Senior Manager, Benefits

PEAK6 Services LLC; Chicago (IL); Hybrid; USD 131,000 - 164,000; Full time

Benefits offered by this job

Healthcare benefits

PTO

401k match

Parental leave

HSA contribution

Calm app subscription

Tuition reimbursement

Hybrid remote 2 days/wk

Discretionary bonus

Job summary

PEAK6 is seeking a Senior Manager, Benefits to design and oversee comprehensive employee benefits programs across US entities and international locations. You will lead strategic program management, implement competitive plans, and partner with brokers and carriers to deliver value.

You will also manage enrollment, compliance with ERISA/ HIPAA/ ACA, and cross‑border initiatives while enabling a positive employee experience. This hybrid role supports growth in a fast-paced fintech environment.

Qualifications

• Minimum 5–7 years of progressive experience managing employee benefits.
• Experience with benefits design, vendor negotiation, and regulatory compliance.
• Experience supporting global benefits programs across multiple countries.

Responsibilities

• Oversee strategic benefits program management across US and international locations.
• Manage day-to-day benefits administration including enrollments and inquiries.
• Ensure compliance with ERISA, HIPAA, ACA, FMLA, COBRA, and related regulations.
• Lead annual open enrollment and vendor management activities.
• Oversee Workday benefits administration and retirement plan services.

Skills

Benefits design

Vendor management

Regulatory compliance

Global benefits

Data analysis

Education

Bachelor's degree in HR/BA or related field

Tools

Workday

HRIS

Job description

WHO WE ARE

We are PEAK6, a leading investment firm, using technology to find a better way of doing things. The company’s first tech-based solution was developed in 1997 to optimize options trading, and over the past two decades, the same formula has been used across a range of industries, asset classes, and business stages to consistently deliver superior results. Today, PEAK6 seeks transformational opportunities to provide capital and strategic support to entrepreneurs and forward-thinking businesses. PEAK6’s core brands include PEAK6 Capital Management, PEAK6 Strategic Capital, Apex Fintech Solutions, FOCUS, We Insure, Evil Geniuses, Poker Power, Zogo, and Bruce Markets.

ABOUT THIS ROLE

We are PEAK6, a financial technology firm headquartered in the historic Chicago Board of Trade building, where we first opened our doors more than 20 years ago. Our first tech-based solution was developed in 1997 to optimize options trading and, over the past two decades, we have applied the same formula across a range of industries, asset classes and business stages to consistently deliver superior results. Today, PEAK6 seeks transformational opportunities to provide capital and strategic support to entrepreneurs and forward-thinking businesses, helping to unlock their potential.

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. This role ensures benefits 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 enhance the overall employee experience.

KEY RESPONSIBILITIES

Strategic Benefits Program Management (40%)

• Oversee the design, implementation, and management of comprehensive employee benefits programs, including medical, dental, vision, life insurance, retirement, wellness, leaves of absence, and disability benefits.
• Evaluate existing benefits offerings for competitiveness, effectiveness, and alignment with organizational objectives, and recommend enhancements as appropriate.
• Monitor industry trends and emerging benefits practices to identify opportunities for program improvements and an enhanced employee experience.
• Partner with regional HR teams, benefits brokers, and international vendors to oversee benefits programs across multiple U.S. business entities and international locations, including the UK and Philippines.
• Responsibilities include oversight of annual renewals, evaluation of financial analyses and plan design recommendations, and consideration of applicable local requirements.
• Plan and oversee annual open enrollment activities, ensuring effective coordination with internal teams, brokers, vendors, and other stakeholders.

Benefits Administration (30%)

• Oversee day-to-day administration of employee benefits programs, ensuring accurate and timely processing of enrollments, eligibility changes, and employee inquiries.
• Manage relationships with benefits brokers, insurance carriers, third-party administrators, and other service providers to support effective program administration, resolve escalations, and monitor service delivery.
• Partner with HR and Employee Relations to oversee leave of absence, disability, return-to-work, and workplace accommodation processes, including coordination with third-party administrators.
• Oversee benefits administration processes within Workday and other benefits systems, including open enrollment, system testing, eligibility, data accuracy, and coordination with HRIS and Payroll.
• Provide oversight of retirement plan administration and service‑provider relationships, coordinating with internal stakeholders and external partners as appropriate.

Compliance and Risk Management (20%)

• Ensure benefits programs are administered in accordance with applicable federal, state, local, and international laws and regulations, including ERISA, HIPAA, FMLA, COBRA, and ACA.
• Oversee required benefits compliance activities, including Form 5500 filings, nondiscrimination testing, employee notices, and other regulatory requirements, in partnership with internal teams and external service providers.
• Coordinate benefits-related audits and monitor vendor compliance with contractual and regulatory obligations.
• Stay informed of legislative and regulatory developments, assess potential impacts on benefits programs, and recommend appropriate actions to maintain compliance.

Employee Communication and Engagement (10%)

• Oversee the development and delivery of 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 ensure employees receive clear, timely, and accurate benefits information.
• Support employee understanding and engagement through presentations, educational resources, and ongoing benefits communications.

EDUCATION

Preferred: Bachelor's degree in Human Resources, Business Administration, or a related field.

WORK EXPERIENCE

Required: 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.

Proven ability to conduct data analysis and present findings on benefits usage, costs, and trends to senior leadership.

Experience working with HRIS systems (Workday), payroll systems, and benefits administration platforms.

Preferred: Experience in fast-paced or highly regulated industries (e.g., technology, healthcare, or finance).

KNOWLEDGE, SKILLS, AND ABILITIES

Benefits Expertise Strong understanding of health and welfare benefits, retirement plans, wellness programs, and leave management.

Knowledge of applicable federal and state regulations, such as ACA, ERISA, HIPAA, FMLA, ADA, and COBRA.

Familiarity with global benefits practices, including country-specific statutory benefits, market-competitive offerings, and multinational vendor management.

Analytical and Problem‑Solving Skills Ability to analyze benefits usage data and costs to propose improvements and ensure cost effectiveness.

Proactive problem‑solving skills for resolving employee benefit issues and optimizing processes.

Project Management and Organizational Skills Capable of handling multiple responsibilities and balancing long‑term strategy with daily operations.

Experience planning and managing complex projects such as open enrollment and system migrations.

Vendor Management Proven ability to evaluate and work closely with third‑party vendors and brokers, negotiating contracts and ensuring service quality.

Communication and Training Strong written and verbal communication skills to convey complex benefits matters to employees and executives.

Ability to prepare visually engaging presentations, materials, and training programs for employees.

Technical Proficiency Advanced proficiency in Microsoft Office Suite (Excel, PowerPoint, and Word) for data analysis and managing benefits materials.

Familiarity with HRIS systems, benefits platforms, and compliance tracking tools

MANAGER LEVEL

Responsible for leading the oversight and administration of employee benefits programs, ensuring compliance, operational effectiveness, and employee satisfaction. Collaborates with HR leadership and cross‑functional teams to support benefits strategy, program improvements, and organizational objectives.

SUPERVISORY RESPONSIBILITY

Lead, coach, and develop benefits team members, providing guidance and support for professional growth.

Establish team priorities, delegate responsibilities, and oversee the effective execution of ongoing benefits operations and strategic initiatives.

Provide oversight of external benefits resources, including brokers, consultants, insurance carriers, and third‑party administrators.

Promote effective team collaboration, process documentation, and continuity of benefits operations.

ORGANIZATIONAL STRUCTURE

The Senior Manager, Benefits reports directly to the SVP of HR and works closely with:

Internal Stakeholders: HR Business Partners, payroll teams, finance, and employee relations, to ensure seamless benefits delivery.

External Stakeholders: Brokers, insurance carriers, and benefits administration vendors, to manage plans and contracts.

Executive Leadership: Delivers regular updates on benefits trends, costs, and employee feedback to inform leadership decisions.

WORKING CONDITIONS

Environment: Office‑based role with potential for hybrid or remote flexibility in accordance with organizational policies.

Schedule: Full‑time position, with occasional extended hours during open enrollment, audits, or system updates.

Travel Requirements: Minimal travel, with potential visits to vendor meetings, benefits fairs, or off‑site HR events.

Physical Demands: Primarily desk‑based with significant use of computers and communication platforms.

FLSA STATUS

Exempt. This is a salaried position and is not eligible for overtime under the Fair Labor Standards Act (FLSA).

OUR REWARDS

We offer a robust package of employee perks and benefits, including healthcare benefits (medical, dental and vision, EAP), competitive PTO, 401k match, parental leave, and HSA contribution match. We also provide our employees with a paid subscription to the Calm app and offer generous external learning and tuition reimbursement benefits.

As a hybrid workforce, we offer our employees the ability to work remotely up to two days a week. Base pay offered may vary depending on job‑related knowledge, skills, experience, and office location. This position also may be eligible for a discretionary annual bonus in addition to a range of health & wellness benefits, enhancing your overall compensation package.

Base Salary Range $130,800-$163,500

PEAK6 is proud to be an equal opportunity employer that does not discriminate on the basis of race, color, religion, sex (including pregnancy, sexual orientation, and gender identity), national origin, age, disability, veteran status, marital status, or any other protected characteristic. Our hiring practices ensure that all qualified applicants receive fair consideration without regard to these characteristics.

PEAK6 is committed to creating an inclusive and accessible workplace for all candidates, including those with disabilities. We are dedicated to ensuring equal employment opportunities and providing reasonable accommodations to qualified individuals with disabilities. If you require reasonable accommodations to participate in the application or interview process, please contact our HR department at [e-mail]. We will work with you to provide the necessary accommodations to ensure your full participation in our hiring process.

#PEAK6 Application data may be reviewed, including through automated tools, for security and fraud‑prevention purposes. This review is conducted by our information security team and is separate from hiring decisions.

We’re In The Business Of What Ought To Be The business of doing, creating, and building the world the way we see fit. We seek out the transformational opportunity, making it better, more useful, more valuable. At PEAK6, we activate what is into what ought to be through world‑class technology, operational excellence and purposeful design. Headquartered in the Chicago Board of Trade Building, PEAK6 is not your typical investment firm. While trading got us our start and still powers our center, we quickly realized that our vision was to embrace and empower today’s consumer through technology, simplifying processes, improving performance and creating new wealth.