Senior Manager, Benefits

PEAK6•Chicago, IL

3d•Hybrid

About The Position

The Senior Manager, Benefits is responsible for the strategic oversight, implementation, administration, and evaluation of employee benefits programs across multiple U.S. business entities and international locations. The role ensures programs remain competitive, compliant, cost-effective, and aligned with organizational objectives. The Manager partners with HR leadership, internal stakeholders, benefits brokers, insurance carriers, and third-party administrators to oversee program delivery, evaluate recommendations, support strategic decisions, and improve the employee experience. The position oversees benefits program design and administration, including medical, dental, vision, life insurance, retirement, wellness, leaves of absence, and disability benefits. It also oversees annual renewals and open enrollment, benefits systems and service providers, retirement plan administration, regulatory compliance, audits, and employee communications. The Senior Manager leads and develops benefits team members and oversees external benefits resources. This is a salaried, exempt, full-time role reporting directly to the SVP of HR. It is office-based with potential hybrid or remote flexibility under organizational policies; the company describes its workforce as hybrid and allows remote work up to two days per week. The role may involve occasional extended hours during open enrollment, audits, or system updates, and minimal travel. It is primarily desk-based, with significant use of computers and communication platforms.

Requirements

Minimum of 5–7 years of progressive experience managing employee benefits, wellness programs, or HR-related processes.
Demonstrated experience in benefits plan design, vendor negotiation, and regulatory compliance.
Experience supporting or administering global benefits programs across multiple countries, including coordination with international brokers, carriers, and local statutory requirements.
Ability to conduct data analysis and present findings on benefits usage, costs, and trends to senior leadership.
Experience working with HRIS systems such as Workday, payroll systems, and benefits administration platforms.
Strong understanding of health and welfare benefits, retirement plans, wellness programs, and leave management.
Knowledge of applicable federal and state regulations, including ACA, ERISA, HIPAA, FMLA, ADA, and COBRA.
Familiarity with global benefits practices, including country-specific statutory benefits, market-competitive offerings, and multinational vendor management.
Ability to analyze benefits usage data and costs to propose improvements and support cost effectiveness.
Proactive problem-solving skills for resolving employee benefits issues and optimizing processes.
Ability to handle multiple responsibilities and balance long-term strategy with daily operations.
Experience planning and managing complex projects such as open enrollment and system migrations.
Proven ability to evaluate and work closely with third-party vendors and brokers, negotiate contracts, and ensure service quality.
Strong written and verbal communication skills for conveying complex benefits matters to employees and executives.
Ability to prepare visually engaging presentations, materials, and employee training programs.
Advanced proficiency in Microsoft Office Suite, including Excel, PowerPoint, and Word, for data analysis and benefits materials.
Familiarity with HRIS systems, benefits platforms, and compliance tracking tools.
Ability to lead, coach, and develop benefits team members and oversee external benefits resources.

Nice To Haves

Bachelor’s degree in Human Resources, Business Administration, or a related field.
Experience in fast-paced or highly regulated industries, such as technology, healthcare, or finance.

Responsibilities

Oversee the design, implementation, and management of employee benefits programs, including medical, dental, vision, life insurance, retirement, wellness, leave, and disability benefits.
Evaluate benefits offerings for competitiveness, effectiveness, and alignment with organizational objectives, and recommend enhancements.
Monitor industry trends and emerging benefits practices to identify opportunities to improve programs and employee experience.
Partner with regional HR teams, brokers, and international vendors to oversee programs across U.S. business entities and international locations, including the UK and Philippines.
Oversee annual renewals, evaluate financial analyses and plan design recommendations, and consider applicable local requirements.
Plan and oversee annual open enrollment activities in coordination with internal teams, brokers, vendors, and other stakeholders.
Oversee day-to-day benefits administration, including timely and accurate enrollments, eligibility changes, and employee inquiries.
Manage relationships with brokers, insurance carriers, third-party administrators, and other providers; resolve escalations and monitor service delivery.
Partner with HR and Employee Relations to oversee leave, disability, return-to-work, and workplace accommodation processes, including coordination with third-party administrators.
Oversee benefits administration in Workday and other benefits systems, including open enrollment, system testing, eligibility, data accuracy, and coordination with HRIS and Payroll.
Oversee retirement plan administration and service-provider relationships, coordinating with internal and external partners.
Ensure benefits programs comply with applicable federal, state, local, and international laws and regulations, including ERISA, HIPAA, FMLA, COBRA, and ACA.
Oversee compliance activities such as Form 5500 filings, nondiscrimination testing, employee notices, and other regulatory requirements, in partnership with internal teams and service providers.
Coordinate benefits-related audits and monitor vendor compliance with contractual and regulatory obligations.
Monitor legislative and regulatory developments, assess their potential impacts, and recommend actions to maintain compliance.
Oversee development and delivery of benefits and wellness communications, including open enrollment materials, new-hire orientations, education, and wellness initiatives.
Partner with HR and internal communications teams to provide employees with clear, timely, and accurate benefits information.
Support employee understanding and engagement through presentations, educational resources, and ongoing communications.
Lead, coach, and develop benefits team members; establish priorities, delegate responsibilities, and oversee execution of operations and strategic initiatives.
Oversee external benefits resources, promote team collaboration and process documentation, and support continuity of benefits operations.
Deliver regular updates to executive leadership on benefits trends, costs, and employee feedback.