Sr. Director of Benefits, Compensation, and HR Tech

Post Date

Mar 12, 2026

Location

Orlando,
Florida

ZIP/Postal Code

32801
US
May 22, 2026 Insight Global

Job Type

Perm

Category

Corporate Operations

Req #

ORL-5ad12a2b-dcfc-4908-8e38-006723473ee8

Pay Rate

$175k - $185k (estimate)

Job Description

A client of Insight Global is seeking a Sr. Director of Benefits, Compensation, and HR Technology to lead the strategic design and execution of all total rewards programs across a multistate workforce. This role oversees health and welfare benefits, retirement plan operations, compensation program design, and enterprise-wide leave of absence governance.
The Sr. Director will manage vendor relationships, ensure compliance with federal and state regulations, and guide compensation structures for both hourly and salaried employees. The role also leads HR technology strategy to support systems optimization and data-driven decision-making. This leader will partner closely with HR, Finance, Payroll, Legal, Operations, and IT, while managing teams across Benefits, Compensation, and HR Technology.

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 related field
10+ years experience leading Benefits and Compensation in a multistate environment
Experience overseeing 401(k) and retirement plan governance and compliance
Strong knowledge of ERISA, ACA, FMLA, ADA, PWFA, COBRA, HIPAA
Experience in leave of absence governance
Background managing compensation programs including salary structures, incentives, and benchmarking
Experience with HR technology strategy or HRIS optimization
Strong vendor management and analytical skills

Nice to Have Skills & Experience

Master’s degree
Experience working in a large, complex organization
Background with HR tech transformation initiatives

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.