Agenda: Guidewire Executive Symposium 2026

Throughout the Day	Main Arrival Day Transportation provided from Fort Lauderdale and Palm Beach Airports to The Boca Raton Hotel for customers.
8:00 AM–1:30 PM	Hosted Golf Tee Times Sponsored by One, Inc. Location: The Boca Raton Harborside Golf Course This activity is optional and requires pre-registration. The golf course is located on property. Sleeping rooms will be available for those attendees arriving the evening of Tuesday, March 24.
1:00 PM–4:30 PM	Catamaran Tour Departs from the Hotel Set sail aboard the Palm Breeze Catamaran and soak up the South Florida sunshine as ocean breezes carry you across the Atlantic. This spacious 55-foot sailing catamaran, featuring a wide 30-foot beam and towering 75-foot mast, offers the perfect blend of relaxation and adventure on the open water. This activity is optional and requires pre-registration.
1:00 PM-5:00 PM	Delray Food Tour Departs from the Hotel – 25 Minute Transfer Time Taste your way through downtown Delray Beach on a guided stroll along Atlantic Avenue. Enjoy samples from local restaurants, hear insider stories from chefs and mixologists, and get a flavorful glimpse into the city’s culture and history. Bon Appétit! This activity is optional and requires pre-registration. Vegetarian and pescatarian options are available, but we are unable to provide vegan or gluten-free selections on this tour.
10:30 AM–6:00 PM	Event Registration and Hospitality Area Open Location: Registration South
7:00 PM–9:00 PM	Welcome Reception Sponsored by Hi Marley Location: Harborside Lawn – Guests invited

7:45 AM–9:00 AM	Group Breakfast Sponsored by Smart Communications Location: Alhambra Lawn – Guests invited
9:00 AM–10:30 AM	Guidewire Keynote Mike Rosenbaum, Chief Executive Officer, Guidewire John Mullen, President, Guidewire Christina Colby, Chief Customer Officer, Guidewire Join CEO Mike Rosenbaum and Guidewire’s leadership team for a keynote on the next chapter of intelligent insurance, enabled by our intelligent insurance platform that brings together modern core systems, unified data, analytics, and AI. The team will introduce our latest innovations and highlight how they help insurers accelerate speed to market, improve operational efficiency, strengthen decision making, and deliver better experiences for customers and agents. Mike and the team will outline the strategic shifts and technology capabilities that will define competitive advantage in the years ahead. Location: Royal Ballroom – All Attendees
10:30 AM–11:00 AM	Mid-Morning Break Location: Royal Assembly
11:00 AM-11:20 AM	ProNavigator: Activating Knowledge for Intelligent Insurance Joseph D’Souza, Founder, ProNavigator, Guidewire Graham Haigh, Advisor, Former COO, Wawanesa Join host Joseph D’Souza, founder of ProNavigator (acquired by Guidewire), and special guest Graham Haigh, former COO of Wawanesa, for a discussion enabling Intelligent Insurance. This session explores how ProNavigator transforms fragmented, static information into real-time, actionable guidance across underwriting, claims, and distribution. Attendees will gain insight into how intelligent knowledge management improves decision quality, operational efficiency. Together, they will unpack the “Build vs. Buy" decision, the necessity of human-in-the-loop workflows, and the leadership strategies required to ensure AI tools are adopted by the frontline. Location: Royal Ballroom - All Attendees
11:20 AM–11:45 AM	Intelligent Insurance in Action: How Guidewire Insurtech Innovators Deliver Smarter Claims Decisions Sponsored by PwC Laura Drabik, Chief Evangelist, Guidewire Michael Flanagan, Chief Executive Officer, Xtract Alex Johnson, Vice President of Insurance, Quantexa Emmanuel Singletary, Senior Solution Consultant, Guidewire Michael Balarezo, Chief Executive Officer, Adjusto Chrysa Jones, Co-founder & Chief Operating Officer, StreamSettle Join Guidewire Chief Evangelist Laura Drabik for a dynamic demonstration of how new innovations in data and automation are elevating intelligence and decision-making across the claims value chain. Our graduating Insurtech Vanguards – Xtract and Quantexa, will show how their solutions work in concert with Guidewire to deliver clarity, context, and confidence at every step of the claims journey. Location: Royal Ballroom - All Attendees
11:45 AM–12:05 PM	Scaling Innovation: Modernizing Bond & Specialty Insurance at Travelers Tracey Cournoyer, Senior Vice President and Chief Information and Operations Officer Bond & Specialty Insurance, Travelers Travelers is driving a global digital transformation by balancing the "Perform and Transform" framework, executing reliably today while building the architecture for tomorrow. This session explores the Bond & Specialty Insurance journey, including the transition to Guidewire Cloud and the use of modern architecture to improve data accessibility and integrate AI. Join Chief Information and Operations Officer, Tracey Cournoyer, as she provides an executive roadmap for reimagining processes to deliver industry-leading results and enhanced customer experiences. Location: Royal Ballroom - InsuranceSuite Attendees
11:45 AM–12:30 PM	InsuranceNow 2026: Accelerating the Future of Core Insurance Sponsored by Ogon Consulting Ben Guyer, Senior Director of Product Management, InsuranceNow, Guidewire Gain an executive‑level view of the strategic direction and long‑term vision for the Guidewire InsuranceNow platform. Presented and moderated by Ben Guyer, Senior Director of Product Management for InsuranceNow, this session looks beyond the near‑term roadmap to show how InsuranceNow will continue to lead as an all‑in‑one, cloud‑native core system for the P&C industry’s next decade. Designed for InsuranceNow customers and key stakeholders, this forward‑looking session will focus on using your core platform to drive market differentiation, efficiency, and growth. Key innovation areas include: Agentic AI and the future of core Next‑generation data and pricing Cloud‑native platform evolution Strategic line of business expansion Join us to see how your core platform is evolving to stay ahead of critical industry shifts and position your organization for long‑term success in a rapidly changing market. Location: Royal Salon IX – InsuranceNow Attendees
12:05 PM–2:00 PM	Lunch Sponsored by Accenture Location: Alhambra Lawn
2:00 PM–2:30 PM	A Conversation with Dame Inga Beale, former CEO of Lloyd’s Sponsored by EY Dame Inga Beale, former CEO of Lloyd’s Moderator: Brian Desmond, Chief Marketing Officer, Guidewire Join Dame Inga Beale, former CEO of Lloyd’s, for a strategic conversation on the forces reshaping the insurance industry and what they mean for today’s leaders. Drawing on her extensive global experience, Inga will explore how AI is transforming operations and outcomes, how organizational structures and talent models must evolve, and where the most significant opportunities and risks are emerging. She will also share her hopes for the industry’s future and offer practical guidance on the decisions and priorities that matter most as leaders navigate this era of change. This session offers executives a rare opportunity to learn from one of the industry’s most respected and influential voices as they position their organizations for what comes next. Location: Royal Ballroom – All Attendees
2:30 PM–2:50 PM	Navigating Market Volatility: Heritage’s Strategy for Multi-State Agility and Transformation Ernie Garateix, Chief Executive Officer, Heritage Holdings Join Heritage Insurance CEO Ernie Garateix to explore how this Florida-headquartered insurer maintains stability and growth across 16 states. Ernie discusses replacing legacy systems with Guidewire to achieve the scalability and speed to market required for diverse geographic expansion. Learn how Heritage leverages AI and a shift into Excess & Surplus lines to bypass regulatory bottlenecks and proactively manage catastrophe risk in a shifting insurance landscape. Location: Royal Ballroom – InsuranceSuite Attendees
2:30 PM–3:00 PM	From Tribal Knowledge to Institutional Intelligence Preparing Regional, Mutual and MGA Insurers for the Next Five Years Sponsored by Ogon Consulting Joseph D’Souza, Founder, ProNavigator, Guidewire Moderator: Zachary Gustafson, GM, Claims & InsuranceNow, Guidewire Regional carriers, mutuals, and MGAs depend on expertise that lives in people, not systems. As retirements, turnover, and complexity increase, critical tribal knowledge is at growing risk of being lost. In this thought-leadership session, the founder of ProNavigator and the GM of InsuranceNow will share how insurers are turning person-dependent expertise into durable institutional intelligence—without large IT teams or major transformation programs. Key focus areas include: Why tribal knowledge is now a critical operational risk How to start capturing and structuring expertise A practical 12–18 month roadmap to build a more resilient, future-ready operating model Join us to learn how to protect and scale your organization’s expertise for the next five years. Location: Royal Salon IX – InsuranceNow Attendees
2:50 PM–3:30 PM	Mid-Afternoon Break Location: Royal Assembly
3:30 PM–4:00 PM	What’s Next for Pricing in P&C *Sponsored by ValueMomentum* Baiju Devani, Chief Technology Officer and Co-Founder, Armilla AI Moderator: Chris Folkman, Vice President, Product Management, Guidewire Join Guidewire’s Chris Folkman for a forward-looking conversation with a leading pricing and actuarial expert on how pricing is rapidly evolving in P&C insurance. The discussion will examine the growing role of data, analytics, and AI in shaping pricing strategies; how organizations are rethinking structures and skills; and what leaders must prioritize to strengthen profitability and competitiveness. Attendees will gain practical insights and strategic perspective on how advanced pricing capabilities can become a true performance differentiator. Location: Royal Ballroom – All Attendees
4:00 PM–4:40 PM	A Conversation with Tennis Legend, John McEnroe Sponsored by Deloitte John McEnroe, Tennis Legend Moderator: Brian Desmond, Chief Marketing Officer, Guidewire Enjoy an entertaining and candid conversation with tennis legend John McEnroe. Known for his unmatched talent, fierce competitive spirit, and unmistakable personality, McEnroe will share stories from his remarkable career, his experiences on and off the court, and the moments that shaped his life in tennis and beyond. Expect humor, honesty, and the unexpected as one of sport’s most iconic figures takes the stage for an unforgettable session. Location: Royal Ballroom – All Attendees (Guests Included)
4:40 PM–4:45 PM	Closing Remarks Brian Desmond, Chief Marketing Officer, Guidewire Location: Royal Ballroom – All Attendees (Guests Included
4:45 PM–5:00 PM	Meet & Greet with John McEnroe *Sponsored by Deloitte* John McEnroe, Tennis Legend Location: Royal Ballroom – All Attendees (Guests Included)
6:30 PM–9:30 PM	Executive Symposium Main Day Reception Sponsored by PwC Location: Boat located at the dock outside the Palm Court Bar (Cloister Lobby). See the mobile app for details. The boat will stay docked for easy access. (Guests Invited)