Director, Ai Enablement

Headspace

Remote, US
Base: $138,600-$220,000 (up to $250,000 in sf/nyc/...
Remote
7+ years product management or operations experience
Enterprise-level transformation leadership
Ai strategy and roadmap development
Headspace is building an AI-first operating model grounded in member safety, privacy, and measurable business impact

Job Summary

  • Headspace is building an AI-first operating model grounded in member safety, privacy, and measurable business impact.
  • This role reports directly to the COO/Founder and will define the strategy for adopting AI thoughtfully and responsibly across the enterprise.
  • The position offers a robust total rewards package including base salary, stock awards, comprehensive healthcare, and a monthly wellness stipend.

Matching Summary

Headspace is building an AI-first operating model grounded in member safety, privacy, and measurable business impact.

Salary

Base: $138,600-$220,000 (up to $250,000 in SF/NYC/Seattle); Equity: Included; Benefits: Comprehensive healthcare, wellness stipend, retirement match

Skills & Requirements

Must-have

  • 7+ years product management or operations experience
  • Enterprise-level transformation leadership
  • AI strategy and roadmap development
  • Cross-functional stakeholder management
  • People leadership and team building
  • LLM concepts and prompt design skills
  • Experience with Legal, Privacy, and Security

Nice-to-have

  • Healthcare or digital health background
  • Champion network and training program creation
  • Vendor selection and contract evaluation
  • Hands-on prototyping and workflow design
  • Change management methodologies
  • PMP, CSM, or AI certifications

Key Requirements

  • 7+ years of relevant experience
  • US permanent residency required
  • Leadership experience in matrixed organizations
  • Proven track record in AI enablement

Work Rights

Must permanently reside in the US full-time

Tailored Resume

Cover Letter