Chief of Staff

Probook is the AI dispatcher for the home services industry, transforming how plumbing, HVAC, and electrical businesses operate.

Our impact is real. Dispatching the right technician to the right job can mean the difference between a $300 band-aid fix and a $20,000 system replacement. By automating previously high-touch workflows around the clock, Probook ensures a consistent customer experience without the need for 24/7 live staffing. We unify our customers' processes into a single, scalable platform, giving businesses one place to run their entire dispatch operation.

This is a role for someone who wants to build — and is willing to do whatever it takes to make that happen.

You are the founder's right hand. Your job is to clear the path — executing on his highest priorities so his time is spent only on what he uniquely can do. That means owning the unglamorous work without being asked, and the high-leverage work without needing direction. At under 40 people, both show up every day.

An operator. You have built things, run processes, and delivered outputs under pressure without a playbook. You are not learning how to execute — you already know.

A thought partner. You come to meetings with a point of view. You push back when something doesn't add up and bring context the founder doesn't have.

A synthesizer. You turn messy conversations and disorganized inputs into a clear picture of what matters and what happens next.

CEO-grade output. Everything you produce could go directly to a board member or customer without editing.

Low ego. You will do work that is below your capability because it needs to be done. That doesn't bother you.

• High-priority special projects across every function — you own them start to finish

• Decision and action tracking: capture commitments from key meetings, follow up with owners, surface blockers early

• Board prep: materials, data packages, and pre-reads delivered on time, every time

• Company culture: all hands to team rituals to everything in between

• Lightweight operational systems that create order without adding overhead

  
  

• 5+ years of experience, with at least 3 in a high-output role: management consulting, investment banking, startup operations, or a prior CoS / BizOps seat

• NYC-based; 5 days/week in-office

• Proven track record producing board- and CEO-ready materials independently

• Strong written communication — your first draft doesn't need to be rewritten

• Comfortable making judgment calls with incomplete information

The People: One of the most talent-dense startups in NYC (MIT, Harvard, UPenn, Waterloo, ICPC world finalists, IMO Gold Medalists, Ex-Meta, Citadel, YC).

The Market: $700B industry with clear tailwinds — AI adoption, labor shortages, generational transitions. We're defining the category.

The Traction: $XXM ARR in 18 months. Cash-flow positive. PMF proven; now scaling.

The Front Seat: Full context on every major decision at the company. Few roles anywhere compound this fast.

Salary: $180K - $220K

Equity: Meaningful early-stage equity

Health: Comprehensive medical, dental, and vision

Perks: $1,000/month stipend (food, gym, Uber) + really good office snacks

Access: Direct exposure to world-class investors and advisors