Strategic Projects Lead
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.
Responsibilities
- Leverage your analytical and data-driven skills to launch new AI product offerings, validate product-market fit, and build new AI-powered products from concept to revenue.
- 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, and 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, and lead structured hiring processes for VP- and C-level roles.
- 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.
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.
- Scrubby, high-ownership, and relentless about execution quality and speed.
- Energized by operating in high-stakes environments with significant autonomy and visibility.
Qualifications
- Proven track record of success in high-growth startups or similar fast-paced environments.
- Experience in launching and scaling new products or services.
- Strong project management and organizational skills.
- Ability to work independently and as part of a team.
- Excellent communication and interpersonal skills.
Skills
- Strategic thinking and problem-solving.
- Project management and organizational skills.
- Leadership and team-building abilities.
- Outreach and sales experience.
- Market analysis and business development skills.
- Financial modeling and analysis.
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
- Opportunity to help accelerate our mission to make excellent child care accessible to all
Pay
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.
Schedule
The Playground team is fully in-office in NYC and Denver. This role will be based in our NYC office.
Contact
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. 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.