Guidewire

Guidewire Canadian Executive Forum

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Guidewire Canadian Executive Forum

Four Seasons Hotel Toronto

 May 26-27, 2026

The Guidewire Canadian Executive Forum will bring together Canada's leaders and Guidewire executives to explore the industry’s next era. This year, we extend the theme of Intelligent Insurance, an evolution powered by modern core platforms, data, analytics and AI.

Discover how Intelligent Insurance is creating smarter, faster, and more customer-focused experiences, and be part of the energy driving it forward across Canada.

Our discussions will focus on the most critical levers for success in today’s market:

  • Harnessing Generative AI: Moving from experimentation to high-impact implementation.
  • Data-Driven Foundations: Building the infrastructure required for sustained, profitable growth.
  • Organizational Agility: Techniques to launch new products with the speed the market now demands.
  • Peer Collaboration: Facilitated networking to share insights on the path forward.


Please contact [email protected] for any questions.

Event Registration

"Guidewire has a history of investing in R&D to continually improve its system, which gives us confidence that as our needs evolve, they will evolve with us."

Matt Myers

Senior Vice President
Erie Insurance

Agenda

Agenda Overview

Tuesday, May 26

Time


12:00 – 1:30 pm

Canadian Insurance Guidewire Alliance Lunch

1:30 – 4:00 pm

Canadian Insurance Guidewire Alliance Board Meeting

6:00 – 7:30 pm 

Welcome Reception


Wednesday, May 27

Time

7:30 – 9:00 am
Breakfast Buffet
9:00 – 9:05 am
Welcome
 
Jolene Mierau, Customer Success Manager, Guidewire
9:05 – 10:35 am
Guidewire Keynote  
 
Mike Rosenbaum, CEO, Guidewire 
Ian Drysdale, CEO, One, Inc.
 
Join the Guidewire executive team for a keynote introducing Intelligent Insurance, a new era enabled by modern insurance platforms and AI. The session will explore how platform innovation is driving faster development, greater efficiency, and smarter automation, and how new applications such as PricingCenter, UnderwritingCenter, and ProNavigator are supporting Intelligent Insurance, enabling more adaptive pricing, stronger risk decisions, and faster, more consistent claims and underwriting outcomes for insurers across Canada.
10:35 – 11:00 am
Mid-Morning Break
11:00 – 11:30 am
ProNavigator: Activating Knowledge for Intelligent Insurance
 
Joseph D’Souza, ProNavigator Founder, Guidewire 
 
Natalie Simms, Executive Product Owner, Claims Journey, TD Insurance
 
Join Joseph D’Souza, former CEO of ProNavigator, the P&C knowledge management specialist recently acquired by Guidewire, for a discussion on how insurers can enable Intelligent Insurance by activating their organizational knowledge. 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, and the agent experience, and how insurers can convert institutional knowledge into a durable competitive advantage.
11:30 am – 12:00 pm
Redefining Injury Outcomes: GenAI’s Role in Transforming Care, Claims, and Carrier Strategy
 
Laura Drabik, Chief Evangelist, Guidewire 
 
Gavan Pokan, Chief Operating Officer, Workplace Safety and Insurance Board
 
Join Guidewire’s Chief Evangelist Laura Drabik and Gavan Pokan, Chief Operation Officer, Workplace Safety and Insurance Board as they unpack the Guidewire and PwC joint report Reimagining Workers’ Compensation in the Age of Generative AI, exploring how generative AI is reshaping not just workers’ compensation, but the way carriers approach injury outcomes, risk, and recovery. Laura will highlight customer voices and the five forces of change driving a shift from process-centric models to worker-centric, predictive, and proactive strategies.
12:00 – 1:30 pm
Lunch
1:30 – 1:50 pm
Customer Case Study: Red River Mutual
 
Brenda Gibson, President & CEO, Red River Mutual
1:50 – 2:15 pm
Unifying Pricing and Rating: Accelerating the Future of Insurance 
 
Alex Prajescu
Director, Product Management Pricing & Rating, Guidewire
 
Amanda Evenson, Vice President, Data & Analytics, Red River Mutual
 
Pricing and rating are at the heart of every insurer’s success. Discover how insurers can move from fragmented pricing and rating processes to a cohesive, end-to-end solution natively built on the Guidewire Cloud Platform. This session highlights Guidewire’s strategic evolution, the Quantee acquisition, and the launch of PricingCenter, which brings advanced analytics, speed, and unified configuration to both actuarial and IT teams.
2:15 – 2:35 pm 
Customer Case Study: Beneva
 
Sylvain Nolet, Vice President, Beneva
2:35 – 2:55 pm
Accelerating Innovation with Insurtech Vanguards
 
Laura Drabik, Chief Evangelist, Guidewire 
 
Jodi Scarlett, Chief Executive Officer, EcoClaim
 
Aren Mirzaian, Co-founder, CEO, MyChoice
 
Alexis Vertefeuille, CEO, Sinistar
 
Facilitated by Laura Drabik, Chief Evangelist at Guidewire, this session will educate attendees on the solutions available in today’s market. Each featured company is part of Guidewire’s Insurtech Vanguards program and will share its core value proposition — the specific problems it solves and the measurable impact it delivers to insurers. Join us to discover what’s possible and how these innovators are helping insurers move faster and compete smarter.
2:55 – 3:00 pm
Closing Remarks 
 
Jolene Mierau, Customer Success Manager, Guidewire
3:00 – 4:00 pm
End of Program Reception

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Four Seasons Toronto

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Speakers

Brenda Gibson

President and CEO

Red River Mutual

Since being appointed President and CEO of Red River Mutual in 2023, Brenda Gibson has leveraged her nearly 20 years of expertise in financial management and national insurance leadership to drive the company’s strategic evolution. A CPA, CA, and University of Manitoba Commerce graduate, Gibson has successfully accelerated Red River Mutual’s digital transformation by prioritizing technology, data-driven decision-making, and product innovation. Under her direction, the organization has achieved sustainable growth and secured a competitive market position, earning recognition as a Top Insurance Employer and receiving multiple national award nominations. Her executive approach emphasizes accountability and operational excellence, ensuring the company remains a robust, purpose-driven leader within the regional and national insurance landscape.

Amanda Evenson

Vice President, Data and Analytics

Red River Mutual

With over 25 years of diverse experience in the insurance industry, Amanda Evenson is a seasoned professional currently serving as the Vice President of Data and Analytics at Red River Mutual. Her career is marked by a strong track record in both operational leadership and large-scale transformation, including the successful deployment of an enterprise data warehouse that has modernized pricing strategies and accelerated business growth. Having held key roles such as Director of Strategy and Director of Innovation, Amanda excels at building new organizational competencies and executing strategic plans that earn high-level endorsement from executive boards. Her technical expertise spans business strategy, product management, and the implementation of design thinking frameworks, all underpinned by a collaborative leadership style that translates complex data into actionable, high-impact business insights.

Gavin Pokan

Chief Recovery and Care Officer

Workplace Safety and Insurance Board (WSIB)

Gavin Pokan is the Chief Recovery and Care Officer at the Workplace Safety and Insurance Board (WSIB), bringing more than 26 years of experience across the organization. He leads the Operations cluster, with accountability for large-scale, end-to-end claims management and service delivery, driving operational excellence and continuous improvement. Starting his career as an adjudicator, Gavin has advanced through senior leadership roles spanning digital solutions, employer services, and enterprise planning, shaping how the organization delivers results for workers and employers. He holds a Certificate in Strategic Leadership and Innovation from the Schulich School of Business, a Six Sigma Green Belt, and a Bachelor of Science in Psychology from the University of Toronto.

Aren Mirzaian

Co-Founder and CEO

MyChoice

Aren Mirzaian is the Co-Founder and CEO of MyChoice, a Google-accelerated Canadian insurtech platform focused on underwriting and pre-risk assessment. Starting his career in insurance technology 13 years ago, Aren has been passionate about advancing the space ever since. Drawing on his experience scaling digital architecture and consumer facing products at Omnicom for global brands like Apple, McDonald's, and Volkswagen Group, he now builds AI-driven solutions that modernize broker and carrier workflows. Backed by MyChoice’s published insurance studies and data pieces, his industry insights are frequently featured on major publications like CBC, Globe and Mail and Canadian Underwriter.

Jodi Scarlett

CEO

EcoClaim

Drawing on over 20 years of experience as a restoration business owner and operator, Jodi Scarlett now leads EcoClaim in delivering high-impact sustainability solutions for the insurance, construction, and restoration sectors. Her proven track record of scaling enterprises is evidenced by her three-year streak on the W100 Top Female Entrepreneurs in Canada list, as well as recognition from Alberta Venture’s Fast Growth 50 and Chase Morgan’s Women 2 Watch. Today, Jodi leverages this deep industry expertise to drive innovation at EcoClaim, providing the insurance industry with the vital tools needed to measure, manage, and reduce supply-chain emissions through circular economy practices.

Kevin Michael

Co-Founder and CEO

Tempo

  

Natalie Simms

VP, Executive Product Owner, Claims Journey

TD Insurance

Natalie Simms is the Vice President, Operations & Modernization for Claims at TD Insurance where she leads large‑scale, end‑to‑end transformations focused on improving customer experience, operational performance, and colleague enablement.

With over 20 years of experience in Financial Services, Natalie is recognized for bridging strategy, operations, and people outcomes to drive measurable business results. Her career spans senior Human Resources leadership and enterprise operations, bringing a distinctive people‑first lens to complex modernization initiatives.

Natalie holds an MBA from McMaster University and a Bachelor of Human Resource Management from York University, and is a CHRP‑designated professional.

Doris Munoz

Senior IT Director, Brokerage, Modernization, and IT Transformation

Beneva

Doris Munoz is an experienced IT executive with over 25 years in technology leadership, including 15 years as a director and more than two decades in project management. Recognized for her strategic mindset and people‑focused leadership, she excels at mobilizing people, driving transformation, and delivering solutions that balance innovation and pragmatism. Doris has led diverse IT teams, coached IT managers, and built strong partnerships across business, IT, and external providers. Passionate about developing future talent, she actively promotes technology careers among youth and women through initiatives such as Mon Avenir TI, Techno‑compétences, Numérique au féminin, and Les codes des filles. She is driven by integrity, curiosity, and a commitment to empowering people and advancing inclusive IT leadership.

Olivier Guillot-Lafrance

Senior Director, Actuarial, Commercial Lines

Beneva

A graduate of Université Laval and a Fellow of both the Canadian Institute of Actuaries and the Casualty Actuarial Society, Olivier Guillot-Lafrance has held various management positions in both personal lines and commercial insurance with several Canadian insurers.

Currently senior director of actuarial for Commercial Lines at Beneva, and with nearly 20 years of experience in the property and casualty insurance industry, Olivier has developed expertise in pricing, product development, and project management.

Ian Drysdale

CEO

One Inc.

Since assuming the role of CEO in 2021, Ian Drysdale has transformed One Inc into the insurance industry's premier digital payments network. His strategic vision culminated in a 2024 recapitalization led by Nordic Capital and Great Hill Partners at a unicorn valuation—a fivefold increase since 2020. Recognized as a top Insurtech CEO in 2025, Ian draws on over 30 years of executive experience from industry giants such as Zelis, Elavon, and WorldPay. Previously an Executive in Residence at Great Hill Partners, he holds a BA from Bishop’s University and an MBA in International Business from Florida Atlantic University.

 

Mike Rosenbaum

CEO

Guidewire

Mike Rosenbaum joined Guidewire as Chief Executive Officer in 2019. Since Mike’s arrival, Guidewire has cemented its position as the leading cloud platform serving the P&C insurance industry, growing cloud adoption by over 500%, tripling cloud revenue, and expanding the Guidewire partner ecosystem to become the largest in P&C insurance. Mike’s focus on delivering value for customers, coupled with his “ship, shipmate, self” approach to prioritization, continue to shape the industry-leading platform, applications, and content trusted by insurers globally. Prior to Guidewire, Mike led product management and go-to-market strategy for core CRM products at Salesforce and served in the US Navy as a submarine officer.

Laura Drabik

Chief Evangelist

Guidewire

Laura Drabik is a trusted advisor to insurers seeking to harness disruptive technologies to their competitive advantage. An accomplished executive, presenter, and product strategist, she's known for turning cogent insights gained in the field into category-leading solutions for Guidewire customers. Her website, blog, videos, email newsletter, and podcast interview series have earned industry acclaim as indispensable resources for understanding the trends transforming the P&C landscape. And her role in launching and leading Guidewire's Insurtech Vanguards incubator program has been pivotal in connecting insurers with vital new technologies. Laura is also renowned for inspiring the next generation of industry leaders through her influential TEDx Talk, keynotes, and advocacy for women in technology.

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