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PlaygroundPlaygroundNew York, NY

Strategic Projects Lead

Serve as the CEO’s right hand on 0-to-1 strategic initiatives including launching new AI products, building outbound sales engines, hiring executives, and leading international expansion.

200k – 300k/yr
On-site3+ YOEBusiness Operations

About the role

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
  • 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
  • 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
  • Lead structured hiring processes for VP- and C-level roles

Lead International Expansion

  • Evaluate new markets, build business cases, navigate operational and regulatory complexity
  • 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
  • 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
  • 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

Compensation & 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

Skills

Management ConsultingCorporate StrategyBusiness OperationsFinancial ModelingExecutive HiringGo-to-Market StrategyAi Product DevelopmentM&A DiligenceInternational ExpansionStakeholder Management

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