Chief of Staff to the CEO

Probook Logo
Probook
Manhattan, NY, United States
130000 - 160000 USD / Year
  • Entertainment
  • FullTime
  • Applications have closed

We’re looking for a founding Chief of Staff who thrives at the intersection of strategy, finance, and execution. This is not a “shadow CEO” role or a note-taking function — it’s an operator seat. You’ll work directly with the CEO to set priorities, drive execution, and own high-leverage initiatives across the business.

With a strong foundation in finance, you’ll help shape our operating model, own critical analyses, and partner on decisions that define the trajectory of the company. This is a rare opportunity to see the full picture of company-building, from strategic planning and capital allocation to day-to-day operations, while sitting in the room where every key decision is made.

Why this role / why now

  • We’re in the earliest chapter of building Probook. Every decision now compounds, and this role sits at the center of those decisions.
  • Recruiting, customer acquisition, fundraising, and strategic finance will all run through you.
  • You’ll develop a 360° view of how a Sequoia-backed company scales from zero to one — the role is a launchpad into future leadership, venture, or founding.

What You’ll Do

  • Partner with the CEO to drive company priorities, ensuring decisions translate into execution.
  • Build and refine financial models that guide strategy, resourcing, and capital planning.
  • Lead special projects: new market entry, pricing strategies, board prep, strategic partnerships.
  • Serve as connective tissue across teams — from recruiting to product to go-to-market.
  • Pressure test decisions with data, structured thinking, and a bias for action.

What We’re Looking For

  • 3–6 years of experience overall

  • 1 -2 in investment banking, consulting, VC/PE

  • 2+ strategic finance at a top-tier startup.

  • Sharp operator instincts: you can drop into ambiguity, build structure, and move fast.

  • Strong finance toolkit: modeling, analysis, and decision support.

  • Hunger to build: you’re motivated by ownership, impact, and learning every part of the business.

  • High trust, low ego: thrives in a founder’s office environment.

Why join us

  • Partner directly with the CEO on the most important problems in the company.
  • Build the muscle to go on and lead, invest, or found.
  • Help scale one of NYC’s most talent-dense startups from the ground floor.

Comp

  • 130 – 160K + Equity
  • 1K monthly food and wellness stipend
  • Full Benefits (dental, health, vision)
  • Unlimited PTO
  • Office Perks: Hang board (for climbers), Office dog, snacks, coffee, espresso, team lunches and dinners.
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