---
title: 'Head of Support at Pylon'
canonical: 'https://feeny.ai/job/head-of-support-pylon-san-francisco-bvkcvmnhgjjs'
type: 'job'
last_seen: '2026-09-10'
---

# Head of Support at Pylon

- **Company:** Pylon
- **Location:** San Francisco, CA
- **Employment:** full-time
- **Work type:** onsite
- **Posted:** 2026-07-08
- **Last confirmed live:** 2026-09-10
- **Apply:** https://jobs.ashbyhq.com/pylon-labs/c8b37f74-66bb-4829-851f-7d2d3afe1560

## Job description

Pylon — the agentic support platform purpose-built for B2B. 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](http://Incident.io) run their support and customer success workflows on Pylon. We're also featured on the [Enterprise Tech 30 List](https://www.enterprisetech30.com/).

## 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 - $280k 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.

## About Pylon

## Company Overview
- **One-liner**: Pylon is an AI-native customer support platform purpose-built for B2B companies, unifying conversations across Slack, Teams, email, and chat into a single intelligent workspace.
- **Entity Type**: Private (Series B – $31M raised August 2025, total funding ~$51.3M)
- **Headquarters**: San Francisco, California, USA
- **Founded**: 2022 (Y Combinator Winter 2023 batch)
- **Founders**: Advith Chelikani (Co-Founder & CEO), Robert Eng (Co-Founder), Marty Kausas (Co-Founder)

## Core Business
- **Primary industry**: Customer Support / Customer Service Software (SaaS)
- **Target customers**: B2B companies of all sizes, from startups (e.g., Vellum, Hightouch, Deel) to mid-market and enterprise.
- **Mission / purpose**: To build the first customer support platform designed for how B2B teams actually work – with complex accounts, multiple stakeholders, and conversations across many platforms.

## Products & Services
- **Omnichannel Support**: A single view for all customer conversations across Slack Connect, Microsoft Teams, Discord, email, in-app chat, WhatsApp, and ticket forms. Manages both internal and external channels.
- **AI Assistants + Agents**: AI-powered tools that automatically route issues based on intent, draft replies and knowledge articles, categorize tickets, surface account insights, generate charts, and answer natural-language questions about customers. Can resolve 50% of eligible inquiries without human intervention.
- **Knowledge Automation**: AI that identifies gaps in the knowledge base, drafts articles, and surfaces the right answers before the support team has to search.
- **Account Intelligence**: Automatically tracks churn signals, feature requests, renewal risk, and other key account data, surfacing full customer context in seconds for support, success, and sales teams.

## Market Standing
- **Valuation / Market Cap**: Not publicly disclosed
- **Key Metric**: Total funding of **$51.3M** (Pre-Seed $125K from Y Combinator, Seed $3.2M led by General Catalyst, Series A $17M led by a16z, Series B $31M led by Bain Capital Ventures and a16z). Estimated annual revenue of **~$2.3M** as of mid-2025 (LinkedIn estimate).
- **Notable Investors / Partners**: Andreessen Horowitz (a16z), Bain Capital Ventures, General Catalyst, Y Combinator.
- **Growth Signals**:
  - Headcount grew **158% YoY** to ~87 employees (July 2025).
  - Claims **90% decrease in First Response Time** (from 35 minutes to <3.5 minutes) and **8x faster resolution time** despite 76% more ticket volume.
  - Customers include YC companies like Vellum, Hightouch, and Deel.
  - 50% of eligible inquiries resolved without human intervention.
  - Active hiring across engineering, customer success, sales, product, and GTM roles.

## Competitive Advantages
- **AI-native architecture**: Built from the ground up with AI, rather than bolting AI onto legacy platforms like Zendesk or Intercom.
- **B2B-specific channel support**: First platform to natively integrate Slack Connect, Microsoft Teams, and community channels (Discord) – critical for B2B workflows.
- **Account Intelligence**: Proactive detection of churn risk, feature requests, and renewal signals from support conversations, shared across support, success, and sales.
- **Compliance & security**: SOC 2 Type II, GDPR, ISO 27001, and HIPAA compliant, making it suitable for regulated industries.

## Strategic Focus
- **Current priorities**: Deepening AI automation (agents, knowledge base, routing), expanding omnichannel integrations, and scaling the go-to-market organization to capture more mid-market and enterprise customers migrating off legacy tools (e.g., Zendesk, Intercom, Freshdesk, Salesforce Service Cloud).
- **Direction for growth**: Become the default support platform for all B2B companies, leveraging AI to handle routine issues while empowering agents with full context.

## Why Work Here
- **Culture highlights**: Mission-driven team building the “first B2B support platform,” with a strong engineering background (founders from Caltech, Airbnb, Samsara, Affinity). Fast-paced startup environment.
- **Remote/hybrid policy**: In-person at the San Francisco office.
- **Notable perks/engineering culture**: Cutting-edge AI work; chance to shape product from early stage; exposure to founders and experienced leaders (e.g., Head of Engineering from Samsara). High growth means opportunity for impact and career acceleration.

## Sources
1. [usepylon.com](https://www.usepylon.com/)
2. [Pylon Jobs (Ashby)](https://jobs.ashbyhq.com/pylon-labs)
3. [Y Combinator – Pylon](https://www.ycombinator.com/companies/pylon-2)
4. [LinkedIn – Pylon](https://www.linkedin.com/company/usepylon)

## Other roles at Pylon

- [Financial Controller](https://feeny.ai/job/financial-controller-pylon-san-francisco-snfmn7m5fana) — San Francisco, CA
- [Founding Account Executive, EMEA](https://feeny.ai/job/founding-account-executive-emea-pylon-london-ep3g8daxg3sf) — London, United Kingdom
- [Head of Marketing](https://feeny.ai/job/head-of-marketing-pylon-san-francisco-ddytw6s979a0) — San Francisco, CA
- [Group Product Manager](https://feeny.ai/job/group-product-manager-pylon-san-francisco-cwztqhdgy02c) — San Francisco, CA
- [Marketing Operations Lead](https://feeny.ai/job/marketing-operations-lead-pylon-san-francisco-ark6j6hk8e39) — San Francisco, CA
- [Software Engineer, Intern](https://feeny.ai/job/software-engineer-intern-pylon-san-francisco-arbcpptxzwx7) — San Francisco, CA
- [Software Engineer, AI](https://feeny.ai/job/software-engineer-ai-pylon-san-francisco-wn7yjd0aadyt) — San Francisco, CA
- [Software Engineer, New Grad](https://feeny.ai/job/software-engineer-new-grad-pylon-san-francisco-qj78fzaa0rv4) — San Francisco, CA
- [Software Engineer, Security](https://feeny.ai/job/software-engineer-security-pylon-san-francisco-ysnmbrj39pzz) — San Francisco, CA
- [Software Engineer, Infrastructure](https://feeny.ai/job/software-engineer-infrastructure-pylon-san-francisco-ytb536zjw32v) — San Francisco, CA