View all jobs Director, Payments & Financial Services Canada • Toronto • Halifax • Calgary • Vancouver • Ottawa • Kitchener • Waterloo • Hamilton • Truro General Managers Remote Full-time About the role 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. With Payments as a core growth engine for Fresh Books, 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. They translate multi-year strategy into quarterly delivery, hold teams accountable for measurable results, and intervene decisively when the numbers require a course correction — while personally rolling up their sleeves on execution, not just directing it. 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 (surcharging, repricing, embedded product expansion) while keeping the day-to-day machine running.
What You’ll Do
Run the Payments Business — Operating Rhythm, Metrics, and Delivery
Own the operating rhythm: weekly business reviews (WBR), monthly business reviews (MBR), monthly P&L; reviews, and the monthly KPI report in partnership with FP&A; and Data & Analytics.
Own the TPV and revenue forecast as source of truth; monitor performance against net revenue, TPV, and net Payments-attached-user targets, and drive the actions to close gaps.
Translate performance insights into transparent, executive-ready recommendations and deliver them in leadership and cross-LOB forums.
Drive Execution on Priority Initiatives
Lead delivery on the highest-value Payments initiatives — surcharging, repricing, Auto Pay phases, Optimized Payments / interchange work, and launch readiness for BNPL and embedded partners (Klarna, Cash App, Affi… and embedded IPO).
Manage the Payments portfolio: prioritize across initiatives, influence resource allocation, and hold cross-functional partners accountable for delivery, results, and learnings.
Challenge or adjust decisions that could limit business impact — default configurations, pricing changes, rollout sequencing.
Own

📌 Director, payments (Winnipeg)
🏢 FreshBooks
📍 Winnipeg