Chief of Staff, CEO

Handshake • San Francisco, CA

1d

About The Position

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 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. You'll be the CEO's 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. We've 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.

Requirements

• 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 don't 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

Nice To Haves

• 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

Responsibilities

• Drive the CEO's 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 CEO's thinking with precision and reflect Handshake's strategy externally

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed
• Number of Employees: 501-1,000 employees