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