AI Enablement Director - Strategy & Transformation

OpenTalent; San Francisco (CA); On-site; USD 210,000 - 260,000; Full time

Job summary

Headspace is seeking a Director, AI Enablement to define and drive the enterprise AI strategy, ensuring responsible, scalable adoption. You will partner with the COO/Founder and senior leaders to translate priorities into a tight AI roadmap and governance framework, guiding cross-functional teams through discovery, pilots, and launches.

You will lead a high-impact team, cultivate talent, and build the organizational muscle needed to scale AI while upholding safety, privacy, and company values.

Qualifications

• 7+ years of experience in product management, operations, strategy, or related roles delivering software/AI projects end-to-end.

Responsibilities

• Define and lead Headspace’s enterprise AI enablement strategy, roadmap, and operating model.
• Partner with executives to identify high-value AI opportunities and build a scalable portfolio of work.
• Own AI intake and prioritization with a transparent queue.
• Lead AI initiatives end-to-end from discovery to launch with clear milestones and metrics.
• Develop and coach cross-functional teams to scale AI adoption within responsible guardrails.
• Drive alignment with senior stakeholders across Product, Engineering, Legal, Privacy, Security, and Procurement.
• Define enterprise standards and governance for AI vendor evaluation and build-versus-buy decisions.
• Scale AI enablement through programs like leadership engagement, playbooks, and training.
• Oversee portfolio health with measurable business impact and lessons learned.
• Unblock critical integration work and identify next-wave AI opportunities for adoption.

Skills

Experience 7+ yrs

Cross-functional leadership

AI strategy roadmaps

Executive stakeholder mgmt

People leadership

AI concepts (LLMs/agents)

LLM prompts design

Adoption metrics

Data dashboards

AI use-case evaluation

Legal/Privacy liaison

Analytical rigor

Strong communication

Tools

Looker

Tableau

Job description

Headspace is seeking a Director, AI Enablement to define and drive the enterprise AI strategy, ensuring responsible, scalable adoption. You will partner with the COO/Founder and senior leaders to translate priorities into a tight AI roadmap and governance framework, guiding cross-functional teams through discovery, pilots, and launches.

You will lead a high-impact team, cultivate talent, and build the organizational muscle needed to scale AI while upholding safety, privacy, and company values.