Head of Agentic Customer Success & Growth

pylon-labs; San Francisco (CA); Hybrid; USD 220,000 - 320,000; Full time

Job summary

Pylon seeks a Head of Customer Success to own how post-sales works and scale it across SF, NYC, and London. You’ll inherit a 15+ person CS team, forecast results, and drive renewal, expansion, and customer migrations to agentic workflows. You’ll shape strategy for AI-driven CS and represent Pylon in the CS community.

You’ll lead a strategic, hands-on team that partners with product, sales, and support to ensure durable growth and high NRR across our 1,600+ customers.

Qualifications

• Experience leading customer success at a company with agentic or usage-based billing.
• Proven ability to scale a CS organization across multiple offices.
• Track record of owning NRR, GRR, and expansion targets at scale.

Responsibilities

• Own NRR, GRR, and churn; forecast weekly and present to the board.
• Own expansion numbers; lead cross-sell and upsell as a core part of the role.
• Run the commercial system: goal setting, pipeline reviews, renewals, and compensation design.
• Lead the Agentic Motion; drive deployment and usage of agentic CS across customers.
• Shape how AI changes the CS role and implement it internally.
• Scale the Org: hire and develop managers; segment design for Enterprise, Mid-Market, and Scaled.
• Manage Sales-to-CS relationship and post-sales customer expectations.
• Run CS as Customer Zero; dogfooding and champion programs with PMs.
• Be Pylon’s voice in the CS community through speaking, writing, podcasts.

Skills

Leadership

Forecasting

Strategic thinking

People management

Job description

Pylon seeks a Head of Customer Success to own how post-sales works and scale it across SF, NYC, and London. You’ll inherit a 15+ person CS team, forecast results, and drive renewal, expansion, and customer migrations to agentic workflows. You’ll shape strategy for AI-driven CS and represent Pylon in the CS community.

You’ll lead a strategic, hands-on team that partners with product, sales, and support to ensure durable growth and high NRR across our 1,600+ customers.