Leads FreshBooks’ Payments and Financial Services business, owning operating rhythm, forecasts, P&L impact, pricing, payment operations, risk, compliance, partner relationships, and priority initiatives. Oversees cross-functional execution across Product, Engineering, Marketing, Sales, Operations, Support, and Risk. Manages processors, card networks, and BNPL partners while driving TPV, revenue, margin, customer growth, and operational performance. Partners with the General Manager on strategy, planning, embedded finance expansion, and commercial decisions.
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
- 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, 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 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 escalate 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 action and forward strategy.
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
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.
Perks and BenefitsWe understand that you'll weigh many factors when deciding if FreshBooks is the right next step in your career. Here are some of our offerings for our employees (we call ourselves ✨ FreshBookers✨) to support their growth:
- 🩺 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.
- 📚 Perks that matter. Including a Peer Recognition Program, an Employee Assistance Program, headphone credit, meaningful in-person gatherings to bring onsite and remote employees together, and more perks matched to your local cluster.
- 🌱 Working environments to help you thrive. Beautiful office spaces welcome you in Toronto, Amsterdam, and San Luis Potosi. If you don't have access to a FreshBooks office, you receive a home office credit to set up your home office.
- 🤗 Supportive peer group, mentors, and leaders. We care about each other across the organization and have programs to support this so everyone feels a strong sense of belonging, and believes in collective impact.
- 🚀 Accelerated growth. Comprehensive company onboarding, career development through continuous coaching, training, and learning on the job.
You've probably learned a bit about FreshBooks before making it to this point, but let us take a moment to introduce ourselves: At FreshBooks, we believe that small business owners are the backbone of the economy, yet they are often the most underserved when it comes to technology. For over 20 years, we’ve been on a mission to support owners, from the scrappy solopreneur with a big dream to the growing business with employees to manage.
Our leading platform is more than just business software; it’s an all-in-one financial toolkit that automates invoicing, expenses, payments and payroll, allowing our customers to spend less time on paperwork and more time doing the work they love.
We believe in human-centric connections that empower teams to do their best work. Headquartered in Toronto, Canada, our team operates in clusters across North America and Europe using a variety of working environments - remote, hybrid, and in-office - all based on what’s best for the team, collaboration, and mental well-being. 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.
Even if your experience doesn't meet every bullet on the above lists, we'd love to learn more about you and why you think FreshBooks is the next step in your career. FreshBooks is an equal-opportunity employer. We do not discriminate based on gender, religion, race, mental disability, sexual orientation, age, or any other status. All applicants are considered based on their qualifications and merits. At FreshBooks, we inspire an environment of mutual respect and we believe diversity and inclusion are crucial to our success. FreshBooks provides employment accommodation during the recruitment process. Should you require any accommodation, please indicate this on your application and we will work with you to meet your accessibility needs. For any questions, suggestions or required documents regarding accessibility in a different format, please contact us by phone at 1-416-780-2700 and/or email at [email protected].
Similar Jobs
Software
Leads FreshBooks’ Payments and Financial Services business, owning operating cadence, TPV and revenue forecasting, P&L impact, pricing, partner relationships, payment operations, risk, compliance, and strategic initiatives. Drives execution across Product, Engineering, Marketing, Sales, Operations, Support, and Risk while managing processors, networks, BNPL partners, payouts, reconciliation, PayFac controls, and customer pricing. Develops near-term strategy, supports annual planning, and delivers executive recommendations and measurable commercial outcomes.
Top Skills:
AffirmCash AppDiscoverKlarnaMastercardStripe ConnectVisa
Cloud • Security • Software • Cybersecurity • Automation
Owns and improves the operational toolkit supporting Solutions Architects, including systems, workflows, reporting, documentation, support requests, engagement tracking, capacity planning, and data quality. Partners with revenue technology, analytics, and system owners to translate field needs into requirements, automate processes, improve handoffs, and sustain adoption. Supports SA leadership through reporting, business reviews, operating rhythms, testing, rollouts, and continuous operational improvements.
Top Skills:
AICRMDevsecopsExcelGitlabGoogle SheetsSalesforceSQL
Artificial Intelligence • Fintech • Information Technology • Logistics • Payments • Business Intelligence • Generative AI
Lead Coupa’s growth marketing strategy across the full customer funnel, integrating product-led, marketing-led, and sales-led growth. Optimize conversion through experimentation, lifecycle campaigns, in-app engagement, and assisted trial programs. Manage and develop marketing staff, establish operating rhythms, and build analytics and attribution systems measuring CAC, LTV, activation, and pipeline conversion. Use CRM, product analytics, and automation tools to create behavior-driven customer journeys and scale data-informed campaigns.
Top Skills:
HubspotPendoSalesforce
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
