Executive Team

Reliability ∙ Growth ∙ Innovation

Get to know your FIRST Canada Executive Team

As our company is evolving, so is our team of esteemed leaders whose experience and industry knowledge has proven to be the ideal combination to create a product offering like never before. See their biographies below.


Stuart Bruce, CPA, CA
Chairman, Chief Executive Officer

Stuart has spent over 20 years in the premium finance market place in Canada. He founded Insurance Pay Canada in 2001 (now FIRST Insurance Funding of Canada) and successfully built the finance management system, team and broker network from start up to one of the largest premium finance company in Canada. In 2007, after Insurance Pay was sold to an Australian based investment bank, Stuart founded Policy Billing Services Inc. and was appointed CEO of FIRST Canada after the merger of Policy Bill and FIRST Canada in April 2014. Stuart is a CPA chartered accountant and holds an Honors Business Administration degree from the Richard Ivey School of Business, University of Western Ontario.



David Caringi
Chief Sales Officer

David has been working in the premium finance industry for over 20 years. In his role as Chief Sales Officer, David is responsible for overseeing the overall sales strategy and building key relationships with valued partners across the country. In 2002 David joined Insurance Pay as a Business Development Manager. David was an original partner in the launch and success of the company, contributing a major role in sales and marketing. In 2010 David was a partner in the launch and growth of a specialized premium finance service company (Policy Bill) which ultimately merged with First Insurance Funding in 2014.




John Martin, CPA, CA
Senior Vice President, Finance

John has been in the premium finance industry for over 10 years. In his role, John provides corporate leadership of all financial functions, including financial and corporate reporting, strategic analytics, financial planning, budgeting and treasury management. Prior to joining the company in 2005, he primarily held public and private sector auditor roles, focusing on a variety of industries. John graduated from Dalhousie University with a Bachelor of Commerce, and has been a member of the Ontario Institute of Chartered Accountants since 2002.




Brian Day
Senior Vice President, Credit and Operations

Brian has over 25 years of experience in the financial services industry. Brian joined FIRST Canada with banking and premium finance experience including positions in client services, credit and operations. In his role, Brian drives efficiency and productivity while controlling risk and oversees the daily operations of FIRST Canada. Brian has a wealth of financial and banking experience gained from his 19 years at major banking institution in a variety of positions including senior collections manager, operations and client services. Brian graduated from York University with a BA in Economics.




Crystal Macklin, CM
Senior Vice President, Marketing and Communications

Crystal has more than 15 years of marketing experience, over 10 of which were in the insurance industry. Crystal spearheads the growth and direction of FIRST Canada’s National marketing strategy, channel development, brand, and client experience. Crystal oversees FIRST Canada's traditional and digital marketing, advertising, social media, website, and corporate communications.

Crystal brings with her previous experience from an insurance carrier, technology, and retail sectors, where she held various senior marketing positions. Crystal is a Chartered Marketer and holds a Masters in Marketing Communications from Schulich School of Business at York University.




Jamie Ugarte, PMP
Senior Vice President, Business Solutions

Jamie has been in the premium finance industry for over 10 years with experience in various roles including Account and Project Management. As the VP Business Solutions, Jamie manages a team of technical and project management specialists and oversees the development, delivery, and implementation of FIRST Canada’s technical solutions to our insurance partners. Jamie is a certified Project Management Professional with a BA in Political Science from the University of Western Ontario.





Lesley Orr

Lesley Orr
Associate Vice President, Talent Manager

Lesley has nearly 10 years of Human Resources experience in the Premium Finance, Commercial Real Estate, and Retail industries. In her role, Lesley leads our people and culture strategy to ensure that FIRST Canada is a first choice employer. Lesley oversees all Talent Management operations and programming, specializing in talent development, culture, and engagement. Prior to joining the company in 2021, Lesley held various leadership positions with oversight across Canada and the United States. Lesley is a graduate of the University of King’s College.