Enterprise Customer Success Manager
Probook · Manhattan
- On site
- Fulltime
- Manhattan
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Subject: Interested in the Enterprise Customer Success Manager role at Probook
Hi Casey — I came across the Enterprise Customer Success Manager opening and wanted to reach out directly. I've spent the last few years doing exactly this kind of work, and Probook stood out because…
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About the role
ABOUT PROBOOK
Probook is the AI Operating System 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
3-10 years in B2B SaaS Customer Success with a 3M+ book of business
Startup experience preferred (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 Tailwinds: $700B industry with clear tailwinds: AI adoption, labor shortages, and generational transitions creating demand for operational modernization. We are defining the category, not fighting for share.
The Traction: $XXM ARR in 18 months. Product-market fit proven; now we're scaling.
Funding: $40M raised from Sequoia and Andreessen Horowitz
The Team: >60 people, our founding team comes from the space and has spent thousands of days onsite with our customers. We live the space. We're also becoming one of the most talent-dense start-ups in NYC (MIT, Harvard, UPenn M&T, Waterloo, Citadel, Palantir).
The Greenfield Ownership: You own the outcomes, not just the relationships. And we have a lot of strategic accounts that need owning.
Compensation & Benefits
Equity: Meaningful early-stage equity
Base Salary: $140K – $160K (can go above range depending on experience)
Variable: $20K – $40K OTE tied directly to GRR, NRR, and expansion targets — uncapped upside above quota
Health: Comprehensive medical, dental, and vision
Perks: $500 monthly Ramp card for commuting, meals, gym, etc. (plus $25 in nightly meal delivery credit) and really good office snacks
Access: Direct access to world-class investors and advisors