VP of Customer Success
About The Position
The Mission About Probook 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 proactive communication and around-the-clock workflows, Probook ensures a consistent customer experience without the need for 24/7 manual staffing. We unify these 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 Your Goal: Transition from Founder-Dependent to Scalable Excellence. To date, we've onboarded every single customer in person. We've learned an enormous amount about what drives successful adoption—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 no step gets dropped and every touch meets the standards our founders have set. The Mandate "Zero-Defect" Customer Operations Architecture: Build a standardized Post-Sales Playbook that coordinates complex configurations and training across multiple products simultaneously across customer segments. Achieve 100% pre-launch completion and drive down Time-to-First-Value. Build systems that drive down response times and create real-time Health Score visibility tracking for customer performance against success metrics. Net Revenue Retention (NRR) Engineering: Engineer renewals, don't force them. Track Health Scores and intervene proactively. Target 95%+ Gross Revenue Retention and ensure top accounts renew early. Strategic Expansion & Entrenchment: Operationalize "Land and Expand"— drive outcomes and communicate value so crisply that customers expand usage organically. Drive deep product adoption measured by activity levels—your proxy for entrenchment. Identify and close expansion opportunities. Target 120%+ Net Revenue Retention with customers pulling from you. The "Scale-Ready" Organization: Deconstruct the "Founder Instinct"— codify what George does intuitively into playbooks that new teammates can execute from day one. Build a training machine that gets new hires fully productive within 60 days. Split the team into specialized roles as you scale while maintaining talent density by hiring A-Players who raise the team average. 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. A Technical Project Manager: While this is not an IC role, you will have to do the job in order to build out processes that are able to sustain complex, multi-stakeholder implementations with precision. Your systems coordinate hundreds of inputs across hundreds of customers simultaneously and hold teammates accountable to not dropping threads. 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 or training/enablement leadership in B2B SaaS (Series A-C stage preferred)
- Proven transition experience: You have successfully taken a company from founder-led customer success to a scalable post-sales organization
- Complex training/implementation chops: Experience managing technical onboarding for high-value vertical solutions ($50k+ ACV) with non-technical buyers
- Commercial track record: You have owned NRR targets and hit 115%+ through a combination of retention and expansion
- Player-coach mentality: You have personally managed strategic accounts while simultaneously building the team and systems around you
- NYC based: Excited to work in-office 5 days/week in our high-intensity, high-collaboration culture (~9am - 6pm)
Nice To Haves
- Background in field services, logistics, or operational software
- Track record of building Implementation, CS, and Support functions from scratch
Benefits
- Competitive Compensation: 200-300K base and performance-based bonus tied to GRR, NRR, and TTFV milestones
- Equity: Significant equity stake—you are a founding member of the CS team
- Health: Comprehensive medical, dental, and vision coverage
- Lifestyle: "Take what you need" vacation policy, monthly food stipend, and unlimited office snacks
- Access: Direct access to world-class investors and advisors
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What This Job Offers
Job Type
Full-time
Career Level
Executive
Education Level
No Education Listed
