Enterprise Customer Success Manager
$130k - $160k USD
Who We Are
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 carry a portfolio of Probook's highest-ACV accounts and own their success — from post-deployment through renewal and expansion. You drive outcomes, not just relationships. GRR, NRR, and expansion are your numbers to hit.
Who You Are
An operator first: You run your book like a business. You track health scores, flag churn risk before it surfaces, and hold customers accountable to the outcomes they signed up for.
Commercially sharp: You spot expansion opportunities naturally, build airtight business cases, and are comfortable asking for the renewal and the upsell in the same conversation.
A strong executor: You manage a portfolio of complex, multi-stakeholder accounts without dropping anything. Your project management and follow-through skills are airtight.
Direct and confident: You communicate clearly and concisely with executives, operators, and economic buyers alike. You deliver hard messages without hedging and earn trust through follow-through, not warmth.
Low ego, high output: No task is beneath you. You do whatever it takes to make your accounts successful.
What You Will Own
A portfolio of Probook's largest and most strategic accounts, with full ownership of GRR, NRR, and expansion targets
The full post-launch relationship: Go-Live through renewal, including QBRs, health checks, escalation management, and expansion plays
Cross-functional accountability: work directly with Deployment, Product, and Leadership to surface customer feedback, resolve blockers, and close product gaps that affect retention
Requirements
NYC-based; 5 days/week in-office
3+ years in B2B SaaS Customer Success or Account Management with direct ownership of GRR, NRR, and expansion metrics
Startup experience required (Series A–D)
Demonstrated ownership of a book with $100K+ ACV accounts
Experience managing multi-stakeholder accounts with 3+ decision makers or business units
Proven track record running executive-level business reviews and owning commercial conversations — renewals, upsells, escalations
Vertical SaaS or field operations software experience is a strong plus
Home services industry experience is a plus, though by no means required
Why Join Probook?
The People: Becoming one of the most talent-dense start-ups in NYC (MIT, Harvard, UPenn, Waterloo, ICPC world finalists, IMO Gold Medalists, Ex-Meta, Citadel, YC).
The Market: $700B industry with clear tailwinds. AI adoption, labor shortages, and generational transitions. We are defining the category, not fighting for share.
The Traction: $XXM ARR in 18 months. Cash-flow positive. PMF proven; now we are scaling.
The Greenfield Ownership: You own the outcomes, not just the relationships. And we have a lot of strategic accounts that need owning.
Compensation & Benefits
Base: $130K – $160K
Variable: $20K – $40K OTE tied directly to GRR, NRR, and expansion targets — uncapped upside above quota
Equity: Meaningful early-stage equity
Health: Comprehensive medical, dental, and vision
Perks: $1,000/month stipend (food, gym, Uber) + really good office snacks
Access: Direct line to world-class investors and advisors