Director, AI Enablement

Benefits

Parental leave

Not verified not verified - source URL not recorded

Non-birth-parent leave

Not verified

Family-building benefits

• Fertility benefits: Not verified
• Adoption assistance: Not verified
• Surrogacy assistance: Not verified

Mental health support

Offered From the posting source checked Jun 20, 2026

Relocation assistance

Not verified

Childcare support

Not verified

Learning budget

Not verified

Verification

Not verified checked Jun 7, 2026

Salary

$177K-$250K From the posting source checked Jun 20, 2026

401(k) match

Reported from DOL Form 5500 industry filing (not employer-specific)

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Market context

U.S. role benchmark (BLS OEWS)

$61,842 U.S. median for this role

Projected growth (BLS Employment Projections)

+1.9% - Slower

245% above the BLS role benchmark for operations aggregate.

Posted salary is far from this role benchmark; treat it as low confidence.

Matched to SOC 11-1021 - Operations aggregate by role bucket.

Source: U.S. Bureau of Labor Statistics, OEWS, May 2024 and Employment Projections, 2024-2034.

Role

Role function

Operations From the posting source checked Jun 20, 2026

Seniority

Director Plus From the posting source checked Jun 20, 2026

Work mode

Hybrid From the posting source checked Jun 20, 2026

In-office days

2 days From the posting source checked Jun 20, 2026

Schedule

Shift type

Not verified

Weekend work

Not verified

Company

Equity

Offered From the posting source checked Jun 20, 2026

Application

Cover letter

Not verified

Assessment

Not verified

Deadline

Not stated

Where they hire

State eligibility is not yet verified.

About this role

Director, AI Enablement Remote - United States; San Francisco - Hybrid About the Director, AI Enablement at Headspace: Headspace is building an AI-first operating model grounded in member safety, privacy, and measurable business impact. As Director, AI Enablement, you will define and drive the strategy that helps Headspace adopt AI thoughtfully, responsibly, and at scale across the enterprise. This is a highly visible role, reporting to the COO/Founder, with the opportunity to shape how teams across Headspace evaluate, build, govern, and scale AI-powered workflows, tools, and operating practices. You will partner closely with executive leaders and senior stakeholders across Product, Engineering, Legal, Privacy, Security, Procurement, Care, and Go-to-Market to translate company priorities into an AI roadmap that delivers meaningful outcomes for our teams and the members we serve. 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. 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: - Define and lead Headspace's enterprise AI enablement strategy, roadmap, and operating model, aligning investments and priorities to

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