Chief of Staff, CEO

Handshake was founded on a simple belief that everyone deserves a path to a great career, regardless of where they went to school or who they know. Today, we power 25 million job seekers, 1 million+ employers, and 1,600 educational institutions.

In 2025, we started Handshake AI and built the fastest-growing AI data business in history. We work directly with frontier AI lab researchers to create evaluations, publish benchmarks, and push the boundary of data. We’ve grown from $0 to ~$1B run rate and pay ~$60M to over 30K individuals every month.

Human data is the core infrastructure to AI advancement. Frontier AI labs currently improve model capabilities with various data-intensive post-training techniques. We believe that data spend for AI training will increase by 3-5x in the next few years and continue for much longer as models take on new domains. Handshake AI supports all of the frontier AI labs, working on their most complex data at the largest scale.

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.

• 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

• 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

• 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