People Operations Generalist - Compliance & Benefits

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
• 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

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.

Internal Employees - R365 is committed to growing talent from within. If you see a role that excites you and you meet the qualifications, we encourage you to apply -regardless of your current location or work arrangement. Reach out to your People Business Partner if you have questions.

DYN365, Inc d/b/a Restaurant365 is an equal opportunity employer.