Chief of Staff

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 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