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 universe. This is
a high-impact, high-visibility role at the intersection of fintech and vertical SaaS. You’ll be the
single point of ownership for our Stripe partnership, payment processing infrastructure, margin
optimization, connected accounts architecture, and future pricing strategy.
Today, Playground operates as a registered ISO (Independent Sales Organization) for Stripe,
processing credit card and ACH payments for thousands of childcare providers through Stripe
Connect. This role will take what we’ve built and elevate it—driving margin improvement,
building reporting infrastructure, optimizing our connected accounts model, and shaping the
strategic roadmap for payments at Playground.
This is not a project manager role. We need a builder—someone who has lived in the payments
ecosystem, understands the mechanics of interchange, network fees, and platform economics,
and can translate that knowledge into strategy and execution

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, KYC, 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

Reporting & Analytics
• 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

Strategy & Roadmap
• 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 payment

• 7+ 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
• 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

• Experience at a high-growth startup

• Experience with childcare management software

• Experience in early childcare

Salary for this position is $175,000 – $225,000 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
  

How to Apply: 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.