Head of Support

Pylon•San Francisco, CA

8d•$180,000 - $240,000•Onsite

About The Position

About Pylon Pylon is building the future of B2B customer support. We believe support should be a strategic advantage: deeply technical, tightly connected to the product, and increasingly powered by AI. Because support is our product, our own support organization should set the standard. We are looking for a Head of Support to build a world-class customer experience today while defining what an AI-native support organization should look like for the next several years. The Role 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.

Requirements

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

Nice To Haves

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

Responsibilities

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