AI Enablement Lead

About the AI Enablement Lead at Headspace:

Headspace is building an AI-first operating model grounded in member safety, privacy, and measurable business impact. This role is for a hands-on AI builder and adoption leader—a curious, product-minded problem solver who moves fast, spots leverage, and turns messy ambiguity into shipped workflows, tools, and outcomes across the company. 

As the AI Enablement Lead, you’ll drive company-wide adoption end-to-end: building repeatable intake and prioritization, moving pilots to production, equipping teams with playbooks and training, and helping initiatives clear governance smoothly. You’ll influence across all teams at Headspace, building the muscle for experimentation and scaled adoption through enablement, evangelization, and hands-on execution. 

You’re fearless and constructively contrarian: willing to challenge defaults, run smart experiments, and unblock teams while staying inside responsible AI guardrails. Help build AI agents that give our teams the leverage they need to #make-the-mission-matter.

What you will do:

• 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.
• Build and run AI enablement (training, office hours, playbooks, and an AI Champions network) to drive adoption and fluency.
• Grow awareness and adoption of existing AI tools with functional leaders to expand use cases and impact.
• Standardize AI vendor evaluation and guide tools through governance with Product, Legal, Privacy, Security, Procurement.
• Champion responsible AI through measurement, training, and org-wide communication.
• Deliver lightweight reporting and exec-ready updates on pipeline health, outcomes, and trade-offs.
• Unblock high-leverage technical/integration work and identify next-wave AI opportunities to scale adoption and cultural change.

What success looks like (first 90 days):

• A single, working AI intake + prioritization system is live, with clear criteria and a visible queue.
• An AI enablement cadence is running (office hours + champions network + basic playbook library).
• At least 1–2 pilots move from idea → UAT/launch with measurable outcomes.
• A repeatable vendor evaluation + governance checklist exists (privacy/security/procurement artifacts), reducing cycle time for new tools and pilots.

Required Skills:

• 5+ years of experience in Product Ops, Technical Program Management, Business Operations, or equivalent roles delivering software/AI projects end-to-end.
• Strong cross-functional leadership, change management, and stakeholder management; ability to influence without authority across Product/Eng, Legal/Privacy/Security, Procurement, and functional leaders.
• Comfort operating in ambiguity and driving crisp decisions, scope, milestones, and delivery plans.
• 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 success metrics for initiatives and measure outcomes (directly or in partnership with analytics/data teams).
• Excellent written and verbal communication (exec one-pagers, workshops, playbooks, enablement sessions).
• Strong judgment and commitment to member safety, privacy, and Headspace’s mission.

Preferred Skills:

• Experience building internal enablement programs (champions networks, training, office hours, templates) for new tools or major process shifts.
• Experience coordinating AI governance / risk reviews and embedding responsible AI practices.
• Vendor evaluation experience and partnership with Procurement.
• Experience in healthcare/wellness/consumer products where privacy and safety are critical.
• PMP/CSM or relevant program management / AI certificates.

Location:

This is a hybrid role located in our San Francisco office, working 3 days per week from the office. 

Pay & Benefits:

The anticipated new hire base salary range for this full-time position is $118,800-$189,750 + equity + benefits. 

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

Headspace exists to provide every person access to lifelong mental health support. 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.

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. These values shape our decisions, guide our collaborations, and define our culture. 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.

Why You’ll Love Working Here:

• A mission that matters—with impact you can see and feel
• A culture that’s collaborative, inclusive, and grounded in our values
• The chance to shape what mental health care looks like next
• Competitive pay and benefits that support your whole self

How we feel about Diversity, Equity, Inclusion and Belonging:

Headspace is committed to bringing together humans from different backgrounds and perspectives, providing employees with a safe and welcoming work environment free of discrimination and harassment. We strive to create a diverse & inclusive environment where everyone can thrive, feel a sense of belonging, and do impactful work together. 

As an equal opportunity employer, we prohibit any unlawful discrimination against a job applicant on the basis of their race, color, religion, gender, gender identity, gender expression, sexual orientation, national origin, family or parental status, disability*, age, veteran status, or any other status protected by the laws or regulations in the locations where we operate. We respect the laws enforced by the EEOC and are dedicated to going above and beyond in fostering diversity across our workplace. 

*Applicants with disabilities may be entitled to reasonable accommodation under the terms of the Americans with Disabilities Act and certain state or local laws. A reasonable accommodation is a change in the way things are normally done which will ensure an equal employment opportunity without imposing undue hardship on Headspace. Please inform our Talent team by filling out this form if you need any assistance completing any forms or to otherwise participate in the application or interview process.

Headspace participates in the E-Verify Program.

Privacy Statement

All member records are protected according to our Privacy Policy. Further, while employees of Headspace (formerly Ginger) cannot access Headspace products/services, they will be offered benefits according to the company's benefit plan. To ensure we are adhering to best practice and ethical guidelines in the field of mental health, we take care to avoid dual relationships. 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.  

As such, Headspace requests that individuals who have received coaching or clinical services at Headspace wait until their care with Headspace is complete before applying for a position. If someone with a Headspace account is hired for a position, please note their account will be deactivated and they will not be able to use Headspace services for the duration of their employment. 

Further, if Headspace cannot find a role that fails to resolve an ethical issue associated with a dual relationship, Headspace may need to take steps to ensure ethical obligations are being adhered to, including a delayed start date or a potential leave of absence. Such steps would be taken to protect both the former member, as well as any relevant individuals from their care team, from impairment, risk of exploitation, or harm.

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