Founding Executive Assistant

About Probook

Probook is an AI-driven operating system built for the home services sector, helping plumbing, HVAC, and electrical companies run more efficiently.

The business addresses a real operational gap: assigning the right technician to the right job can be the difference between a modest repair and a major replacement project. By automating high-touch processes around the clock, Probook helps deliver a reliable customer experience without requiring live 24/7 staffing. Its platform brings a customer’s workflows into one scalable system so dispatch teams can manage everything in one place.

The Role

This position places you as the primary support partner to three founders at one of New York City’s fastest-growing startups, backed by two top-tier venture capital firms. It is a role with a high degree of trust and ownership, suited to someone who is exceptionally strong in executive support.

You will assist three senior leaders across scheduling, communication, travel, coordination between executives, and day-to-day operational reliability. You’ll be present for confidential discussions, manage shifting priorities in real time, and make sound decisions that help all three executives keep pace with the business.

What You’ll Own

• Protecting executive time by fully managing the founders’ calendars, filtering and prioritizing requests, preparing meeting materials 24 hours ahead of time, and flagging scheduling conflicts early.
• Handling communications across all inboxes by reviewing, drafting, routing, and following up on messages, with same-day responses for priority items.
• Managing travel and logistics from start to finish, including flights, hotels, ground transport, itineraries, and backup plans, while resolving disruptions before the executives are affected and processing expenses within 5 business days.
• Coordinating across the founders to keep shared commitments aligned, including ownership of board meetings, all-hands meetings, and investor events, and ensuring information moves cleanly between all three leaders.
• Overseeing office and operational reliability by managing vendors, office systems, recurring workflows, team events, off-sites, and executive onboarding logistics.

Who You Are

• You have supported multiple senior executives at the same time and can point to concrete examples of doing so.
• You are extremely dependable and consistently catch issues before they become problems.
• You anticipate needs ahead of time rather than waiting to be asked.
• You communicate in a polished, professional way and adapt quickly to different priorities and people.
• You handle confidential information with care, maturity, and discretion.
• You are committed to mastering executive support rather than using the role as a stepping stone.

Requirements

• Must be based in New York City and available to work onsite 5 days a week; this requirement is non-negotiable.
• 2 to 5 years of experience in a similar role.
• Experience in startups is a strong advantage, though not mandatory.
• Proven experience supporting more than one senior executive at the same time.
• Excellent written communication skills, since you will communicate on behalf of three executives.
• Comfort working with fast-moving, high-expectation leaders in an intense startup environment.
• Strong ownership mindset with the ability to deliver results independently and without close supervision.
• Startup background is strongly preferred, though outstanding judgment and speed can compensate for lack of it.

Why Join Probook?

• The opportunity: Probook operates in a $700B industry shaped by AI adoption, labor shortages, and leadership changes that are driving demand for modernization. The company aims to define the category rather than compete for existing share.
• The traction: The business has reached $XXM ARR in 18 months, with product-market fit already established and scaling now underway.
• The funding: Probook has raised $40M from Sequoia and Andreessen Horowitz.
• The team: The company has a team of more than 60 people, and its founding team has spent thousands of days on site with customers. The organization is also building a highly talented NYC startup team with experience from MIT, Harvard, UPenn M&T, Waterloo, Citadel, and Palantir.

Compensation and Benefits

• Base salary of $100,000 to $125,000, with flexibility for the right candidate, plus equity.
• Comprehensive medical, dental, and vision coverage.
• $500 monthly stipend that can be used for food, gym, Uber, and similar expenses.
• Direct daily access to highly accomplished founders and investors.