Chief of Staff, Handshake AI CBO

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. 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.