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 Tailwinds: $700B industry with clear tailwinds: AI adoption, labor shortages, and generational transitions creating demand for operational modernization. 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're scaling.

• The Team: >30 people, our founding team comes from the space and has spent thousands of days onsite with our customers. We live the space. We're also becoming one of the most talent-dense start-ups in NYC (MIT, Harvard, UPenn M&T, Waterloo, Citadel, Palantir).

• 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

• Equity: Meaningful early-stage equity

• Salary: $120K – $145K

• Health: Comprehensive medical, dental, and vision

• Perks: $500 monthly Ramp card for commuting, meals, gym, etc. (plus $25 in nightly DoorDash credit) and really good office snacks

• Access: Direct access to world-class investors and advisors