Chief of Staff

A Note From The Founder

We're 30 people, ~$10M ARR, and a lack of process is getting in the way of scaling.

We're talking customer health metrics strewn across half a dozen spreadsheets. Months of uncashed physical checks are piling up on my desk. GTM playbooks half-documented. You'll build our entire operational foundation from scratch: finance, admin, people ops, systems, special projects. You'll work directly with me to free our team's bandwidth and help us scale.

Fair warning: this role starts neither glamorous nor strategic. Your first few months will be a lot of grunt work: coordinating calendars, chasing receivables, and office management.

But if you're energized by building from zero and getting shit done, this is once-in-a-career. Work directly with founders. Front row seat to hypergrowth.
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

Founder Leverage You'll own all admin: calendars, travel, logistics, office management. You'll do the work yourself first, build the systems to scale it, then hire an EA to run it as you take on higher-leverage work.

Operational Foundation Build financial infrastructure with real-time visibility into cash, burn, and unit economics. Fix accounts receivable. Implement core HR/people systems.

Strategic Projects You solve our hardest problems without a playbook: operationalizing GTM strategies, building customer success tooling, and key one-off hires. That way, the team can focus on building product, closing deals, and taking care of customers.

Who You Are

• Energized by Doing: You'll start off personally booking travel, managing calendars, and chasing receivables. No task is beneath you. You do the work yourself before building systems or hiring others to scale it.
• 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.
• Relentlessly Proactive: You anticipate needs before being asked. You see a problem, dig into context, and solve it without hand-holding.
  
  No playbook needed.
• Calm Under Pressure: You can take heat. When things break, you solve without drama.

Requirements

• 2-5 years in high-agency roles: operations, COS at high-growth startups (seed to Series C/D), top-tier consulting/banking, or founder experience.
• 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 the office.

Why Join Probook?

• Founding Role: First operations hire. Build systems from scratch with zero bureaucracy and direct CEO access.
• The Market: $700B industry with clear tailwinds-AI adoption, labor shortages, generational transitions. We're defining the category, not fighting for share.
• The Traction: $XXM ARR in under 18 months. Cash-flow positive. Product-market fit proven; now we're scaling.
• The Upside: Meaningful equity in a company that controls its own destiny.

Compensation & Benefits

• Equity: Meaningful equity as a founding member of the operations team.
• Salary: Competitive base compensation.
• Health: Comprehensive medical, dental, and vision.
• Perks: Monthly food stipend and unlimited office snacks.
• Direct access to world-class investors and advisors.