Strategic Projects Lead
About The Position
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.
Requirements
- 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.
Responsibilities
- 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.
Benefits
- 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
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
