COO for over 10 years.

• Provided leadership and operational management beginning in 1993 for SAN Group (SIAA's founding and largest Master Agency), as President and CEO.

• Published Insurance Agency 4.0 (Nov 2020), a book depicting how IAs can prepare their agency for the future, develop a digital road map, and increase profit, scalability and time.

• Received the IBA Hot 100 Award in 2017, as a leader shaping the future of the insurance industry.

• Led SIAA, its Member Agencies, Master Agencies and Strategic Partners in raising hundreds of thousands of dollars for Dana-Farber Cancer Institute & The Jimmy Fund, Wounded Warriors Project, Veterans Count, and a number of other philanthropic organizations.

In the last 30 years, Matt has become a subject-matter expert in the field of insurance distribution and agency development. He is a frequent contributor to many industry publications, including Insurance Journal, Property Casualty 360, National Underwriter Magazine, PIA Magazine, Independent Agent, Best's Review and The Standard. Matt is also a frequent presenter and speaker at a variety of insurance conferences, meetings and events.

He has served on regional and national advisory councils for numerous insurance companies and serves on the Board of Trustees of Tilton School. Matt resides on the seacoast of New Hampshire with his wife and three sons. When not working, you can find him and his family boating, fishing, hiking, traveling, or skiing.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Karen Eckert SVP, Personal Insurance Agent Distribution Travelers
Biography

Karen Eckert is Senior Vice President of Personal Insurance Agent Distribution at Travelers. She oversees the Agent Distribution organization for Personal Insurance, which includes seven regional sales teams, inside sales, a national partners sales team, an agency enablement circle and a home office field sales operations group. Her team is comprised of 260 sales professionals who support over $14 billion in premium across more than 20,000 independent agency locations in the U.S. With over 35 years of agency experience in both Business and Personal Insurance, Karen joined Travelers in 2009 in the Select business unit, leading several regions before moving to Personal Insurance and assuming her current role leading the Personal Insurance Agent Distribution Team in 2023.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Hunter Moss CEO SIAA Xchange
Biography

Hunter Moss is Chief Executive Officer of Xchange, SIAA's embedded wholesale and MGA platform, built to simplify E&S placement for members. He sets the strategic vision, owns the platform and program roadmap, and secures the carrier and Lloyd's capacity behind new programs. Hunter has spent his career building MGAs, launching carrier relationships, structuring reinsurance programs, and navigating the Lloyd's of London market. He has also led M&A transactions, raised capital from strategic investors, and created underwriting platforms from the ground up.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Graham Blackwell CEO, President and Incoming CEO Applied Systems
Biography
Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Tim deRosa President Sequel Insurance Agencies
Biography
Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM
Learn More
12:40 PM

Putting Data and AI-Supported Insights to Work

See how agencies can use better intelligence to identify opportunities, prioritize growth conversations, focus producer ...

Putting Data and AI-Supported Insights to Work

See how agencies can use better intelligence to identify opportunities, prioritize growth conversations, focus producer effort, and make more confident business decisions. This practical session connects data and AI-supported insights to everyday agency planning, client engagement, and growth execution.

Learn More
01:50 PM

Modern Retail Agency Operations: Tools, Technology, and AI at Work

Hear directly from agency owners in a main stage panel discussion focused on how retail agencies are modernizing day-to-...

Modern Retail Agency Operations: Tools, Technology, and AI at Work

Hear directly from agency owners in a main stage panel discussion focused on how retail agencies are modernizing day-to-day operations. This session explores practical approaches to workflows, automation, agency management systems, data, and AI-supported processes, with real-world perspective on what is working, what is challenging, and how agencies can improve efficiency, execution, productivity, and client experience without losing the human connection that defines independent agencies.

Session Speakers

 

speaker headshot
Frank Sentner Sentwood Consulting
Biography

Frank Sentner has been providing technology solutions to the insurance industry for 50 years. His consulting practice is focused on improving the business processes of insurers, insurance brokerage firms, and insurance technology solution providers. He has managed major policy, billing, and claims system replacement projects for insurers and has provided strategic technology consulting for large insurance brokerage firms. Frank led the development of the first ACORD Forms-based agency management system while working for Insurnet in 1976. He started his consulting firm in 1982, then merged it with two other founders in 1984 to form Creative Information Systems (CISCo) where he designed and developed Sagitta, the first ACORD AL3-based agency system, which is still used today by some of the largest insurance brokers in the world. For the last decade, Frank has focused on mentoring Startup InsurTech firms and is currently on the board or advisory board for eight startups. His only remaining corporate consulting client is ACORD.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Evan Silverio Silverio Insurance Agency
Biography

Evan Silverio is President & CEO of Silverio Insurance Group consisting of Silverio Insurance, Woodcome Insurance and Secky Insurance; independent P&C agencies operating across Massachusetts, New Hampshire, and Rhode Island. Building on a family business founded in 1986, he has grown the group into a multi-agency platform serving a diverse, multilingual client base built through organic growth, agency acquisitions and talent development. He is also a real estate investor and an active civic leader in the Merrimack Valley of Massachusetts.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Chris Paradiso Paradiso Finacial and Insurance Services
Biography

Chris Paradiso stands as one of the most influential and forward-thinking agency owners in the insurance industry today. With over 25 years of experience as a licensed insurance agent, Chris’s relentless commitment to exceptional customer service has propelled his agency, Paradiso Insurance, into a thriving operation of 50+ employees. Founded in 2006, the agency has achieved remarkable milestones, including winning Safeco and Liberty Mutual’s prestigious National Agent for the Future Award in 2019. Currently licensed in 44 states, Paradiso Insurance is on track to achieve nationwide licensing in all 50 states. Chris’s visionary leadership extends beyond his agency. Through his coaching platform, Paradiso Presents, he has inspired and guided hundreds of insurance agencies to innovate and achieve success. His influence is further amplified by his roles on the advisory boards of Rough Notes, a leading insurance publication, 101 Weston Labs, Phase 4 Veterans Wall, and the Flagpole Committee. In 2010, Chris was recognized for his work within his local community and throughout Connecticut when he received the Community Service Award from Rough Notes spotlighting the various ways, he gives back including the Bikes for Reading program, Reverse Trick-or-Treat and Annual Flag Day Event. In 2011, Chris launched “Paradiso Presents,” a groundbreaking program focused on social media marketing, data utilization, and process optimization. This initiative equips insurance agencies with the tools to thrive in today’s complex, technology-driven landscape. His innovative marketing strategies have been widely adopted across the industry, earning him a reputation as a digital trailblazer in a field often slow to embrace technological advancements. Chris’s work with Aureus Analytics exemplifies his commitment to leveraging data for enhanced customer insights and service. By championing the use of cutting-edge analytics, he is helping agencies nationwide improve their customer relationships and financial performance. At his core, Chris Paradiso is a family man who leads with the belief that family is everything and that passion for one’s work transforms it into a lifelong joy. His dedication to innovation, community, and mentorship continues to shape the future of the insurance industry.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Anurag Shah Chief Data Officer SIAA
Biography

As SIAA’s Chief Data Officer, Anurag is responsible for developing and executing the overall Data, Analytics and AI Strategy across the organization. This includes deploying data platforms across members as well as Master agencies and strategic carrier partners. He is also responsible for developing the analytics and AI roadmap that will help the organization achieve its vision. Anurag has over 25 years of experience of building and scaling technology products and services. Before joining SIAA, Anurag was the CEO and Co-Founder of DONNA.ai (Aureus Analytics) where he led the organization's overall growth, product roadmap and execution strategy and the eventual sale to SIAA. At DONNA ai he worked closely with a large number of independent insurance agencies across the US and helped them grow their businesses using AI and Data. Anurag started his first technology venture – ESI, at the age of 24, which was later acquired by Omnitech, where he served as the COO & Head of Global Operations. Prior to ESI, he worked for IBM & CBay systems. Anurag's strengths lie at the intersection of business and technology, focusing on artificial intelligence and machine learning. He is a co-author of two patents: Network Analysis and SentiMeter®. Anurag is an engineering graduate from the University of Mumbai and has studied management at NMIMS in Mumbai and executive management from the ISB, Hyderabad. He has also studied Machine Learning from Stanford. As a technology entrepreneur and artificial intelligence subject matter expert, Anurag is continuously thinking of disruptive ways to connect the evolution of AI and its application to various industries, including insurance. Anurag lives in Connecticut with his wife and two sons.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Brandon Hill Stockton-Hill Insurance
Biography
Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Frank Sentner Sentwood Consulting
Biography

Frank Sentner has been providing technology solutions to the insurance industry for 50 years. His consulting practice is focused on improving the business processes of insurers, insurance brokerage firms, and insurance technology solution providers. He has managed major policy, billing, and claims system replacement projects for insurers and has provided strategic technology consulting for large insurance brokerage firms. Frank led the development of the first ACORD Forms-based agency management system while working for Insurnet in 1976. He started his consulting firm in 1982, then merged it with two other founders in 1984 to form Creative Information Systems (CISCo) where he designed and developed Sagitta, the first ACORD AL3-based agency system, which is still used today by some of the largest insurance brokers in the world. For the last decade, Frank has focused on mentoring Startup InsurTech firms and is currently on the board or advisory board for eight startups. His only remaining corporate consulting client is ACORD.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Evan Silverio Silverio Insurance Agency
Biography

Evan Silverio is President & CEO of Silverio Insurance Group consisting of Silverio Insurance, Woodcome Insurance and Secky Insurance; independent P&C agencies operating across Massachusetts, New Hampshire, and Rhode Island. Building on a family business founded in 1986, he has grown the group into a multi-agency platform serving a diverse, multilingual client base built through organic growth, agency acquisitions and talent development. He is also a real estate investor and an active civic leader in the Merrimack Valley of Massachusetts.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Chris Paradiso Paradiso Finacial and Insurance Services
Biography

Chris Paradiso stands as one of the most influential and forward-thinking agency owners in the insurance industry today. With over 25 years of experience as a licensed insurance agent, Chris’s relentless commitment to exceptional customer service has propelled his agency, Paradiso Insurance, into a thriving operation of 50+ employees. Founded in 2006, the agency has achieved remarkable milestones, including winning Safeco and Liberty Mutual’s prestigious National Agent for the Future Award in 2019. Currently licensed in 44 states, Paradiso Insurance is on track to achieve nationwide licensing in all 50 states. Chris’s visionary leadership extends beyond his agency. Through his coaching platform, Paradiso Presents, he has inspired and guided hundreds of insurance agencies to innovate and achieve success. His influence is further amplified by his roles on the advisory boards of Rough Notes, a leading insurance publication, 101 Weston Labs, Phase 4 Veterans Wall, and the Flagpole Committee. In 2010, Chris was recognized for his work within his local community and throughout Connecticut when he received the Community Service Award from Rough Notes spotlighting the various ways, he gives back including the Bikes for Reading program, Reverse Trick-or-Treat and Annual Flag Day Event. In 2011, Chris launched “Paradiso Presents,” a groundbreaking program focused on social media marketing, data utilization, and process optimization. This initiative equips insurance agencies with the tools to thrive in today’s complex, technology-driven landscape. His innovative marketing strategies have been widely adopted across the industry, earning him a reputation as a digital trailblazer in a field often slow to embrace technological advancements. Chris’s work with Aureus Analytics exemplifies his commitment to leveraging data for enhanced customer insights and service. By championing the use of cutting-edge analytics, he is helping agencies nationwide improve their customer relationships and financial performance. At his core, Chris Paradiso is a family man who leads with the belief that family is everything and that passion for one’s work transforms it into a lifelong joy. His dedication to innovation, community, and mentorship continues to shape the future of the insurance industry.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Anurag Shah Chief Data Officer SIAA
Biography

As SIAA’s Chief Data Officer, Anurag is responsible for developing and executing the overall Data, Analytics and AI Strategy across the organization. This includes deploying data platforms across members as well as Master agencies and strategic carrier partners. He is also responsible for developing the analytics and AI roadmap that will help the organization achieve its vision. Anurag has over 25 years of experience of building and scaling technology products and services. Before joining SIAA, Anurag was the CEO and Co-Founder of DONNA.ai (Aureus Analytics) where he led the organization's overall growth, product roadmap and execution strategy and the eventual sale to SIAA. At DONNA ai he worked closely with a large number of independent insurance agencies across the US and helped them grow their businesses using AI and Data. Anurag started his first technology venture – ESI, at the age of 24, which was later acquired by Omnitech, where he served as the COO & Head of Global Operations. Prior to ESI, he worked for IBM & CBay systems. Anurag's strengths lie at the intersection of business and technology, focusing on artificial intelligence and machine learning. He is a co-author of two patents: Network Analysis and SentiMeter®. Anurag is an engineering graduate from the University of Mumbai and has studied management at NMIMS in Mumbai and executive management from the ISB, Hyderabad. He has also studied Machine Learning from Stanford. As a technology entrepreneur and artificial intelligence subject matter expert, Anurag is continuously thinking of disruptive ways to connect the evolution of AI and its application to various industries, including insurance. Anurag lives in Connecticut with his wife and two sons.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Brandon Hill Stockton-Hill Insurance
Biography
Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM
Learn More
02:40 PM

Practical AI for Everyday Agency Work

Move beyond broad AI trends and focus on realistic, high-value use cases for independent agencies and the partners who s...

Practical AI for Everyday Agency Work

Move beyond broad AI trends and focus on realistic, high-value use cases for independent agencies and the partners who support them. This session highlights practical ways AI can support client communications, renewal preparation, account summaries, follow-up, internal handoffs, first drafts of marketing content, and administrative efficiency—while keeping privacy, accuracy review, and human judgment at the center.

Learn More
03:50 PM

The Modern Agency Tech Stack

Understand the core systems, integrations, and workflow decisions that shape how an agency operates day to day. This ses...

The Modern Agency Tech Stack

Understand the core systems, integrations, and workflow decisions that shape how an agency operates day to day. This session helps agency owners evaluate technology more clearly, avoid unnecessary complexity, and identify where tools can create immediate operational efficiency.

Learn More
04:25 PM

From Quote to Bind: Reducing Friction in the Agency Workflow

Take a tactical look at the pain points that slow agency teams down—from intake, quoting, submissions, remarketing, co...

From Quote to Bind: Reducing Friction in the Agency Workflow

Take a tactical look at the pain points that slow agency teams down—from intake, quoting, submissions, remarketing, comparative rating, and document management to handoffs and follow-up. This session helps agency owners identify workflow improvements that can save time, reduce friction, and support better execution.

Learn More
11:30 AM

Opening Main Stage: Reimagining Agency Growth - What's Next is Now

Kick off IA Evolve with opening remarks from Matt Masiello, CEO of SIAA, followed by a main stage conversation with indu...

Opening Main Stage: Reimagining Agency Growth - What's Next is Now

Kick off IA Evolve with opening remarks from Matt Masiello, CEO of SIAA, followed by a main stage conversation with industry leaders from across the independent agency ecosystem. This session will explore how agency growth, carrier relationships, technology, market access, and client expectations are evolving—and what those changes mean for independent agency owners, producers, future owners, carriers, technology partners, and others across the P&C industry.

Session Speakers

 

speaker headshot
Matt Masiello CEO SIAA
Biography

As CEO of SIAA, Matt Masiello has responsibility for executive management of the largest alliance of independent insurance agencies in the United States and its related companies, providing leadership to senior executives of SIAA and Master Agencies across the country.

His more than 30 years of industry experience have instilled in him the skills, knowledge, and expertise to lead SIAA. Matt has responsibility for the organization's overall success,including providing strategic vision for its future and piloting the organization in the execution of that vision. SIAA includes the following strategic business units:

• The Agent Alliance has 49 regional Master Agencies covering all 50 states with over 5,200 independent insurance agencies as Members, which write over $17 billion in P&C premium.

• Sequel Insurance Agencies is a Top 100 retail agency.

• Xchange – Powered by SIAA is a wholesale and MGA platform dedicated to providing member agencies with faster, easier, and frictionless processes in conjunction with non-standard submissions.

• Portfolio IQ is a data driven platform utilizing AI to provide business intelligence that improves growth quality and operational efficiencies for members and partners. In his tenure with SIAA and the insurance industry, Matt has:

• Developed SIAA's internal operations and executed its strategic direction as COO for over 10 years.

• Provided leadership and operational management beginning in 1993 for SAN Group (SIAA's founding and largest Master Agency), as President and CEO.

• Published Insurance Agency 4.0 (Nov 2020), a book depicting how IAs can prepare their agency for the future, develop a digital road map, and increase profit, scalability and time.

• Received the IBA Hot 100 Award in 2017, as a leader shaping the future of the insurance industry.

• Led SIAA, its Member Agencies, Master Agencies and Strategic Partners in raising hundreds of thousands of dollars for Dana-Farber Cancer Institute & The Jimmy Fund, Wounded Warriors Project, Veterans Count, and a number of other philanthropic organizations.

In the last 30 years, Matt has become a subject-matter expert in the field of insurance distribution and agency development. He is a frequent contributor to many industry publications, including Insurance Journal, Property Casualty 360, National Underwriter Magazine, PIA Magazine, Independent Agent, Best's Review and The Standard. Matt is also a frequent presenter and speaker at a variety of insurance conferences, meetings and events.

He has served on regional and national advisory councils for numerous insurance companies and serves on the Board of Trustees of Tilton School. Matt resides on the seacoast of New Hampshire with his wife and three sons. When not working, you can find him and his family boating, fishing, hiking, traveling, or skiing.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Karen Eckert SVP, Personal Insurance Agent Distribution Travelers
Biography

Karen Eckert is Senior Vice President of Personal Insurance Agent Distribution at Travelers. She oversees the Agent Distribution organization for Personal Insurance, which includes seven regional sales teams, inside sales, a national partners sales team, an agency enablement circle and a home office field sales operations group. Her team is comprised of 260 sales professionals who support over $14 billion in premium across more than 20,000 independent agency locations in the U.S. With over 35 years of agency experience in both Business and Personal Insurance, Karen joined Travelers in 2009 in the Select business unit, leading several regions before moving to Personal Insurance and assuming her current role leading the Personal Insurance Agent Distribution Team in 2023.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Hunter Moss CEO SIAA Xchange
Biography

Hunter Moss is Chief Executive Officer of Xchange, SIAA's embedded wholesale and MGA platform, built to simplify E&S placement for members. He sets the strategic vision, owns the platform and program roadmap, and secures the carrier and Lloyd's capacity behind new programs. Hunter has spent his career building MGAs, launching carrier relationships, structuring reinsurance programs, and navigating the Lloyd's of London market. He has also led M&A transactions, raised capital from strategic investors, and created underwriting platforms from the ground up.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Graham Blackwell CEO, President and Incoming CEO Applied Systems
Biography
Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Tim deRosa President Sequel Insurance Agencies
Biography
Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Matt Masiello CEO SIAA
Biography

As CEO of SIAA, Matt Masiello has responsibility for executive management of the largest alliance of independent insurance agencies in the United States and its related companies, providing leadership to senior executives of SIAA and Master Agencies across the country.

His more than 30 years of industry experience have instilled in him the skills, knowledge, and expertise to lead SIAA. Matt has responsibility for the organization's overall success,including providing strategic vision for its future and piloting the organization in the execution of that vision. SIAA includes the following strategic business units:

• The Agent Alliance has 49 regional Master Agencies covering all 50 states with over 5,200 independent insurance agencies as Members, which write over $17 billion in P&C premium.

• Sequel Insurance Agencies is a Top 100 retail agency.

• Xchange – Powered by SIAA is a wholesale and MGA platform dedicated to providing member agencies with faster, easier, and frictionless processes in conjunction with non-standard submissions.

• Portfolio IQ is a data driven platform utilizing AI to provide business intelligence that improves growth quality and operational efficiencies for members and partners. In his tenure with SIAA and the insurance industry, Matt has:

• Developed SIAA's internal operations and executed its strategic direction as COO for over 10 years.

• Provided leadership and operational management beginning in 1993 for SAN Group (SIAA's founding and largest Master Agency), as President and CEO.

• Published Insurance Agency 4.0 (Nov 2020), a book depicting how IAs can prepare their agency for the future, develop a digital road map, and increase profit, scalability and time.

• Received the IBA Hot 100 Award in 2017, as a leader shaping the future of the insurance industry.

• Led SIAA, its Member Agencies, Master Agencies and Strategic Partners in raising hundreds of thousands of dollars for Dana-Farber Cancer Institute & The Jimmy Fund, Wounded Warriors Project, Veterans Count, and a number of other philanthropic organizations.

In the last 30 years, Matt has become a subject-matter expert in the field of insurance distribution and agency development. He is a frequent contributor to many industry publications, including Insurance Journal, Property Casualty 360, National Underwriter Magazine, PIA Magazine, Independent Agent, Best's Review and The Standard. Matt is also a frequent presenter and speaker at a variety of insurance conferences, meetings and events.

He has served on regional and national advisory councils for numerous insurance companies and serves on the Board of Trustees of Tilton School. Matt resides on the seacoast of New Hampshire with his wife and three sons. When not working, you can find him and his family boating, fishing, hiking, traveling, or skiing.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Karen Eckert SVP, Personal Insurance Agent Distribution Travelers
Biography

Karen Eckert is Senior Vice President of Personal Insurance Agent Distribution at Travelers. She oversees the Agent Distribution organization for Personal Insurance, which includes seven regional sales teams, inside sales, a national partners sales team, an agency enablement circle and a home office field sales operations group. Her team is comprised of 260 sales professionals who support over $14 billion in premium across more than 20,000 independent agency locations in the U.S. With over 35 years of agency experience in both Business and Personal Insurance, Karen joined Travelers in 2009 in the Select business unit, leading several regions before moving to Personal Insurance and assuming her current role leading the Personal Insurance Agent Distribution Team in 2023.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Hunter Moss CEO SIAA Xchange
Biography

Hunter Moss is Chief Executive Officer of Xchange, SIAA's embedded wholesale and MGA platform, built to simplify E&S placement for members. He sets the strategic vision, owns the platform and program roadmap, and secures the carrier and Lloyd's capacity behind new programs. Hunter has spent his career building MGAs, launching carrier relationships, structuring reinsurance programs, and navigating the Lloyd's of London market. He has also led M&A transactions, raised capital from strategic investors, and created underwriting platforms from the ground up.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Graham Blackwell CEO, President and Incoming CEO Applied Systems
Biography
Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Tim deRosa President Sequel Insurance Agencies
Biography
Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM
Learn More
01:50 PM

Modern Retail Agency Operations: Tools, Technology, and AI at Work

Hear directly from agency owners in a main stage panel discussion focused on how retail agencies are modernizing day-to-...

Modern Retail Agency Operations: Tools, Technology, and AI at Work

Hear directly from agency owners in a main stage panel discussion focused on how retail agencies are modernizing day-to-day operations. This session explores practical approaches to workflows, automation, agency management systems, data, and AI-supported processes, with real-world perspective on what is working, what is challenging, and how agencies can improve efficiency, execution, productivity, and client experience without losing the human connection that defines independent agencies.

Session Speakers

 

speaker headshot
Frank Sentner Sentwood Consulting
Biography

Frank Sentner has been providing technology solutions to the insurance industry for 50 years. His consulting practice is focused on improving the business processes of insurers, insurance brokerage firms, and insurance technology solution providers. He has managed major policy, billing, and claims system replacement projects for insurers and has provided strategic technology consulting for large insurance brokerage firms. Frank led the development of the first ACORD Forms-based agency management system while working for Insurnet in 1976. He started his consulting firm in 1982, then merged it with two other founders in 1984 to form Creative Information Systems (CISCo) where he designed and developed Sagitta, the first ACORD AL3-based agency system, which is still used today by some of the largest insurance brokers in the world. For the last decade, Frank has focused on mentoring Startup InsurTech firms and is currently on the board or advisory board for eight startups. His only remaining corporate consulting client is ACORD.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Evan Silverio Silverio Insurance Agency
Biography

Evan Silverio is President & CEO of Silverio Insurance Group consisting of Silverio Insurance, Woodcome Insurance and Secky Insurance; independent P&C agencies operating across Massachusetts, New Hampshire, and Rhode Island. Building on a family business founded in 1986, he has grown the group into a multi-agency platform serving a diverse, multilingual client base built through organic growth, agency acquisitions and talent development. He is also a real estate investor and an active civic leader in the Merrimack Valley of Massachusetts.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Chris Paradiso Paradiso Finacial and Insurance Services
Biography

Chris Paradiso stands as one of the most influential and forward-thinking agency owners in the insurance industry today. With over 25 years of experience as a licensed insurance agent, Chris’s relentless commitment to exceptional customer service has propelled his agency, Paradiso Insurance, into a thriving operation of 50+ employees. Founded in 2006, the agency has achieved remarkable milestones, including winning Safeco and Liberty Mutual’s prestigious National Agent for the Future Award in 2019. Currently licensed in 44 states, Paradiso Insurance is on track to achieve nationwide licensing in all 50 states. Chris’s visionary leadership extends beyond his agency. Through his coaching platform, Paradiso Presents, he has inspired and guided hundreds of insurance agencies to innovate and achieve success. His influence is further amplified by his roles on the advisory boards of Rough Notes, a leading insurance publication, 101 Weston Labs, Phase 4 Veterans Wall, and the Flagpole Committee. In 2010, Chris was recognized for his work within his local community and throughout Connecticut when he received the Community Service Award from Rough Notes spotlighting the various ways, he gives back including the Bikes for Reading program, Reverse Trick-or-Treat and Annual Flag Day Event. In 2011, Chris launched “Paradiso Presents,” a groundbreaking program focused on social media marketing, data utilization, and process optimization. This initiative equips insurance agencies with the tools to thrive in today’s complex, technology-driven landscape. His innovative marketing strategies have been widely adopted across the industry, earning him a reputation as a digital trailblazer in a field often slow to embrace technological advancements. Chris’s work with Aureus Analytics exemplifies his commitment to leveraging data for enhanced customer insights and service. By championing the use of cutting-edge analytics, he is helping agencies nationwide improve their customer relationships and financial performance. At his core, Chris Paradiso is a family man who leads with the belief that family is everything and that passion for one’s work transforms it into a lifelong joy. His dedication to innovation, community, and mentorship continues to shape the future of the insurance industry.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Anurag Shah Chief Data Officer SIAA
Biography

As SIAA’s Chief Data Officer, Anurag is responsible for developing and executing the overall Data, Analytics and AI Strategy across the organization. This includes deploying data platforms across members as well as Master agencies and strategic carrier partners. He is also responsible for developing the analytics and AI roadmap that will help the organization achieve its vision. Anurag has over 25 years of experience of building and scaling technology products and services. Before joining SIAA, Anurag was the CEO and Co-Founder of DONNA.ai (Aureus Analytics) where he led the organization's overall growth, product roadmap and execution strategy and the eventual sale to SIAA. At DONNA ai he worked closely with a large number of independent insurance agencies across the US and helped them grow their businesses using AI and Data. Anurag started his first technology venture – ESI, at the age of 24, which was later acquired by Omnitech, where he served as the COO & Head of Global Operations. Prior to ESI, he worked for IBM & CBay systems. Anurag's strengths lie at the intersection of business and technology, focusing on artificial intelligence and machine learning. He is a co-author of two patents: Network Analysis and SentiMeter®. Anurag is an engineering graduate from the University of Mumbai and has studied management at NMIMS in Mumbai and executive management from the ISB, Hyderabad. He has also studied Machine Learning from Stanford. As a technology entrepreneur and artificial intelligence subject matter expert, Anurag is continuously thinking of disruptive ways to connect the evolution of AI and its application to various industries, including insurance. Anurag lives in Connecticut with his wife and two sons.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Brandon Hill Stockton-Hill Insurance
Biography
Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Frank Sentner Sentwood Consulting
Biography

Frank Sentner has been providing technology solutions to the insurance industry for 50 years. His consulting practice is focused on improving the business processes of insurers, insurance brokerage firms, and insurance technology solution providers. He has managed major policy, billing, and claims system replacement projects for insurers and has provided strategic technology consulting for large insurance brokerage firms. Frank led the development of the first ACORD Forms-based agency management system while working for Insurnet in 1976. He started his consulting firm in 1982, then merged it with two other founders in 1984 to form Creative Information Systems (CISCo) where he designed and developed Sagitta, the first ACORD AL3-based agency system, which is still used today by some of the largest insurance brokers in the world. For the last decade, Frank has focused on mentoring Startup InsurTech firms and is currently on the board or advisory board for eight startups. His only remaining corporate consulting client is ACORD.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Evan Silverio Silverio Insurance Agency
Biography

Evan Silverio is President & CEO of Silverio Insurance Group consisting of Silverio Insurance, Woodcome Insurance and Secky Insurance; independent P&C agencies operating across Massachusetts, New Hampshire, and Rhode Island. Building on a family business founded in 1986, he has grown the group into a multi-agency platform serving a diverse, multilingual client base built through organic growth, agency acquisitions and talent development. He is also a real estate investor and an active civic leader in the Merrimack Valley of Massachusetts.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Chris Paradiso Paradiso Finacial and Insurance Services
Biography

Chris Paradiso stands as one of the most influential and forward-thinking agency owners in the insurance industry today. With over 25 years of experience as a licensed insurance agent, Chris’s relentless commitment to exceptional customer service has propelled his agency, Paradiso Insurance, into a thriving operation of 50+ employees. Founded in 2006, the agency has achieved remarkable milestones, including winning Safeco and Liberty Mutual’s prestigious National Agent for the Future Award in 2019. Currently licensed in 44 states, Paradiso Insurance is on track to achieve nationwide licensing in all 50 states. Chris’s visionary leadership extends beyond his agency. Through his coaching platform, Paradiso Presents, he has inspired and guided hundreds of insurance agencies to innovate and achieve success. His influence is further amplified by his roles on the advisory boards of Rough Notes, a leading insurance publication, 101 Weston Labs, Phase 4 Veterans Wall, and the Flagpole Committee. In 2010, Chris was recognized for his work within his local community and throughout Connecticut when he received the Community Service Award from Rough Notes spotlighting the various ways, he gives back including the Bikes for Reading program, Reverse Trick-or-Treat and Annual Flag Day Event. In 2011, Chris launched “Paradiso Presents,” a groundbreaking program focused on social media marketing, data utilization, and process optimization. This initiative equips insurance agencies with the tools to thrive in today’s complex, technology-driven landscape. His innovative marketing strategies have been widely adopted across the industry, earning him a reputation as a digital trailblazer in a field often slow to embrace technological advancements. Chris’s work with Aureus Analytics exemplifies his commitment to leveraging data for enhanced customer insights and service. By championing the use of cutting-edge analytics, he is helping agencies nationwide improve their customer relationships and financial performance. At his core, Chris Paradiso is a family man who leads with the belief that family is everything and that passion for one’s work transforms it into a lifelong joy. His dedication to innovation, community, and mentorship continues to shape the future of the insurance industry.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Anurag Shah Chief Data Officer SIAA
Biography

As SIAA’s Chief Data Officer, Anurag is responsible for developing and executing the overall Data, Analytics and AI Strategy across the organization. This includes deploying data platforms across members as well as Master agencies and strategic carrier partners. He is also responsible for developing the analytics and AI roadmap that will help the organization achieve its vision. Anurag has over 25 years of experience of building and scaling technology products and services. Before joining SIAA, Anurag was the CEO and Co-Founder of DONNA.ai (Aureus Analytics) where he led the organization's overall growth, product roadmap and execution strategy and the eventual sale to SIAA. At DONNA ai he worked closely with a large number of independent insurance agencies across the US and helped them grow their businesses using AI and Data. Anurag started his first technology venture – ESI, at the age of 24, which was later acquired by Omnitech, where he served as the COO & Head of Global Operations. Prior to ESI, he worked for IBM & CBay systems. Anurag's strengths lie at the intersection of business and technology, focusing on artificial intelligence and machine learning. He is a co-author of two patents: Network Analysis and SentiMeter®. Anurag is an engineering graduate from the University of Mumbai and has studied management at NMIMS in Mumbai and executive management from the ISB, Hyderabad. He has also studied Machine Learning from Stanford. As a technology entrepreneur and artificial intelligence subject matter expert, Anurag is continuously thinking of disruptive ways to connect the evolution of AI and its application to various industries, including insurance. Anurag lives in Connecticut with his wife and two sons.

Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM

 

speaker headshot
Brandon Hill Stockton-Hill Insurance
Biography
Sessions (1)
ZOOMAPI All
Modern Retail Agency Operations: Tools, Technology, and AI at Work
01:50 PM
Learn More
02:40 PM

Practical AI for Everyday Agency Work

Move beyond broad AI trends and focus on realistic, high-value use cases for independent agencies and the partners who s...

Practical AI for Everyday Agency Work

Move beyond broad AI trends and focus on realistic, high-value use cases for independent agencies and the partners who support them. This session highlights practical ways AI can support client communications, renewal preparation, account summaries, follow-up, internal handoffs, first drafts of marketing content, and administrative efficiency—while keeping privacy, accuracy review, and human judgment at the center.

Learn More
03:15 PM

Smarter Specialty Placement: Taking the Pain Out of E&S

Improve confidence in placing complex risks by focusing on submission quality, underwriting expectations, wholesale coll...

Smarter Specialty Placement: Taking the Pain Out of E&S

Improve confidence in placing complex risks by focusing on submission quality, underwriting expectations, wholesale collaboration, and practical market access. This session helps agency owners understand when to seek specialty support, how to package risk details clearly, and how to improve placement outcomes for hard-to-place accounts.

Learn More
03:50 PM

The Modern Agency Tech Stack

Understand the core systems, integrations, and workflow decisions that shape how an agency operates day to day. This ses...

The Modern Agency Tech Stack

Understand the core systems, integrations, and workflow decisions that shape how an agency operates day to day. This session helps agency owners evaluate technology more clearly, avoid unnecessary complexity, and identify where tools can create immediate operational efficiency.

Learn More

Producer Productivity and Sales Execution

Focus on practical tactics agencies can use to improve producer productivity, sales follow-up, pipeline visibility, rene...

Producer Productivity and Sales Execution

Focus on practical tactics agencies can use to improve producer productivity, sales follow-up, pipeline visibility, renewal preparation, cross-sell opportunities, and account prioritization. This session gives agency owners, leaders, producers, and future owners actionable ideas for strengthening business development discipline and helping teams focus time on the right opportunities

Learn More
04:25 PM

From Quote to Bind: Reducing Friction in the Agency Workflow

Take a tactical look at the pain points that slow agency teams down—from intake, quoting, submissions, remarketing, co...

From Quote to Bind: Reducing Friction in the Agency Workflow

Take a tactical look at the pain points that slow agency teams down—from intake, quoting, submissions, remarketing, comparative rating, and document management to handoffs and follow-up. This session helps agency owners identify workflow improvements that can save time, reduce friction, and support better execution.

Learn More

Marketing, Retention, and Client Experience

Explore how communication, marketing automation, client segmentation, retention strategies, and digital engagement can s...

Marketing, Retention, and Client Experience

Explore how communication, marketing automation, client segmentation, retention strategies, and digital engagement can strengthen relationships and create more consistent client touchpoints. This session helps agency owners think more intentionally about client experience as a driver of retention and growth.

Learn More
11:30 AM

Opening Main Stage: Reimagining Agency Growth - What's Next is Now

Kick off IA Evolve with opening remarks from Matt Masiello, CEO of SIAA, followed by a main stage conversation with indu...

Opening Main Stage: Reimagining Agency Growth - What's Next is Now

Kick off IA Evolve with opening remarks from Matt Masiello, CEO of SIAA, followed by a main stage conversation with industry leaders from across the independent agency ecosystem. This session will explore how agency growth, carrier relationships, technology, market access, and client expectations are evolving—and what those changes mean for independent agency owners, producers, future owners, carriers, technology partners, and others across the P&C industry.

Session Speakers

 

speaker headshot
Matt Masiello CEO SIAA
Biography

As CEO of SIAA, Matt Masiello has responsibility for executive management of the largest alliance of independent insurance agencies in the United States and its related companies, providing leadership to senior executives of SIAA and Master Agencies across the country.

His more than 30 years of industry experience have instilled in him the skills, knowledge, and expertise to lead SIAA. Matt has responsibility for the organization's overall success,including providing strategic vision for its future and piloting the organization in the execution of that vision. SIAA includes the following strategic business units:

• The Agent Alliance has 49 regional Master Agencies covering all 50 states with over 5,200 independent insurance agencies as Members, which write over $17 billion in P&C premium.

• Sequel Insurance Agencies is a Top 100 retail agency.

• Xchange – Powered by SIAA is a wholesale and MGA platform dedicated to providing member agencies with faster, easier, and frictionless processes in conjunction with non-standard submissions.

• Portfolio IQ is a data driven platform utilizing AI to provide business intelligence that improves growth quality and operational efficiencies for members and partners. In his tenure with SIAA and the insurance industry, Matt has:

• Developed SIAA's internal operations and executed its strategic direction as COO for over 10 years.

• Provided leadership and operational management beginning in 1993 for SAN Group (SIAA's founding and largest Master Agency), as President and CEO.

• Published Insurance Agency 4.0 (Nov 2020), a book depicting how IAs can prepare their agency for the future, develop a digital road map, and increase profit, scalability and time.

• Received the IBA Hot 100 Award in 2017, as a leader shaping the future of the insurance industry.

• Led SIAA, its Member Agencies, Master Agencies and Strategic Partners in raising hundreds of thousands of dollars for Dana-Farber Cancer Institute & The Jimmy Fund, Wounded Warriors Project, Veterans Count, and a number of other philanthropic organizations.

In the last 30 years, Matt has become a subject-matter expert in the field of insurance distribution and agency development. He is a frequent contributor to many industry publications, including Insurance Journal, Property Casualty 360, National Underwriter Magazine, PIA Magazine, Independent Agent, Best's Review and The Standard. Matt is also a frequent presenter and speaker at a variety of insurance conferences, meetings and events.

He has served on regional and national advisory councils for numerous insurance companies and serves on the Board of Trustees of Tilton School. Matt resides on the seacoast of New Hampshire with his wife and three sons. When not working, you can find him and his family boating, fishing, hiking, traveling, or skiing.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Karen Eckert SVP, Personal Insurance Agent Distribution Travelers
Biography

Karen Eckert is Senior Vice President of Personal Insurance Agent Distribution at Travelers. She oversees the Agent Distribution organization for Personal Insurance, which includes seven regional sales teams, inside sales, a national partners sales team, an agency enablement circle and a home office field sales operations group. Her team is comprised of 260 sales professionals who support over $14 billion in premium across more than 20,000 independent agency locations in the U.S. With over 35 years of agency experience in both Business and Personal Insurance, Karen joined Travelers in 2009 in the Select business unit, leading several regions before moving to Personal Insurance and assuming her current role leading the Personal Insurance Agent Distribution Team in 2023.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Hunter Moss CEO SIAA Xchange
Biography

Hunter Moss is Chief Executive Officer of Xchange, SIAA's embedded wholesale and MGA platform, built to simplify E&S placement for members. He sets the strategic vision, owns the platform and program roadmap, and secures the carrier and Lloyd's capacity behind new programs. Hunter has spent his career building MGAs, launching carrier relationships, structuring reinsurance programs, and navigating the Lloyd's of London market. He has also led M&A transactions, raised capital from strategic investors, and created underwriting platforms from the ground up.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Graham Blackwell CEO, President and Incoming CEO Applied Systems
Biography
Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Tim deRosa President Sequel Insurance Agencies
Biography
Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Matt Masiello CEO SIAA
Biography

As CEO of SIAA, Matt Masiello has responsibility for executive management of the largest alliance of independent insurance agencies in the United States and its related companies, providing leadership to senior executives of SIAA and Master Agencies across the country.

His more than 30 years of industry experience have instilled in him the skills, knowledge, and expertise to lead SIAA. Matt has responsibility for the organization's overall success,including providing strategic vision for its future and piloting the organization in the execution of that vision. SIAA includes the following strategic business units:

• The Agent Alliance has 49 regional Master Agencies covering all 50 states with over 5,200 independent insurance agencies as Members, which write over $17 billion in P&C premium.

• Sequel Insurance Agencies is a Top 100 retail agency.

• Xchange – Powered by SIAA is a wholesale and MGA platform dedicated to providing member agencies with faster, easier, and frictionless processes in conjunction with non-standard submissions.

• Portfolio IQ is a data driven platform utilizing AI to provide business intelligence that improves growth quality and operational efficiencies for members and partners. In his tenure with SIAA and the insurance industry, Matt has:

• Developed SIAA's internal operations and executed its strategic direction as COO for over 10 years.

• Provided leadership and operational management beginning in 1993 for SAN Group (SIAA's founding and largest Master Agency), as President and CEO.

• Published Insurance Agency 4.0 (Nov 2020), a book depicting how IAs can prepare their agency for the future, develop a digital road map, and increase profit, scalability and time.

• Received the IBA Hot 100 Award in 2017, as a leader shaping the future of the insurance industry.

• Led SIAA, its Member Agencies, Master Agencies and Strategic Partners in raising hundreds of thousands of dollars for Dana-Farber Cancer Institute & The Jimmy Fund, Wounded Warriors Project, Veterans Count, and a number of other philanthropic organizations.

In the last 30 years, Matt has become a subject-matter expert in the field of insurance distribution and agency development. He is a frequent contributor to many industry publications, including Insurance Journal, Property Casualty 360, National Underwriter Magazine, PIA Magazine, Independent Agent, Best's Review and The Standard. Matt is also a frequent presenter and speaker at a variety of insurance conferences, meetings and events.

He has served on regional and national advisory councils for numerous insurance companies and serves on the Board of Trustees of Tilton School. Matt resides on the seacoast of New Hampshire with his wife and three sons. When not working, you can find him and his family boating, fishing, hiking, traveling, or skiing.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Karen Eckert SVP, Personal Insurance Agent Distribution Travelers
Biography

Karen Eckert is Senior Vice President of Personal Insurance Agent Distribution at Travelers. She oversees the Agent Distribution organization for Personal Insurance, which includes seven regional sales teams, inside sales, a national partners sales team, an agency enablement circle and a home office field sales operations group. Her team is comprised of 260 sales professionals who support over $14 billion in premium across more than 20,000 independent agency locations in the U.S. With over 35 years of agency experience in both Business and Personal Insurance, Karen joined Travelers in 2009 in the Select business unit, leading several regions before moving to Personal Insurance and assuming her current role leading the Personal Insurance Agent Distribution Team in 2023.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Hunter Moss CEO SIAA Xchange
Biography

Hunter Moss is Chief Executive Officer of Xchange, SIAA's embedded wholesale and MGA platform, built to simplify E&S placement for members. He sets the strategic vision, owns the platform and program roadmap, and secures the carrier and Lloyd's capacity behind new programs. Hunter has spent his career building MGAs, launching carrier relationships, structuring reinsurance programs, and navigating the Lloyd's of London market. He has also led M&A transactions, raised capital from strategic investors, and created underwriting platforms from the ground up.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Graham Blackwell CEO, President and Incoming CEO Applied Systems
Biography
Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Tim deRosa President Sequel Insurance Agencies
Biography
Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM
Learn More
12:40 PM

Innovation, Underwriting Discipline, and Growth in the Independent Agency Channel

Explore how carrier priorities, product strategy, underwriting discipline, and market trends are shaping growth opportun...

Innovation, Underwriting Discipline, and Growth in the Independent Agency Channel

Explore how carrier priorities, product strategy, underwriting discipline, and market trends are shaping growth opportunities across the independent agency channel. This session will help agency principals, producers, carrier partners, and industry professionals better understand how alignment can support profitable, sustainable growth.

Learn More
01:15 PM

Commercial Lines Innovation and Smarter Agency Growth

Gain perspective on commercial lines trends, product evolution, underwriting expectations, and small business opportunit...

Commercial Lines Innovation and Smarter Agency Growth

Gain perspective on commercial lines trends, product evolution, underwriting expectations, and small business opportunities that matter to independent agencies and their partners. This session is designed to help attendees understand where the market is moving and how agencies and carriers can support stronger client value and growth.

Learn More

How to Access More Opportunity, Support, and Scale

Learn how independent agencies can expand market access, strengthen operations, use smarter intelligence, tap specialty ...

How to Access More Opportunity, Support, and Scale

Learn how independent agencies can expand market access, strengthen operations, use smarter intelligence, tap specialty resources, and connect with growth support designed around real agency needs. This session is useful for current members looking to maximize available capabilities, producers and future owners exploring what growth can look like, and prospective members evaluating the value of joining a larger independent agency network.

Learn More
03:15 PM

Risk Management, Underwriting Insight, and Agency Value Creation

Learn how risk management trends, underwriting insight, customer education, and carrier expertise can strengthen client ...

Risk Management, Underwriting Insight, and Agency Value Creation

Learn how risk management trends, underwriting insight, customer education, and carrier expertise can strengthen client relationships and improve outcomes across the independent agency channel. This session is designed to help agencies and carrier partners deepen advisory value, improve collaboration, and identify opportunities to support better decisions for clients.

Learn More

Smarter Specialty Placement: Taking the Pain Out of E&S

Improve confidence in placing complex risks by focusing on submission quality, underwriting expectations, wholesale coll...

Smarter Specialty Placement: Taking the Pain Out of E&S

Improve confidence in placing complex risks by focusing on submission quality, underwriting expectations, wholesale collaboration, and practical market access. This session helps agency owners understand when to seek specialty support, how to package risk details clearly, and how to improve placement outcomes for hard-to-place accounts.

Learn More
11:30 AM

Opening Main Stage: Reimagining Agency Growth - What's Next is Now

Kick off IA Evolve with opening remarks from Matt Masiello, CEO of SIAA, followed by a main stage conversation with indu...

Opening Main Stage: Reimagining Agency Growth - What's Next is Now

Kick off IA Evolve with opening remarks from Matt Masiello, CEO of SIAA, followed by a main stage conversation with industry leaders from across the independent agency ecosystem. This session will explore how agency growth, carrier relationships, technology, market access, and client expectations are evolving—and what those changes mean for independent agency owners, producers, future owners, carriers, technology partners, and others across the P&C industry.

Session Speakers

 

speaker headshot
Matt Masiello CEO SIAA
Biography

As CEO of SIAA, Matt Masiello has responsibility for executive management of the largest alliance of independent insurance agencies in the United States and its related companies, providing leadership to senior executives of SIAA and Master Agencies across the country.

His more than 30 years of industry experience have instilled in him the skills, knowledge, and expertise to lead SIAA. Matt has responsibility for the organization's overall success,including providing strategic vision for its future and piloting the organization in the execution of that vision. SIAA includes the following strategic business units:

• The Agent Alliance has 49 regional Master Agencies covering all 50 states with over 5,200 independent insurance agencies as Members, which write over $17 billion in P&C premium.

• Sequel Insurance Agencies is a Top 100 retail agency.

• Xchange – Powered by SIAA is a wholesale and MGA platform dedicated to providing member agencies with faster, easier, and frictionless processes in conjunction with non-standard submissions.

• Portfolio IQ is a data driven platform utilizing AI to provide business intelligence that improves growth quality and operational efficiencies for members and partners. In his tenure with SIAA and the insurance industry, Matt has:

• Developed SIAA's internal operations and executed its strategic direction as COO for over 10 years.

• Provided leadership and operational management beginning in 1993 for SAN Group (SIAA's founding and largest Master Agency), as President and CEO.

• Published Insurance Agency 4.0 (Nov 2020), a book depicting how IAs can prepare their agency for the future, develop a digital road map, and increase profit, scalability and time.

• Received the IBA Hot 100 Award in 2017, as a leader shaping the future of the insurance industry.

• Led SIAA, its Member Agencies, Master Agencies and Strategic Partners in raising hundreds of thousands of dollars for Dana-Farber Cancer Institute & The Jimmy Fund, Wounded Warriors Project, Veterans Count, and a number of other philanthropic organizations.

In the last 30 years, Matt has become a subject-matter expert in the field of insurance distribution and agency development. He is a frequent contributor to many industry publications, including Insurance Journal, Property Casualty 360, National Underwriter Magazine, PIA Magazine, Independent Agent, Best's Review and The Standard. Matt is also a frequent presenter and speaker at a variety of insurance conferences, meetings and events.

He has served on regional and national advisory councils for numerous insurance companies and serves on the Board of Trustees of Tilton School. Matt resides on the seacoast of New Hampshire with his wife and three sons. When not working, you can find him and his family boating, fishing, hiking, traveling, or skiing.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Karen Eckert SVP, Personal Insurance Agent Distribution Travelers
Biography

Karen Eckert is Senior Vice President of Personal Insurance Agent Distribution at Travelers. She oversees the Agent Distribution organization for Personal Insurance, which includes seven regional sales teams, inside sales, a national partners sales team, an agency enablement circle and a home office field sales operations group. Her team is comprised of 260 sales professionals who support over $14 billion in premium across more than 20,000 independent agency locations in the U.S. With over 35 years of agency experience in both Business and Personal Insurance, Karen joined Travelers in 2009 in the Select business unit, leading several regions before moving to Personal Insurance and assuming her current role leading the Personal Insurance Agent Distribution Team in 2023.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Hunter Moss CEO SIAA Xchange
Biography

Hunter Moss is Chief Executive Officer of Xchange, SIAA's embedded wholesale and MGA platform, built to simplify E&S placement for members. He sets the strategic vision, owns the platform and program roadmap, and secures the carrier and Lloyd's capacity behind new programs. Hunter has spent his career building MGAs, launching carrier relationships, structuring reinsurance programs, and navigating the Lloyd's of London market. He has also led M&A transactions, raised capital from strategic investors, and created underwriting platforms from the ground up.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Graham Blackwell CEO, President and Incoming CEO Applied Systems
Biography
Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Tim deRosa President Sequel Insurance Agencies
Biography
Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Matt Masiello CEO SIAA
Biography

As CEO of SIAA, Matt Masiello has responsibility for executive management of the largest alliance of independent insurance agencies in the United States and its related companies, providing leadership to senior executives of SIAA and Master Agencies across the country.

His more than 30 years of industry experience have instilled in him the skills, knowledge, and expertise to lead SIAA. Matt has responsibility for the organization's overall success,including providing strategic vision for its future and piloting the organization in the execution of that vision. SIAA includes the following strategic business units:

• The Agent Alliance has 49 regional Master Agencies covering all 50 states with over 5,200 independent insurance agencies as Members, which write over $17 billion in P&C premium.

• Sequel Insurance Agencies is a Top 100 retail agency.

• Xchange – Powered by SIAA is a wholesale and MGA platform dedicated to providing member agencies with faster, easier, and frictionless processes in conjunction with non-standard submissions.

• Portfolio IQ is a data driven platform utilizing AI to provide business intelligence that improves growth quality and operational efficiencies for members and partners. In his tenure with SIAA and the insurance industry, Matt has:

• Developed SIAA's internal operations and executed its strategic direction as COO for over 10 years.

• Provided leadership and operational management beginning in 1993 for SAN Group (SIAA's founding and largest Master Agency), as President and CEO.

• Published Insurance Agency 4.0 (Nov 2020), a book depicting how IAs can prepare their agency for the future, develop a digital road map, and increase profit, scalability and time.

• Received the IBA Hot 100 Award in 2017, as a leader shaping the future of the insurance industry.

• Led SIAA, its Member Agencies, Master Agencies and Strategic Partners in raising hundreds of thousands of dollars for Dana-Farber Cancer Institute & The Jimmy Fund, Wounded Warriors Project, Veterans Count, and a number of other philanthropic organizations.

In the last 30 years, Matt has become a subject-matter expert in the field of insurance distribution and agency development. He is a frequent contributor to many industry publications, including Insurance Journal, Property Casualty 360, National Underwriter Magazine, PIA Magazine, Independent Agent, Best's Review and The Standard. Matt is also a frequent presenter and speaker at a variety of insurance conferences, meetings and events.

He has served on regional and national advisory councils for numerous insurance companies and serves on the Board of Trustees of Tilton School. Matt resides on the seacoast of New Hampshire with his wife and three sons. When not working, you can find him and his family boating, fishing, hiking, traveling, or skiing.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Karen Eckert SVP, Personal Insurance Agent Distribution Travelers
Biography

Karen Eckert is Senior Vice President of Personal Insurance Agent Distribution at Travelers. She oversees the Agent Distribution organization for Personal Insurance, which includes seven regional sales teams, inside sales, a national partners sales team, an agency enablement circle and a home office field sales operations group. Her team is comprised of 260 sales professionals who support over $14 billion in premium across more than 20,000 independent agency locations in the U.S. With over 35 years of agency experience in both Business and Personal Insurance, Karen joined Travelers in 2009 in the Select business unit, leading several regions before moving to Personal Insurance and assuming her current role leading the Personal Insurance Agent Distribution Team in 2023.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Hunter Moss CEO SIAA Xchange
Biography

Hunter Moss is Chief Executive Officer of Xchange, SIAA's embedded wholesale and MGA platform, built to simplify E&S placement for members. He sets the strategic vision, owns the platform and program roadmap, and secures the carrier and Lloyd's capacity behind new programs. Hunter has spent his career building MGAs, launching carrier relationships, structuring reinsurance programs, and navigating the Lloyd's of London market. He has also led M&A transactions, raised capital from strategic investors, and created underwriting platforms from the ground up.

Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Graham Blackwell CEO, President and Incoming CEO Applied Systems
Biography
Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM

 

speaker headshot
Tim deRosa President Sequel Insurance Agencies
Biography
Sessions (1)
ZOOMAPI All
Opening Main Stage: Reimagining Agency Growth - What's Next is Now
11:30 AM
Learn More
12:40 PM

Innovation, Underwriting Discipline, and Growth in the Independent Agency Channel

Explore how carrier priorities, product strategy, underwriting discipline, and market trends are shaping growth opportun...

Innovation, Underwriting Discipline, and Growth in the Independent Agency Channel

Explore how carrier priorities, product strategy, underwriting discipline, and market trends are shaping growth opportunities across the independent agency channel. This session will help agency principals, producers, carrier partners, and industry professionals better understand how alignment can support profitable, sustainable growth.

Learn More

Putting Data and AI-Supported Insights to Work

See how agencies can use better intelligence to identify opportunities, prioritize growth conversations, focus producer ...

Putting Data and AI-Supported Insights to Work

See how agencies can use better intelligence to identify opportunities, prioritize growth conversations, focus producer effort, and make more confident business decisions. This practical session connects data and AI-supported insights to everyday agency planning, client engagement, and growth execution.

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01:15 PM

Commercial Lines Innovation and Smarter Agency Growth

Gain perspective on commercial lines trends, product evolution, underwriting expectations, and small business opportunit...

Commercial Lines Innovation and Smarter Agency Growth

Gain perspective on commercial lines trends, product evolution, underwriting expectations, and small business opportunities that matter to independent agencies and their partners. This session is designed to help attendees understand where the market is moving and how agencies and carriers can support stronger client value and growth.

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How to Access More Opportunity, Support, and Scale

Learn how independent agencies can expand market access, strengthen operations, use smarter intelligence, tap specialty ...

How to Access More Opportunity, Support, and Scale

Learn how independent agencies can expand market access, strengthen operations, use smarter intelligence, tap specialty resources, and connect with growth support designed around real agency needs. This session is useful for current members looking to maximize available capabilities, producers and future owners exploring what growth can look like, and prospective members evaluating the value of joining a larger independent agency network.

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03:50 PM

Producer Productivity and Sales Execution

Focus on practical tactics agencies can use to improve producer productivity, sales follow-up, pipeline visibility, rene...

Producer Productivity and Sales Execution

Focus on practical tactics agencies can use to improve producer productivity, sales follow-up, pipeline visibility, renewal preparation, cross-sell opportunities, and account prioritization. This session gives agency owners, leaders, producers, and future owners actionable ideas for strengthening business development discipline and helping teams focus time on the right opportunities

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04:25 PM

Marketing, Retention, and Client Experience

Explore how communication, marketing automation, client segmentation, retention strategies, and digital engagement can s...

Marketing, Retention, and Client Experience

Explore how communication, marketing automation, client segmentation, retention strategies, and digital engagement can strengthen relationships and create more consistent client touchpoints. This session helps agency owners think more intentionally about client experience as a driver of retention and growth.

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Built for the Independent Agency

Whether you’re running an agency, building one, selling insurance, supporting agencies, or helping shape the future of the industry, IA Evolve gives you a clearer view of what’s ahead


Agency Leaders

Discover new opportunities, improve operations, and build a stronger path to growth.

Producers & Sales Leaders

Sharpen sales execution, improve follow-up, and focus time where it matters most.

Operations & Service Teams

Find practical ways to reduce friction, improve workflows, and create a better client experience.

Carriers & Industry Partners

Better understand agency priorities and discover new ways to create value together.

Event Exhibitors

PortfolioIQ

PortfolioIQ

Xchange

Xchange

Vertafore

Vertafore

About 1

Welcome to [Event Name]! Join us for an unforgettable experience filled with excitement, inspiration, and connection. Our event brings together industry leaders, experts, and enthusiasts to share knowledge, engage in meaningful discussions, and foster valuable connections. Explore innovative ideas, discover new opportunities, and be a part of this vibrant gathering. Whether you’re a seasoned professional or a curious newcomer, there’s something for everyone at [Event Name]. Get ready for a day of learning, networking, and fun. See you there!