Chief of Staff, CEO

About this role

ABOUT HANDSHAKE

Handshake is the career network for the AI economy. 20 million knowledge workers, 1,600 educational institutions, 1 million employers (including 100% of the Fortune 50), and every foundational AI lab trust Handshake to power career discovery, hiring, and upskilling, from freelance AI training gigs to first internships to full-time careers and beyond. This unique value is leading to unparalleled growth; in 2025, we tripled our ARR at scale.

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

The Chief of Staff to the CEO is Garrett Lord's closest execution partner — the person who helps him get things done at extraordinary speed across Handshake's mutually reinforcing business lines: our network, recruiting platform, and AI data work. You'll turn his priorities into structured action, run the operating rhythm that keeps a fast-growing organization aligned, and pick up whatever needs to move — owning the systems-building and follow-through that a founder-led company needs but doesn't run on its own. It's a high-trust, high-leverage seat and a proven springboard into senior operating roles at Handshake.

- Run the operating cadence — board prep, executive staff, planning, and KPI reviews — so decisions get made and priorities stay clear across the company

- Drive high-stakes cross-functional initiatives, from GTM alignment and org design to M&A and AI adoption, from idea to executed outcome with clear owners

- Build the analytical foundation behind key decisions by interrogating data, modeling scenarios, and distilling crisp, actionable recommendations for the CEO and board

- Produce world-class communications — board decks, investor memos, and all-hands narratives — that represent the CEO's thinking with precision

YOU HAVE

- 5+ years of standout performance and rapid progression in a high-bar environment — top-tier consulting, investing (PE/VC/IB), or high-growth operating

- Has been the right-hand person to a senior leader and personally owned initiatives end to end — not just supported a team

- Exceptional horsepower and work ethic — you move fast, outwork the problem, and get things done without being asked

- AI fluency and enthusiasm — you actively use AI to create leverage in your work and are excited about where it's headed (formal AI experience not required)

- Intellectual humility and coachability — you learn fast, update your views, and take direct feedback in stride

- Calm under pressure and highly collaborative — you build trust fast and work well with everyone amid chaos

- Sharp analytical and written communication — fluent with data and models; decks and memos that don't need editing

- Energized by Handshake's mission to expand access to opportunity in the AI economy

Bonus points:

- Experience across company stages, from early-stage to scaled

- Familiarity with marketplaces, multi-sided platforms, or AI/SaaS go-to-market

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 http://joinhandshake.com/careers.