Head of Finance

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 finance organization and joining a collaborative, high-growth startup — please apply!

As the Head of Finance, you will be the key financial partner to the CEO and Executive Leadership Team, responsible for driving Playground’s long-term financial strategy, planning, and operational efficiency. This is a highly visible and critical leadership role that sits at the intersection of Finance, Strategy, and Operations.

You will own the company’s operating model and planning cadence, prepare all Board and investor materials, evaluate complex corporate development opportunities including M&A and fundraising, and build the finance function from the ground up. Your mandate is to provide the quantitative framework for all major strategic decisions as Playground scales from a high-growth startup into a category-defining company.

The Playground team is fully in-office in NYC and Denver. Note that this role will be in-person in NYC.

• Strategic Finance: Own and manage the company’s integrated financial model, including long-range planning, annual operating plan, and rolling forecasts. Translate operational goals into financial targets and establish the right planning cadences across the organization.

• AI Systems & Processes: Build an AI-native finance function — deploy AI tools to automate forecasting, reporting, and financial workflows so the team operates faster and leaner than traditional finance orgs..

• Board Reporting & Investor Relations: Prepare all quarterly Board materials, investor presentations, and management dashboards.

• Build the Finance Team: Hire, mentor, and develop a high-performing Finance function from the ground up — spanning FP&A, accounting, and strategic finance — capable of scaling with Playground’s growth trajectory.

• M&A: Source, evaluate, and execute acquisition opportunities end-to-end. Lead financial diligence, build deal models, negotiate terms, and manage post-acquisition integration planning to ensure Playground captures full strategic value.

• 4-8 years of experience in Finance, with at least 2+ years at a technology investment firm or high growth SaaS / AI company. Prior experience in Investment Banking, Private Equity, or Venture Capital is highly desirable

• Direct experience with M&A execution (deal sourcing, financial diligence, modeling, negotiation) and/or fundraising (building data rooms, investor materials, managing due diligence)

• Deep knowledge of SaaS business model, advanced modeling techniques, valuation methodologies, and GAAP principles

• Proven ability to operate at a tactical level and a strategic level simultaneously — you can build the model yourself and present the insights to the Board

• A strong curiosity and proactive approach to applying AI toward the evolution of finance operations

• Competitive salary + equity

• 3 weeks of PTO

• Health, vision, and dental benefits

• $1200/year education stipend

• 401(k)

• Free lunch daily

• New MacBook and any equipment you need

• 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!

Salary for this position is $250,000 - 300,000 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.