Senior Manager, Benefits

PEAK6•Chicago, IL

4d•$130,800 - $163,500•Hybrid

About The Position

The Senior Manager, Benefits is responsible for strategic oversight, implementation, administration, and evaluation of employee benefits programs across multiple U.S. business entities and international locations. The role ensures programs are 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, assess recommendations, support strategic decisions, and improve the employee experience. The role leads benefits program design and administration, including health and welfare, retirement, wellness, leave, and disability benefits. It oversees annual renewals and open enrollment; benefits systems and service providers; retirement plan administration; regulatory compliance and audits; and employee communications. The manager also leads, coaches, and develops benefits team members and provides oversight of external benefits resources. The position reports directly to the SVP of HR and works with HR business partners, payroll, finance, employee relations, vendors, and executive leadership. It is a full-time, salaried, exempt role. The environment is office-based, with potential hybrid or remote flexibility under organizational policies. The role involves minimal travel and occasional extended hours during open enrollment, audits, or system updates. Work is primarily desk-based and involves significant computer and communication-platform use.

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 manage 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.

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, leaves of absence, 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 program improvements and enhance the employee experience.
Oversee benefits programs across multiple U.S. business entities and international locations, including the UK and Philippines; manage annual renewals, evaluate financial analyses and plan design recommendations, and consider local requirements.
Plan and oversee annual open enrollment in coordination with internal teams, brokers, vendors, and other stakeholders.
Oversee day-to-day benefits administration, including accurate and timely enrollment, eligibility changes, and responses to employee inquiries.
Manage relationships with brokers, insurance carriers, third-party administrators, and other service providers; resolve escalations and monitor service delivery.
Partner with HR and Employee Relations on leave of absence, 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 in coordination with internal stakeholders 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.
Coordinate benefits-related audits and monitor vendor compliance with contractual and regulatory obligations.
Track legislative and regulatory developments, assess their potential impact on benefits programs, and recommend actions to maintain compliance.
Oversee employee benefits and wellness communications, including open enrollment materials, new hire orientations, benefits education, and wellness initiatives.
Partner with HR and internal communications teams to provide clear, timely, and accurate benefits information to employees.
Support employee understanding and engagement through presentations, educational resources, and ongoing benefits communications.
Lead, coach, and develop benefits team members; establish priorities, delegate work, and oversee ongoing operations and strategic initiatives.
Provide oversight of external benefits resources, including brokers, consultants, insurance carriers, and third-party administrators.
Promote team collaboration, process documentation, and continuity of benefits operations.
Deliver regular updates to executive leadership on benefits trends, costs, and employee feedback.

Benefits

Healthcare benefits, including medical, dental, vision, and EAP.
Competitive PTO.
401(k) match.
Parental leave.
HSA contribution match.
Paid subscription to the Calm app.
External learning benefits.
Tuition reimbursement.
Hybrid work arrangement allowing remote work up to two days a week, subject to organizational policies.
Potential eligibility for a discretionary annual bonus.
Health and wellness benefits.