Shelby Austin

Co-Founder and CEO, Arteria AI

Shelby Austin is the founder and CEO of Arteria AI Inc., an award-winning digital documentation software that was incubated and then spun out of the world’s largest consulting firm.  Arteria works with large financial institutions around the world providing infrastructure for them to document and monitor deals with clients.  

Shelby was previously the Managing Partner of Growth & Investments and Omnia AI at Deloitte. Shelby had responsibility for the Canadian firm’s inorganic and accelerated growth investments through acquisitions, ventures, incubation and scale-up and asset development activities and its AI and data footprint. 

Shelby joined Deloitte through its acquisition of her first company, a high-growth startup that also focused on documentation. Previously, Shelby was a Partner at a Canadian “Seven Sister” law firm where her practice focused on complex corporate and commercial litigation matters. 

Shelby was named to the Maclean’s 2024 list of the 100 Most Powerful Canadians, one of 10 in the AI category. In the past, Shelby has received the Canada’s Most Powerful Women: Top 100 award given by The Women’s Executive Network (WXN) and the Rising Stars award given by Lexpert Magazine to Canada’s leading lawyers under 40. In 2023, Arteria was recognized by CB Insights in its AI 100 rankings and by Gartner as one of three identified “Cool Vendors in Applying Generative AI to Banking” report. 

Dax Dasilva

Founder and CEO, Lightspeed

Dax Dasilva is the creative mind behind Lightspeed Commerce. Founded in 2005, Lightspeed is the unified POS and payments platform for ambitious entrepreneurs to accelerate growth, provide the best customer experience and become a go-to destination in their space. It powers the world's best businesses in over 100 countries globally. 

Dasilva was reappointed as CEO on February 15, 2024. Prior to that, he served as Executive Chair of Lightspeed’s board of directors for two years, and previously led the company’s operations as Chief Executive Officer since its founding in 2005. 

Lightspeed employs thousands of staff, and powers hundreds of thousands of customer locations worldwide. During Dasilva’s leadership as CEO, the company went public in March 2019 on the Toronto Stock Exchange under the symbol LSPD, becoming one of Canada’s top 10 technology IPOs. In September 2020, the company listed on the New York Stock Exchange. Lightspeed also undertook 9 acquisitions over the course of a four year period to consolidate the global market and launch two, best-in-class flagship products: Lightspeed Retail and Lightspeed Restaurant. 

Harley Finkelstein

President, Shopify

Harley Finkelstein is an entrepreneur, lawyer, and the President of Shopify. He founded his first company at age 17 while a student at McGill. Harley completed his law degree as well as his MBA at the University of Ottawa. Harley was one of the “Dragons” on CBC’s Next Gen Den and starred on Discovery Channel’s I Quit. He received the Canadian Angel Investor of the Year Award, Canada’s Top 40 Under 40 Award, Fortune’s 40 Under 40, and was inducted into the Order of Ottawa. From 2014 to 2017 Harley was on the Board of Directors of the C100, and from 2017 to 2020 he was on to the Board of Directors of the Canadian Broadcasting Corporation (CBC). He is currently on the Board of Directors of the National Retail Federation, Operation Hope, and the Montreal Children’s Hospital Foundation. Harley recently co-founded Firebelly, a modern high-end tea brand, and created Big Shot, a project and podcast that archives the stories of the greatest Jewish entrepreneurs of the last century. 

Roham Gharegozlou

Co-Founder and CEO, Dapper Labs

Roham Gharegozlou is a seasoned founder and active startup investor with a particular interest in consumer software and social trends. He has co-founded five companies and invested in nearly 100 others over the past 15 years.  

Roham is currently founder and CEO of Dapper Labs, the company that owns and operates social commerce platforms including NBA Top Shot, NFL ALL DAY, and Disney Pinnacle.  Roham was previously founder and CEO of Axiom Zen, an award-winning venture studio. Prior to starting Axiom Zen, Roham served as a Partner at Rising Tide Fund, an early-stage VC based in Silicon Valley.  

Outside of work, Roham is an avid traveler most comfortable on the slopes or out on the water. Roham holds BA, BS, and MS degrees from Stanford University in Economics and Biological Sciences.  

Marc Hollenberg

Chief Operations Officer, Moneris

Marc Hollenberg is the Chief Operations Officer (COO) at Moneris. Marc joined Moneris in 2014 to lead our Customer Experience Team.  Marc brings over 20 years of leadership experience in the financial services and customer experience fields, driving strategies to deepen relationships with customers and enhance organizational effectiveness.  

As COO, Marc leads Moneris’ customer engagement stragegy as well as our Customer Enablement, Business Transformation, Chargebacks and Field Services teams.   His mandate is to enhance digital service/support offerings and develop future support strategies that serve to differentiate Moneris and support our long term strategy of strong customer and employee engagement.   

Prior to joining Moneris, Marc held senior positions at Rakuten Inc. as well as American Express. Marc has a proven track record leading large teams to execute on customer experience improvement and operational excellence strategies.  Marc is originally from Montreal and moved to Toronto in 1998. Marc and his wife have been together for 20 years and have a daughter and 2 dogs. 

Jil Macdonald

Chief Operating Officer, Walnut Insurance

Jil Macdonald is a pioneering technology executive renowned for her transformative work in digital and AI product innovation. With decades of experience, she has successfully led the creation and scaling of over 200 cutting-edge products across Insurance, Finance, Environmental, and Energy sectors, generating $285M+ in industry savings. 

As Chief Operating Officer at Walnut Insurance, Jil is at the forefront of developing revolutionary embedded insurance programs. She has forged strategic partnerships with major brands such as Telus, Tim Hortons, National Bank, Pineapple, and NEO, reshaping the insurance landscape by helping organizations launch their own insurance arms and unlock new revenue streams. 

Her distinguished career includes executive roles at AltaML, Alberta Energy Regulator, and Ernst & Young, where she has showcased her strategic vision and expertise. Beyond her corporate accomplishments, Jil is an influential board director and dedicated community and cancer volunteer, actively supporting startups and venture initiatives. 

Recognized with accolades like Top 40 Under 40, Young Women in Energy, and Women of Inspiration awards, Jil Macdonald stands out as a visionary leader driving innovation and excellence in technology. 

Mara Reiff

CEO (Interim) and Chief Customer Officer, FreshBooks

As CEO (Interim) and Chief Customer Officer, Mara leads FreshBooks with a strategic, customer-centric approach. Formerly an executive in the telecommunications industry, Mara brings a powerful blend of data-driven insight, technical skill, and business operations expertise to FreshBooks. One of IBM’s Global Women Leaders in AI, Mara holds an engineering degree in Applied Mathematics and Chemical Engineering, as well as an MBA. 

Darryl White

CEO, BMO Financial Group

Darryl is Chief Executive Officer of BMO, the eighth largest bank in North America by assets, serving over 13 million customers across Canada, the United States, and in select global markets for over 200 years. Darryl chairs BMO’s Executive Committee and serves as a director of BMO Financial Group and its U.S. subsidiary, BMO Financial Corp. 

Darryl joined BMO as an investment banking analyst in 1994. He returned to his hometown of Montreal in 2006 to lead the bank’s Quebec Investment & Corporate Banking team. In 2014, he was named CEO and Group Head, BMO Capital Markets, and in 2016 appointed BMO’s Chief Operating Officer. 

Driven by the bank’s Purpose, to Boldly Grow the Good in business and life, Darryl is committed to supporting a thriving economy, a sustainable future and inclusive society. He is a member of Washington, D.C-based, The Business Council, Ottawa-based Business Council of Canada, the Business Council of Toronto, the Mayor of Beijing’s International Business Leaders Advisory Council, and the Bank Policy Institute. In partnership with United Way Greater Toronto, Darryl also Co-Chairs the Inclusive Local Economic Opportunity Roundtable, uniting business and community leaders in approaches to reduce economic disparity in the region. 

An advocate for eliminating barriers to inclusion, Darryl serves as a Director and Executive Committee member of Catalyst, and its Canada Advisory Board. He is the Campaign Cabinet Co-President for the Montréal Children’s Hospital Foundation, a member of Toronto's University Health Network Board of Trustees and Honourary Campaign Co-Chair for Kids Help Phone. A lifelong sports fan, Darryl serves as a director of Alpine Canada, the governing body for alpine, para-alpine and ski cross racing in Canada and chairs the board of the NHL’s Montreal Canadiens.  

Darryl holds an Honours Business Administration degree and an honorary Doctor of Laws degree from the Ivey Business School at Western University and is a graduate of Harvard Business School’s Advanced Management Program. Darryl is a past recipient of Canada’s Top 40 under 40® Award and was named 2023 CEO of the Year and Strategist of the Year by The Globe and Mail.