other
Posted 2 weeks agoDirector, AI Enablement
at Headspace
United StatesHybrid
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.
- 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.
- 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.
- Deliver executive-ready communication, recommendations, and reporting on AI strategy, portfolio health, risks, trade-offs, and realized impact.
Requirements
- About the Director, AI Enablement at Headspace:
- 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:
- 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.
- Unblock high-leverage technical/integration work and identify next-wave AI opportunities to scale adoption and cultural change.
- 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.
- 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
- 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. Preferred Skills: • •
- 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). Location:
- We strive to create a diverse & inclusive environment where everyone can thrive, feel a sense of belonging, and do impactful work together.
Experience
- Required Skills: 7+ years of
Benefits
- 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.
- Your recruiter will share more details about our hybrid model. Pay & Benefits :
- The anticipated new hire base salary range for this full-time position is $138,600-$220,000 + equity + benefits.
- For roles based in San Francisco, New York City, or Seattle, a separate salary range of $177,100-$250,000 applies, consistent with our location-based compensation philosophy.
- 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.
- 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.
- Your recruiter will provide more details on the specific salary range for your location during the hiring process.
- At Headspace, base salary is but one component of our Total Rewards package.
- We’re proud of our robust package inclusive of: base salary, stock awards, comprehensive healthcare coverage, monthly wellness stipend, retirement savings match, lifetime Headspace membership, generous parental leave, and more.
- Additional details about our Total Rewards package will be provided during the recruitment process. About Headspace
- We combine evidence-based content, clinical care, and innovative technology to help millions of members around the world get support that’s effective, personalized, and truly accessible whenever and wherever they need it.
- 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
- How we feel about Diversity, Equity, Inclusion and Belonging:
- A dual relationship occurs when a mental health care provider has a second, significantly different relationship with their client in addition to the traditional client-therapist relationship—including, for example, a managerial relationship.
Contact
- For how how we will use the personal information you provide as part of the application process, please see: https://www.headspace.com/applicant-notice #LI- Hybrid
Additional details
- 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 building enterprise enablement programs such as champion networks, training curricula, playbooks, and adoption frameworks. •
- Experience balancing strategic leadership with hands-on prototyping, workflow design, prompt iteration, or early-stage solution development.
- We are currently hiring this role remotely in the US and Hybrid for San Francisco (SF). Candidates must permanently reside in the US full-time.
- For candidates with a primary residence in the greater SF area, this role will follow our hybrid model.
- You’ll work 3 days per week from our office, allowing for impactful in-office collaboration and connection, while enjoying the flexibility of remote work for the rest of the week.
- Headspace exists to provide every person access to lifelong mental health support.
- At Headspace, our values aren’t just what we believe, they’re how we work, grow, and make an impact together.
- We live them daily: Make the Mission Matter, Iterate to Great, Own the Outcome, and Connect with Courage.