Manager, People Operations

Flock Freight; Chicago (IL); Hybrid; USD 125,000 - 140,000; Full time

Benefits offered by this job

Hybrid Work Model

Medical, Dental & Vision

Job summary

Flock Freight, based in Chicago, IL, is hiring a strategic and hands-on Manager, People Operations to strengthen the employee experience and the operational HR foundation. You will lead the HR technology, total rewards, and people analytics, partnering with the VP of People to enable scalable, data-driven initiatives.

This role shapes the systems, programs, and reporting that reduce manual work, improve service quality, and support growth.

Qualifications

• Senior-level People Operations leadership experience.
• Experience building workforce analytics and executive dashboards.
• Hands-on UKG Pro administration or similar enterprise HRIS.
• Strong knowledge of compensation, benefits, pay-transparency rules.
• Ability to translate business goals into operational plans.

Responsibilities

• Lead HRIS administration and HR systems improvements.
• Develop workforce dashboards to inform People decisions.
• Own total rewards program strategy, governance, and communication.
• Oversee annual Open Enrollment and vendor coordination.
• Design scalable operating models to improve service quality.
• Identify automation and AI opportunities to boost productivity.
• Partner with Finance and Legal on equity reporting and payroll.
• Ensure compliance across federal and state employment laws.

Skills

People Operations leadership

HR analytics

UKG Pro administration

Compensation & benefits

Multi-state employment law

Excel/Google Sheets

Project management

Communication

Privacy & compliance

Education

Bachelor's degree in Human Resources

Tools

UKG Pro

Job description

Company Overview

Flock Freight is the largest Shared Truckload (STL) freight brokerage in the U.S., transforming underutilized truckload capacity into tangible value: cost savings for shippers, increased earnings for carriers, and a smaller carbon footprint.

Company Overview

Flock Freight is the largest Shared Truckload (STL) freight brokerage in the U.S., transforming underutilized truckload capacity into tangible value: cost savings for shippers, increased earnings for carriers, and a smaller carbon footprint.

Their AI-powered, patented pooling technology optimizes across Flock's entire customer network, combining shipments from thousands of businesses into efficient Shared Truckloads. With STL, shippers enjoy truckload-level service while only paying for the space they need. Trusted by thousands of customers, from some of the largest enterprises to growing brands, Flock Freight delivers an unmatched combination of cost efficiency, exceptional service, and a streamlined shipping experience.

Flock Freight has been a Certified B Corp since 2020, meeting high social, environmental, transparency, and accountability standards to all of our stakeholders.

Team/Department Overview

People Operations - Reporting directly to the VP, People

About The Role

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.

What You’ll Do

• 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.

What You’ll Bring

• 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.

Compensation

The base salary range for this position is $125,00 - $140,000 per year. This reflects typical earning potential in this role based on market data and individual factors including skill sets, experience, and geographic location. In addition to salary, full-time employees are eligible for an equity package and competitive benefits that support you and your family as part of your total rewards package at Flock Freight. This role is eligible for an annual bonus plan in addition to the base salary.

Life & Benefits Of The Flock

• Hybrid Work Model: As an organization we value in-office collaboration, working cross-functionally, and winning together. Through three scheduled in-office days and two work-from-home days, we are able to work more efficiently and collaboratively.
• Medical, Dental & Vision: Generous coverage for employees and dependents. Both HMO and PPO options provided.

Our Promise To You

We're interested in your inherent abilities, not just the skills you bring from your last role - if you think you have what it takes to succeed in the role but don't check every box, please still get in touch. We'd love to start a conversation with you.

Flock Freight has zero tolerance for behavior that negatively impacts marginalized groups, including women, people of color, veterans, immigrants, people with disabilities, and members of the LGBTQIA+ community. We invite people of all identities to join the Flock!

We are targeting talent in both San Diego, CA and Chicago, IL.

Equal Opportunity Employer

This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights notice from the Department of Labor.