Chief of Staff, President & COO
Handshake was founded on the 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 launched Handshake AI and built the fastest-growing AI data business in history, working directly with frontier AI lab researchers to create evaluations, publish benchmarks, and push the boundary of data. We've grown from $0 to a ~$1B run rate and pay ~$60M to over 30K individuals every month.
About the Role
You will be the execution partner to Jonathan Stull, Handshake's President & COO. He has built Handshake alongside CEO Garrett Lord for the past decade and 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 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, moving it forward. This role is a proven accelerator at Handshake: previous holders have gone on to run functions as VPs and GMs. If you perform, your next role is a big one.
Responsibilities
- Own the operating rhythm of the business: planning, staff meetings, operating reviews, and board prep. Ensure decisions are made, owners are named, and threads never drop.
- Deliver first drafts before anyone asks. When a problem is flagged, you show up with a proposed answer that reflects your principal’s thinking and priorities.
- Maintain an independent, data-driven view of business performance. Interrogate datasets, build models, and communicate insights—even when inconvenient.
- Craft high-impact communications: board materials, exec memos, and partner-facing narratives with zero filler.
- Drive strategic projects with no natural owner, end to end. Treat pushback as input and keep moving.
- Leverage AI across the business. Identify and implement AI workflows to accelerate the team, starting with your own work.
- Represent your principal in rooms they cannot attend, with judgment, discretion, and calm.
Requirements
- 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 demonstrate this through artifacts from past roles.
- Proactive to the point of impatience. You never wait to be told what to do, and your former managers will confirm this.
- Able to distill messy debates into a one-page summary capturing decisions, next steps, and your principal’s perspective.
- Keep projects moving through pushback. Pausing at resistance is the failure mode for this role.
- Analytically self-sufficient: build financial models, work with large datasets, and use SQL (or learn it fast).
- Your writing requires minimal editing.
- Low ego, high trust. You earn influence through judgment, clarity, and follow-through.
Qualifications
- 5+ years producing decision-ready work for senior leaders: strategy consulting, banking, 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 work (formal AI experience not required).
- Energized by Handshake’s mission to expand access to opportunity in the AI economy.
Nice to Have
- Experience with marketplaces or multi-sided platforms.
- Exposure to board, financing, or public-market milestones.
- Familiarity with the AI data, evaluation, or annotation ecosystem.
Benefits
- 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 coverage; mental health support; $500 wellness stipend.
- Growth: $2,000 learning stipend, ongoing development opportunities.
- Remote & Office: Internet stipend, commuting benefits, free lunch and gym in the SF office.
- Time Off: Flexible PTO, 15 holidays + 2 flex days.
- Connection: Team outings and referral bonuses.
Pay
Compensation range: $224,000 – $280,000.