Head of Customer Success

Pylon•San Francisco, CA

1d•Onsite

About The Position

Pylon is seeking a Head of Customer Success to lead and scale its post-sales operations. The role involves managing a Customer Success organization with strong NRR and expansion goals, overseeing a team of over 15 people across multiple locations, and driving the adoption of agentic support among Pylon's 1,600+ customers. This is a strategic position at the forefront of the next generation of Customer Success, offering opportunities for thought leadership. The ideal candidate will be responsible for post-sales revenue, expansion targets, and the commercial systems that support them. A key focus will be driving the deployment and usage of agentic support and managing the customer migration to a usage-based billing model. The role also requires scaling the organization by hiring and developing managers, designing segment strategies, and managing the relationship between Sales and CS. Additionally, the Head of Customer Success will act as 'Customer Zero,' using Pylon daily for their own workflows and contributing to product development. The role also involves representing Pylon externally in the CS community through speaking, writing, and other engagements.

Requirements

Experience leading customer success at a company with an agentic and/or usage-based billing product.
5+ years in post-sales, with 2+ years leading customer success organizations, including managing managers in an org of 15+ people across segments and geographies.
A track record of personally owning and exceeding NRR and expansion targets in B2B SaaS.
Experience scaling a CS org through an inflection point: hypergrowth, multi-geo expansion, or a pricing model shift.
Based in San Francisco or willing to relocate, with real enthusiasm for working in person.
Ability to move fluidly between strategic and hands-on tasks.
Ability to develop managers and lead a large team effectively.
Experience scaling systems that already work by understanding them first.
Experience managing a large account base with diverse customer segments.
Experience using agents in personal workflows and a strong point of view on agentic CS.
Ability to credibly demo Pylon's agentic capabilities to a skeptical CCO.

Nice To Haves

Existing public presence in the CS community (speaking, writing, or communities like Support Driven).
EMEA team experience.

Responsibilities

Own NRR, GRR, and churn, including weekly forecasting to the board.
Own the expansion number through cross-selling and upselling.
Run the commercial system, including quarterly goal setting, pipeline reviews, renewal and save motions, deal approvals, and comp/SPIFF design.
Drive Agentic Support deployment and usage across the customer base.
Own the customer migration motion to agentic, usage-based billing, driving adoption and guiding customers through the transition.
Develop and implement strategies for how AI changes the customer success role.
Grow the team across three offices, including hiring and developing managers, owning segment design, and capacity planning.
Own the Sales to CS relationship, including qualification criteria, deal review, and customer expectations.
Lead the dogfooding and Championship programs, using Pylon daily for own workflows.
Represent Pylon externally through speaking, writing, podcasts, and community engagement.