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Handshake

Chief of Staff, Handshake AI CBO

📍 San Francisco, CA
🏢 General & Administrative
⏱️ FullTime
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About Handshake

Handshake is the career network for the AI economy. We connect over 20 million knowledge workers, 1,600 educational institutions, and 1 million employers (including 100% of the Fortune 50), powering career discovery, hiring, and upskilling from freelance AI training gigs to first internships to full-time careers and beyond. Our unified platform brings everything together: the network creates recruiting matches, recruiting generates rich career data, and that data powers AI systems—each part strengthening the others in a continuous cycle of value creation. In 2025, this unique position helped us triple ARR at scale as the AI economy accelerated.

Why join Handshake now:

  • Shape how every career evolves in the AI economy, at global scale, with impact your friends, family and peers can see and feel

  • Work hand-in-hand with world-class AI labs, Fortune 500 partners and the world’s top educational institutions

  • Join a team with leadership from Scale AI, Meta, xAI, Notion, Coinbase, and Palantir, among others

  • Build a massive, fast-growing business with billions in revenue

The Role

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. Handshake AI is one of the fastest-scaling businesses in the AI economy — and this role exists to ensure the CBO and the broader leadership team can operate with clarity, alignment, and speed as the business grows.

  • Own the rhythm of the Handshake AI business — standing up and running WBRs, planning cycles, and operating reviews that create visibility, surface risks early, and keep the CBO and leadership team free from surprises and fire drills

  • Drive cross-functional alignment across product, GTM, and operations by translating ambiguous priorities into structured workstreams with clear 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

You Have

  • 7+ years in consulting, strategy & operations, business operations, or a similarly analytical role at a tech or AI-focused company

  • A track record of building and running operating cadences — WBRs, planning cycles, cross-functional reviews — that bring alignment and accountability to fast-moving organizations

  • Experience creating alignment across senior stakeholders — you bring clarity to cross-functional priorities and know how to move a leadership team toward decisions

  • 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

  • Thrives in fast-moving, high-growth environments where priorities shift and structure is still being built

Bonus Points:

  • Experience with marketplaces, multi-sided platforms, or AI/ML products

  • Background in business operations or strategy & operations — with experience moving from insight to execution across a fast-moving org

We Offer

Handshake delivers benefits that help you feel supported – and thrive at work and in life.

The below benefits are for full-time US employees.

  • 🎯 Ownership: Equity in a fast-growing company

  • 💰 Financial Wellness: 401(k) match, competitive compensation, financial coaching

  • 🍼 Family Support: Paid parental leave, fertility benefits, parental coaching

  • 💝 Wellbeing: Medical, dental, and vision, mental health support, $500 wellness stipend

  • 📚 Growth: $2,000 learning stipend, ongoing development

  • 💻 Remote & Office: Internet, commuting, and free lunch/gym in our SF office

  • 🏝 Time Off: Flexible PTO, 15 holidays + 2 flex days

  • 🤝 Connection: Team outings & referral bonuses

Explore our mission, values, and comprehensive US benefits at joinhandshake.com/careers.