Geared toward mid-level technical B2B support leaders comfortable with defining AI-driven support workflows and scaling global teams.
Derived from job-description analysis by Serendipath's career intelligence engine.
Original posting from Pylon Labs via Ashby
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.
WHAT YOU'LL DO
- 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
WHAT WE'RE LOOKING FOR
- 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
OUR PERKS
🚆 Commuter benefits
🌱 Parental leave
🏝️ 14 company holidays + unlimited PTO
🗺️ Annual offsite
🍽 Lunch, dinner, and snacks at the office
🏋️ Fitness stipend
MORE ABOUT PYLON
Funding: Series B led by a16z and BCV ($51M total raised)
Founders: Advith Chelikani https://www.linkedin.com/in/advith/, Robert Eng https://www.linkedin.com/in/robert-eng/, and Marty Kausas https://www.linkedin.com/in/martykausas
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.
Source: Pylon Labs careers (Ashby)