People Operations Generalist - Compliance & Benefits

Job description

Restaurant365 is a SaaS company disrupting the restaurant industry! Our cloud-based platform provides a unique, centralized solution for accounting and back-office operations for restaurants. Restaurant365’s culture is focused on empowering team members to produce top-notch results while elevating their skills. We’re constantly evolving and improving to make sure we are and always will be “Best in Class” ... and we want that for you too! 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. ### How you'll add value: 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 ### What you'll need to be successful in this role: - 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