Chief of Staff, President & COO

Handshake was founded on a simple belief that everyone deserves a path to a great career, regardless of where they went to school or who they know. Today, we power 25 million job seekers, 1 million+ employers, and 1,600 educational institutions.

In 2025, we started Handshake AI and built the fastest-growing AI data business in history. We work directly with frontier AI lab researchers to create evaluations, publish benchmarks, and push the boundary of data. We've grown from $0 to ~$1B run rate and pay ~$60M to over 30K individuals every month.

Why join Handshake now:

• Shape how every career evolves in the AI economy, at global scale, with impact your friends, family and peers can see and feel

• Partner hand-in-hand with world-class AI labs, Fortune 500 partners and the world's top educational institutions

• Work together with engineers, scientists, operators, and more from Palantir, Meta, Scale AI, and former YC founders

• Build a massive, fast-growing business with billions in revenue

You will be the execution partner to Jonathan Stull, Handshake's President & COO. He has built Handshake hand in hand with CEO Garrett Lord for the past decade, and he partners with Garrett and the board on strategy and execution across the company.

He directly leads the Handshake Network and its global growth, plus the Careers revenue lines: Learning, Recruiting, and International. The Handshake network is compounding fast (new user acquisition up 200%, WAU up 70%), and we're investing hard to accelerate that growth by opening new international markets and broadening the product suite to 10x our TAM, with two major acquisitions closed in the past two months.

Every major question about AI and work runs through this business, and you will sit inside every major decision and be expected to move it forward. This seat is a proven accelerator at Handshake: the people who have held roles like this have gone on to run functions as VPs and GMs. If you perform, your next role is a big one.

What you will own:

• The operating rhythm of the business: planning, staff meetings, operating reviews, and board prep. Decisions get made, owners get named, and threads never drop on your watch

• First drafts before anyone asks. When a problem gets flagged on Monday, you show up with a proposed answer, and the answer reflects what your principal actually thinks and where his focus is

• An independent, data-driven view of business performance. You interrogate the datasets, build the models, and say what the numbers show even when it is inconvenient

• Communications that impact the company and the market: board materials, exec memos, and partner-facing narratives with zero filler

• Strategic projects with no natural owner, carried end to end. Projects here hit resistance. You treat pushback as input to the next draft and keep moving

• AI leverage across the business. Finding and installing AI workflows that make the whole team faster is a recurring part of the job, and you should be doing it to your own work first

• Representing him in rooms he cannot be in, with judgment, discretion, and calm

This is not a 9 to 5 job. The pace is intense, context switches fast, and your principal will lean on you heavily.

• You have been the right hand to a demanding senior leader and carried work end to end yourself. You can walk us through the artifacts

• You are proactive to the point of impatience. You have never waited to be told what to do, and your former managers will say so. We will ask them

• You can sit in a messy hour of debate and produce the one page that captures what your principal thinks, what was decided, and what happens next

• You keep projects moving through pushback. Pausing at the first sign of resistance is the failure mode for this role

• You are analytically self-sufficient: financial models, large datasets, SQL or the ability to pick it up fast

• Your writing does not need editing

• Low ego, high trust. You earn influence through judgment, clarity, and follow-through

• 5+ years where producing decision-ready work for senior leaders was the job itself: strategy consulting, banking or investing, corp dev, or strategy & ops in direct service of a C-level executive

• Rapid progression in a high-bar environment that rewarded speed over process

• AI fluency: you use AI daily to create leverage in your own work (formal AI experience not required)

• Energized by Handshake's mission to expand access to opportunity in the AI economy

Bonus points:

• Experience with marketplaces or multi-sided platforms

• Exposure to board, financing, or public-market milestones

• Familiarity with the AI data, evaluation, or annotation ecosystem

Handshake delivers benefits that help you feel supported—and thrive at work and in life.

The below benefits are for full-time US employees.

🎯 Ownership: Equity in a fast-growing company

💰 Financial Wellness: 401(k) match, competitive compensation, financial coaching

🍼 Family Support: Paid parental leave, fertility benefits, parental coaching

💝 Wellbeing: Medical, dental, and vision, mental health support, $500 wellness stipend

📚 Growth: $2,000 learning stipend, ongoing development

💻 Remote & Office: Internet, commuting, and free lunch/gym in our SF office

🏝 Time Off: Flexible PTO, 15 holidays + 2 flex days

🤝 Connection: Team outings & referral bonuses

Explore our mission, values, and comprehensive US benefits at joinhandshake.com/careers.