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Handshake is a platform powering 25 million job seekers, 1 million+ employers, and 1,600 educational institutions. The company recently launched Handshake AI, which has grown to ~$1B run rate by partnering with frontier AI labs to create evaluations and benchmarks. You will serve as Chief of Staff to Jonathan Stull, the President & COO, who leads the Handshake Network (experiencing 200% new user acquisition growth and 70% WAU growth) and the Careers revenue lines including Learning, Recruiting, and International.
You will own the operating rhythm of the business: planning, staff meetings, operating reviews, and board preparation. You will produce first-draft analyses and strategic recommendations before being asked, develop an independent data-driven view of business performance, create high-impact communications (board materials, executive memos, partner narratives), and drive strategic projects with no natural owner through to completion. You will also identify and implement AI workflows that increase team velocity.
This role requires representing the President & COO in high-stakes meetings with judgment and discretion. You will work at an intense pace with frequent context switches and heavy reliance from your principal. Success requires 5+ years producing decision-ready work for senior leaders (strategy consulting, banking, investing, corp dev, or strategy & ops in direct service of C-level executives), rapid progression in high-bar environments, daily AI fluency, and strong writing skills requiring minimal editing. You should be analytically self-sufficient with financial modeling and SQL capabilities. Experience with marketplaces, board/financing milestones, or the AI data ecosystem is a bonus. The role has been a proven accelerator at Handshake, with previous holders advancing to VP and GM positions.
