Head of Finance

About the role

The Head of Finance will serve as the key financial partner to the CEO and Executive Leadership Team, driving Playground's long-term financial strategy, planning, and operational efficiency. This role is highly visible and critical, sitting at the intersection of Finance, Strategy, and Operations.

Responsibilities

• 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.

• 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.

• 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.

• 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.

Requirements

• 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—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.

Qualifications

• Master’s degree in Finance, Accounting, Business Administration, or a related field.

• CPA certification preferred.

Skills

• Strong analytical and problem-solving skills.

• Excellent communication and interpersonal skills.

• Experience with financial modeling and analysis.

• Ability to work effectively in a fast-paced, dynamic environment.

• Experience with SaaS business models and advanced financial systems.

Benefits

• 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!

Pay

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.

Schedule

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