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
Probook is at an inflection point, and the next phase of growth requires the founder to operate at a different level. This role exists to make that possible.
The Chief of Staff is the founder's primary execution partner. You own the founder's most important priorities at any given moment, and being a company with under 40 means those priorities are often gritty and unglamorous.
But to be clear, this is not an EA role. This is a role that we hope will slope into a functional leader within Probook.
Who You Are
An operator: You have built things, run processes, and delivered outputs under time pressure without a playbook. You are not learning how to execute. You already know.
A thought partner to the founder: You come to meetings with a point of view, not just a summary. You push back when something does not add up and bring context the founder does not have
A synthesizer: You take a messy conversation, a disorganized meeting, or a pile of functional updates and turn them into a clear picture of what matters and what needs to happen next.
CEO-grade output: Everything you produce could go directly to a board member, investor, or executive without editing. You do not submit drafts.
Low ego: You will do work that is below your capability because it needs to be done. That does not bother you.
Professional: You sit inside every sensitive conversation at this company. You treat that access with the seriousness it deserves.
What You Will Own
Board preparation: own the end-to-end process for every board meeting, including materials, data packages, and pre-read distribution on time, every time.
Action item tracking: capture decisions and commitments from the founder's key meetings, follow up with functional owners, and surface blockers before they stall progress.
Functional leader updates: filter, synthesize, and distill cross-functional status into what the founder actually needs to see.
Special projects: own high-priority, time-bound initiatives that do not have a clear functional home and cannot wait.
Operational systems: build and maintain the lightweight processes that create order around the founder's work without adding overhead.
Requirements
NYC Based: Excited to work in-office 5 days/week in our high-collaboration culture.
5+ years of professional experience
3 or more years in a high-output role: management consulting, investment banking, venture-backed startup operations, or a prior Chief of Staff or BizOps role.
Demonstrated track record of producing CEO or board-ready materials independently, including financial summaries, strategic memos, and executive presentations.
Experience managing cross-functional workstreams with multiple stakeholders and competing deadlines.
Strong written communication. Your first draft is clean, concise, and does not need to be rewritten.
Comfortable operating with incomplete information and making judgment calls without waiting to be told.
Why Join Probook?
The People: Becoming one of the most talent-dense start-ups in NYC (Waterloo, GT, Berkeley, UPenn, ICPC world finalist, IMO Gold Medalist, Ex-Tennr, Metta, Citadel, YC).
The Market: $700B industry with clear tailwinds. AI adoption, labor shortages, generational transitions. We are defining the category, not fighting for share.
The Traction: $XXM ARR in 18 months. Cash-flow positive. Product-market fit proven; now we are scaling.
The Seat: You will be inside every major decision this company makes. There are very few roles at any company where the work compounds this fast.
Compensation & Benefits
Equity: Meaningful equity.
Salary: $200K - $250K Base comp
Health: Comprehensive medical, dental, and vision
Perks: $1,000 Monthly stipend (food, gym, Uber, etc) and really good office snacks
Access: Direct access to world-class investors and advisors
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