Senior Manager - Benefits

Uber-Freight-4; Chicago (IL); On-site; USD 130,000 - 160,000; Full time

Job summary

Uber Freight is seeking a Senior Manager, Benefits to lead the administration, governance, and continuous improvement of employee benefits programs across the U.S. and global locations. The role blends strategic oversight with hands‑on execution to deliver compliant, engaging programs and an outstanding employee experience.

You will partner with Payroll, HRIS, Finance, Legal, and HR leadership to drive operational excellence and lead annual enrollment, audits, and vendor governance.

Qualifications

• 8+ years of progressive benefits experience with health, welfare, retirement, leave, and wellbeing programs.
• International benefits administration knowledge and global brokers/vendors experience.
• Managed multi‑million dollar benefit operations with vendor accountability.
• Led cross‑functional initiatives with Payroll, HRIS, Finance, and Legal.
• Data-driven with HRIS/benefits system integration expertise.
• Benchmarking and scalable benefits solutions for fast-paced environments.
• Experience as a player-coach in benefits leadership.

Responsibilities

• Lead administration and ongoing management of health, welfare, retirement, leave, and wellbeing programs.
• Own strategic relationships with benefits vendors, brokers, consultants, carriers, and third‑party admins.
• Partner with Employee Experience, Payroll, HRIS, Finance, Legal, and HR leadership to drive operational excellence.
• Lead annual enrollment strategy, execution, communications, and governance activities.
• Oversee benefits compliance, audits, reporting requirements, and controls.
• Manage U.S. benefits programs and support Mexico programs with local stakeholders.
• Lead vendor performance reviews, service governance, and issue resolution.
• Identify and implement process improvements to enhance efficiency and scalability.
• Lead benefits projects, vendor implementations, and operational transformations.
• Coach and develop benefits team members with a culture of accountability.

Skills

Benefits administration

Vendor management

Cross-functional leadership

HRIS proficiency

Data-driven analysis

Strategic planning

Player-coach leadership

Education

CEBS certification

Tools

HRIS platforms

Benefits administration systems

Job description

No immigration sponsorship or transfer available for this role.

About the Role

The Senior Manager, Benefits is responsible for leading the administration, governance, and continuous improvement of employee benefits programs across the U.S. and global locations. This role provides leadership for benefits operations, vendor management, and cross-functional initiatives while ensuring programs are delivered efficiently, compliantly, and with a strong employee experience.

The ideal candidate is a collaborative hands‑on player/coach who pairs strategic vision with deep benefits expertise to execute operational excellence, and streamline processes.

What the Candidate Will Do

• Lead the administration and ongoing management of health, welfare, retirement, leave, and wellbeing programs.
• Serve as the strategic relationship owner for benefits vendors, brokers, consultants, carriers, and third‑party administrators.
• Partner with Employee Experience, Payroll, HRIS, Finance, Legal, and HR leadership to drive operational excellence.
• Lead annual enrollment strategy, execution, communications, and governance activities.
• Oversee benefits compliance, audits, reporting requirements, and operational controls.
• Manage benefits programs in the U.S. and support employee benefits programs in Mexico while partnering with local stakeholders and vendors.
• Lead vendor performance reviews, service governance, and issue resolution activities.
• Identify and implement process improvements that enhance efficiency, scalability, compliance, and employee experience.
• Lead benefits‑related projects, vendor implementations, and operational transformation initiatives.
• Coach, develop, and support benefits team members while fostering a culture of accountability and continuous improvement.

Basic Qualifications

• 8+ years of progressive benefits experience focused on managing health, welfare, retirement, leave, and wellbeing programs.
• Current understanding of international benefits administration, statutory requirements, and working with global benefit brokers/vendors.
• Managed multi‑million dollar benefit operations, driving vendor accountability and performance across brokers, consultants, carriers, and third party administrators.
• Led cross‑functional initiatives involving Payroll, HRIS, Finance, and Legal.
• Data driven with technical expertise in HRIS platforms, benefits administration systems, and vendor integrations.
• Proven track record of benchmarking 'what great looks like,' proactively identifying operational gaps, and pitching/executing scalable benefits solutions in fast‑paced environments.
• Experience and a desire to lead as a "player-coach".

Preferred Qualifications

• 3+ years of people management experience.
• Experience in a multinational organization and supporting employee benefits programs abroad.
• Experience with a benefits consultancy or a benefits broker.
• CEBS or similar benefits certification.

Benefits & Compensation for U.S. Employees

Employees working more than 30 hours in the US at Uber Freight are eligible for benefits like a company sponsored health plan, dental and vision benefits, 401k match, financial and mental wellness benefits, parental leave, short- and long‑term disability coverage, life insurance and more. US based employees may also be eligible for a performance or sales incentive bonus program, participation in Uber Freight equity awards, and other types of compensation depending upon the role.

• Illinois: The salary range for this role is $130,000 to $160,000 a year.

About Uber Freight

Uber Freight helps companies move goods more reliably and efficiently. We bring together the technology, people, and transportation capacity they need, using real‑time data from millions of shipments to guide smarter decisions. That helps customers spot issues early, avoid costly surprises, and deliver on time. Uber Freight works with 1 in 3 Fortune 500 shippers across North America and manages over $17B in freight. Learn more at www.uberfreight.com.

Candidate Privacy Notice

Uber Freight is committed to protecting the privacy of our candidates. We collect and process personal data in accordance with applicable data protection laws. For detailed information on how we handle candidate data, please review our Candidate Privacy Notice .

EEOC

Uber Freight is proud to be an Equal Opportunity/Affirmative Action employer. All qualified applicants will receive consideration for employment without regards to sex, gender identity, sexual orientation, race, color, religion, national origin, disability, protected Veteran status, age, or any other characteristic protected by law. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements.