CEO PANEL

Wednesday, April 8 | 11:15 AM - 12:15 PM | Winnipeg Ballroom

Moderated by Pete Tessier

Pete Tessier | Founder / Co-Host / Producer / Speaker, The Insurance Podcast

Pete hosts and produces two podcasts, one creatively named The Insurance Podcast as well as What’s on Dec? for Canadian Underwriter. Pete has been a co-owner in an insurance brokerage, IBAM President, a director on IBAC, and past chair of the Insurance Council of Manitoba.

Aside from moderating CEO panels at insurance broker conferences, Pete has been a speaker and presenter for insurance and insuretech events including Trufla’s Amplify, IBAO, IBANS, IBAS, the National Insurance Conference of Canada, Insuretech Connect Las Vegas, and for the international organization The Strategy Institute at the Digital Marketing Summit for Financial Services.

When Pete is not booking guests and trying to make sense of the insurance marketplace, he is the President of the new tech-powered start-up MGA, Taycon Risk who is bringing a broker-centric approach to underwriting.

Panelists


Kathy Boychuk, CPA, CMA	Cara Cameron, CPA, FCIP	Brenda Gibson, CPA, CA, CIP	Penny McCune

Kathy Boychuk, CPA, CMA | President & CEO, Peace Hills Insurance

Kathy is an accomplished business leader of a privately Indigenous owned Western Canadian insurer. Peace Hills Insurance is proudly owned by the Samson Cree Nation in Alberta and writes close to $500M in annual premiums.

Kathy has held the position of President and CEO for the past 9 years and was previously the Chief Financial Officer. She is a Chartered Professional Accountant with more than 33 years of experience in the insurance industry. Kathy has demonstrated the drive to deliver results in a fast paced, dynamic industry. Her skills include team building, communication, financial analysis, and effective management of risk. As the leader of a mid sized regional insurer that competes with major national and international competitors, Kathy prioritizes the value of connecting with people and building relationships to make an impact.

With strong attention to detail and excellent data-driven analytical capabilities, Kathy’s finance background is balanced with strong strategic insights and sound decision making which has contributed to long term business growth and success.

Kathy also serves as a member of the Board of the Insurance Bureau of Canada.

Cara Cameron, CPA, FCIP | Chief Strategy Officer, Incoming President & CEO, Portage Mutual Insurance

Cara Cameron is a leadership and strategic executive with over 19 years of experience in the insurance industry. She is currently the Chief Strategy Officer & Incoming President & CEO (effective July 1st, 2026) at Portage Mutual Insurance. Portage Mutual Insurance is a Canadian national property and casualty insurer with gross written premiums of approximately $430 million and 320 employees.

Ms. Cameron is very passionate about aligning people-centric environments with strategy and has developed expertise in the areas of strategic development, implementation, collaborative cultures and elevated leadership. She has held various executive positions including Vice-President Finance, Chief Operating Officer and President & CEO within the mutual insurance industry prior to joining Portage Mutual. In her former positions, Cara played a key role in strategy, merger & acquisition activities, governance, reinsurance, information technology, and human resources.

Cara is a proud maritimer having been born and raised in Nova Scotia. She is a graduate of Acadia University where she completed a Bachelor of Business Administration. She earned a Chartered Professional Accountant (CPA, CA) Designation in 2004 and holds a Fellow Chartered Insurance Professional (FCIP) Designation. She is a life-long learner; and served on the Board of Farm Mutual Re and various National Association of Mutual Insurance Company committees supporting industry learning and development.

Cara presently resides in Burlington, Ontario, and is a proud mom of four children and two mini-labradoodles. She loves spending time in nature, time on her yoga mat and is very excited to step into the role as President & CEO of Portage Mutual Insurance.

Brenda Gibson, CPA, CA, CIP | President & CEO, Red River Mutual

Brenda Gibson was appointed President and CEO of Red River Mutual in 2023. She is a graduate of the University of Manitoba with a Bachelor of Commerce (Honours) and holds the CPA, CA and CIP designations.

With nearly two decades of experience across regional operations, financial management, product development, and national insurance leadership, Brenda brings a broad and balanced perspective to guiding Red River Mutual’s continued evolution.

Since joining the company, she has advanced RRM’s strategic plan with a focus on technology, data, innovation, and sustainable growth. Under her leadership, the company has been recognized as a Top Insurance Employer and has received multiple national award nominations.

Brenda’s leadership philosophy centres on clarity, collaboration, and accountability. She believes in empowering teams with purpose, trusting people to lead in their areas of expertise, and fostering a culture that values continuous improvement and doing what’s right for employees, customers, partners, and communities.

Penny McCune | President & CEO, SGI

Penny McCune is SGI’s President and CEO. She was entrusted with the prestigious role in June 2022, 36 years into her career at the corporation. 

McCune joined SGI in 1985 as a temporary Junior Clerk in the Auto Fund. Shortly afterward she moved into a permanent position and, before she celebrated her first anniversary with the company, had promoted to a supervisory role. In the years since, she’s held many strategic leadership roles, including serving as the Executive Vice President and Chief Operating Officer of the Auto Fund (2016-2022), Executive Vice President of Claims and Salvage (2014-2015), Executive Vice President of Customer and Distribution Strategy (2012-2014), and Assistant Vice President for SGI CANADA (2004-2012). 

During her career, she’s been a key part of many important projects and initiatives. Among her accomplishments, she championed a new vision for SGI’s culture that focuses on employee collaboration and connection, led development of a new claims process, led SGI’s transformation into a customer-centric organization, contributed to traffic safety improvements in Saskatchewan and led expansion of SGI CANADA, the competitive property and casualty insurance arm of SGI, into markets outside its home province of Saskatchewan. She’s currently leading SGI’s system modernization project to enhance services for partners and customers.

McCune has worked in nearly every area of SGI during the past four decades, forging strong relationships with brokers, partners and employees. 

McCune was born, raised and educated in Saskatchewan. She has a Bachelor of Administration from the University of Regina and her Chartered Insurance Professional designation from the Insurance Institute of Canada. She has a keen interest in disaster prevention and serves on the Board of Directors for the Institute for Catastrophic Loss Reduction. Outside of work, McCune is passionate about animal welfare and served on the Board of Directors for the Regina Humane Society for 20 years. She lives in Regina and spends many weekends at a place she calls her sanctuary – her cabin. 

From temporary Junior Clerk to the first woman President and CEO of SGI, Penny McCune’s career path is an inspiring story for the next generation of leaders in Saskatchewan.

BROKER PANEL

Thursday, April 9 | 11:15 AM - 12:15 PM | Wellington Ballroom

Moderated by Brett McGregor

Brett McGregor, MBA, FCIP, CAIB | Chief Executive Officer, Guild Insurance Group

Brett McGregor is a seasoned insurance executive with over 25 years of experience in the Canadian insurance industry. Born and raised in Wawanesa, Manitoba, Brett’s strong connection to community and service continues to shape his leadership style.

As President & CEO of Guild Insurance Group, he leads a growing team of 95 employees across eleven locations, delivering customized insurance solutions to individuals and businesses. His leadership has helped shape Guild into a progressive, community-focused firm grounded in service and local expertise.

Brett is a strong advocate for continuous learning and professional development. He holds a Bachelor of Commerce (Honours) degree from the University of Manitoba and has earned the CAIB, CIP, and FCIP designations, along with an MBA completed in 2014.

An active member of the insurance community, Brett contributes to the broader industry dialogue through his involvement with the Insurance Brokers Association of Canada of which he is currently President. Brett is also a Past President of the Insurance Brokers Association of Manitoba.

Dedicated to giving back, Brett has held leadership roles in several local initiatives and continues to be involved in coaching youth sports and community volunteering.

Panelists

Ryan Garriock, CPIB, CAIB

Pamela Gilroy-Rajotte, CAIB

Kevin Neiles

Ryan Garriock, CPIB, CAIB | Owner, Garriock Insurance

Ryan Garriock is a third-generation insurance broker and co-owner of Garriock Insurance. With a career spanning every aspect of brokerage operations, Ryan has helped grow the family business into a respected and well-established brokerage. He holds a CPIB and CAIB designations and is known for combining industry expertise with practical business insights.

Beyond his brokerage, Ryan is an active leader in the insurance community, having served on many boards and committees, as IBAM president and as one of the founders of the Young Broker Network. He is also a proud alumnus of Red River College, where he previously chaired the Alumni Board and mentored emerging professionals.

At the 2026 IBAM Conference, Ryan will share his perspectives on industry trends, professional growth, and client engagement, offering attendees actionable insights from his experience leading a successful, forward-thinking business.

Pamela Gilroy-Rajotte, CAIB | Regional Sales Manager, Westland Insurance Group Ltd.

With over 22 years of insurance leadership, Pamela has built a career on the belief that sustainable growth is the result of two things: relentless operational efficiency and a deep investment in people.

An accomplished insurance industry leader and a lifelong student of leadership, Pamela has navigated some of the industry’s most complex transformations—from launching start-ups and orchestrating major acquisitions to pioneering digital shifts in national brokerages. She has a unique talent for translating high-level strategy into ground-level results, having led dozens of branches through the growing pains of change.

Beyond the numbers, Pamela is known for her extensive industry network and a reputation built on unwavering integrity. As a former President of the Insurance Brokers Association of Manitoba, and a current member of the Insurance Council of Manitoba, she has been a vocal advocate for the profession and a dedicated mentor to the next generation of industry leaders.

Pamela has dedicated her career to the insurance industry and remains deeply committed to community and professional service. Whether she is serving on national committees or contributing to local initiatives, she believes giving back to the industry has defined her career. Pamela brings a wealth of "real-world" insight and a principled approach to every conversation.

Kevin Neiles | Retired Chief Markets Officer, Arthur J. Gallagher Canada | Former President, Western Region | Insurance Industry Leader

Kevin Neiles retired from Arthur J. Gallagher Canada Limited on January 1, 2025, concluding a distinguished career in insurance leadership spanning nearly four decades. In his final roles with Gallagher, he was Chief Markets Officer, President of the Western Region, and a member of the company’s Board of Directors.

Kevin began his insurance career with Ranger Insurance in 1986, became a partner in 1988, and was appointed President and CEO in 1999. He led Ranger through a period of significant growth before guiding the organization through its merger with Arthur J. Gallagher in 2014.

A long-time contributor to the broker community, Kevin held board positions with the Insurance Brokers Association of Manitoba (1992–1998), including serving as President in 1997, and was also a Director with the Insurance Brokers Association of Canada.

He holds a Bachelor of Physical Education degree from the University of Manitoba, is a CAIB Honors graduate, and earned his CRM designation through the University of Toronto School of Continuing Education. Over his career, he participated on numerous local and national insurer advisory panels and was active in YPO and YPO Gold, contributing at the chapter executive level.

Before entering the insurance industry, Kevin played four seasons in the Canadian Football League with Montreal, Winnipeg, and Calgary, and was part of the Grey Cup–championship Winnipeg team in 1984.

Kevin remains engaged in community leadership, including board involvement with the Winnipeg Football Club and the True North Youth Foundation, which supports youth programming across Manitoba.