Director of Payments

ABOUT PLAYGROUND Playground is working to make excellent child care accessible to all. Playground has built best in class software to manage all aspects of running a child care business. We believe that providers should focus on providing incredible child care — the kind of work that only people can do — and that software should manage the rest. We're building the child care management platform that eliminates the administrative work of running a center. Playground is at an inflection point — and poised to grow extremely fast. We recently raised millions of dollars, have several statewide contracts, and are working with thousands of schools across the country. Additionally, our founders were recently honored as Forbes 30 under 30. We are a team of owners, who are not afraid to dive into large, complex projects. If you are excited by the prospect of helping build Playground's account management organization and joining a collaborative, high-growth startup — please apply! ABOUT THE ROLE We’re looking for a Director of Payments to own Playground’s entire payments ecosystem. This is a high-impact, high-visibility role at the intersection of fintech and vertical SaaS. You will serve as the single owner of our Stripe partnership, payment processing infrastructure, margin optimization, connected accounts architecture, and long-term pricing strategy. Today, Playground operates as a registered ISO (Independent Sales Organization) with Stripe, processing credit card and ACH payments for thousands of childcare providers through Stripe Connect. This role will build on that foundation—driving margin expansion, strengthening reporting infrastructure, optimizing our connected accounts model, and shaping the future of payments at Playground. We’re looking for someone who combines strategic payments expertise with hands-on technical depth. The ideal candidate has deep experience within the payments ecosystem, understands the mechanics of interchange, network fees, and platform economics, and has operated at both the strategic and executional level. You’ve either built or led the implementation of payment infrastructure connecting processors to CRMs, core SaaS platforms, and downstream systems. More importantly, you understand how changes across this stack impact billing, reporting, onboarding, and operations—and can lead the cross-functional work required to continuously improve it. WHAT YOU'LL DO STRIPE PARTNERSHIP & RELATIONSHIP MANAGEMENT - Own the day-to-day and strategic relationship with Stripe, serving as Playground’s primary point of contact - Negotiate rates, program terms, and partnership agreements to maximize Playground’s economic position - Stay ahead of Stripe product releases, API changes, and platform updates that impact our business - Manage escalations, disputes, and compliance requirements with Stripe’s partner and risk teams MARGIN OPTIMIZATION & FINANCIAL PERFORMANCE - Own payment processing margins end-to-end: analyze, report on, and improve net margin across card and ACH transactions - Build and maintain margin analysis dashboards and reporting infrastructure for leadership visibility - Identify and execute on opportunities to improve basis-point economics across the portfolio - Develop pricing models for new and existing connected accounts that balance growth with margin targets - Partner with Finance on revenue forecasting, COGS analysis, and payment volume projections CONNECTED ACCOUNTS INFRASTRUCTURE - Oversee the current Stripe Connect connected accounts architecture and identify areas for improvement - Define and execute the migration or optimization strategy for connected account onboarding, and payouts - Design future-state connected account pricing structures that support enterprise, SMB, and family childcare segments - Collaborate with Engineering and Product on API integrations, payment flows, and platform reliability PAYMENT SYSTEMS IMPLEMENTATION & CROSS-SYSTEM ARCHITECTURE - Own the end-to-end architecture of how payment processing infrastructure connects to our CRM, core SaaS platform, and internal operational systems - Lead or directly manage implementation projects that touch payment flows—new integrations, migrations, data pipeline changes, and system upgrades - Evaluate the downstream implications of changes to payment infrastructure on billing, reporting, onboarding, and customer-facing operations before they ship - Build and maintain tactical improvement roadmaps for payment system reliability, data accuracy, and cross-system consistency - Serve as the technical bridge between Engineering, Product, Sales, and Finance—fluent enough to read API documentation and spec requirements, capable of going deeper when the situation demands it REPORTING & ANALYTICS - Build a payments reporting stack: transaction-level data, margin analysis, connected account performance, and anomaly detection - Create ex