Strategic Finance Lead

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 for rapid growth. We recently raised millions of dollars, secured several statewide contracts, and are working with thousands of schools across the country. Our founders were recently honored as Forbes 30 Under 30.

We are a team of owners, unafraid to dive into large, complex projects. If you’re excited about solving high-impact problems across a growing startup and want to work closely with company leadership to build operational and financial excellence from the inside out, we want to hear from you!

We are seeking a Strategic Finance Lead who will have a high degree of impact and visibility. Reporting directly to Playground's CEO, you will identify commercial opportunities, deliver financial discipline, and propel us to the next stage of growth. This role is key in shaping the company's financial strategic direction, focusing on comprehensive financial planning, forecasting, and analysis; providing insights that guide the decision-making processes and support business operations.

This is a high-impact, highly visible role ideal for someone who thrives in ambiguity, enjoys cross-functional collaboration, and wants to influence financial strategy in a fast-growing startup.

• Drive company-wide decision-making with data precision and strategic analysis

• Manage corporate model, financial KPIs, and sales / G&A forecasts

• Produce materials and financial presentations to leadership team

• Serve as operational finance partner to business teams around the organization, helping to define key metrics that will drive our business, measure our progress, and provide key financial insights

• Partner with Sales, Marketing, and Product teams to analyze new revenue streams and product opportunities

• Assist the Executive Team on Board communications, including quarterly presentations and ad hoc analysis to investors

• Play a key role in the annual budgeting process, and lead monthly variance to budget reporting

• Provide monthly financial reporting and insights, cost tracking, and KPI reporting to different teams across the company

• Support capital markets, fundraising, and strategic initiatives including new product analysis & M&A

• Build and own detailed financial and operational models, ensuring the highest quality and accuracy.

• Forecasting revenue and expenses for new partnerships or expansions

• Evaluating financial impact of different market-entry strategies

• Building dashboards to track international business performance

• Streamlining reporting processes to improve decision‑making speed and accuracy

• Investment Banking Background: Must have prior experience in investment banking.
  Priority given to candidates from TMT (Technology, Media & Telecom) and FIG (Financial Institutions Group) groups
  , with exposure to payments and financial technology businesses.

• Startup
  
  Experience:
  
  Must have experience working at a startup after investment banking
  . Candidates for whom this would be their first startup experience are not eligible
  .

• Industry Exposure: Strong understanding of payments, fintech, or financial services is highly preferred.

• Self‑starter capable of independently navigating ambiguity

• Strong communication and interpersonal skills across diverse audiences

• Positive attitude, high attention to detail, and comfort working in a matrix organization

• Ability to thrive in a fast‑paced, high‑growth, and evolving environment

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 Union Square, NYC. Please make sure you are open to a fully…