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. The Outcomes You'll Deliver 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. PlayOn is where high school sports come to life. Through GoFan, NFHS Network, and MaxPreps, we give every fan a front-row seat to the moments that matter most: the buzzer-beaters, the comeback wins, the senior nights, the rivalries that define a town. We built our technology for the people who live and breathe high school athletics — the parents who never miss a game, the alumni still cheering from across the country, the communities that show up week after week. From buying tickets to watching a live stream to reliving the highlights, we make it simple to stay close to the sports and the athletes you love most. Backed by KKR, we build the technology that powers high school athletics from the inside out: Schools trust us to handle ticketing, streaming, fundraising, concessions, merchandise, and more so the people running programs can stay focused on the athletes and fans we all serve together. We're a growth-stage company on a mission to make high school sports more accessible, more memorable, and more connected than ever before. When being there means everything, we make sure you never miss a moment. Why You'll Love Working at PlayOn Product, potential, and people. We’re a leader in the high school event space, constantly evolving our product to meet the needs of administrators. We focus on solving real challenges, learning quickly, and creating impactful solutions. This is a growth-stage company, meaning your contributions have real impact. You’ll have opportunities to grow your skills, tackle meaningful problems, and make a difference in the lives of schools and the students and fans they serve. Our culture is built on accountability, collaboration, growth, and fairness. We don’t just show up—we show up for each other. Everyone wears the same jersey, and we play hard, make the extra pass, and cheer one another on. Losses teach us, challenges motivate us, and persistence drives us forward. We value integrity over shortcuts, choosing to do what’s right even when it’s hard. Together, we strive to be better every day—because we know that’s how we win as a team. The Benefits We Offer Multiple medical insurance plans to choose from Dental, vision life and disability insurance Employee Emergency Fund Company equity (stock options) Open PTO policy 401K plan with company match Hybrid/flexible work environment Note: Must be a full-time employee to participate in the company’s employee health benefit plan. Part-time employees and interns are not eligible to participate.