Manager of Benefits and Retirement

Post Date

Aug 05, 2026

Location

Orlando,
Florida

ZIP/Postal Code

32827
US
Oct 05, 2026 Insight Global

Job Type

Contract-to-perm

Category

Managerial / Professional

Req #

ORL-92f115ae-5ef6-4104-8e00-9767132924ce

Pay Rate

$35 - $43 (hourly estimate)

Job Description

Insight Global is looking for a Manager of Benefits & Retirement. This person will be responsible for the strategic oversight, administration, compliance, and continuous improvement of employee benefits and retirement programs. This role leads benefit operations, vendor management, retirement plan administration, employee support, and regulatory compliance while ensuring programs remain competitive, cost-effective, and aligned with organizational goals. The position also manages a small team and serves as a key advisor on benefits strategy and employee well-being initiatives. This role is a fully onsite Monday-Friday 8am to 5pm.

We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, please send a request to HR@insightglobal.com.To learn more about how we collect, keep, and process your private information, please review Insight Global's Workforce Privacy Policy: https://insightglobal.com/workforce-privacy-policy/.

Required Skills & Experience

Bachelor's degree in Human Resources, Business Administration, Finance, or a related field.
7+ years of progressive experience in employee benefits administration, retirement programs, or total rewards.
2+ years of people leadership or supervisory experience.
Strong knowledge of ERISA, COBRA, HIPAA, FMLA, ACA, and other relevant benefits regulations.
Experience managing health, welfare, retirement, and leave programs.
Experience working directly with benefits vendors, consultants, and third-party administrators.
Strong financial analysis and budgeting experience related to benefits plans.
Advanced Microsoft Excel skills.
Excellent communication and presentation skills.
Experience using HRIS and benefits administration platforms.

Nice to Have Skills & Experience

CEBS (Certified Employee Benefit Specialist).
SHRM-CP, SHRM-SCP, PHR, or SPHR certification.
Retirement certification such as CRPS or QKA.
Pension administration experience.
Experience leading benefits strategy for organizations with 1,000+ employees.
Experience managing self-funded health plans.
Benefits consulting or broker-side experience.
Experience with Workday, UKG, Oracle HCM, SAP SuccessFactors, or similar HR systems.
Experience leading wellness, employee engagement, or total rewards initiatives.
Experience navigating unionized workforces or collective bargaining agreements.

Benefit packages for this role will start on the 1st day of employment and include medical, dental, and vision insurance, as well as HSA, FSA, and DCFSA account options, and 401k retirement account access with employer matching. Employees in this role are also entitled to paid sick leave and/or other paid time off as provided by applicable law.