Head of Customer Success — Scale Agentic CS & Growth

Pylon; San Francisco (CA); On-site; USD 260,000 - 420,000; Full time

Benefits offered by this job

Medical, dental, and vision insurance

401(k) retirement plan

Commuter benefits

Parental leave

14 company holidays

Unlimited PTO

Annual offsite

Lunch, dinner, and snacks

Fitness stipend

Job summary

Pylon is seeking a Head of Customer Success to own post-sales at scale across SF, NYC, and London, with a 15+ person team and 159% NRR. You will lead expansion goals and drive agentic CS adoption, aligning revenue, renewals, and customer outcomes with Pylon’s platform and strategy.

You will shape how AI-native support evolves internally and for customers, while building a durable operating model. This role sits at the intersection of strategy, people leadership, and product impact.

Qualifications

• Must have owned the number (NRR/GRR/expansion) at scale.
• Experience leading teams across multiple geographies.
• Experience building and scaling a CS org in a hypergrowth environment.
• Public presence in the CS community is a plus.

Responsibilities

• Own NRR, GRR, and churn; forecast weekly and present to board.
• Own expansion numbers; drive cross-sell/upsell as core to the role.
• Scale the CS organization across offices and segments; design capacity and book economics.

Skills

NRR ownership

Expansion targets

Leadership of managers

Public thought leadership

Job description

Pylon is seeking a Head of Customer Success to own post-sales at scale across SF, NYC, and London, with a 15+ person team and 159% NRR. You will lead expansion goals and drive agentic CS adoption, aligning revenue, renewals, and customer outcomes with Pylon’s platform and strategy.

You will shape how AI-native support evolves internally and for customers, while building a durable operating model. This role sits at the intersection of strategy, people leadership, and product impact.