AI Enablement Program Manager

Headspace•San Francisco, CA

1d•$118,800 - $189,750•Hybrid

About The Position

About the AI Enablement Program Manager 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 product builder—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 Program Manager, you’ll drive change like an athlete: sprinting from insight → prototype → pilot → production, and building the systems that make AI adoption repeatable (intake, prioritization, playbooks, training, governance). You’re fearless and constructively contrarian—willing to challenge defaults, run smart experiments, and unblock teams—while ensuring everything clears responsible AI guardrails smoothly. 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. 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.

Requirements

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.

Nice To Haves

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.

Responsibilities

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.
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.