Chief of Staff, CEO

The Chief of Staff to the CEO is Garrett Lord's closest execution partner — the person who helps him get things done at extraordinary speed across Handshake's mutually reinforcing business lines: our network, recruiting platform, and AI data work. You'll turn his priorities into structured action, run the operating rhythm that keeps a fast-growing organization aligned, and pick up whatever needs to move — owning the systems-building and follow-through that a founder-led company needs but doesn't run on its own. It's a high-trust, high-leverage seat and a proven springboard into senior operating roles at Handshake.

Responsibilities

Run the operating cadence — board prep, executive staff, planning, and KPI reviews — so decisions get made and priorities stay clear across the company; Drive high-stakes cross-functional initiatives, from GTM alignment and org design to M&A and AI adoption, from idea to executed outcome with clear owners; Build the analytical foundation behind key decisions by interrogating data, modeling scenarios, and distilling crisp, actionable recommendations for the CEO and board; Produce world-class communications — board decks, investor memos, and all-hands narratives — that represent the CEO's thinking with precision

Requirements

5+ years of standout performance and rapid progression in a high-bar environment — top-tier consulting, investing (PE/VC/IB), or high-growth operating; Has been the right-hand person to a senior leader and personally owned initiatives end to end — not just supported a team; Exceptional horsepower and work ethic — you move fast, outwork the problem, and get things done without being asked; AI fluency and enthusiasm — you actively use AI to create leverage in your work and are excited about where it's headed (formal AI experience not required); Intellectual humility and coachability — you learn fast, update your views, and take direct feedback in stride; Calm under pressure and highly collaborative — you build trust fast and work well with everyone amid chaos; Sharp analytical and written communication — fluent with data and models; decks and memos that don't need editing; Energized by Handshake's mission to expand access to opportunity in the AI economy

Nice to have

Experience across company stages, from early-stage to scaled; Familiarity with marketplaces, multi-sided platforms, or AI/SaaS go-to-market

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, 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