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Head of People & Operations

Pylon· Operations
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San FranciscoFull-timePosted 4mo ago

About the role

First dedicated People leader responsible for people ops, HR, performance/comp, recruiting and culture as Pylon scales; player-coach role combining hands-on work with building scalable processes.

Responsibilities

  • Understand and own the vision for the company and be an active voice in pushing the company forward. People and HR should enable the company, not obstruct it.
  • Own People Ops: select and manage HRIS, equity administration, broker, immigration counsel; own onboarding (30/60/90), offboarding, payroll, benefits, compliance, etc.; scale for 10x employees.
  • Own performance and compensation: define comp bands, performance review cycles, PIP processes; coach managers, handle promotions.
  • Nurture culture: serve as the bellwether when culture diverges from core values (Sprint the Marathon, Happy Grinder, Product Fluency, Win as a Team).
  • Act as Head of Recruiting: maintain headcount plan and close gaps between plan and actuals.
  • Be an active player in scaling People from 50 to 500 employees.

Qualifications

  • Been an active player in scaling People somewhere from 50 → 500 employees
  • Bonus: non-traditional background outside of HR to build understanding on how to drive a company forward
  • Lived through performance and employee-relations, including PIPs, terminations, layoffs, and lessons learned
  • Willingness to do grunt work and build processes, not just manage a team

Skills

Required:HRIS managementCompensation designOnboarding/offboardingCoaching & manager development

Benefits

  • Commuter benefits
  • Parental leave
  • 14 company holidays + unlimited PTO
  • Annual offsite
  • Lunch, dinner, and snacks at the office
  • Fitness stipend
Last updated Sep 17, 2026. Interested? Apply on the company site.
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About Pylon

The only customer support platform built for B2B.

Pylon is the modern alternative to Zendesk, Intercom, Freshdesk, and Salesforce Service Cloud. We help B2B companies track customer support issues across common B2B channels including shared Slack channels (Slack Connect), Microsoft Teams, email, in-app chat, ticket forms, Slack community, and more. Hundreds of fast-growing YC companies of all sizes like Vellum, Hightouch, and Deel are customers. Learn more at usepylon.com

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