Senior Benefits Leader - Hybrid, Ops & Vendor Strategy

Uber Freight; Chicago (IL); Hybrid; USD 130,000 - 160,000; Full time

Benefits offered by this job

Health plan

Dental and Vision benefits

401k match

Parental leave

Disability coverage

Life insurance

Equity awards

Job summary

Uber Freight is seeking a Senior Manager, Benefits to lead the administration, governance, and continuous improvement of employee benefits across the U.S. and global locations.

This hands-on leader will drive benefits operations, vendor management, and cross-functional initiatives while ensuring programs are compliant, scalable, and deliver a strong employee experience. The role requires a collaborative player-coach who pairs strategic vision with deep benefits expertise to execute operational

Qualifications

• Bachelor's degree required.
• 8+ years of progressive benefits experience managing health, welfare, retirement, leave, and wellbeing programs.
• Managed multi-million dollar benefit operations, driving vendor accountability and performance across brokers, consultants, carriers, and third party administrators.
• Led major new benefit vendor implementations.
• 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".

Responsibilities

• 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.

Skills

Benefits administration

Vendor management

Cross-functional collaboration

People leadership

HRIS systems

Data-driven decision making

Education

Bachelor's degree

Tools

Oracle

HRIS

Benefits administration systems

Job description

Uber Freight is seeking a Senior Manager, Benefits to lead the administration, governance, and continuous improvement of employee benefits across the U.S. and global locations.

This hands-on leader will drive benefits operations, vendor management, and cross-functional initiatives while ensuring programs are compliant, scalable, and deliver a strong employee experience. The role requires a collaborative player-coach who pairs strategic vision with deep benefits expertise to execute operational