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Open nowPosted 20 days ago

Director, Payments & Financial Services

FreshBooks3 open roles

Where
Halifax, Calgary, Vancouver, Ottawa, Kitchener, Canada, Waterloo, Hamilton, Truro, Toronto
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Your applicationOpen nowDirector, Payments & Financial ServicesFreshBooks · Halifax, Calgary, Vancouver, Ottawa, Kitchener, Canada, Waterloo, Hamilton, Truro, Toronto

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The clock on this job

Early applications get read.

12.3% of postings close within 7 days. Measured by our own scanner across the market.

Share of postings closed within
  1. 2.1%1 day
  2. 4.5%3 days
  3. 12.3%7 days
  4. 19.3%14 days
  5. 35.6%30 days
  6. 58.1%60 days
This job: posted 20 days ago

The posting

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 DeliveryOwn 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 InitiativesLead 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, Affirm, 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 ExecutionOwn 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 RelationshipsManage 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 DecisionsOwn the high-value customer strategy, including strategic account pricing and repricing initiatives. Set and enforce pricing within guardrails; recommend guardrail changes and escalate significant exceptions to the GM. Balance customer growth against margin discipline and PayFac sub-merchant risk exposure.

Partner and Influence Across the OrganizationServe 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 IntelligencePartner 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 action and forward strategy.

Support Strategy and PlanningOwn the sub-12-month strategy (win, grow TPV, optimize revenue) and partner with the GM on annual and 2027 planning. Contribute to positioning, PMM, and GTM thesis, and support evaluation of adjacent product expansion (e.g., embedded banking and card issuing) with business cases, ROI models, and post-launch accountability.

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 (e.g., Stripe, card networks, BNPL providers). 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 (fraud, chargebacks, merchant underwriting, 1099). Hands-on payment operations experience (payouts/reconciliation, processor workflows, automation).

#LI-SR1 #LI-REMOTE

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