Responsibilities

Pylon is looking for a Head of Customer Success to own how post-sales works at Pylon, and to scale it, not rebuild it.
You'll inherit a Customer Success organization that works: 159% NRR, quarterly expansion goals at scale, and a 15+ person team across SF, NYC, and London with team leads already in place. The systems run. Your job is to scale the team, from team leads to a management layer, and from strong quarters to a durable machine, all while leading Pylon's biggest bet: making agentic support the way our 1,600+ customers work.
This is one of the most strategic seats we'll fill this year. Our customers are support and CS leaders themselves, so they look to us for how other companies use Pylon to run support and success, and how we do it internally. You'll sit at the forefront of the next generation of CS, with real room to become a thought leader in the community.
Own NRR, GRR, and churn. Post-sales revenue is yours, forecast weekly and presented to the board.
Own the expansion number. Cross-sell and upsell are not handed off to someone else, they're a core part of how you run the org, and you're directly accountable for hitting the quarterly expansion goal.
Run the commercial system: quarterly goal setting (bottoms-up and top-down), pipeline reviews, renewal and save motions, deal approvals, and comp/SPIFF design tied to the company's bets.
Lead the Agentic Motion
Drive Agentic Support deployment and usage across the customer base, the company's top priority, run through your team.
Own the customer migration motion to agentic, usage-based billing: drive adoption of the usage-based product, guide customers through the transition, and land successful migrations. This isn't ownership of pricing strategy itself, it's ownership of how customers actually get there.
Have a strong point of view on how AI changes the customer success role, and be able to implement that transformation internally as well as help carry it through to our product.
Grow the team across three offices: hire and develop managers (two team leads are already ready for that step), own segment design across Enterprise, Mid-Market, and Scaled, book economics, and capacity planning.
Own the Sales to CS relationship: qualification criteria, deal review, and customer expectations post sales.

Head of Customer Success at Pylon Labs · LumiJobs

Head of Customer Success

Responsibilities

Qualification

Preferred

Benefits

Company

Pylon Labs

More roles at Pylon Labs