People Operations Generalist - Compliance & Benefits

Following the expansion of People Technology & Operations to include Benefits Administration and HR Compliance, this hire closes a critical gap: owning the compliance and benefits function at the practitioner level. With open enrollment targeting early November and multi-country benefit programs in active management, the team needs a practitioner who can: 

• Serve as the primary compliance owner — EEO-1, FMLA/LOA, state/local employment law, I-9, background checks, SOC2 HR controls 

• Own the day-to-day benefits relationship with Sequoia and other benefit partners across US and international footprint 

• Triage and resolve FreshService tickets across Total Rewards queues, and manage Received Mail workflows 

• Support open enrollment planning, communications, and execution alongside the Benefits Specialist 

• Use AI tools proactively to reduce manual work across all of the above: develop workflows to automate / streamline audits, draft communication, identify ticket themes and build self service tools and/or automated responses, and automate routine reporting. 

Compliance — Primary Owner 

• Own the end-to-end HR compliance calendar: EEO-1 reporting, FLSA audits, I-9 program, state/local posting requirements 

• Administer and manage LOA programs (FMLA, state PDL, parental leave, accommodations) in partnership with legal and HRIS  

• Maintain background check program and ensure compliant onboarding across all states and countries 

• Assist with SOC2 HR controls, internal audits, and HR risk assessments 

• Use AI to accelerate compliance drafting, monitoring, and documentation — reducing turnaround time and human error 

 Benefits Administration — Partner & Executor 

• Own end‑to‑end benefits administration, including eligibility, enrollments/life events, carrier file feeds, billing and premium reconciliation, open enrollment planning and execution, and employee issue resolution 

• Manage benefits vendors and broker/consultant relationships; support renewals, plan changes, and service‑level monitoring 

• Partner closely with Payroll to ensure accurate benefit deductions, arrears/retroactivity handling, audits, and resolution of pay‑impacting issues 

• Automate benefits data reconciliation and enrollment communications using workflow automation and AI drafting tools 

 Ticket Management 

• Triage, own, and resolve Total Rewards tickets and support People Ops ticket queue 

• Manage Received Mail queue — process and route correspondence, legal notices, garnishments, and government agency mail 

• Partner on onboarding and offboarding processes as a backup to the People Ops lead 

• Maintain accurate employee records in Workday; run compliance and benefits audit reports 

• Contribute to process documentation and SOPs for the team's compliance and benefits workflows 

• Build AI-powered triage and auto-response workflows to reduce ticket handle time and eliminate repeat volume 

• 5+ years of progressive HR operations experience with significant hands‑on responsibility for HR Compliance and benefits administration 

• Strong working knowledge of benefits operations, including life events, carrier feeds, reconciliation, and vendor management 

• Experience partnering with Payroll on deductions, reconciliations, and pay‑impacting transactions 

• Demonstrated ownership of multi-state or multi-country benefits programs 

• Excellent communication skills and discretion when handling confidential information 

• Experience serving as the primary HR compliance resource for a company with 500+ employees 

• Experience leading open enrollment for 500+ employee populations 

• Working knowledge of FMLA, ADA, FLSA, EEO-1, I-9, COBRA, and state-level employment regulations 

• Comfortable identifying compliance gaps and drafting corrective policy without requiring a template 

• Proficiency in an enterprise HRIS — Workday strongly preferred