Director of Payments

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!

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.

• 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

• 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

• 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

• 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

• Build a payments reporting stack: transaction-level data, margin analysis, connected account performance, and anomaly detection

• Create executive-ready reporting on payment processing volume, revenue, margin trends, and key KPIs

• Establish monitoring and alerting for payment failures, dispute rates, and processing anomalies

• Define the 12–36 month payments strategy, including pricing, product, and partnership initiatives

• Evaluate alternative payment methods, processors, or hybrid models that could enhance Playground’s offering

• Benchmark Playground’s payments economics against industry standards and competitive landscape

• Advise leadership on market trends in embedded finance, payment facilitation, and vertical SaaS payments

• You’ve spent 4+ years working in payments, fintech, or payment facilitation—ideally at a platform, ISO, or PayFac

• You deeply understand Stripe Connect (or equivalent platform payment models), interchange economics, and the mechanics of payment processing margins

• You’ve managed a Stripe, Adyen, or comparable processor relationship at a strategic level—not just integration

• You have experience with connected account models, including onboarding, underwriting, and payout operations

• You’ve been hands-on in implementing or project-managing payment system infrastructure—connecting a processor to CRM, billing, and core product systems—and you understand the cross-system implications when something changes

• You’re technically fluent—comfortable reading API documentation, understanding data flows, and speccing out integration requirements—and you can go deeper when the project demands it

• You’re fluent in the language of basis points, interchange tiers, network fees, and effective rates

• You can build financial models and reporting dashboards, and you’re comfortable getting into the data yourself

• You’re a clear communicator who can translate complex payment mechanics into plain language for leadership, sales, and product teams

• You thrive in fast-paced, high-growth environments where you’re building the plane while flying it

• Previous experience in payments consulting, fintech advisory, or ISO/PayFac operations is strongly preferred

• 4+ years in payments, fintech, or embedded finance roles

• Direct experience managing payment processor partnerships (Stripe strongly preferred)

• Deep knowledge of Stripe Connect, connected accounts, and platform payment models

• Experience at an ISO, PayFac, or payment-facilitation-enabled SaaS platform

• Strong analytical skills with experience building margin analysis and reporting infrastructure

• Demonstrated experience implementing or project-managing payment system integrations across multiple internal systems (e.g., processor ↔ CRM ↔ core platform)

• Technical fluency sufficient to read API documentation, understand data flows, and evaluate the downstream impact of infrastructure changes

• Familiarity with PCI compliance, payment regulations, and risk management

• Previous fintech consulting or payments advisory experience preferred

• Based in or willing to relocate to New York City (5 days/week in-office, Union Square)

• Bachelor’s degree in Finance, Business, Economics, or related field; MBA a plus

Salary for this position is $225,000 ($175,000 Base) subject to standard withholding and applicable taxes. Job level and actual compensation will be decided on factors including, but not limited to, individual qualifications objectively assessed during the interview process (including skills and prior relevant experience, potential impact, and scope of role), market demands, and specific work location. The listed range is a guideline, and the range for this role may be modified.

• Competitive salary + equity

• 3 weeks of PTO

• Health, vision, and dental benefits

• $1200/year education stipend

• Free lunch daily

• Collaborative and supportive work culture with a high level of autonomy and room for growth

• You’ll own the payments function at a company where payments is a core business driver—not an afterthought

• You’ll have a direct line to leadership and the autonomy to shape strategy from day one

• You’re joining a team that’s scaled from 25 to 60+ people in months—with the trajectory to keep going

• You’ll work on real infrastructure that processes millions in payment volume for thousands of childcare centers

• You’ll be part of a mission that matters: making excellent child care accessible to all

If you're a hustler who's excited to join a mission-driven, early-stage company with ownership, craftsmanship, and empathy at the center of what we do, apply now. The Playground Team is fully in-office in Lodo, Denver or Union Square, NYC. Please make sure you are open to a fully in-person role before applying.

Check out: https://www.tryplayground.com/about to learn more about our journey and co-founders Dan, Josh, and Sasha.