AI Strategy & Special Projects

The Role You'll Play

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.

This is not a purely strategic role. You’ll be expected to get hands-on with AI tools like Claude and Codex to prototype, test, and iterate on real workflows. We’re looking for someone who doesn’t just shape AI strategy, but actively builds, turning ideas into lightweight, impactful solutions that drive real outcomes.

You Will: 

• 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 
• Partner across the company to identify high-impact AI opportunities and move them from idea to delivery  
• 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 
• Support responsible AI delivery by aligning on pragmatic guardrails and risk considerations appropriate to each use case  
• Provide clear, decision-ready updates to the CTO and leadership partners on progress, outcomes, and next steps

You’ll thrive in this role with experience in:  

• 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 

It is the Company's intent to pay all Team Members competitive wages and salaries that are motivational, fair and equitable. The goal of Company's compensation program is to be transparent, attract potential employees, meet the needs of all current employees, and encourage Team Members to stay with our organization. Actual compensation packages are based on several factors that are unique to each candidate, including but not limited to skill set, depth of experience, certifications, and specific work location.