VP of Customer Success
$250k - $350k USD
The Mission
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.
Your mandate: Build the "Post-Sales Engine" that turns high-stakes, high-touch customer delivery into a repeatable, scalable machine.
You own the entire customer lifecycle—from signed agreement through implementation, renewal, and expansion.
The Strategic Challenge
To date, we've onboarded every single customer in person. We've learned an enormous amount about what drives success—now we need to document it, systematize it, and scale it. You will architect a repeatable post-sales motion that maintains white-glove quality at scale, where every touch meets the standards our founders have set, and the outcomes follow.
The Mandate
Assemble and Develop the Team: Hire A-players who raise the team average. Build a training machine that gets new hires fully productive within 60 days. Codify what works into playbooks anyone can execute — not just the founders.
Build the Post-Sales Machine: Architect a scalable CS machine — implementation, health scoring, renewals — that runs without you in the room.
Protect the Base: Engineer renewals, don't force them. Proactively manage health scores and intervene early. Target 95%+ Gross Revenue Retention.
Grow the Book: Operationalize land-and-expand. Drive adoption deep enough that expansion becomes the natural next conversation. Target 120%+ Net Revenue Retention with customers pulling from you.
Who You Are
A “Safe” Set of Hands: You ultimately own customer outcomes and their end-to-end experience. When issues arise, you lead de-escalation, bring clarity amid complexity, and drive thorough solutions that support measurable long-term customer success.
A Builder, Not Just a Manager: You thrive in ambiguity. You don't need a pre-existing playbook; you want to write it. You are a player-coach who will manage marquee accounts personally while building the systems for your team.
A Talent Magnet: You already have talent excited to follow you here. You’re capable of building systems for attracting, closing, retaining, and enabling A+ talent.
Operationally Rigorous: You manage by metrics, not vibes. You inspect the business end to end, maintain a deep understanding of the full customer portfolio, and use data to identify themes, surface risks and opportunities early, and drive proactive action.
A Commercial Animal: You are comfortable discussing money. You view "Success" as a revenue function and know how to pivot a "how do I fix this?" conversation into an upsell.
A "Blue Collar Whisperer": You can speak to a PE-backed exec in the morning and a third-generation plumber in the afternoon. You earn trust with people who value action over slides. Buzzwords don't work here—clarity and competence do.
Requirements
5+ years of post-sales leadership in B2B vertical SaaS (Series A-D stage preferred)
Proven transition experience: You have successfully taken a company from founder-led customer success to a scalable post-sales organization
Enterprise training/implementation chops: Experience managing onboarding for high-value vertical solutions ($50k+ ACV) with non-technical buyers
Commercial track record: You have owned GRR/NRR targets and can speak to the numbers you've hit
Player-coach mentality: You have personally managed and triaged strategic accounts while simultaneously building the team and systems around you
NYC based: Excited to work in-office 5 days/week in our high-collaboration culture
Strongly Encouraged:
Background in field services, logistics, or highly-vertical operational software
Track record of building Implementation, CS, and Support functions from scratch
Why Join Probook?
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.
Founder-Market Fit: Our founding team comes from the space and has spent thousands of days onsite with our customers. We live the space.
Traction: Top enterprises nationwide trust Probook. We have generational backing.
Compensation & Benefits
Competitive Compensation: $250K-$350K base, with performance-based bonuses tied to GRR & NRR outcomes
Equity: Significant equity stake—you are our founding CS leader
Health: Comprehensive medical, dental, and vision coverage
Lifestyle: "Take what you need" vacation policy, monthly food stipend, and really good office snacks
Access: Direct access to world-class investors and advisors