Head of Customer Success — Scale Agentic CS & Growth

Socket.dev; San Francisco (CA); On-site; USD 220,000 - 320,000; Full time

Benefits offered by this job

Fully covered medical, dental, and vor

401(k) retirement plan

Commuter benefits

Parental leave

14 company holidays + unlimited PTO

Annual offsite

Lunch, dinner, and snacks at theoffice

Fitness stipend

Job summary

Pylon is seeking a Head of Customer Success to own post-sales performance and scale a 15+ person team across SF, NYC, and London. You’ll lead NRR growth, expansions, and churn reduction while embedding agentic CS across our customers.

This role blends strategic leadership with hands-on execution, shaping how AI-native support partners with product and sales. You’ll build managers, design playbooks, and speak externally to influence the CS community, while ensuring the customer journey aligns

Qualifications

• Experience leading customer success with an agentic or usage-based product.
• Track record of owning NRR, GRR and expansion targets at scale.
• Strategic yet hands-on leader capable of building managers.

Responsibilities

• Own the Number: NRR, GRR, churn forecasting and expansion targets.
• Lead the Agentic Motion: drive usage-based billing adoption and migrations.
• Scale the org across three offices and geographies with managers.
• Run CS as Customer Zero: dogfooding and internal championing of workflows.

Skills

NRR ownership

Leadership experience

AI native

Multi-geo

Job description

Pylon is seeking a Head of Customer Success to own post-sales performance and scale a 15+ person team across SF, NYC, and London. You’ll lead NRR growth, expansions, and churn reduction while embedding agentic CS across our customers.

This role blends strategic leadership with hands-on execution, shaping how AI-native support partners with product and sales. You’ll build managers, design playbooks, and speak externally to influence the CS community, while ensuring the customer journey aligns