Chief of Staff
$180k - $220k USD
Who We Are
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.
The Role
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.
Who You Are
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.
What You Will Own
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
Requirements
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
Why Join Probook
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.
Compensation & Benefits
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