Chief of Staff

Probook•New York, NY

2d•Onsite

About The Position

We're 30 people, ~$10M ARR, and have zero operations people. We’re talking about physical checks sitting uncashed on my desk for months. Zero financial reporting. Zilch. The most critical of admin work happens in stolen moments between customer calls. You’ll build our entire operational foundation from scratch: finance, admin, people ops, systems, everything. You'll work directly to free up my bandwidth and unblock our growth.= Fair warning: this role is not glamorous. You'll spend the next few months personally managing calendars, chasing receipts, and coordinating travel. If you need work to feel “strategic” from day one, this isn't it. But if you're energized by building from zero and just getting shit done— this is once-in-a-career. About Probook Probook is the AI “Front Office” for the home services industry, transforming how plumbing, HVAC, and electrical businesses operate. Our work’s impact is real. Dispatching the right tech to the right job can mean the difference between a $300 service call and a $20,000 system replacement. Proactive outbound keeps revenue steady even when demand dries up. And answering every call on time ensures homeowners convert before looking elsewhere. Probook unifies these workflows into a consistent CX, giving businesses a single, scalable place to run their entire operation. The Mandate Financial Infrastructure & Visibility Build clean financials with real-time visibility into cash, burn, unit economics, and forecasts. Fix accounts receivable. Administrative Excellence & Founder Leverage Own all admin work— calendars, travel, logistics, events, office management. Unlock 10+ hours/week of founder bandwidth. You'll personally handle EA-level work for months before hiring support. Systems, Tools & Operational Infrastructure Implement the core operational stack: people/HR, bills, etc. Make the simple stuff clear so we can focus on hard problems. Special Projects & Strategic Initiatives Own critical one-off projects that don't fit elsewhere. Be the utility player who drives cross-functional work without playbooks. Who You Are Energized by Grunt Work: You'll personally book travel, manage calendars, chase receipts, and handle logistics for months. No task is beneath you. You see grunt work as building trust and learning the business, not paying dues. Safe Hands for Sophisticated Work: The CEO can hand you complex, high-stakes projects with minimal context and trust they'll be handled. You manage volume (50+ tasks) AND depth (financial cleanup, board prep, negotiations) with excellence. Godly Proactivity: You anticipate needs before being asked. You see a problem, dig into context, and solve it without hand-holding. Pure Doer: Excited by zero-to-one. No playbook needed. You do the work yourself before hiring others to do it. Calm Under Pressure: Unflappable. When things break, you solve without drama. Why Join Probook? Founding Role: You're the first operations hire. Full ownership to build systems from scratch with zero bureaucracy and direct CEO access. The Market: A $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: $10M ARR in 18 months. Cash-flow positive. Product-market fit is established; we are now optimizing for scale. The Backing: Funded by Sequoia and a16z—partners who invest in category-defining leaders. The Upside: A meaningful equity stake in a company that controls its own destiny.

Requirements

3+ years in operations or chief of staff roles at high-growth seed-series C startups.
Track record doing both high-volume admin AND complex strategic projects.
Business acumen: Can read a P&L and understand unit economics.
NYC based: Excited to work 6 days/week in-office.

Responsibilities

Build clean financials with real-time visibility into cash, burn, unit economics, and forecasts.
Fix accounts receivable.
Own all admin work— calendars, travel, logistics, events, office management.
Unlock 10+ hours/week of founder bandwidth.
Implement the core operational stack: people/HR, bills, etc.
Own critical one-off projects that don't fit elsewhere.
Drive cross-functional work without playbooks.