Head of Financial Services

ROLLER • Austin, TX

2h

About The Position

ROLLER is seeking a Head of Financial Services to own its embedded financial services business end to end. Reporting to the Chief Product Officer, this senior commercial leader will run the business as a P&L, owning pricing, partner economics, merchant risk, payments operations, and the financial services roadmap. The role works closely with Product, Engineering, Finance, Legal, and go-to-market teams.

The Head of Financial Services will lead key payments-partner relationships, support Sales in enterprise and franchise deals, and represent Financial Services to senior leadership and in board reporting. This is a hands-on leadership role in a lean team, responsible for setting strategy and defending results while staying close to operational areas such as onboarding, payouts, reserves, and disputes.

Requirements

• 10+ years of experience in payments or fintech, including 5+ years leading a function at a high-growth SaaS or technology company; strong tenure in a scaling organization is required.
• Experience owning a P&L, setting pricing, building forecasts, and defending results with a CFO.
• Experience running payments on a platform model such as Adyen for Platforms, Stripe Connect, a PayFac, or a marketplace.
• In-depth understanding of onboarding and KYC, settlement, reserves, disputes, interchange, and scheme-fee economics.
• Experience within a vertical SaaS platform serving SMB and mid-market merchants, including familiarity with payments attach, repricing an existing customer base, and balancing go-to-market objectives with risk.
• Experience negotiating commercial terms with a major acquirer, processor, or financial partner, including revenue share, pricing changes, and contract renewals.
• Sound judgment on merchant risk, including making reserve, fraud, and account decisions under uncertainty and explaining them to merchants and a board.
• Executive-level communication skills, including preparing board-ready materials, presenting to senior leadership, and translating regulatory changes into actionable guidance for venue owners.
• Ability to build processes, playbooks, and data capabilities in a lean, evolving team, and engage with operational detail when needed.
• Comfort operating across regions and time zones, including Australia, the US, Canada, the UK, and Europe.

Nice To Haves

• Experience with embedded lending or merchant cash advances.
• Experience with embedded insurance.
• Experience with payment hardware economics.
• Hands-on use of AI tooling.
• Experience in attractions, leisure, or hospitality.

Responsibilities

• Own the Financial Services P&L, including strategy, annual plan, revenue, margin, pricing, and forecasts across payments, lending, and insurance.
• Scale ROLLER Capital and Instant Cash Out by managing eligibility and offer rules, underwriting and portfolio risk with the lending partner, and go-to-market adoption; take Refund Protection and future products from launch to scale.
• Lead merchant risk and fraud, including onboarding, reserves, fraud monitoring, chargebacks, and account actions, balancing loss exposure with merchant experience.
• Manage the partner portfolio, including commercial terms, revenue share, pricing changes, governance, and escalations with Adyen, Stripe, Cover Genius, and hardware vendors.
• Shape the financial services roadmap with Product and Engineering, develop commercial cases, prioritize with the payments squad, and ensure products deliver value to merchants and the business.
• Own regulatory and scheme compliance, including surcharging, interchange pass-through, and payment acceptance across markets, and translate regulatory changes into merchant guidance.
• Support Sales and enterprise customers with pricing approvals, deal support, enterprise and franchise-group deals and renewals, competitive positioning, and enablement for Sales, Customer Success, and Support.
• Lead and develop the Financial Services team; build runbooks, coverage, and data to manage escalations, and hire as the business grows.

Benefits

• Team Member Assistance Program offering health and wellbeing support, coaching, education modules, and weekly webinars.
• 16 weeks of paid parental leave for primary carers and 4 weeks for secondary carers.
• Highly flexible work environment.
• All Access pass to WeWork, depending on location.
• Individual learning and development budget.
• Career growth opportunities.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed