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.
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.
Senior Customer Engagement Manager
Own end-to-end relationships with strategic US insurance carriers, leading complex AI implementation programs that transform unstructured data workflows. Act as trusted advisor to C-suite stakeholders while driving retention, expansion, and product influence.
Director of Client Engagement
Lead and scale the client engagement function for a robotics platform company. Own post-sale outcomes, manage a small team, drive retention and expansion, and serve as the voice of the customer to Product and Engineering.
Customer Success Manager, Beneficial Deployments
Customer Success Manager supporting Beneficial Deployments team, serving as strategic advisor to global development organizations adopting Claude AI products to amplify social impact.