Head of AI Success
Leads post-sale AI success operations at scale, building automated systems for retention, expansion, health scoring, and support to drive NDR and customer outcomes. Requires 8+ years in strategy/product/ops, AI-native mindset, and analytical revenue focus.
About the job
Responsibilities
- Own everything post-sale: maximize customer happiness, product usage, and NDR.
- Drive retention + expansion, customer outcomes (bookings, revenue, efficiency), deployment speed, and AI-first support.
- Build AI-powered success engine that scales from 500 → 5,000+ customers.
- Create systems for account segmentation + ownership, health scoring, expansion/upsell playbooks.
- Turn customer data into revenue opportunities.
- Redesign onboarding to be fast, repeatable, low-touch.
- Automate support and success workflows using AI.
- Hire and lead teams across Success, Deployment, and Support.
Requirements
- 8+ years of strategy, product, or operations experience (e.g., product manager, engagement manager, consultant, founder).
- Strong interpersonal and relationship-building skills.
- Experience developing new AI solutions in fast-moving, ambiguous environments.
- Systems thinker: design scalable systems, not manual processes; build health scoring, segmentation, playbooks.
- Analytical: live in metrics (NDR, churn, expansion, usage); turn data into actions.
- AI-native: automate workflows using tools like Claude; think leverage first.
- Revenue-driven: see CS as revenue function; own expansion and NDR.
- Builder mindset: create playbooks from scratch; scale messy systems.
Nice-to-Haves
- Knowledge of Customer Success processes, systems, best practices.
- Experience at high-growth startup.
- Background in computer science or AI product management.
Skills
AI, Claude, Health Scoring, Account Segmentation, Ndr, Churn Analysis, Expansion Playbooks, Onboarding Automation, Customer Success Systems, Metrics Analysis
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