Chief of Staff, CEO

Handshake•San Francisco, CA

About The Position

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