Chief of Staff, President & COO

Handshake•San Francisco, CA

2d•$224,000 - $280,000•Hybrid

About The Position

Handshake is a platform that connects job seekers with employers and educational institutions, aiming to provide a path to great careers for everyone. In 2025, Handshake launched Handshake AI, which has rapidly become a significant player in the AI data business, working with frontier AI labs to create evaluations and benchmarks. The company has experienced substantial growth, reaching approximately $1 billion in run rate and paying out around $60 million monthly to over 30,000 individuals. Joining Handshake now offers the opportunity to shape the evolution of careers in the AI economy, collaborate with leading AI labs and Fortune 500 companies, work alongside experienced professionals from top tech companies, and build a rapidly growing business with billions in revenue.

Requirements

Proven experience as the right-hand to a demanding senior leader, with a track record of carrying work end-to-end.
Proactive approach; never waiting to be told what to do.
Ability to distill complex discussions into concise summaries of decisions and next steps.
Capacity to drive projects forward through pushback and resistance.
Analytical self-sufficiency, including financial modeling, working with large datasets, and SQL proficiency or the ability to acquire it quickly.
Exceptional writing skills with minimal need for editing.
Low ego and high trust, earning influence through judgment, clarity, and follow-through.
5+ years of experience in roles such as strategy consulting, banking, investing, corporate development, or strategy & operations directly supporting a C-level executive.
Demonstrated rapid progression in a high-bar environment that values speed.
AI fluency, using AI daily to create leverage in personal work.
Enthusiasm for Handshake's mission to expand access to opportunity in the AI economy.

Nice To Haves

Experience with marketplaces or multi-sided platforms.
Exposure to board, financing, or public-market milestones.
Familiarity with the AI data, evaluation, or annotation ecosystem.

Responsibilities

Serve as the execution partner to Handshake's President & COO, supporting strategy and execution across the company.
Manage the operating rhythm of the business, including planning, staff meetings, operating reviews, and board preparation.
Proactively develop proposed solutions to business problems, reflecting the principal's perspective and focus.
Provide an independent, data-driven view of business performance by analyzing datasets and building models.
Create impactful communications for the company and the market, including board materials, executive memos, and partner-facing narratives.
Lead strategic projects that lack a natural owner, driving them to completion despite resistance.
Identify and implement AI workflows to increase team efficiency and apply this to personal work first.
Represent the President & COO in meetings with judgment, discretion, and calm.