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Director of People Operations and Systems

Whop· People
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Palo Alto, CAFull-timePosted 4w ago

About the role

Director level role responsible for running People Operations and People Systems, owning the employee experience from offer to exit, automating processes, and building an AI-enabled self-service infrastructure to support rapid company growth.

Responsibilities

  • Run day-to-day People Operations, with clear priorities, service levels, and measures of success, and contribute to the People Operations roadmap alongside the Chief People and Talent Officer
  • Execute the full employee lifecycle, including onboarding, employee changes, performance cycles, leaves, accommodations, work authorization, immigration support, offboarding, and records management
  • Run payroll, benefits administration, and employment compliance, and manage policies, audits, and vendor relationships with a high bar for accuracy and employee trust
  • Own the HRIS as the source of truth, including integrations, access controls, data quality, and simple, reliable workflows
  • Build AI-enabled and self-service support that answers routine questions quickly, routes complex issues to the right owner, and reduces administrative work
  • Build dashboards and reporting for headcount, hiring, retention, performance, and compensation so leaders can get accurate answers quickly
  • Partner with the Chief People Officer to connect role approvals, recruiting operations, candidate data, offers, and onboarding into one seamless handoff
  • Work with Finance, Legal, and IT on payroll, equity administration, compliance, security, and headcount data
  • Write the operating playbooks Whop needs, then continuously simplify or automate them as the business changes
  • Spot what will break next and fix it before growth turns it into a larger problem

Qualifications

  • Five or more years in People Operations, HR Operations, or People Systems, including experience owning major programs end to end, and ideally some experience managing or mentoring others
  • Experience building or scaling People Operations at a high-growth technology company, ideally around 100 to several hundred employees
  • Hands-on HRIS ownership, including implementations, integrations, permissions, vendor management, and ongoing optimization
  • Knowledge of payroll, benefits, leaves, immigration, employee data, and US employment compliance; ability to run them accurately and know when to escalate
  • Data fluency with ability to turn ambiguous questions into metrics, analysis, and recommendations
  • Experience using AI and automation to improve speed, accuracy, or service
  • Ability to fix broken workflows and handle sensitive employee cases with discretion
  • Direct communication style, sound judgment, confidentiality, and trust across the organization
  • Ability to move quickly, take ownership, and remain calm with changing priorities
  • Commitment to building an exceptional company culture beyond traditional People playbooks

Skills

Required:People Operations

Benefits

  • Best in class cash compensation and meaningful equity
  • High trust environment with ownership and direct access to company leaders
  • Opportunity to build the People operating system for a company shaping the future of how the next generation earns a living
  • Meals, wellness support, and office benefits designed for an in-person team
Last updated Oct 26, 2026. Interested? Apply on the company site.
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