This role is designed for a technical program or product leader with 5+ years of experience who bridges the gap between AI potential and business execution. It’
Work type: hybrid
Location: San Francisco - Hybrid
Salary: $118,800 – $215,000/yr
Type: Full-time
This role is designed for a technical program or product leader with 5+ years of experience who bridges the gap between AI potential and business execution. It’s ideal for a "hands-on builder" who understands the LLM lifecycle—from prototyping and vendor evaluation to navigating legal and privacy hurdles. If you enjoy creating order out of chaos and driving cultural shifts around technology adoption, this leadership position is for you. The compensation is competitive, reaching up to $189k plus equity and a robust wellness stipend. While the role is hybrid (3 days/week in San Francisco), it offers the unique chance to shape an "AI-first" model for a mission-driven wellness brand where safety and privacy are paramount. You’ll have a high degree of influence, working across every department to build the company’s AI infrastructure from the ground up. **You might be a good fit if you...** * Have successfully moved AI pilots from the idea stage into production in a regulated environment like healthcare. * Are comfortable challenging the status quo and can guide teams through complex governance (Legal, Privacy, InfoSec). * Enjoy creating internal "playbooks" and training programs to evangelize new tools. * Are local to the SF Bay Area and value a blend of in-person collaboration and remote flexibility.
About the Sr. Manager,AI Enablementat 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. You will be reporting to the COO for this role, with broad support across the executive and senior leadership team.
As the Sr. Manager, AI Enablement, 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:
The anticipated new hire base salary range for this full-time position is $118,800-$215,000 + 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: