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.
