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restart

Director, AI Enablement

Remote - United States; San Francisco - Hybrid · Director · Full-time

Sponsorship not specified$139k-$220kDetected 33 days ago
RESTData VisualizationLLMsAgentic AIA/B TestingProduct ManagementProcurementCustomer SuccessPatient CareLeadershipCommunicationCollaborationMentoring

About the role

  • 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.

Responsibilities

  • 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.
  • We live them daily: Make the Mission Matter, Iterate to Great, Own the Outcome, and Connect with Courage.

Requirements

  • 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.
  • 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 define, interpret, and act on adoption and outcome metrics
  • comfort with dashboards (Looker, Tableau, etc.)
  • Experience evaluating AI use cases through a business lens, including feasibility, value, risk, adoption readiness, and return on investment.
  • 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.
  • Required Skills:

Nice to have

  • Preferred Skills:

Skills

  • Demonstrated success influencing and partnering with executive leaders and senior stakeholders in a highly matrixed organization.
  • Ability to define, interpret, and act on adoption and outcome metrics; comfort with dashboards (Looker, Tableau, etc.)
  • Experience with vendor selection, contract evaluation, and budget or portfolio management for AI tools and platforms.
  • 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).
  • Candidates must permanently reside in the US full-time.
  • Your recruiter will share more details about our hybrid model.

Compensation

  • The anticipated new hire base salary range for this full-time position is $138,600-$220,000 + equity + benefits.

Benefits

  • The anticipated new hire base salary range for this full-time position is $138,600-$220,000 + equity + benefits.
  • At Headspace, base salary is but one component of our Total Rewards package.
  • Additional details about our Total Rewards package will be provided during the recruitment process.
  • Headspace exists to provide every person access to lifelong mental health support.
  • They're our shared commitment to building a more connected, human-centered team-one that's redefining how mental health care supports people today and for generations to come.
  • The chance to shape what mental health care looks like next
  • Competitive pay and benefits that support your whole self
  • Within this range, individual compensation is determined by a candidate's location as well as a range of factors including but not limited to: unique relevant experience, job-related skills, and education or training.

Company info

  • 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.
  • At Headspace, our values aren't just what we believe, they're how we work, grow, and make an impact together.
  • These values shape our decisions, guide our collaborations, and define our culture.
  • A culture that's collaborative, inclusive, and grounded in our values
  • Our salary ranges are based on the job, level, and location, and reflect the lowest to highest geographic markets where we are hiring for this role within the United States.
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