Head of Operations

Probook•New York, NY

13h•$200,000 - $250,000•Onsite

About The Position

Probook is scaling fast and our operational foundation needs to catch up. This role owns it. You will report directly to the CEO and take full ownership of finance and internal operations, fixing what's broken, building what's missing, and eventually hiring a small team beneath you to run it. The goal is a lean, clean function that never becomes a bottleneck. Who You Are Finance-first. You are comfortable owning books, cleaning up A/R, managing a bookkeeper, and producing projections the founder can actually use. A systems builder. You see a gap and close it. Operationally self-sufficient. You don't need a team to start executing. You hire when it makes sense, not as a precondition. Low overhead. You build lean by default. You are not here to create a function for its own sake. A credible owner. You manage the full operational surface (Legal, finance, office, vendors) without dropping anything or escalating unnecessarily.

Requirements

NYC-based; 5 days/week in-office
5+ years in finance and operations, with direct ownership of books, reporting, and cross-functional systems
Startup experience required — you have built or significantly cleaned up operational infrastructure before
Comfortable managing external vendors and advisors (bookkeepers, lawyers, benefits brokers)
Strong enough financially to own projections and A/R independently, without a finance team underneath you yet
Track record of hiring and managing ICs

Responsibilities

Finance: billing, A/R cleanup, bookkeeper management, projections, and financial reporting to the founder. You'll also lead fundraising ops
Legal: all agreements and day-to-day legal coordination with outside counsel
Internal systems: own and improve core tooling (Ramp, Gusto, employee onboarding, and whatever else needs to exist)
Office: lead the office move and own office experience on an ongoing basis (or manage team)
Hiring: when the time is right, hire and manage a small team (finance, EA, office) beneath you — keeping the function lean