Head of People & Operations

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 run their support and customer success workflows on Pylon. We're also featured on the Enterprise Tech 30 List .

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 , Robert Eng , and Marty Kausas

Team: Currently 100+ and growing!