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Chief of Staff, Handshake AI

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Location:
United States , San Francisco

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Category:
IT - Administration

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Contract Type:
Not provided

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Salary:

224000.00 - 280000.00 USD / Year
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Job Description:

Join Handshake as the Chief of Staff for Handshake AI, where you'll drive strategic operations and enhance business growth in the AI career network, engaging closely with top executives and partners. 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:

  • Oversee operational strategy
  • Synthesize performance data
  • Create executive narratives
  • Advocate for AI-driven workflows to scale business efforts
  • Drive the operating cadence for Handshake AI
  • Translate ambiguous questions into structured projects
  • Synthesize data across product, GTM, and finance to surface insights on Handshake AI performance and recommend actions
  • Create executive-ready narratives (decks, memos, briefings)
  • Champion AI-powered ways of working inside the business

Requirements:

  • 5+ years in a relevant analytical role
  • Strong analytical skills
  • Exceptional communication abilities
  • Experience in project management
  • A proactive mindset
  • A track record of driving cross-functional projects from idea to impact—especially in fast-paced, ambiguous environments
  • Comfortable working with data and financial models, and using them to inform decisions and tradeoffs
  • Exceptional written and verbal communication
  • High bias to action and “own the outcome” mindset
  • Comfort operating at olympic pace, with frequent context switching and evolving priorities
  • Low ego, high trust

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

Additional Information:

Job Posted:
January 16, 2026

Employment Type:
Fulltime
Work Type:
Hybrid work
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