Founding Executive Assistant

Probook•New York, NY

27d•$100,000 - $125,000•Onsite

About The Position

Probook is seeking an exceptional Executive Assistant to serve as the right hand to its three founders. This is a high-ownership, high-trust role within one of NYC's fastest-growing startups, backed by tier-1 VCs. The Executive Assistant will support senior executives across calendar management, communications, travel, cross-executive coordination, and operational reliability. This role involves being privy to sensitive conversations, managing competing priorities in real time, and making critical judgment calls to ensure the business operates at its demanded pace.

Requirements

NYC-based and required to be in-office 5 days/week.
2-5 years of experience in a related role.
Demonstrated experience supporting more than one senior executive simultaneously.
Exceptional written communication skills, capable of representing three executives in written form.
Comfortable with fast-moving, high-standard personalities; Probook moves fast, and the founders are demanding.
Track record of taking ownership and delivering without being micromanaged.
Startup experience strongly preferred, but not required if the candidate shows exceptional judgment and pace.

Nice To Haves

Startup experience is a great plus.

Responsibilities

Own founders’ calendars completely, filtering and triaging requests, delivering meeting prep 24 hours in advance, and surfacing conflicts before they happen.
Manage all inboxes, triaging, drafting, routing, and following up on communications, ensuring priority items receive a same-day response.
Own all travel end-to-end, including flights, hotels, ground transport, itineraries, and contingencies, resolving disruptions before the executive is aware.
Process expenses within 5 business days.
Keep Founders aligned on shared commitments, owning board meetings, all-hands, and investor events end-to-end.
Route information between the three founders that would otherwise get lost.
Own vendors, office systems, and recurring workflows.
Run team events, off-sites, and execute exec-level onboarding logistics.