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 FreshBooks, 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 clear, 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, AutoPay 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 Payment Operations Execution

Own the operational backbone hands-on: payouts and reconciliation health, processor and payout workflows (e.g., Stripe Connect), and the automation that reduces cost, errors, and support volume.

Oversee 1099 operations, compliance reviews, and PayFac sub-merchant controls (chargeback, fraud, merchant-default monitoring).





Own vendor and partner onboarding and operational performance — uptime, SLAs, and adherence to payment security and compliance standards.

Own Partner, Vendor, and Network Relationships

Manage the day-to-day relationship with Stripe (monthly ops, accelerator program, QBRs) as the most active external surface.

Support and execute partner and vendor negotiations across BNPL providers, processors, and card networks (Visa, Mastercard, Discover), escalating strategic terms to the GM.

Steward external advisor and consultant engagements supporting CoGS, pricing, and PMM work.

Own High-Value Customer and Commercial Decisions

Own the high-value customer strategy, including strategic account pricing and repricing initiatives.

Set and enforce pricing within guardrails; recommend guardrail changes and elevate significant exceptions to the GM.

Balance customer growth against margin discipline and PayFac sub-merchant risk exposure.

Partner and Influence Across the Organization

Serve as a trusted business partner to leaders across Product, Engineering, Marketing, Sales, Operations, Support, and Risk, driving outcomes through cadence and influence rather than direct authority.

Chair the Payments leadership forums (monthly leadership review, bi-weekly POD leadership) and represent the business in cross-LOB and executive forums.

Manage Risk, Compliance, and Market Intelligence

Partner with Risk and Finance on risk strategy and guardrails; oversee compliance reviews and regulatory obligations.

Track the payments and fintech ecosystem — competitive threats, network and regulatory shifts — and translate signals into near-term actio

📌 Director, Payments (Winnipeg)
🏢 FreshBooks
📍 Winnipeg