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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
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.
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.
Matt Masiello
CEO, SIAA
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.
Karen Eckert
SVP, Personal Insurance Agent Distribution, Travelers
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.
Hunter Moss
CEO, SIAA Xchange
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.
Graham Blackwell
CEO, President and Incoming CEO, Applied SystemsTim deRosa
President, Sequel Insurance Agencies
Matt Masiello
CEO, SIAA
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.
Karen Eckert
SVP, Personal Insurance Agent Distribution, Travelers
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.
Hunter Moss
CEO, SIAA Xchange
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.
Graham Blackwell
CEO, President and Incoming CEO, Applied SystemsTim deRosa
President, Sequel Insurance AgenciesTake 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.
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.
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.
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 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.
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.
Frank Sentner
Sentwood Consulting
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.
Evan Silverio
Silverio Insurance Agency
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.
Chris Paradiso
Paradiso Finacial and Insurance Services
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.
Anurag Shah
Chief Data Officer, SIAA
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.
Brandon Hill
Stockton-Hill Insurance
Frank Sentner
Sentwood Consulting
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.
Evan Silverio
Silverio Insurance Agency
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.
Chris Paradiso
Paradiso Finacial and Insurance Services
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.
Anurag Shah
Chief Data Officer, SIAA
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.
Brandon Hill
Stockton-Hill InsuranceMove 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 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.
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.
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
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.
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.
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.
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.
Matt Masiello
CEO, SIAA
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.
Karen Eckert
SVP, Personal Insurance Agent Distribution, Travelers
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.
Hunter Moss
CEO, SIAA Xchange
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.
Graham Blackwell
CEO, President and Incoming CEO, Applied SystemsTim deRosa
President, Sequel Insurance Agencies
Matt Masiello
CEO, SIAA
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.
Karen Eckert
SVP, Personal Insurance Agent Distribution, Travelers
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.
Hunter Moss
CEO, SIAA Xchange
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.
Graham Blackwell
CEO, President and Incoming CEO, Applied SystemsTim deRosa
President, Sequel Insurance AgenciesSee 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.
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.
Frank Sentner
Sentwood Consulting
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.
Evan Silverio
Silverio Insurance Agency
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.
Chris Paradiso
Paradiso Finacial and Insurance Services
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.
Anurag Shah
Chief Data Officer, SIAA
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.
Brandon Hill
Stockton-Hill Insurance
Frank Sentner
Sentwood Consulting
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.
Evan Silverio
Silverio Insurance Agency
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.
Chris Paradiso
Paradiso Finacial and Insurance Services
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.
Anurag Shah
Chief Data Officer, SIAA
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.
Brandon Hill
Stockton-Hill InsuranceMove 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.
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.
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.
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.
Matt Masiello
CEO, SIAA
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.
Karen Eckert
SVP, Personal Insurance Agent Distribution, Travelers
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.
Hunter Moss
CEO, SIAA Xchange
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.
Graham Blackwell
CEO, President and Incoming CEO, Applied SystemsTim deRosa
President, Sequel Insurance Agencies
Matt Masiello
CEO, SIAA
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.
Karen Eckert
SVP, Personal Insurance Agent Distribution, Travelers
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.
Hunter Moss
CEO, SIAA Xchange
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.
Graham Blackwell
CEO, President and Incoming CEO, Applied SystemsTim deRosa
President, Sequel Insurance AgenciesHear 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.
Frank Sentner
Sentwood Consulting
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.
Evan Silverio
Silverio Insurance Agency
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.
Chris Paradiso
Paradiso Finacial and Insurance Services
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.
Anurag Shah
Chief Data Officer, SIAA
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.
Brandon Hill
Stockton-Hill Insurance
Frank Sentner
Sentwood Consulting
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.
Evan Silverio
Silverio Insurance Agency
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.
Chris Paradiso
Paradiso Finacial and Insurance Services
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.
Anurag Shah
Chief Data Officer, SIAA
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.
Brandon Hill
Stockton-Hill InsuranceMove 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.
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.
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.
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
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.
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.
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.
Matt Masiello
CEO, SIAA
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.
Karen Eckert
SVP, Personal Insurance Agent Distribution, Travelers
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.
Hunter Moss
CEO, SIAA Xchange
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.
Graham Blackwell
CEO, President and Incoming CEO, Applied SystemsTim deRosa
President, Sequel Insurance Agencies
Matt Masiello
CEO, SIAA
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.
Karen Eckert
SVP, Personal Insurance Agent Distribution, Travelers
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.
Hunter Moss
CEO, SIAA Xchange
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.
Graham Blackwell
CEO, President and Incoming CEO, Applied SystemsTim deRosa
President, Sequel Insurance AgenciesExplore 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.
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 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 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.
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.
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.
Matt Masiello
CEO, SIAA
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.
Karen Eckert
SVP, Personal Insurance Agent Distribution, Travelers
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.
Hunter Moss
CEO, SIAA Xchange
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.
Graham Blackwell
CEO, President and Incoming CEO, Applied SystemsTim deRosa
President, Sequel Insurance Agencies
Matt Masiello
CEO, SIAA
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.
Karen Eckert
SVP, Personal Insurance Agent Distribution, Travelers
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.
Hunter Moss
CEO, SIAA Xchange
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.
Graham Blackwell
CEO, President and Incoming CEO, Applied SystemsTim deRosa
President, Sequel Insurance AgenciesExplore 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.
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.
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 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.
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
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.
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
Discover new opportunities, improve operations, and build a stronger path to growth.
Sharpen sales execution, improve follow-up, and focus time where it matters most.
Find practical ways to reduce friction, improve workflows, and create a better client experience.
Better understand agency priorities and discover new ways to create value together.
Event Exhibitors
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!
Stockton-Hill Insurance
President, Sequel Insurance Agencies
CEO, President and Incoming CEO, Applied Systems
Chief Data Officer, SIAA
READ BIOSIAA
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.
Paradiso Finacial and Insurance Services
READ BIOParadiso Finacial and Insurance Services
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.
Silverio Insurance Agency
READ BIOSilverio Insurance Agency
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.
Sentwood Consulting
READ BIOSentwood Consulting
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.
CEO, SIAA Xchange
READ BIOSIAA Xchange
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.
SVP, Personal Insurance Agent Distribution, Travelers
READ BIOTravelers
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.
CEO, SIAA
READ BIOSIAA
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.
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