New York City, United States of America On-site USD 200,000 – 300,000 / year

Probook is hiring a VP of Customer Success

As VP of Customer Success, you will design and lead the evolution of our post-sales organization, transforming high-touch delivery into a scalable, data-driven operation. Your mission is to own the full customer journey—from onboarding through renewal and expansion—while institutionalizing the founder’s intuition into systems and playbooks that endure beyond any single individual.

Key Responsibilities

  • Build and operationalize a repeatable, scalable Post-Sales Engine that maintains premium service quality across customer segments
  • Develop a unified Post-Sales Playbook to streamline complex product configurations and training across multiple solutions
  • Drive down Time-to-First-Value and ensure 100% pre-launch completion through disciplined execution
  • Create real-time Health Score tracking to monitor customer progress and proactively guide interventions
  • Engineer renewals through value delivery, targeting 95%+ Gross Revenue Retention and early renewals from top accounts
  • Operationalize 'Land and Expand' by driving deep product adoption and organic customer growth
  • Target 120%+ Net Revenue Retention by identifying and capturing expansion opportunities
  • Systematize onboarding and training to bring new hires to full productivity within 60 days
  • Scale the team through role specialization while maintaining high talent density by hiring top-tier performers
  • Translate intuitive founder-led decisions into documented processes that new team members can execute from day one

Qualifications

You have 5+ years leading post-sales or enablement functions in B2B SaaS, ideally at Series A-C stage. You’ve successfully transitioned customer success from founder-led to scalable operations and have a track record managing technical implementations for high-ACV solutions sold to non-technical buyers. You’ve owned Net Revenue Retention targets and delivered 115%+ through retention and expansion. You thrive as a player-coach—personally managing key accounts while building systems and leading teams. Prior experience building Implementation, Customer Success, and Support functions from scratch is highly valued, especially in operational software, logistics, or field services domains.

Work Environment

This is an onsite role based in New York City, requiring five days per week in-office (~9am–6pm) within a high-intensity, collaborative culture. We value action over presentations, clarity over jargon, and competence over noise. You’ll join as a founding member of the CS leadership team, with direct access to investors and advisors, shaping the future of customer success at a growing company.

Compensation & Benefits

Offer includes $200K–$300K base salary, performance-based bonus tied to GRR, NRR, and TTFV goals, and a significant equity stake. Benefits include comprehensive medical, dental, and vision coverage, unlimited snacks, a monthly food stipend, and a flexible vacation policy.

Required Skills
Customer SuccessB2B SaaSTechnical OnboardingAccount ManagementTeam Building
About company
Probook
Probook is the AI dispatcher for the home services industry, transforming how plumbing, HVAC, and electrical businesses operate by automating proactive communication and around-the-clock workflows into a single, scalable platform.
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Job Details
Department Business Operations
Category management
Posted 3 months ago