Restaurant365 is adding a People Operations Generalist to the People Technology & Operations team to serve as the primary point of accountability for HR compliance and benefits administration across all operating countries. This is a hands-on, execution-focused role for someone who thrives at the intersection of employee experience, regulatory compliance, and benefits program ownership.
The successful candidate will own the benefits relationship with our benefit partners (including Sequoia), drive compliance programs end-to-end, be the first responder on Total Rewards Fresh Service tickets and Received Mail queue management and deploy AI and automation to drive efficiency and reduce manual work.
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
Differentiating Qualities (All Levels)
AI-forward mindset — actively looks for automation opportunities in repetitive HR workflows
Operates with urgency and follows through; treats open tickets and open compliance items as risks to close
Strong communicator who can translate compliance requirements into plain-language employee guidance
High EQ and discretion when handling sensitive employee matters
Comfortable working across time zones to serve a globally distributed workforce
Definition of Success — First 90 Days
Full audit of benefits data feeds between HRIS and benefit partners completed; discrepancies resolved
FreshService ticket SLAs met at ≥ 90% within 30 days of onboarding
Compliance calendar built and owned — EEO-1, state postings, LOA tracker, I-9 audit cycle
Sequoia relationship transitioned; open enrollment readiness confirmed with benefits partner
Received Mail workflow documented with clear handoffs and SLA targets
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