People Operations Generalist - Compliance & Benefits

Restaurant365 is transforming how restaurants run their businesses. Today, we help more than 50,000 restaurant locations manage their finances, operations, and people. As AI changes what's possible, we’re reimagining how restaurant back offices operate—automating routine work, helping teams make better decisions, and giving restaurant leaders more time to focus on growing their businesses.​ 

We're transforming how we work, too. AI is changing how we build products, solve problems, and deliver results for our customers. We're embracing new ways of working, moving faster, and creating opportunities for our people to make a greater impact.​ 

At Restaurant365, our culture is built on ownership, collaboration, and continuous improvement. We believe in challenging ourselves, learning every day, and working together to achieve great results. We’re looking for people who are curious, take initiative, and want to grow while helping shape the future of an industry​ 

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 

• Find opportunities to automate and improve how work gets done across your role with approved AI and other tools, choosing the right tool for each task, refining your prompts, and reviewing outputs for quality and time saved. 

 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 

• 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 

• Curiosity and eagerness to use AI in your daily work, backed by hands-on experience, a good sense of what generative AI can and can't do, and the judgment to verify its outputs.  

• 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 

R365 Team Member Benefits & Compensation

• This position has a salary range of $95,000 - $110,000. The above range represents the expected salary range for this position. The actual salary may vary based upon several factors, including, but not limited to, relevant skills/experience, time in the role, business line, and geographic location. Restaurant365 focuses on equitable pay for our team and aims for transparency with our pay practices.
• Comprehensive medical benefits, 100% paid for employee
• 401k + matching
• Equity Option Grant
• Unlimited PTO + Company holidays
• Wellness initiatives
This role is hybrid, balancing flexibility with the value of in-person collaboration. To support connection, partnership, and team effectiveness, employees are expected to work onsite each Tuesday and Wednesday.