IA EVOLVE

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 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 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, Chief Executive Officer, leads Applied Systems’ overall business strategy, operations, and growth initiatives. Prior to being named CEO, Graham served as President of Applied Systems, where he was responsible for the company’s Strategic Growth Business Units, including Ivans, EZLynx, and Applied Pay.

Graham joined Applied in 2020 from SMS Assist, where he led the company’s sales, marketing, and strategy functions as Chief Revenue Officer. Prior to SMS Assist, he spent nearly eight years with Bain Capital’s Private Equity operating team, partnering closely with the boards and management teams of Bain Capital portfolio companies.

Earlier in his career, Graham was an Associate Partner with McKinsey & Company and a consultant with Accenture.

Graham holds an MBA from the University of Chicago Booth School of Business and a BBA from Ohio University.

As President of Sequel Insurance Agencies, Tim leads the strategic buildout of SIAA’s retail insurance agency venture, designed to extend SIAA – The Agent Alliance’s market-leading position in the network space while creating additional, accretive value and optionality for Master Agency partners and Member Agencies. The launch of Sequel further expands SIAA’s total-solution offering for the independent agency channel. In his role, Tim is responsible for enterprise leadership across the retail platform.

Tim brings more than 25 years of experience across the carrier, wholesale, and retail segments of the insurance industry. He has held senior leadership roles at Chubb, founded and successfully sold

a wholesale/MGA business to a private equity–backed firm, and most recently served as Chief Operating Officer of Risk Strategies Private Client Services, where he specialized in serving high-net-worth clients. Across these roles, Tim has built and scaled insurance operations, integrated acquisitions, developed high-performing teams, and cultivated long-standing industry relationships.

In addition to his professional leadership, Tim remains actively engaged in both industry and community organizations. He holds the CIC designation and has served as a member of the Boston Estate Planning Council and the Family Office Exchange (FOX). He also served on AIG Private Client Group’s National Strategic Broker Council and currently serves as Vice President of the Board of Directors of Bend FC, combining his leadership experience with a passion for youth sports.

Tim earned a Bachelor of Arts in Political Science with a concentration in international government and politics from Drew University, where he was a member of the men’s soccer team and received both all-conference and academic all-conference honors. He resides in Bend, Oregon, with his wife and three children, and enjoys backcountry skiing, mountain biking, and golf.

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 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 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.

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.

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 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 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, Chief Executive Officer, leads Applied Systems’ overall business strategy, operations, and growth initiatives. Prior to being named CEO, Graham served as President of Applied Systems, where he was responsible for the company’s Strategic Growth Business Units, including Ivans, EZLynx, and Applied Pay.

Graham joined Applied in 2020 from SMS Assist, where he led the company’s sales, marketing, and strategy functions as Chief Revenue Officer. Prior to SMS Assist, he spent nearly eight years with Bain Capital’s Private Equity operating team, partnering closely with the boards and management teams of Bain Capital portfolio companies.

Earlier in his career, Graham was an Associate Partner with McKinsey & Company and a consultant with Accenture.

Graham holds an MBA from the University of Chicago Booth School of Business and a BBA from Ohio University.

As President of Sequel Insurance Agencies, Tim leads the strategic buildout of SIAA’s retail insurance agency venture, designed to extend SIAA – The Agent Alliance’s market-leading position in the network space while creating additional, accretive value and optionality for Master Agency partners and Member Agencies. The launch of Sequel further expands SIAA’s total-solution offering for the independent agency channel. In his role, Tim is responsible for enterprise leadership across the retail platform.

Tim brings more than 25 years of experience across the carrier, wholesale, and retail segments of the insurance industry. He has held senior leadership roles at Chubb, founded and successfully sold

a wholesale/MGA business to a private equity–backed firm, and most recently served as Chief Operating Officer of Risk Strategies Private Client Services, where he specialized in serving high-net-worth clients. Across these roles, Tim has built and scaled insurance operations, integrated acquisitions, developed high-performing teams, and cultivated long-standing industry relationships.

In addition to his professional leadership, Tim remains actively engaged in both industry and community organizations. He holds the CIC designation and has served as a member of the Boston Estate Planning Council and the Family Office Exchange (FOX). He also served on AIG Private Client Group’s National Strategic Broker Council and currently serves as Vice President of the Board of Directors of Bend FC, combining his leadership experience with a passion for youth sports.

Tim earned a Bachelor of Arts in Political Science with a concentration in international government and politics from Drew University, where he was a member of the men’s soccer team and received both all-conference and academic all-conference honors. He resides in Bend, Oregon, with his wife and three children, and enjoys backcountry skiing, mountain biking, and golf.

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 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 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, Chief Executive Officer, leads Applied Systems’ overall business strategy, operations, and growth initiatives. Prior to being named CEO, Graham served as President of Applied Systems, where he was responsible for the company’s Strategic Growth Business Units, including Ivans, EZLynx, and Applied Pay.

Graham joined Applied in 2020 from SMS Assist, where he led the company’s sales, marketing, and strategy functions as Chief Revenue Officer. Prior to SMS Assist, he spent nearly eight years with Bain Capital’s Private Equity operating team, partnering closely with the boards and management teams of Bain Capital portfolio companies.

Earlier in his career, Graham was an Associate Partner with McKinsey & Company and a consultant with Accenture.

Graham holds an MBA from the University of Chicago Booth School of Business and a BBA from Ohio University.

As President of Sequel Insurance Agencies, Tim leads the strategic buildout of SIAA’s retail insurance agency venture, designed to extend SIAA – The Agent Alliance’s market-leading position in the network space while creating additional, accretive value and optionality for Master Agency partners and Member Agencies. The launch of Sequel further expands SIAA’s total-solution offering for the independent agency channel. In his role, Tim is responsible for enterprise leadership across the retail platform.

Tim brings more than 25 years of experience across the carrier, wholesale, and retail segments of the insurance industry. He has held senior leadership roles at Chubb, founded and successfully sold

a wholesale/MGA business to a private equity–backed firm, and most recently served as Chief Operating Officer of Risk Strategies Private Client Services, where he specialized in serving high-net-worth clients. Across these roles, Tim has built and scaled insurance operations, integrated acquisitions, developed high-performing teams, and cultivated long-standing industry relationships.

In addition to his professional leadership, Tim remains actively engaged in both industry and community organizations. He holds the CIC designation and has served as a member of the Boston Estate Planning Council and the Family Office Exchange (FOX). He also served on AIG Private Client Group’s National Strategic Broker Council and currently serves as Vice President of the Board of Directors of Bend FC, combining his leadership experience with a passion for youth sports.

Tim earned a Bachelor of Arts in Political Science with a concentration in international government and politics from Drew University, where he was a member of the men’s soccer team and received both all-conference and academic all-conference honors. He resides in Bend, Oregon, with his wife and three children, and enjoys backcountry skiing, mountain biking, and golf.

Business Leader, National Accounts, Progressive Insurance Jeff Hannon joined Progressive in 2005 as the Ohio Regional Sales Manager and has held a variety of roles within Agency Distribution. Since 2021, Jeff has led National Accounts, responsible for large account strategy and execution focused on profitably growing our share within Progressive’s largest relationships. Jeff has spent the vast majority of his career working with independent agents. Immediately prior to joining Progressive, Jeff was the AVP of Agency Management for Liberty Mutual’s Agency Markets. Jeff holds a bachelor's degree from John Carroll University. Jeff lives in Chagrin Falls, Ohio, with his wife, Dawn, and they have two grown sons.

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 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 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, Chief Executive Officer, leads Applied Systems’ overall business strategy, operations, and growth initiatives. Prior to being named CEO, Graham served as President of Applied Systems, where he was responsible for the company’s Strategic Growth Business Units, including Ivans, EZLynx, and Applied Pay.

Graham joined Applied in 2020 from SMS Assist, where he led the company’s sales, marketing, and strategy functions as Chief Revenue Officer. Prior to SMS Assist, he spent nearly eight years with Bain Capital’s Private Equity operating team, partnering closely with the boards and management teams of Bain Capital portfolio companies.

Earlier in his career, Graham was an Associate Partner with McKinsey & Company and a consultant with Accenture.

Graham holds an MBA from the University of Chicago Booth School of Business and a BBA from Ohio University.

As President of Sequel Insurance Agencies, Tim leads the strategic buildout of SIAA’s retail insurance agency venture, designed to extend SIAA – The Agent Alliance’s market-leading position in the network space while creating additional, accretive value and optionality for Master Agency partners and Member Agencies. The launch of Sequel further expands SIAA’s total-solution offering for the independent agency channel. In his role, Tim is responsible for enterprise leadership across the retail platform.

Tim brings more than 25 years of experience across the carrier, wholesale, and retail segments of the insurance industry. He has held senior leadership roles at Chubb, founded and successfully sold

a wholesale/MGA business to a private equity–backed firm, and most recently served as Chief Operating Officer of Risk Strategies Private Client Services, where he specialized in serving high-net-worth clients. Across these roles, Tim has built and scaled insurance operations, integrated acquisitions, developed high-performing teams, and cultivated long-standing industry relationships.

In addition to his professional leadership, Tim remains actively engaged in both industry and community organizations. He holds the CIC designation and has served as a member of the Boston Estate Planning Council and the Family Office Exchange (FOX). He also served on AIG Private Client Group’s National Strategic Broker Council and currently serves as Vice President of the Board of Directors of Bend FC, combining his leadership experience with a passion for youth sports.

Tim earned a Bachelor of Arts in Political Science with a concentration in international government and politics from Drew University, where he was a member of the men’s soccer team and received both all-conference and academic all-conference honors. He resides in Bend, Oregon, with his wife and three children, and enjoys backcountry skiing, mountain biking, and golf.

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 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 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.

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.

D.J. Postles is Chief Underwriting Officer of Xchange, SIAA's embedded wholesale and MGA platform, built to simplify E&S placement for members. He owns underwriting strategy, portfolio performance, and carrier relationships. He brings more than 25 years of underwriting and leadership experience across global carriers, specialty MGAs, and reinsurance organizations. D.J. has built and managed diversified portfolios in both regional and national markets, driving profitable growth through disciplined underwriting and strong broker and carrier partnerships

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 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 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, Chief Executive Officer, leads Applied Systems’ overall business strategy, operations, and growth initiatives. Prior to being named CEO, Graham served as President of Applied Systems, where he was responsible for the company’s Strategic Growth Business Units, including Ivans, EZLynx, and Applied Pay.

Graham joined Applied in 2020 from SMS Assist, where he led the company’s sales, marketing, and strategy functions as Chief Revenue Officer. Prior to SMS Assist, he spent nearly eight years with Bain Capital’s Private Equity operating team, partnering closely with the boards and management teams of Bain Capital portfolio companies.

Earlier in his career, Graham was an Associate Partner with McKinsey & Company and a consultant with Accenture.

Graham holds an MBA from the University of Chicago Booth School of Business and a BBA from Ohio University.

As President of Sequel Insurance Agencies, Tim leads the strategic buildout of SIAA’s retail insurance agency venture, designed to extend SIAA – The Agent Alliance’s market-leading position in the network space while creating additional, accretive value and optionality for Master Agency partners and Member Agencies. The launch of Sequel further expands SIAA’s total-solution offering for the independent agency channel. In his role, Tim is responsible for enterprise leadership across the retail platform.

Tim brings more than 25 years of experience across the carrier, wholesale, and retail segments of the insurance industry. He has held senior leadership roles at Chubb, founded and successfully sold

a wholesale/MGA business to a private equity–backed firm, and most recently served as Chief Operating Officer of Risk Strategies Private Client Services, where he specialized in serving high-net-worth clients. Across these roles, Tim has built and scaled insurance operations, integrated acquisitions, developed high-performing teams, and cultivated long-standing industry relationships.

In addition to his professional leadership, Tim remains actively engaged in both industry and community organizations. He holds the CIC designation and has served as a member of the Boston Estate Planning Council and the Family Office Exchange (FOX). He also served on AIG Private Client Group’s National Strategic Broker Council and currently serves as Vice President of the Board of Directors of Bend FC, combining his leadership experience with a passion for youth sports.

Tim earned a Bachelor of Arts in Political Science with a concentration in international government and politics from Drew University, where he was a member of the men’s soccer team and received both all-conference and academic all-conference honors. He resides in Bend, Oregon, with his wife and three children, and enjoys backcountry skiing, mountain biking, and golf.

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 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 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.

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.

Rob Bourne is the SVP and General Manager of EZLynx. He previously served as SVP at Applied Systems, overseeing Inside Sales, Account Management, Business Development, and Alliance Partnerships. Before that, he held senior roles at Athelas and Podium, where he spearheaded growth, revenue strategy, and operations. With an MBA from Cornell University and extensive experience in AI-driven platforms, Bourne brings strategic insight and proven expertise in scaling innovative technology solutions.