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. Playground has raised millions of dollars in funding, has several Statewide contracts, and is working with thousands of schools across the country. Our founders were recently recognized by Forbes as 30 under 30, and our work has been recognized across the country.

Playground is at an inflection point, growing at a quick pace, and we are looking to expand our Product team as quickly as possible. Playground is a team of owners who are not afraid to dive into large, complex projects.

Job Description

We're looking for someone who came up through engineering, understands how systems are built, and has the scar tissue from owning a product end-to-end at a fast-moving company. You'll be the connective tissue between Engineering, Product, CS, Onboarding, and Sales cutting through the noise of competing priorities to identify what actually matters for our users and drive it to completion.

Responsibilities

• Own core product areas end-to-end, from discovery through delivery and iteration

• Deeply understand the childcare industry, our users (childcare providers and parents/guardians), and the problems they face

• Communicate directly with users through calls, chats, research, and feedback loops

• Synthesize feedback from customer-facing teams (CS, Onboarding, Sales) into a clear, prioritized roadmap that reflects what matters most across our customer base and business

• Partner closely with Engineering to translate customer and business needs into well-scoped, technically grounded specs

• Operate as the connective tissue across teams — you'll be the person who keeps everyone aligned and moving

• Make hard prioritization calls and defend them with data and customer insight

• Proactively identify gaps in product experience and drive improvements without waiting to be asked

• Own the payments roadmap end-to-end: transaction flows, billing, payouts, reconciliation, and compliance

• Partner with Engineering on payment infrastructure decisions (processors, rails, ledger design, fraud/risk tradeoffs)

Requirements

• 6-10+ years of PM experience, with 3+ years specifically owning payments products in B2B SaaS or FinTech

• Deep working knowledge of payment processing, transaction lifecycles, and reconciliation

• Experience working with payment processors/PSPs (Stripe, Adyen, etc.) and understanding of interchange, chargebacks, and settlement

• Technical background — prior software engineering experience or a degree in a technical discipline (CS, engineering, or similar)

• Proven ability to deeply understand engineering systems, architecture decisions, and technical tradeoffs without needing to write the code

• Experience owning a significant product or function at a startup, with real accountability for outcomes

• Strong prioritization instincts — you've managed a flood of inbound requests and know how to say no clearly and credibly

• Excellent communication skills across technical and non-technical audiences

Nice To Have

• B2B SaaS or FinTech experience

• Former founder or a long history of launched side projects

• Background in childcare, education, or a related vertical

Compensation

• The annual salary range for this position is $175,000–$220,000 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.

Why Join Playground

• Competitive salary + equity

• 3 weeks of PTO

• Health, vision, and dental benefits

• $1200/year education stipend

• Free lunch daily

• New MacBook

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

• Help accelerate our mission to make excellent child care accessible to all!

How to Apply
If you're excited to join a mission-driven, early-stage company where ownership, craftsmanship, and empathy are at the center of what we do, apply now. The Playground Team is fully in-office in Union Square, NYC. Please ensure you are open to a fully in-person role before applying.

Check out our journey to learn more about our co-founders Dan, Josh, and Sasha.