Director, Compliance - Canada


Toronto, ON



Uplift Pay Monthly was founded by a passionate team of travel industry veterans to make travel more accessible, affordable, and rewarding for everyone. By offering simple, flexible payments, Uplift helps travelers book early while prices are low, and pay for their trip over time. Uplift is a well-financed Series C startup serving the $1.4 Trillion consumer travel segment.

Uplift Pay Monthly is used by top travel brands such as Sunwing,,,, Carnival, United and many more. Learn more at

We are looking for a Director of Compliance who will be a key member of the company-wide Compliance team and who will take the lead on compliance for our Canadian business. The role will report to the General Counsel and Chief Compliance Officer. A successful candidate will be highly motivated and experienced compliance professional with excellent leadership, interpersonal, communication, organizational, team management, project management and decision-making skills.


  • Demonstrate leadership and execution of Uplift’s compliance program in Canada and the United States
  • Collaborate with the Product and Commercial teams on new products, services and initiatives
  • Communicate legal and regulatory requirements and industry standards to impacted stakeholders
  • Evaluate business processes and procedures to identify compliance risks and make recommendations to address them
  • Establish and maintain policies, standards and procedures to mitigate compliance risks
  • Foster a culture of compliance within the growing Toronto office and across the wider company


  • 7+ years of relevant compliance and/or legal experience; preferably in financial services e.g. lending, payments, risks, etc.
  • Bachelor’s degree, legal qualifications, or comparable experience
  • Strong understanding of Canadian consumer-lending, collections, payments, privacy and AML/KYC requirements. Knowledge of United States policies are a plus
  • Fluency in French a plus
  • Excellent interpersonal, cross-functional, communication, writing, and presentation skills
  • Entrepreneurial spirit, persistence and detail oriented
  • Comfortable working in a startup culture with the ability to demonstrate value and earn trust


  • Medical, dental, and vision insurance
  • 11 company paid holidays and unlimited PTO
  • Life insurance
  • Registered Retirement Savings Plan (RRSP)
  • Pre-IPO stock options
  • Pick-A-Perk program
  • Wellness program
  • Credit for daily lunches
  • Snacks and drinks provided
  • Downtown Toronto office location
Uplift is committed to providing accessible employment practices that are in compliance with the Accessibility for Ontarians with Disabilities Act (AODA). Accommodations are available upon request for candidates taking part in all aspects of the selection process.

Note: Uplift does not accept agency resumes. Please do not forward resumes to any recruiting alias or employee. Uplift is not responsible for any fees related to unsolicited resumes.