The RoleYou 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
