VP of Customer Success

Probook is seeking a VP of Customer Success to build the post-sales engine and drive scalability. The role involves architecting a repeatable post-sales motion, improving customer outcomes, and building systems for scalability. The ideal candidate has experience in post-sales or training/enablement leadership in B2B SaaS, with a proven track record of transitioning companies from founder-led customer success to scalable post-sales organizations.

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)
• Massive Plus: 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