Chief of Staff, President & COO

Handshake•San Francisco, CA

12d

About The Position

We are looking for a Chief of Staff to serve as a force multiplier to the President / COO. This role is designed as a high-growth platform that prepares exceptional operators for future leadership opportunities within Handshake. As Chief of Staff, you will sit at the center of decision-making, execution, and analytical insight for one of the company’s most complex and impactful marketplace businesses. You will help shape strategy, improve operating cadence, drive cross-functional alignment, and ensure the President / COO shows up with the highest possible leverage in every room. This is a rare opportunity to operate at the intersection of marketplaces, analytics, AI, and GTM, working closely with leaders across Product, Sales, Marketing, EDU Partnerships, Finance, and Handshake AI. The pace is fast, expectations are high, and the opportunity to grow is substantial.

Requirements

5+ years in consulting, strategy & operations, product management, business operations, or a similarly analytical role at a tech company
Exceptional analytical ability; comfortable working with large datasets and financial models (SQL a plus)
Elite written and verbal communication skills; able to create clarity and narrative from complexity
High bias to action; anticipates needs and operates proactively
Thrives in fast-paced, high-expectation environments with frequent context switching
Low ego, high trust - earns influence through judgment, clarity, and follow-through

Nice To Haves

Strong commercial instincts; experience with marketplaces or multi-sided platforms is a plus

Responsibilities

Run the rhythm of the business—planning, staff meetings, operating reviews, and follow-through.
Surface decisions, clarify priorities, and ensure the organization moves in sync.
Attend many exec-level discussions; represent Jonathan where needed with calm, maturity, and judgment.
Develop an independent, data-driven view of business performance and trends.
Interrogate complex datasets, build models, analyze financials, and distill insights into actionable recommendations.
Produce crisp, narrative-driven materials for executives, partners, and occasionally external audiences.
Lead strategic projects—GTM alignment, AI leverage, marketplace strategy, operational improvement, forecasting frameworks, etc.
Bring clarity to ambiguous questions and proactively identify opportunities to elevate execution.
Support Jonathan’s preparation for high-stakes internal and external moments.
Translate thinking, meetings, and strategy into world-class written communication—presentations, memos, speeches, and narratives.
Champion the adoption of AI tools and workflows that materially increase speed and quality across the business.
Build trust across teams; become a reliable sounding board for leaders who need support or clarity.
Maintain impeccable discretion, judgment, and emotional intelligence.
Be available when needed—including occasional evenings—as part of supporting a high-velocity operating environment.