Head of Support

Pylon is the only agentic support platform, purpose-built for B2B companies. For leaders scaling AI-native support teams, Pylon lets humans and agents collaborate on customer work – investigating, resolving, and acting on every signal across every channel that matters.
Unlike platforms built before the AI era, Pylon enriches every interaction with deep account-level context, automates the low impact customer work, and surfaces answers before your team even has to ask. The result: faster responses, happier customers, and a system that continuously improves itself.

We're backed by a16z, BCV, General Catalyst, and Y Combinator. More than 1,500 companies including Linear, Cognition (makers of Devin), Modal Labs, and Incident.io run their support and customer success workflows on Pylon. We're also featured on the Enterprise Tech 30 List.

You'll lead our global Support org across the US and EMEA, stand up our new New York team, and build the layer of managers and leads who scale it with you. This isn't a conventional support leader role: you're setting the bar for customer experience, building the systems underneath it, and redesigning how the work gets done as AI transforms support. You'll work closely with Product, Engineering, Customer Success, and Sales, and should be just as comfortable reviewing an escalated ticket as presenting a multi-year strategy to the leadership team.

• Define how AI changes support at Pylon: what people should own, what gets automated, and what the resulting team, workflows, and career paths look like

• Own the operating cadence for response times, resolution times, quality, escalations, and customer sentiment as our customer base grows more complex

• Build the systems support runs on, including knowledge management, QA, onboarding, incident response, and capacity planning, each with a real owner and a regular review

• Be customer zero: drive dogfooding of Pylon's workflows across the team, and own the feedback loop that turns support interactions into product insights and roadmap input

• Lead US and EMEA support and stand up the New York team, hiring ahead of demand without fragmenting standards across regions

• Grow team leads and managers, and build the levels and career paths that let them run day-to-day execution without you

• Test whether there's a real support-led revenue opportunity for Pylon and make the call based on what customers actually want

• You've led and scaled a technical B2B support org, ideally at a dev tools, infra, API, or data company, and you've managed managers, not just ICs

• You've built systems and teams from scratch, and you turn recurring pain into an owned, measurable process rather than another one-off fix

• You're technically fluent and curious. You can reason about integrations, APIs, logs, and engineering tradeoffs without needing to be an engineer, and you want to understand why something broke, not just route the escalation

• You have a real, opinionated point of view on how AI changes support, backed by something you've actually built or shipped

• You're high-agency and low-ego. You're comfortable presenting to leadership one hour and inspecting an escalated ticket the next, and you hold a high bar while keeping trust in hard conversations

• Experience launching a new support location or regional team

• Experience building structured dogfooding and product-feedback systems

• Experience operating in a fast-changing, founder-led environment

🚆 Commuter benefits

🌱 Parental leave

🏝️ 14 company holidays + unlimited PTO

🗺️ Annual offsite

🍽 Lunch, dinner, and snacks at the office

🏋️ Fitness stipend

Funding: Series B led by a16z and BCV ($51M total raised)

Founders: Advith Chelikani, Robert Eng, and Marty Kausas

Team: Currently 100+ and growing!
Additional Job details

The base salary range for this position is $180k - $240k annually.

Compensation may vary outside of this range depending on a number of factors, including a candidate’s qualifications, skills, competencies and experience. Base pay is one part of the Total Package that is provided to compensate and recognize employees for their work at Pylon. This role is eligible for stock options, as well as a comprehensive benefits package.