Chief of Staff, CEO

Role Overview

Chief of Staff to the CEO at Handshake — the CEO’s closest execution partner. You translate the CEO’s priorities into structured action, run the operating rhythm of a fast-growing company, and take ownership of key systems-building and follow-through across multiple business lines (network, recruiting platform, and AI data work).

Responsibilities

• Run operating cadence: board prep, executive staff, planning, and KPI reviews to keep the company aligned
• Lead high-stakes cross-functional initiatives: GTM alignment, org design, M&A, and AI adoption (from idea to executed outcome with clear owners)
• Build analytical foundations for decisions: interrogate data, model scenarios, and deliver crisp recommendations to the CEO and board
• Produce executive communications: board decks, investor memos, and all-hands narratives that reflect the CEO’s thinking precisely
• Act as an end-to-end owner for whatever needs to move in a founder-led environment

Requirements

• 5+ years of standout performance with rapid progression in a high-bar environment (e.g., top consulting, investing, or high-growth operations)
• Proven experience as a right-hand person to a senior leader, owning initiatives end to end
• Exceptional drive and ability to move fast and execute without needing to be managed
• AI fluency and enthusiasm; actively uses AI for leverage (formal AI experience not required)
• Intellectual humility and coachability; learns quickly and takes feedback directly
• Calm under pressure; highly collaborative and trust-building
• Strong analytical and written communication skills (data/models + executive-ready decks/memos)
• Motivation aligned with Handshake’s mission to expand access to opportunity in the AI economy

Bonus Points

• Experience across company stages (early to scaled)
• Familiarity with marketplaces / multi-sided platforms or AI/SaaS GTM