Role Overview
Pylon Labs is hiring a director-level Head of People. This is a full-time role in San Francisco. Full responsibilities, required qualifications, and the apply link are listed in the description below.
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Job description
AT PYLON, WE'RE BUILDING THE FUTURE OF B2B POST SALES.
We’re building the all-in-one B2B post-sales support platform powered by conversational data and layered with intelligence to help our customers run their operations in real-time.
We’re backed by a16z, BCV, General Catalyst, Y Combinator.
Currently more than 1300+ companies including Linear, Cognition (makers of Devin), Modal Labs, and Incident.io http://Incident.io run their support and customer success workflows with Pylon. You'll also find us on the Enterprise Tech 30 List https://www.enterprisetech30.com/.
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.
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 Labs
Frequently Asked Questions
How do I apply for the Head of People position at Pylon Labs?
Use the Apply button above to submit your application directly to Pylon Labs. Most applications take less than 5 minutes if your resume and contact details are ready, and you'll be routed to the employer's official application system to finish.
Where is the Head of People position at Pylon Labs located?
This position is based in San Francisco. Pylon Labs has not indicated remote or hybrid options for this role, so candidates should plan for on-site work.
What does a Head of People at Pylon Labs earn?
Pylon Labs has not disclosed a salary range in this posting. Many employers share specifics later in the interview process; you can also ask during a recruiter screen if compensation transparency is important to you.
When was the Head of People role at Pylon Labs posted?
This role was posted on May 28, 2026 (42 days ago). It's still listed as actively hiring; we re-confirm openings against the source system multiple times per day and remove closed roles.
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