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Handshake Logo Handshake · IT - Administration

Chief of Staff, Handshake AI CBO

United States, San Francisco 224000.00 - 280000.00 USD / Year · Job Posted February 20, 2026
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Job Description

We’re looking for a Chief of Staff, Handshake AI to be a senior operational and strategic partner to Handshake AI’s Chief Business Officer, with a primary focus on building and scaling the Handshake AI business. You’ll sit close to decision-making across product, GTM, and operations, turning strategy into execution, keeping priorities sharp, and making sure AI is used to its full potential across the platform.

Job Responsibility

  • Drive the operating cadence for Handshake AI – owning staff meetings, planning cycles, and operating reviews to keep priorities clear and execution on track
  • Translate ambiguous questions into structured projects, turning open-ended problems (e.g., adoption, positioning, or churn drivers) into clear workstreams with owners, milestones, and measurable outcomes
  • Synthesize data across product, GTM, and finance to surface insights on Handshake AI performance and recommend actions that improve growth, efficiency, and customer impact
  • Create executive-ready narratives (decks, memos, briefings) that align leaders, customers, and partners around Handshake AI’s strategy, roadmap, and results
  • Champion AI-powered ways of working inside the business, piloting and scaling tools and workflows that materially increase speed, quality, and leverage for the broader team

Requirements

  • 5+ years in consulting, strategy & operations, product management, business operations, or a similarly analytical role at a tech or AI-focused company
  • A track record of driving cross-functional projects from idea to impact—especially in fast-paced, ambiguous environments
  • Strong analytical skills
  • comfortable working with data and financial models, and using them to inform decisions and tradeoffs
  • Exceptional written and verbal communication
  • you can distill complexity into clear narratives tailored for executives and cross-functional partners
  • High bias to action and “own the outcome” mindset—you anticipate needs, move quickly, and follow through without heavy oversight
  • Comfort operating at olympic pace, with frequent context switching and evolving priorities
  • Low ego, high trust—you build credibility through judgment, clarity, reliability, and discretion rather than formal authority

Nice to have

  • Experience with marketplaces or multi-sided platforms
  • Experience working on AI, ML, or data products (or partnering closely with those teams)
  • Prior experience in a Chief of Staff, Strategic Projects, or BizOps role supporting senior executives

What we offer

  • Equity in a fast-growing company
  • 401(k) match, competitive compensation, financial coaching
  • Paid parental leave, fertility benefits, parental coaching
  • Medical, dental, and vision, mental health support, $500 wellness stipend
  • $2,000 learning stipend, ongoing development
  • Internet, commuting, and free lunch/gym in our SF office
  • Flexible PTO, 15 holidays + 2 flex days
  • Team outings & referral bonuses
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