Head of AI Success

This is not a traditional Head of Customer Success role (and previous experience leading customer success is a plus, but not required).
We’re not hiring someone to just manage relationships or coach people. We’re hiring someone deeply analytical, systems-driven, and AI-native — someone who can design and build a machine that drives retention and expansion at scale, not manage it manually.
What you’ll own
Everything post-sale. Your goals are to maximize customer happiness, product usage, and NDR. You'll own:
Retention + Expansion
Customer outcomes (bookings, revenue, efficiency)
Deployment speed (time-to-value in days, not weeks)
Support (AI-first, proactive, scalable)
What you’ll do
Build the AI-powered success engine that scales from 500 → 5,000+ customers
Create systems for:
Account segmentation + ownership
Health scoring
Expansion and upsell playbooks
Turn customer data into revenue opportunities
Redesign onboarding to be fast, repeatable, and low-touch
Automate support and success workflows using AI
Hire and lead teams across Success, Deployment, and Support
What success looks like
Best-in-class NDR (expansion becomes predictable)
Faster deployments, lower support load
Clear, repeatable expansion engine
A lean, high-leverage team powered by AI
How you operate
Systems thinker
You design scalable systems, not manual processes
You’ve built (or can build) health scoring, segmentation, and playbooks
Analytical
You live in metrics: NDR, churn, expansion, usage
You turn messy data into clear actions
AI-native
You instinctively automate workflows using tools like Claude
You think leverage first, headcount last
Revenue-driven
You see CS as a revenue function, not support
You’re comfortable owning expansion and NDR
Builder
You want to create the playbook, not inherit one
You’ve scaled or want to scale messy systems into machines
Your background
8+ years of strategy, product, or operations experience (e.g., product manager, engagement manager, consultant, founder, etc.)
Strong interpersonal and relationship-building skills
Experience developing new AI solutions in fast-moving, ambiguous environments
Bonus:
Knowledge of Customer Success processes, systems, and best practices
Experience at a high-growth startup environment
Background in computer science or AI product management

Experience
6+ years

Work arrangement
No