Director of Payments

Playground•Denver, CO

3d•$175,000 - $225,000•Onsite

About The Position

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

Requirements

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
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

Nice To Haves

Experience at a high-growth startup
Experience with childcare management software
Experience in early childcare
Previous fintech consulting or payments advisory experience preferred

Responsibilities

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, 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
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 payment

Benefits

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