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.
Top Skills
What We Do
Increase flip rates, boost ticket sizes, and reduce windshield time— all without scaling your dispatch department.
Probook learns from your historical sales data and sends your technicians to the right calls every time.
Our dispatcher-friendly interface overlays your dispatch board so you never have to leave ServiceTitan.
Dispatchers can now focus on higher-value tasks like verifying job info and keeping customers updated.
See why top operators nationwide trust Probook!
