Head of GTM Enablement
PlaygroundDenver, Colorado, United States • New York, New York, United States
Posted May 4, 2026
150000 - 180000 USD
Full Time
About the Company
Playground is a mission-driven, early-stage company working to make excellent child care accessible to all.
Job Description
Playground is hiring a founding Head of GTM Enablement to design and build a best-in-class enablement program for Sales and Customer Success teams. The role involves designing and delivering enablement programs, partnering strategically across teams, and measuring and optimizing enablement impact.
Requirements
- 5+ years of experience in Sales Enablement, Customer Success Enablement, or Learning & Development within high-growth B2B SaaS environments
- Experience owning and running enablement programs
- Proven track record in building and delivering Sales Academy programs and upskilling initiatives
- Strong facilitation, instructional design, and storytelling skills
- Excellent communication and presentation abilities
- Familiarity with enablement and learning tools
- A builder mindset
- Empathy for both Sales and Customer Success teams
Benefits
- Competitive salary + equity
- 3 weeks of PTO
- Health, vision, and dental benefits
- $1200/year education stipend
- 401(k)
- Free lunch daily
- New MacBook and any equipment you need
