Chief of Staff, Handshake AI CBO

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. 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.

• 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.

You Have

• 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.

Bonus points

• 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.

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.