We’re hiring a founding Chief of Staff who will operate as an extension of the CEO’s mind.
This is not a calendar-and-decks support role - you’ll sit at the center of how we decide, execute, and scale at Probook.
Probook is an arbitrage opportunity with Series B/C growth and PMF but still under 30 people.
We have no GTM team, just pure founder-led growth through word of mouth and customer obsession. We are not not guessing here, we are building with clear demand and without the fear of “pivot hell” most startups go through.
Run the company with the CEO
Partner to define priorities, turn decisions into crisp plans, and keep the company pointed at the highest-leverage problems
Create the operating cadence: weekly reviews, goal tracking, metrics, and rituals that keep everyone aligned and accountable
Own strategic finance and decision support
Build and refine financial and operating models that guide strategy, resourcing, and capital planning
Translate numbers into clear tradeoffs, scenarios, and recommendations
Lead high-leverage, zero-to-one projects
Drive special projects: new market entry, pricing strategy, strategic partnerships, board preparation
Stand up new systems and processes from scratch, then hand them off cleanly once they work
Be the connective layer across teams
Ensure recruiting, product, GTM, and operations are working from the same priorities and truth
Connect customer learnings, product roadmaps, and GTM execution so we move as one unit
Pressure-test decisions
Use structured reasoning, data, and a bias toward action to challenge assumptions and sharpen decisions
Identify blind spots, surface risks, and propose solutions before problems crystallize
Raise the bar on execution
Catch what falls between the cracks and close loops relentlessly
Build simple, sharp systems so the company can move faster with more precision
3–6 years of experience that shows analytical rigor and real operating judgment
1–2 years in investment banking, consulting, or VC/PE
2+ years in operating roles at a top-tier startup
Salary: $160,000 - $200,000 + meaningful equity
Stipend: $1K monthly food and wellness stipend
Benefits: Full medical, dental, and vision
Time off: Unlimited PTO (impact over hours logged)
Office & culture perks:
In‑office culture in NYC
Hang board, office dog, great snacks, coffee, espresso
Team lunches and dinners with people you’ll actually want to spend time with
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!
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