Director, Payments & Financial Services

This is a fully remote position, open to applicants in Canada.

📋 Description

• Oversee the daily operations of the Payments business and achieve in-year P&L impact across Payments and Financial Services.

• Lead weekly and monthly P&L and KPI operational reviews alongside FP&A and Data & Analytics.

• Manage TPV and revenue forecasts; track net revenue, TPV, and Payments-attached-user targets while addressing performance gaps.

• Convert performance insights into recommendations suitable for executive presentation.

• Direct significant Payments initiatives such as surcharging, repricing, AutoPay, Optimized Payments/interchange, BNPL, and launches with embedded partners.

• Govern the Payments portfolio by prioritizing initiatives, influencing resources, and ensuring partner accountability.

• Oversee payouts, reconciliation, processor and payout workflows, as well as automation of cost/error/support-volume processes.

• Supervise 1099 operations, compliance reviews, and PayFac sub-merchant controls related to chargebacks, fraud, and merchant-default monitoring.

• Manage vendor and partner onboarding and ensure operational performance, including uptime, SLAs, security, and compliance.

• Handle relationships with Stripe and assist in partner/vendor negotiations involving BNPL providers, processors, and card networks.

• Guide external advisor and consultant engagements.

• Take ownership of high-value customer strategies, strategic pricing, repricing, and pricing guardrails.

• Balance customer growth, margin discipline, and PayFac sub-merchant risk management.

• Collaborate across Product, Engineering, Marketing, Sales, Operations, Support, and Risk to drive results.

• Chair Payments leadership forums and represent the business in cross-LOB and executive discussions.

• Collaborate with Risk and Finance on risk strategy, guardrails, compliance, and regulatory responsibilities.

• Monitor developments in the payments and fintech ecosystem and convert them into actionable strategies.

• Own the sub-12-month strategy and collaborate with the GM on annual and 2027 planning.

• Contribute to positioning, PMM, GTM, adjacent product expansion, business cases, ROI models, and post-launch accountability.

⛳️ Requirements

• A minimum of 8 years in payments, fintech, embedded finance, or SaaS financial services, showcasing commercial ownership of revenue, margin, pricing, or partner economics.

• Extensive, hands-on knowledge of processing and interchange, PayFac/sub-merchant models, BNPL, TPV and attach-rate dynamics, pricing, repricing, and margin management.

• Proven track record of managing or contributing to a P&L.

• Strong financial and analytical skills.

• Demonstrated experience leading cross-functional execution across Product, Engineering, Marketing, Sales, Operations, Support, and Risk.

• Experience in managing external partners, processors, or networks, including Stripe, card networks, and BNPL providers.

• Excellent executive communication and influencing capabilities without direct authority.

• Ability to operate both strategically and tactically within a dynamic, fast-paced environment.

• Bachelor's degree in Business, Finance, Economics, or a related discipline.

🏝️ Benefits

• Incentive programs.

• Equity grant.

• Comprehensive health and wellness benefits.

• Flexible vacation plan.

• Retirement savings program or pension plan matched to the local office.

• Stock options for all full-time employees.

• Parental leave and support for new parents.

• Annual healthy living credit.

• Comprehensive medical and dental benefits.

• Fertility and gender-affirming benefits based on region.

• Peer Recognition Program.

• Employee Assistance Program.

• Headphone credit.

• Meaningful in-person gatherings for both onsite and remote employees.

• Attractive office spaces in Toronto, Amsterdam, and San Luis Potosi.

• Home office credit where a FreshBooks office is not accessible.

• Supportive peer group, mentors, and leaders.

• Comprehensive company onboarding.

• Career development opportunities through continuous coaching, training, and on-the-job learning.

• Employment accommodation during the recruitment process.