Senior Product Manager, Payments

PlayOn is looking for a Senior Product Manager, Payments to own the payments delivery roadmap for one of the largest digital ticketing platforms in high school athletics.

This role sits at the intersection of financial technology, school-facing product, and internal operations tooling. You'll own a broad and complex roadmap spanning financial reporting, payout operations, refunds and disputes, tax compliance, and the rollout of GoFan's Stripe Connect / PFaaS model — directly shaping how 10,000+ schools, districts, and state associations receive funds, reconcile revenue, and manage their financial relationships with GoFan.

You'll partner closely with Engineering, Finance, Customer Success, and school-facing stakeholders to ship product that is accurate, compliant, and trusted. The work spans external customer experiences (bookkeepers, athletic directors, fans) and internal operations tooling (Finance, Accounting, Support) — both sides of the platform need to work flawlessly for payments to be trustworthy.

Critically, we expect this PM to be AI-forward: using AI to accelerate spec writing, data analysis, and prototyping, and to process customer and support feedback at scale so that delivery moves faster from insight to ship.

• Ship financial reporting that helps schools, districts, and internal teams close their books with confidence — settlement statements (SPE), event-level reporting, and the HQ Financial Performance dashboard
• Drive the delivery roadmap for GoFan's Stripe Connect / PFaaS rollout — onboarding flows, settlement service configuration, order service integration, and NetSuite reconciliation as schools migrate off legacy ACH
• Improve refund and dispute tooling for school operators and internal teams — reducing manual intervention and shortening resolution time
• Own the infrastructure behind pricing, tax, and payout accuracy — sales tax for ticketing, fee and rebate configuration (rate service), revenue share automation, and cash reconciliation
• Reduce Support and Finance ticket volume on reconciliation issues by improving the accuracy and traceability of payment data end-to-end

In this role, you can expect to

Own the end-to-end payments delivery roadmap across financial reporting, payout operations, refunds and disputes, tax, and Stripe Connect execution
Translate strategy from the Sr. Manager, Payments Strategy & Product into sequenced, shippable delivery plans with clear acceptance criteria
Partner with Engineering on technical scoping, sequencing, and integration with banking partners (Wells Fargo, NetSuite) and payment processors
Work directly with Finance and Accounting stakeholders — speak their language, earn their trust, and translate their operational needs into product requirements
Use AI tools to accelerate spec writing, query and validate data, and prototype workflows before committing engineering capacity
Validate decisions with data and direct customer input — bookkeeper interviews, support ticket analysis, and behavioral analytics from HQ
Manage a large, complex backlog across multiple workstreams with competing priorities, executive scrutiny, and compliance constraints
Collaborate across Customer Success, Support, and school-facing teams to ensure delivery aligns with the realities of how bookkeepers and athletic directors actually work

To thrive in this role, you have

5-8+ years in product management or a related discipline (accounting, compliance, finance operations) with working knowledge of software product development
Experience in payments, fintech, financial services, or a domain with similar complexity — settlements, payouts, reconciliation, or compliance
Comfort working with Finance and Accounting stakeholders — you can speak their language, read a GL, and earn their trust on accuracy and audit
Proven ability to manage a large, complex backlog across multiple workstreams with competing priorities and executive visibility
Comfort with ambiguity — this role requires judgment, not just execution; the right answer is often not in the ticket
A demonstrated AI-forward approach — actively uses AI tools (Claude, ChatGPT, Cursor, or similar) to accelerate spec writing, data analysis, prototyping, and customer feedback synthesis
Strong communication skills — you can articulate the why behind the work to engineers, finance leaders, and executive stakeholders alike
Strongly preferred: experience with payout or settlement products, familiarity with payment processor ecosystems (doesn't need to be Stripe specifically), and experience supporting internal tools users (Finance, Ops, Accounting) alongside external customers
Strongly preferred: ability to read and interpret data — SQL familiarity or comfort working directly with data teams to answer your own questions

How You Play

Ownership over Participation – You take responsibility for delivering outcomes against real milestones: annotation review in production within six months, a fan-facing AI feature live within nine.

Team over Stars – You partner across engineering, data, product, and external collaborators to make AI systems usable by the whole company and delightful for fans.

Growth over Comfort – You embrace rapid experimentation, AI-forward development, and the ambiguity of building new product categories where no established playbook exists.

Fairness over Popularity – You evaluate tools, patterns, and approaches objectively, choosing what’s right for the platform over what’s fashionable.