Sr. Manager, AI Enablement
San Francisco - Hybrid
About the Sr. Manager, AI Enablement 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. 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:
- 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.
- Strong judgment in selecting AI approaches that balance user impact with scalability and cost, ensuring solutions are viable beyond pilot and can operate efficiently at scale.
- Experience ensuring AI products deliver consistent, reliable user experiences by defining success criteria, embedding evaluation and monitoring practices, and planning for edge cases and failure modes.
- 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-$215,000 + equity + benefits.