About the Role

We're looking for a Strategic Projects Lead to serve as the CEO's right hand on Playground's most critical 0-to-1 initiatives. This is a highly entrepreneurial role designed for someone who thrives in ambiguity, moves quickly, and is energized by solving high-impact business problems from the ground up.

You'll identify, scope, and drive entirely new workstreams that sit outside the existing org chart - from launching new AI product lines to leading M&A and international expansion. One month, you may be building and scaling a new AI-powered offering and owning its P&L. The next, you could be designing an outbound sales engine from scratch or leading diligence on an acquisition target.

This role is ideal for someone who operates like a founder within the company: building the roadmap, aligning stakeholders, assembling teams, and owning outcomes end-to-end. You'll work directly with company leadership on Playground's most strategic priorities and have the opportunity to shape the future of the business in real time.

What You'll Do

Launch New AI Product Offerings

Identify whitespace opportunities, validate product-market fit, and build new AI-powered products from concept to revenue. You'll define the roadmap, hire initial team members, and scale successful initiatives.

Build and Systematize Outbound Go-to-Market

Design Playground's outbound sales motion from the ground up. Develop targeting, messaging, and sequencing strategies, then leverage AI and automation tools to create scalable systems that drive growth efficiently.

Hire Key Executives

Partner closely with the CEO to identify, recruit, and close senior leadership talent across the organization. Lead structured hiring processes for VP- and C-level roles that will significantly influence Playground's trajectory.

Lead International Expansion

Evaluate new markets, build business cases, navigate operational and regulatory complexity, and establish Playground's presence in new geographies - from first hire to first customers.

Drive High-Impact Strategic Initiatives

Take ownership of ambiguous, cross-functional projects that don't fit neatly into existing teams. Build structure where none exists, move quickly, and deliver outcomes that materially impact the business.

Who You Are

• 3-10 years of experience in management consulting, investing, corporate strategy, business operations, or as a founder - ideally within a high-growth startup or similarly fast-paced environment.
• A highly structured thinker who can take ambiguous problems and turn them into clear execution plans.
• Entrepreneurial and resourceful, with a proven ability to build from scratch and operate effectively without a playbook.
• Analytical and data-driven, comfortable building financial models, running analyses, and using insights to drive decisions.
• An exceptional communicator who can confidently write executive-level materials, lead meetings, and influence stakeholders across functions.
• Scrappy, high-ownership, and relentless about execution quality and speed.
• Energized by operating in high-stakes environments with significant autonomy and visibility.

Why Join Playground

• Competitive salary + equity
• 3 weeks of PTO
• Health, vision, and dental benefits
• $1,200/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
• Opportunity to work directly with company leadership on some of Playground's most important strategic initiatives
• Help accelerate our mission to make excellent child care accessible to all

Compensation

Salary for this position is $200,000 - $300,000 subject to standard withholding and applicable taxes. Job level and actual compensation will be determined based on factors including, but not limited to, individual qualifications assessed during the interview process (including skills, prior relevant experience, potential impact, and scope of role), market demands, and work location. The listed range is a guideline and may be modified.

How to Apply

If you're an entrepreneurial builder excited by ownership, ambiguity, and the opportunity to help shape a rapidly growing company, we'd love to hear from you.

The Playground team is fully in-office in NYC and Denver. This role will be based in our NYC office. Please ensure you are comfortable with a fully in-person environment before applying.

Check out Playground's About Page to learn more about our journey and co-founders.