Enterprise Customer Success Manager

ABOUT PROBOOK

Probook is the AI Operating System for the home services industry and is backed by two of the top VC's in the world (Sequoia & a16z)

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
• 5-7+ years in B2B SaaS Customer Success with a 3M+ book of business
• Startup experience is needed unless you can prove you have built playbooks 0-1 (Series A–D)
• Demonstrated ownership of enterprise/strategic accounts (10-30 clients max)
• Experience managing multi-stakeholder accounts with 3+ decision makers or business units
• Vertical SaaS OR field operations software OR 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: $160,000 - $200,000 OTE
• 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