---
title: 'Head of People & Operations at Pylon'
canonical: 'https://feeny.ai/job/head-of-people-operations-pylon-san-francisco-d8z5308fpbf9'
type: 'job'
last_seen: '2026-10-15'
---

# Head of People & Operations at Pylon

- **Company:** Pylon
- **Location:** San Francisco, CA
- **Employment:** full-time
- **Work type:** onsite
- **Posted:** 2026-05-28
- **Last confirmed live:** 2026-10-15
- **Apply:** https://jobs.ashbyhq.com/pylon-labs/0fbe0993-fd9e-4678-a565-d44bda1c5263

## 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 hiring our first dedicated People leader. Someone who can own several sub functions: people ops, HR, perf / comp, recruiting and culture as we scale. Player-coach role - you are capable of being the super IC that builds the function and processes not just a team builder. 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/).

## What You'll Do

- There are three levels. 1) Don’t be afraid of the grunt work. 2) Process build process build process build. 3) own the strategic vision and tackle the unknown unknowns.
- Understand and own the vision for the company and be an active voice in pushing the company forward. People and HR should not be viewed as an obstruction in the company, but as an enabler for the company.
- Own People Ops. Pick and run the HRIS, equity admin, broker, and immigration counsel. Own onboarding (30/60/90), offboarding, payroll, benefits, compliance, etc. Answer how we scale as a company for the next 10x employees.
- Own performance and comp. From the nuts and bolts (comp bands, review cycles, PIPing etc) to enabling people to be their best selves (manager coaching, promos).
- Nurture the culture. Be the bellwether when culture diverges from our core values. Be the embodiment of Sprint the Marathon, Happy Grinder, Product Fluency, and Win as a Team.
- Act as Head of Recruiting. Maintain the headcount plan and close the gap between the plan and actuals.

## What You've Done

- Been an active player in scaling People somewhere from 50 → 500 employees
- Bonus: Non traditional background outside of HR to build an understanding on how to drive a company forward.
- Lived through real performance and employee-relations calls - PIPs, terminations, layoffs - and can speak to what you learned
- Been through the mud and done the schlep work

## Why Join Pylon

- First dedicated People hire - define what the function looks like here from day one
- Direct partnership with the founders on org design and leadership decisions
- Build a high-bar, in-person culture in SF, not a remote-first People function

This Role Might NOT Be For You If

- You want to manage a team without doing the work yourself - for the first 12+ months you are the team, including running payroll and closing offers
- You can’t connect how your role fits into the broader org
- You are looking for an established function with playbooks to operate - we are building it, which is exciting but messy
- You think People is mostly programs and culture - at our stage it is mostly recruiting and the comp / performance machinery underneath
- You want remote or hybrid

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!

## 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

- [Product Designer](https://feeny.ai/job/product-designer-pylon-san-francisco-8eccmp19j35t) — San Francisco, CA
- [Head of Customer Success](https://feeny.ai/job/head-of-customer-success-pylon-san-francisco-rbrzwr2v0z9n) — San Francisco, CA
- [Financial Controller](https://feeny.ai/job/financial-controller-pylon-san-francisco-snfmn7m5fana) — 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
- [Software Engineer, Product](https://feeny.ai/job/software-engineer-product-pylon-san-francisco-773cqvajaaxq) — San Francisco, CA
- [Head of Support](https://feeny.ai/job/head-of-support-pylon-san-francisco-bvkcvmnhgjjs) — San Francisco, CA