Chief of Staff, Handshake AI CBO

Handshake • Full-time • Hybrid in San Francisco, California, United States • $224,000 - $280,000 / year • 1m ago

Fast Facts

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.

Responsibilities: Oversee operational strategy, synthesize performance data, create executive narratives, and advocate for AI-driven workflows to scale business efforts.

Skills: Strong analytical skills, exceptional communication abilities, experience in project management, and a proactive mindset are essential.

Qualifications: 5+ years in a relevant analytical role, with a successful track record in cross-functional project driving and operations management preferred.

Location: This position is based in San Francisco, California, United States.

Compensation: $224000 - $280000 / Annually

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