Chief of Staff, Handshake AI CBO Job at Handshake (San Francisco)

Job Description

We’re looking for a Chief of Staff, Handshake AI to be a senior operational and strategic partner to Handshake AI’s Chief Business Officer, with a primary focus on building and scaling the Handshake AI business. You’ll sit close to decision-making across product, GTM, and operations, turning strategy into execution, keeping priorities sharp, and making sure AI is used to its full potential across the platform.

Job Responsibility

Drive the operating cadence for Handshake AI – owning staff meetings, planning cycles, and operating reviews to keep priorities clear and execution on track
Translate ambiguous questions into structured projects, turning open-ended problems (e.g., adoption, positioning, or churn drivers) into clear workstreams with owners, milestones, and measurable outcomes
Synthesize data across product, GTM, and finance to surface insights on Handshake AI performance and recommend actions that improve growth, efficiency, and customer impact
Create executive-ready narratives (decks, memos, briefings) that align leaders, customers, and partners around Handshake AI’s strategy, roadmap, and results
Champion AI-powered ways of working inside the business, piloting and scaling tools and workflows that materially increase speed, quality, and leverage for the broader team

Requirements

5+ years in consulting, strategy & operations, product management, business operations, or a similarly analytical role at a tech or AI-focused company
A track record of driving cross-functional projects from idea to impact—especially in fast-paced, ambiguous environments
Strong analytical skills
comfortable working with data and financial models, and using them to inform decisions and tradeoffs
Exceptional written and verbal communication
you can distill complexity into clear narratives tailored for executives and cross-functional partners
High bias to action and “own the outcome” mindset—you anticipate needs, move quickly, and follow through without heavy oversight
Comfort operating at olympic pace, with frequent context switching and evolving priorities
Low ego, high trust—you build credibility through judgment, clarity, reliability, and discretion rather than formal authority

Nice to have

Experience with marketplaces or multi-sided platforms
Experience working on AI, ML, or data products (or partnering closely with those teams)
Prior experience in a Chief of Staff, Strategic Projects, or BizOps role supporting senior executives

What we offer

Equity in a fast-growing company
401(k) match, competitive compensation, financial coaching
Paid parental leave, fertility benefits, parental coaching
Medical, dental, and vision, mental health support, $500 wellness stipend
$2,000 learning stipend, ongoing development
Internet, commuting, and free lunch/gym in our SF office
Flexible PTO, 15 holidays + 2 flex days
Team outings & referral bonuses

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Chief of Staff, Handshake AI CBO

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