Probook is hiring a VP of Customer Success to build the 'Post-Sales Engine' that transforms high-stakes customer delivery into a repeatable, scalable machine. You will own the entire customer lifecycle from signed agreement through implementation, renewal, and expansion. This founding role is central to defining a category in a $700B industry with significant tailwinds.
What You'll Do
- Build a standardized Post-Sales Playbook coordinating complex configurations and training across multiple products and customer segments.
- Achieve 100% pre-launch completion and drive down Time-to-First-Value.
- Build systems to drive down response times and create real-time Health Score visibility.
- Engineer renewals by tracking Health Scores and intervening proactively, targeting 95%+ Gross Revenue Retention.
- Operationalize 'Land and Expand' to drive deep product adoption and organic expansion, targeting 120%+ Net Revenue Retention.
- Codify founder instincts into playbooks and build a training machine to get new hires productive within 60 days.
- Build a scale-ready organization by splitting the team into specialized roles and hiring A-Players.
What We're Looking For
- 5+ years of post-sales or training/enablement leadership in B2B SaaS (Series A-C stage preferred).
- Proven experience successfully taking a company from founder-led customer success to a scalable post-sales organization.
- Experience managing technical onboarding for high-value vertical solutions ($50k+ ACV) with non-technical buyers.
- Commercial track record owning NRR targets and hitting 115%+ through retention and expansion.
- Player-coach mentality with experience personally managing strategic accounts while building team and systems.
- NYC based and excited to work in-office 5 days/week (~9am - 6pm).
Nice to Have
- Background in field services, logistics, or operational software.
- Track record of building Implementation, CS, and Support functions from scratch.
Team & Environment
This role is the founding member of the Customer Success team, building the team and function from scratch. You will join a high-intensity, high-collaboration culture.
Benefits & Compensation
- 200-300K base + equity: Significant equity stake.
- Comprehensive medical, dental, and vision coverage.
- 'Take what you need' vacation policy.
- Monthly food stipend.
- Unlimited office snacks.
- Direct access to world-class investors and advisors.
Work Mode
This is an on-site position based in New York, NY.
