Chief of Staff

A Note From The Founder

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

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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.

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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.

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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.

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About Probook

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Probook is the AI dispatcher for the home services industry, transforming how plumbing, HVAC, and electrical businesses operate.

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Our impact is real. Dispatching the right technician to the right job can mean the difference between a $300 "band-aid" fix and a $20,000 system replacement. By automating proactive communication and around-the-clock workflows, Probook ensures a consistent customer experience without the need for 24/7 manual staffing. We unify these processes into a single, scalable platform, giving businesses one place to run their entire dispatch operation.

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The Mandate

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• 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.

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Who You Are

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• 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.

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Requirements

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• 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.

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Why Join Probook?

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• 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.

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Compensation & Benefits

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• Equity: Meaningful equity as a founding member of the operations team.
• Salary: 140K - 200K Base Comp + Meaningful Equity  
• Health: Comprehensive medical, dental, and vision.
• Perks: Monthly food stipend and unlimited office snacks.
• Direct access to world-class investors and advisors.