About the Role
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.
Required Skills
- 7+ years of experience in product management/operations, technical program management, business operations, strategy, digital transformation, or related roles delivering software/AI projects end-to-end.
- Significant experience leading cross-functional, enterprise-level transformation work with demonstrated impact across multiple functions or business units.
- Experience setting strategy, building roadmaps, and establishing operating mechanisms for AI, automation, or other emerging technology initiatives in a fast-paced environment.
- Demonstrated success influencing and partnering with executive leaders and senior stakeholders in a highly matrixed organization.
- People leadership experience, including building, managing, mentoring, and developing high-performing teams and/or standing up a new function or capability.
- Strong aptitude of AI concepts (LLMs/agents, common tradeoffs, prototype→pilot→scale lifecycle) and ability to translate technical constraints into clear timelines and decision points.
- Ability to design, evaluate, and iterate on prompts for LLM-based workflows; essential for building and reviewing AI agents.
- Ability to define, interpret, and act on adoption and outcome metrics; comfort with dashboards (e.g., Looker, Tableau).
- Experience evaluating AI use cases through a business lens, including feasibility, value, risk, adoption readiness, and return on investment.
- Experience partnering with Legal, Privacy, Security, and Procurement or equivalent functions to implement AI responsibly in regulated or high-trust environments.
- Strong analytical and operational rigor, with the ability to define success metrics, assess outcomes, and make clear prioritization decisions.
- Excellent written and verbal communication skills, with the ability to synthesize complexity into crisp recommendations, executive updates, and change-ready messaging.
Preferred Skills
- Experience leading AI enablement, transformation, or internal adoption work in healthcare, digital health, wellness, or another privacy- and safety-sensitive environment.
- Experience building enterprise enablement programs such as champion networks, training curricula, playbooks, and adoption frameworks.
- Experience with vendor selection, contract evaluation, and budget or portfolio management for AI tools and platforms.
- Experience balancing strategic leadership with hands-on prototyping, workflow design, prompt iteration, or early-stage solution development.
- Familiarity with change management approaches that help organizations adopt new tools and ways of working at scale.
- Relevant certifications in program management, product management, change management, or AI-related disciplines (PMP/CSM/AI certificates).