Chief of Staff, CEO

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 worlds 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 one of the highest-leverage roles at Handshake - a seat at the center of our most consequential decisions as we our next phase of growth. Youll be the CEOs closest partner: driving operating cadence, leading strategic initiatives, and ensuring the company moves in sync across every function.

This is a pivotal moment at Handshake. Weve tripled ARR at scale, launched a new AI business, and are building fast in one of the most consequential markets in tech. The Chief of Staff to the CEO will be a key partner in shaping how we grow - bringing structure to ambiguity, alignment across teams, and leverage to every high-stakes decision the CEO faces.

• Drive the CEOs operating rhythm - from board prep and executive staff meetings to annual planning - so decisions get made and priorities stay clear across the company
• Lead high-stakes cross-functional initiatives (GTM alignment, org design, IPO readiness) from ambiguous idea to structured execution with clear owners and measurable outcomes
• Build the analytical foundation behind key decisions by interrogating complex datasets, modeling financials, and distilling insights into crisp, actionable recommendations for the CEO and board
• Produce world-class communications - board decks, investor memos, all-hands narratives - that represent the CEOs thinking with precision and reflect Handshakes strategy externally

You Have

• 8+ years in consulting, strategy & operations, investment banking, or a senior operating role at a technology company
• Experience inside scaled organizations (500+ employees), with exposure to the complexity of late-stage growth - board dynamics, cross-functional alignment, and high-stakes external relationships
• Exceptional analytical ability: you build the analytical foundation that shapes exec-level decisions, including financial models and business cases that influence board-level strategy (SQL a plus)
• Elite written communication skills - board-quality decks, executive memos, and all-hands messaging that dont need much editing
• High bias to action and low ego: you anticipate needs, act before being asked, and measure success entirely by the outcomes of the people you support
• Track record of influencing senior leaders and driving alignment across an executive team without direct authority, in fast-moving, ambiguous environments
• Track record of driving complex, cross-functional projects from ambiguity to execution in fast-moving environments

Bonus Points:

• Background in business operations, strategy & operations, or strategic finance - with experience moving from insight to execution across a fast-moving org
• Experience operating across company stages - from early-stage, high-growth environments to scaled organizations - and the ability to adapt your operating style accordingly
• Familiarity with marketplace businesses, multi-sided platforms, or AI/SaaS go-to-market motions

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.