Director, Payments & Financial Services

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.

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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, 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.

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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.

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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.

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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 escalate significant exceptions to the GM.
- Balance customer growth against margin discipline and PayFac sub-merchant risk exposure.

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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.

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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 action and forward strategy.

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Support Strategy and Planning

- Own 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.
Other duties as may be assigned.

- Bulleted list of responsibilities and activities, no more than 7

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

Compensation

At FreshBooks, we approach each individual's compensation with a promise of fair market value and internal equity commensurate with experience and specific skill set.
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, detailed below.
NOTE: This posting is reflective of an existing vacancy at FreshBooks.