Chief of Staff to the CTO - AI Strategy & Special Projects

About the role

Reporting directly to the CTO, you’ll lead hands-on AI special projects across Playlist and our portfolio (including Mindbody and ClassPass).

This role blends technical program leadership with a Chief of Staff-style operating cadence: you’ll bring clarity to ambiguous work, create momentum across teams, and translate AI capabilities into practical leverage for how we build, support, and scale our products.

Responsibilities

• Prototype and iterate on AI workflows and lightweight solutions using tools like Claude or Codex, focusing on adoption and impact
• Independently scope and execute on AI-driven projects, taking a hands-on role from initial idea through lightweight implementation and iteration, and stepping in to drive work forward
• Turn AI strategy into a clear, executable program with scoped initiatives, owners, milestones, and measurable outcomes
• Possess the ability to identify high-impact AI opportunities and move them from idea to delivery
• Partner across the company to establish and run the operating rhythm for AI work, including OKR support, program updates, and stakeholder communications
• Unblock progress by coordinating dependencies, clarifying tradeoffs, and keeping teams aligned on decisions
• Provide clear, decision-ready updates to the CTO and leadership partners on progress, outcomes, and next steps

Requirements

• 5+ years leading cross-functional technical programs, initiatives, or special AI projects with multiple stakeholders
• Strong ability to turn ambiguity into structured plans and drive consistent follow-through
• Clear, concise writing and communication skills, including executive-ready updates and effective meeting facilitation
• Hands-on comfort with modern AI tools and workflows, including LLMs such as Claude, to test, learn, and iterate
• High ownership mindset with a bias toward action and the ability to drive work forward without needing heavy direction
• Technical fluency that helps you collaborate credibly with engineering partners while staying focused on outcomes
• Sound judgment, balancing speed, quality, and responsible use when introducing AI into existing workflows
• Strong stakeholder management skills, including influencing without authority and navigating competing priorities
• Experience operating in fast-moving environments where priorities evolve, and progress depends on collaboration

Qualifications

• Competitive base salary range in the United States: $99,450 to $130,000
• Additional compensation may include a performance bonus, benefits, and/or other applicable incentive compensation plans

Benefits

The Company is committed to providing competitive wages and salaries that are motivational, fair, and equitable. Actual compensation packages are based on several factors unique to each candidate, including but not limited to skill set, depth of experience, certifications, and specific work location.

We are an Equal Opportunity Employer and highly value diversity at our company. We encourage people of all different backgrounds, experiences, abilities, and perspectives to apply.