Founding Executive Assistant

ABOUT PROBOOK

Probook is the AI Operating System 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
You’ll sit front row as the right hand to 3 founders building one of the fastest-growing startups in NYC, backed by two tier-1 VCs. This is a high-ownership, high-trust role built for someone exceptional at this craft.

You will support three senior executives across calendar management, communications, travel, cross-executive coordination, and operational reliability. You will be in the room for sensitive conversations, managing competing priorities in real time, and making judgment calls that keep three leaders moving at the pace this business demands.

WHO YOU ARE

• You have supported multiple senior executives at the same time and have specific stories to prove it.
• Nothing falls through the cracks on your watch.
• You see two steps ahead, already preparing for what hasn’t been asked yet.
• You write clearly and professionally, and you calibrate quickly.
• You are discreet. You handle sensitive information with maturity and zero leakage.
• You are not here on the way to something else. You are here because you are good at this and you want to master it.

WHAT YOU WILL OWN

• Executive time protection: Own founders’ calendars completely. Filter and triage requests, deliver meeting prep 24 hours in advance, and surface conflicts before they happen.
• Communications: Manage all inboxes. Triage, draft, route, and follow up. Priority items get a same-day response. Nothing drops.
• Travel and logistics: Own all travel end-to-end; flights, hotels, ground transport, itineraries, contingencies. Fix disruptions before the exec finds out. Process expenses within 5 business days.
• Cross-executive coordination: Keep Founders aligned on shared commitments. Own board meetings, all-hands, and investor events end-to-end. Route information between the three that would otherwise get lost.
• Office and operational reliability: Own vendors, office systems, and recurring workflows. Run team events, off-sites, and exec-level onboarding logistics.

REQUIREMENTS

• NYC-based. In-office 5 days/week. This is not negotiable.
• 2-5 years of experience in a related role.
• Start-up experience is a great plus, but not required.
• Demonstrated experience supporting more than one senior executive simultaneously.
• Exceptional written communication — you will represent three executives in written form.
• Comfortable with fast-moving, high-standard personalities. Probook moves fast, and the founders are demanding. This is expected, not exceptional.
• Track record of taking ownership and delivering without being micromanaged.
• Startup experience strongly preferred. Not required if the candidate shows exceptional judgment and pace.

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. Product-market fit proven; now we’re scaling.
• Funding: $40M raised from Sequoia and Andreessen Horowitz
• The Team: >60 people, our founding team comes from the space and has spent thousands of days onsite with our customers. We live in the space. We’re also becoming one of the most talent-dense start-ups in NYC (MIT, Harvard, UPenn M&T, Waterloo, Citadel, Palantir).

COMPENSATION & BENEFITS

• Salary: $100,000 - $125,000 (can flex for the right candidate) + Equity
• Health: Comprehensive medical, dental, and vision
• Perks: $500 monthly stipend (food, gym, Uber, etc.)
• Access: Direct daily exposure to world-class founders and investors.