Manager, People Operations

Flock Freight • Chicago, IL

2d • $125,000 - $140,000 • Hybrid

About The Position

Flock Freight is looking for a strategic and hands-on Manager, People Operations to support the operational foundation behind our exceptional employee experience. You will lead and continuously improve our HR technology, total rewards and people analytics. Partnering closely with the VP of People and Manager of HR Business Partnering, you will create the operational foundation that enables strategic HR initiatives. You will shape the systems, programs, and operating rhythms that make it easier for employees and managers to do their best work. Your impact will be felt in every stage of the employee experience—and in the insights, efficiency, and confidence the business gains from a modern People Operations function.

Requirements

• Bachelor’s degree in Human Resources, Business Administration, or a related field.
• 7+ years of progressive HR experience, including meaningful People Operations leadership experience.
• 2+ years of hands-on UKG Pro administration experience, or experience with a comparable enterprise HRIS.
• Strong knowledge of compensation practices, benefits administration, FLSA, pay-transparency requirements, equity programs, DOL requirements, and multi-state employment law.
• Experience building workforce analytics, executive dashboards, and operational reporting that drives action.
• Advanced Excel or Google Sheets skills.
• Strong business acumen and the ability to connect operational excellence with measurable business outcomes.
• Excellent project management, prioritization, and organizational skills in a fast-changing environment.
• Sound judgment, exceptional attention to detail, and a commitment to accuracy, confidentiality, and compliance.
• A collaborative, credible communication style and the ability to build trust and influence partners at every level.
• Strong written, verbal, and presentation skills, with the adaptability to adjust plans as business needs evolve.

Responsibilities

• Lead the administration and evolution of our HRIS (UKG) and related People systems; partner with Payroll and IT to maintain data integrity, strengthen integrations, and improve the employee experience.
• Develop clear, actionable workforce dashboards and recurring or ad hoc reporting using UKG Business Intelligence to inform business and People decisions.
• Own the strategy, administration, and continuous improvement of Flock Freight’s total rewards programs, including compensation, benefits, wellness, retirement, leave, and voluntary benefits.
• Build and maintain practical total rewards resources, including salary and equity guidelines, offer-development tools, manager resources, and employee communications.
• Lead the annual Open Enrollment program end to end—from strategy and vendor coordination through testing, communications, and execution.
• Design scalable operating models, documentation, and processes that improve service quality, simplify work, and reduce manual effort.
• Identify and implement automation and emerging AI capabilities that enhance HR service delivery, decision-making, and organizational productivity.
• Partner with Finance and Legal on equity administration and reporting, and with Payroll on leave-of-absence payroll processing.
• Ensure People operations, policies, and documentation meet applicable federal, state, and international employment requirements.
• Manage and develop the People Operations Generalist
• Collaborate with People leadership to translate enterprise People priorities into focused operational plans and reliable execution.

Benefits

• Equity package
• Competitive benefits that support you and your family
• Annual bonus plan
• Hybrid Work Model
• Medical, Dental & Vision: Generous coverage for employees and dependents. Both HMO and PPO options provided.

What This Job Offers

• Job Type: Full-time
• Career Level: Manager