At a Glance
- Tasks: Lead the Payments business, driving execution and strategy across teams.
- Company: Join FreshBooks, a mission-driven tech company supporting small businesses.
- Benefits: Competitive salary, stock options, comprehensive health benefits, and flexible vacation.
- Other info: Dynamic work environment with opportunities for mentorship and growth.
- Why this job: Make a real impact in the fintech space while growing your career.
- Qualifications: 8+ years in payments or fintech with strong leadership and analytical skills.
The predicted salary is between 129690 - 158510 $ per year.
The Director, Payments & Financial Services is a senior leadership role within the Payments and Financial Services Line of Business, reporting directly to the General Manager, Financial Services and Payments. This leader is accountable for running the Payments business day-to-day and delivering in-year P&L impact across the Payments and Financial Services Lines of Business.
This is the operational heart of the LOB, and it is a hands-on, player-coach role. The Director owns the rhythm of the business, drives cross-functional execution across Product, Engineering, Marketing, Sales, Operations, Support, and Risk, and makes the trade-offs between customer experience, operational feasibility, risk exposure, and financial performance.
The ideal candidate is a deep payments operator ready to grow into full commercial ownership — analytically rigorous, commercially sharp, and a confident executive communicator — who does the work rather than only delegating it, and who can own delivery on the biggest bets while keeping the day-to-day machine running.
What You’ll Do
- Run the Payments Business — Operating Rhythm, Metrics, and Delivery
- Drive Execution on Priority Initiatives
- Own Payment Operations Execution
- Own Partner, Vendor, and Network Relationships
- Own High-Value Customer and Commercial Decisions
- Partner and Influence Across the Organization
- Manage Risk, Compliance, and Market Intelligence
- Support Strategy and Planning
What You’ll Bring
8+ years in payments, fintech, embedded finance, or SaaS financial services, including demonstrated commercial ownership — revenue, margin, pricing, or partner economics (not operations alone). Deep, hands-on understanding of payments economics: processing and interchange, PayFac / sub-merchant models, BNPL, TPV and attach-rate dynamics, pricing, repricing, and margin management.
Proven experience owning or delivering to a P&L, with strong financial and analytical acumen. Track record leading cross-functional execution across Product, Engineering, Marketing, Sales, Operations, Support, and Risk. Experience managing external partners, processors, or networks.
Strong executive communicator and influencer who can drive alignment across stakeholders without direct authority. Comfortable operating strategically and tactically; thrives in a dynamic, fast-paced environment with a strong bias for execution. Bachelor's degree in Business, Finance, Economics, or a related field.
You’ll Stand Out If You Have
MBA or equivalent experience preferred. Direct experience with embedded finance, card issuing, or treasury/banking-as-a-service. Familiarity with payments risk and compliance. Hands-on payment operations experience.
Compensation
The total compensation for this role ranges from CA$153,000 - CA$190,000 per year, which may include participation in our incentive programs. Additionally, this position offers an equity grant and immediate enrollment in FreshBooks' comprehensive benefits program.
Perks and Benefits
Comprehensive health and wellness benefits. Generous time off including a flexible vacation plan, a retirement savings program or pension plan matched to your local office, stock options for every full-time employee, parental leave and new parent support, annual healthy living credit, comprehensive medical and dental benefits, fertility and gender-affirming benefits dependent on your region, and more.
We are committed to creating a supportive and flexible workplace where everyone can thrive, grow, and make an impact on the lives of small business owners worldwide.
Director, Payments & Financial Services in Winnipeg employer: FreshBooks
FreshBooks is an exceptional employer that prioritizes the well-being and growth of its employees, offering comprehensive health benefits, generous time off, and a supportive work culture that fosters collaboration and belonging. With a commitment to professional development and a flexible working environment across various locations in Canada, including Toronto, FreshBooks empowers its team members to thrive while making a meaningful impact on small business owners worldwide.
