Director, AI Enablement

About the Director, AI Enablement at Headspace:

Headspace is building an AI-first operating model grounded in member safety, privacy, and measurable business impact. As Director, AI Enablement, you will define and drive the strategy that helps Headspace adopt AI thoughtfully, responsibly, and at scale across the enterprise.

This is a highly visible role, reporting to the COO/Founder, with the opportunity to shape how teams across Headspace evaluate, build, govern, and scale AI-powered workflows, tools, and operating practices. You will partner closely with executive leaders and senior stakeholders across Product, Engineering, Legal, Privacy, Security, Procurement, Care, and Go-to-Market to translate company priorities into an AI roadmap that delivers meaningful outcomes for our teams and the members we serve.

This role is ideal for a strategic and hands-on leader who can move fluidly from vision to execution: setting direction, building operating mechanisms, developing talent, and leading cross-functional change in a fast-moving environment. You bring strong judgment, a bias toward learning, and a commitment to responsible AI. You’re willing to challenge defaults, run smart experiments, and unblock teams while staying inside responsible AI guardrails. In doing so, you will help Headspace build the capabilities, guardrails, and cultural momentum needed to make AI a durable advantage in service of our mission to provide every person access to lifelong mental health support.

What you will do:

• Define and lead Headspace’s enterprise AI enablement strategy, roadmap, and operating model, aligning investments and priorities to company goals, member outcomes, and measurable business impact.
• Partner with the COO/Founder, executive team, and senior leadership team to identify high-value opportunities for AI across the business and turn them into a focused, transparent, and scalable portfolio of work.
• Own AI intake and prioritization: triage requests, refine problem statements, size value, and maintain a transparent queue.
• Lead AI initiatives end-to-end (discovery → pilot → launch), aligning scope, milestones, success metrics, and stakeholders. Own the outcome and drive real impact by building.
• Lead a high-impact team, while also leading/influencing crossfunctionally to coach talent and build the organizational muscle needed to scale AI adoption, experimentation, and responsible execution over time.
• Drive cross-functional alignment with senior stakeholders across Product, Engineering, Legal, Privacy, Security, Procurement, and functional leadership to accelerate delivery while managing risk appropriately.
• Define the enterprise standards, frameworks, and guardrails for AI vendor evaluation, implementation, and use, including build-versus-buy recommendations, governance pathways, and responsible AI practices.
• Drive Headspace’s AI enablement capability through scalable programs such as leadership engagement, functional playbooks, training, office hours, and champion networks that increase fluency and adoption across teams.
• Oversee a portfolio of AI initiatives and ensure teams are delivering against clear business cases, adoption metrics, operational improvements, and lessons learned that inform future investment.
• Unblock high-leverage technical/integration work and identify next-wave AI opportunities to scale adoption and cultural change.
• Deliver executive-ready communication, recommendations, and reporting on AI strategy, portfolio health, risks, trade-offs, and realized impact.
• Act as a strategic thought partner and visible leader for AI adoption at Headspace, helping shape a culture that is ambitious, practical, and grounded in safety, privacy, and our values.