People Operations Manager

Roadie, a UPS company, is a leading logistics and delivery platform that helps businesses tackle the complexities of modern retail with unmatched delivery coverage, flexibility and visibility. Reaching 97% of U.S. households across more than 30,000 zip codes — from urban hubs to rural communities — Roadie provides seamless, scalable solutions that meet a variety of delivery needs.

With a network of more than 310,000 independent drivers nationwide, Roadie offers flexible delivery solutions that make complex logistics challenges easy, including solutions for local same-day delivery, delivery of big and bulky items, ship-from-store and DC-to-door. For more information, visit www.roadie.com.

We're hiring a People Operations Manager to own day-to-day people operations and the systems, processes, and services supporting the employee lifecycle. You'll build lightweight, scalable processes that keep things running smoothly as we grow, and you'll help shape our upcoming HRIS and payroll implementation instead of inheriting it later. We're a lean, fast-moving team, so you'll own real work and see the impact quickly.

What You’ll Do

• Serve as the frontline for employee questions and own the employee lifecycle from onboarding to offboarding, so every step feels consistent and easy
• Be the go-to owner for our HR and people systems, and play a key role in our HRIS implementation, including data migration, configuration, testing, training, go-live, and ongoing improvements
• Keep the HRIS the source of truth for people data, with regular audits so it stays accurate across the employee lifecycle
• Build an efficient people operations system and infrastructure: streamline workflows, permissions, and reporting, build automation wherever it saves time
• Partner closely with Payroll on employee changes, benefits deductions, leave-related pay, timekeeping and issue resolution, supporting both hourly and salaried team members
• Run benefits administration and open enrollment, manage our broker and carrier relationships, and partner with the VP on benefits strategy and design, using our systems to optimize and automate wherever possible
• Oversee multistate leave administration, coordinating company, statutory, disability, and payroll and benefits requirements
• Keep us compliant across the states where we operate, including audits and filings, and support employment verifications, documentation, and immigration matters
• Track operational metrics to spot gaps, patterns, and risks, explain the why behind them, and recommend what to do next so the employee experience keeps getting better
• Create and maintain clear procedures, employee resources, and communications that make people processes easy to navigate, and train employees and managers on new systems and workflows
• Lead the way on using AI and automation to cut repetitive admin work, raise accuracy, and make the employee experience great

What You Bring

• 5+ years of progressive HR experience, including meaningful time in a lean or scale-up environment
• Bachelor’s degree or equivalent practical experience; SPHR certification a plus
• Hands-on experience administering HR systems, including configuration and workflow improvement; direct Rippling administration and implementation experience, strongly preferred
• Hands-on benefits administration experience, including working with brokers and carriers
• Working knowledge of multistate employment, including leave programs, payroll, and compliance
• Curiosity about automation, and a track record of using tools to cut manual work
• Strong analytical skills, with the ability to turn data into clear insight and recommendations
• A service mindset and sound judgment: you make systems and compliance easy to navigate, handle sensitive information with care, and know when to resolve issues independently or bring others in
• Resourceful self-starter with a “roll up your sleeves” mentality

Why Roadie?

• Competitive compensation packages
• 100% covered health insurance premiums for yourself
• 401k with company match
• Tuition and student loan repayment assistance (that’s right - Roadie will contribute directly to your existing student loans!)
• Flexible work schedule with unlimited PTO
• Monthly 3-day weekends
• Monthly WFH stipend
• Paid sabbatical leave - tenured team members are given time to rest, relax, and explore
• The technology you need to get the job done

This role is not eligible for visa sponsorship. Applicants must be authorized to work for any employer in the U.S.