Strategic Projects 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 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 building category-defining initiatives and joining a collaborative, high-growth startup — please apply!

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 work streams 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.

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.

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.

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.

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.

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.

• 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.

• Competitive salary + equity

• 3 weeks of PTO

• Health, vision, and dental…