Founders Associate
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
Our CEO is running many critical functions of this company simultaneously. This role exists to make sure his time reflects his priorities and that nothing falls through the cracks while he's moving fast.
You will own his calendar, inbox, and logistics end-to-end. You will operate with full context on what matters most, exercise independent judgment, and keep things moving without being asked twice. Every major decision and conversation at Probook runs through the person you support — you will have a front-row seat to all of it.
Who You Are
Ahead of the ask. Briefings are ready before meetings. Logistics are confirmed before they're requested. You don't wait to be told.
A calendar operator. You sequence meetings with intent, protect focused work time, and resolve conflicts before they surface.
Professional under pressure. You handle sensitive information and high-stakes relationships with consistent judgment — even when things move fast.
Available. Weekend pings, last-minute changes, and urgent requests are part of the job. You handle them without friction.
Fast and reliable. You are never a bottleneck.
What You Will Own
Full ownership of the founder's calendar: scheduling, sequencing, conflict resolution, and focus time protection
Inbox management: triage, draft responses, and flag what requires direct attention
Travel logistics: flights, hotels, ground transport, and itineraries built around the founder's schedule and working style
Meeting preparation: briefing documents, context summaries, and next-step tracking
Expense management: accurate and timely
Ad hoc personal and professional logistics, handled with discretion
Requirements
NYC-based; 5 days/week in-office + available on weekends as needed
3+ years supporting a founder or C-suite executive at a high-growth startup, VC-backed company, or investment firm
Proven track record managing a complex, high-volume calendar with frequent last-minute changes
Available outside standard hours; willing to travel with or on behalf of the founder as needed
Strong written communication — you can draft correspondence that doesn't need to be rewritten
Fluent in Google Workspace and modern scheduling and productivity tools
Why Join Probook
The People: Becoming one of the most talent-dense start-ups 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, and generational transitions. We are defining the category, not fighting for share.
The Traction: $XXM ARR in 18 months. Cash-flow positive. PMF proven; now we are scaling.
The Access: You will have full context on every major decision at the company. For the right person, this is an unmatched window into what it takes to build and scale a venture-backed startup.
Compensation & Benefits
Salary: $120K – $145K
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
Average salary estimate
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