About Probook
Probook is the AI dispatcher for the home services industry, transforming how plumbing, HVAC, and electrical businesses operate.
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 previously high-touch workflows around-the-clock, Probook ensures a consistent customer experience without the need for 24/7 live staffing. We unify our customers' processes into a single, scalable platform, giving businesses one place to run their entire dispatch operation.
The Role
You will sit at the intersection of implementation, retention, and revenue: running our onboarding engine, building the systems that prevent churn before it happens, and operationalizing the expansion path that turns happy customers into growing ones.
You're not walking into a playbook. You're writing it. You'll work directly with the CEO on four mandates: reconciling every existing customer account and building a real health score system; cutting Time-to-Value by designing the definitive implementation playbook; owning the CS tech stack and building dashboards that surface churn risk before it hits; and operationalizing the renewal and expansion workflow end-to-end. This is a high-autonomy, high-accountability role for someone who sees operational drag and immediately starts designing the system to eliminate it.
What you will own:
The "Clean Sweep": You will reconcile every existing customer, ensuring health scores match reality and plans are in place. You will stand in to help with critical accounts as needed.
The Deployment Factory: You will cut our "Time-to-Value" drastically. You will shape the definitive Implementation Playbook, operationalizing the "Pre-Flight Checklists" that ensure every customer receives a white-glove onboarding experience.
CS Intelligence: You will provide a "Single Source of Truth." You'll own the CS tech stack and build the dashboards that tell us who is going to churn before it happens.
Revenue Leverage: You will operationalize the renewal path. Streamline the notification workflows and operationalize the "Value Reports" our teams need to close expansions.
Who You Are
"Safe Hands": Project managing hundreds of enterprise customers doesn't phase you. No bottleneck can't be broken down into first principles and resolved. You can toggle between the database and presenting a churn analysis to the Board, and not let anything get by.
Willing to fight fires: You understand that the quickest way to solve some problems is manually. You can hold your own with the CFO of a 6-figure enterprise client that doesn't see value. You know how to work with tricky customers if the need presents itself.
A Process Architect: You hate doing the same manual task twice. You build structure as a reflex. You see operational drag and design the workflow to eliminate it. You know how to use AI to multiply work without sacrificing quality or creating slop.
Technically Empathetic: You understand the "blue-collar reality" of our users. You can translate a technician's frustration in Oklahoma into a specific product bug or process gap.
Requirements
4+ years of experience
1–3 years in high-agency roles: CS Ops, Implementation, COS, RevOps or Strategy at high-growth B2B SaaS (Seed to Series C)
Tech forward: Expert at Sheets, comfortable with CS metrics, data visualization tools & AI
Experience managing high-touch strategic/enterprise accounts, partnering with established businesses (not startups), and supporting complex, consultative customer relationships — not transactional sales
NYC Based: Excited to work in-office 5 days/week in our high-collaboration culture
Why Join Probook?
The People: Becoming one of the most talent-dense start-ups in NYC (Waterloo, GT, Berkeley, UPenn, ICPC world finalist, IMO Gold Medalist, Ex-Tenner, Metta, Citadel, YC)
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 18 months. Cash-flow positive. Product-market fit proven; now we're scaling.
Compensation & Benefits
Equity: Meaningful equity for being the ground-floor of our CS function
Salary: $160K – $200K
Health: Comprehensive medical, dental, and vision
Perks: $1,000 monthly stipend (food, gym, Uber, etc) and really good office snacks
Access: Direct access to world-class investors and advisors
probook