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