Executive Team

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

David Caringi

Chief Executive Officer

With more than 20 years of experience in the premium finance industry, David provides strategic leadership and vision as Chief Executive Officer of FIRST Insurance Funding of Canada. He is responsible for guiding the company’s long-term growth strategy, fostering innovation, and strengthening relationships with key partners across Canada.

David joined Insurance Pay in 2002 as a Business Development Manager and was a founding partner in the company’s growth and success, playing a pivotal role in expanding its market presence and shaping its sales and marketing strategy. In 2010, he co-founded Policy Bill, a specialized premium finance services company and helped lead its growth until its successful merger with FIRST Insurance Funding of Canada in 2014.

Drawing on extensive industry expertise and entrepreneurial experience, David remains focused on delivering exceptional value to brokers, carriers, and business partners while driving FIRST Insurance Funding of Canada’s continued growth and leadership in the premium finance marketplace.

Jamie Ugarte, PMP 

Chief Operating Officer

Jamie brings more than 15 years of experience in the premium finance industry, with expertise spanning account management, product development, and operations. As Chief Operating Officer, she leads FIRST Canada's core business operations, driving operational excellence, service delivery, and strategic initiatives that support the company's growth and long-term success. Jamie also oversees the development and implementation of innovative technology solutions that enhance efficiency and deliver value for FIRST Canada's insurance partners. She is a certified Project Management Professional (PMP) and holds a Bachelor of Arts degree from the University of Western Ontario.

John Martin, CPA, CA

Chief Financial Officer

John has been in the premium finance industry for over 20 years. As Chief Financial Officer, John provides corporate leadership of all financial functions, including financial and corporate reporting, strategic analytics, financial planning, budgeting, and treasury management. His mandate also extends to aligning FIRST Canada’s financial data, controls, and reporting to a shared standard across the wider organization. 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 a 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 20 years of marketing experience, over 15 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.

Lesley Orr

Vice President, Administration

Lesley brings over 10 years of Human Resources experience in the Insurance, Retail, and Commercial Real Estate industries. In her role, Lesley oversees our people and culture strategy, driving strategies that foster a dynamic workplace and position FIRST Canada as a first choice employer. Prior to joining the company in 2021, Lesley held leadership positions with oversight across Canada and the United States. Lesley holds a degree from the University of King’s College.