Benefits Operations Manager

The Trade Desk • Chicago, IL

3h

About The Position

The Benefits Operations Manager is responsible for the accurate execution, compliance, and optimization of all employee benefit programs. This role ensures a seamless employee experience through operational efficiency and integrity using process management, data validation, and system integration oversight. The position serves as the primary point of accountability for benefits-related compliance with federal and state regulations North American Retirement Plan matters. In partnership with People Technology drives continuous improvement in plan administration by leveraging HRIS platforms to drive automation, resolving escalated issues, managing file feeds, and ensuring the accurate flow of data between internal systems and external partners.

Requirements

• Ability to create and maintain dashboards and produce actionable data insights.
• Strategic thinker with a strong continuous improvement mindset and attention to detail.
• Agility in navigating ambiguity and adapting to evolving regulatory landscapes.
• High diligence and ability to manage multiple deadlines.
• Strong analytical and problem-solving skills with the ability to translate complex data into clear recommendations.
• Experience conducting benchmarking, trend analysis, and benefits plan optimization.
• Ability to align benefit operations with broader HR strategy and total rewards goals.
• Highly effective written and verbal communication skills to interact with all levels of leadership.
• Collaboration effectiveness and ability to work cross-functionally with multiple stakeholders.
• Advanced Excel and Microsoft Office skills.
• Bachelor's degree in Human Resources, Business Administration, or a related field.
• 7–10 years of progressive experience in benefits operations and managing retirement plans in a corporate setting.
• Knowledge of compliance requirements related to ERISA, ACA, COBRA, 5500 Filings, EPCRS.
• Project Management experience within benefits or HR Operations.
• Strong qualified defined contribution administration and analysis is a must - familiarity with 401(k) regulations as detailed in ERISA, EPCRS, and by the IRS.
• Experience with system integrations and file feed troubleshooting.
• Ability to maintain strict confidentiality and handle sensitive employee information with discretion.
• People Management experience required - this role will have direct reports.

Nice To Haves

• Experience with Workday.
• Experience managing multiple vendor partner relationships.
• Familiarity with ServiceNow or similar ticketing/workflow system.

Responsibilities

• Identify and implement operational improvements, including automation of manual processes and policy enhancements.
• Lead initiatives to align benefits operations with the function's direction – included but not limited to billing, employee inquiries, data discrepancy resolution, eligibility files and other reporting needs.
• Develop and maintain dashboards, reports, and metrics for internal stakeholders and leadership teams to support benefits program performance, compliance, and strategic planning.
• Partner with technology teams to ensure data integrity by resolving file errors and ensuring smooth data flows between HRIS and vendor platforms.
• Contribute to risk mitigation strategies by proactively identifying regulatory or vendor performance issues and developing resolution plans.
• Ensure timely and accurate execution of state filings, federal filings, and compliance documentation.
• Experience managing day-to-day aspects of both 401(k) and RRSP Plans – including annual audits, payroll reconciliation processes and funding.
• Continually analyze, review and improve the working processes and controls of the administration and related transactions and matters impacting 401(k) and RRSP plans.
• For US and Canada inquiries, serve as point of escalation for complex employee inquiries.

Benefits

• comprehensive healthcare (medical, dental, and vision) with premiums paid in full for employees and dependents
• retirement benefits such as a 401k plan and company match
• short and long-term disability coverage
• basic life insurance
• well-being benefits
• reimbursement for certain tuition expenses
• parental leave
• sick time of 1 hour per 30 hours worked
• vacation time for full-time employees up to 120 hours thru the first year and 160 hours thereafter
• around 13 paid holidays per year
• Employees can also purchase The Trade Desk stock at a discount through The Trade Desk’s Employee Stock Purchase Plan

What This Job Offers

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