Demo

Head of Total Rewards

World Insurance Associates, LLC.
Chicago, IL Full Time
POSTED ON 10/1/2025 CLOSED ON 12/31/2025

What are the responsibilities and job description for the Head of Total Rewards position at World Insurance Associates, LLC.?

Summary
World Insurance Associates is a unique insurance organization offering top products and services from major providers, combined with attentive service from local agents.
Founded in 2011, World is one of the fastest-growing insurance brokers in the U.S. with over 2,800 employees in over 260 offices across North America.  We specialize in personal and commercial insurance lines, surety and bonding, employee benefits, financial and retirement services, and human capital management solutions.
Position Overview
The Head of Total Rewards is responsible for developing and implementing the organization’s compensation, benefits, and recognition strategies. Working in a fast paced, high growth environment, the successful candidate will be skilled at creating and building best practices across total rewards. This role ensures the company remains competitive in attracting and retaining top talent while aligning with business goals and maintaining compliance with regulatory requirements.
Primary Responsibilities
  • Lead the design and execution of a comprehensive total rewards strategy, including compensation, benefits, and recognition programs, to support the organization’s goals and culture.
  • Analyze market trends to ensure competitive positioning while maintaining budgetary alignment.
  • Partner with senior leadership and HR teams to assess and evolve total rewards offerings.
  • Develop and deploy scalable job architecture frameworks, including job families, leveling, and pay structures.
  • Oversee the design, development and management of compensation structures, including salary bands, incentive plans, and executive compensation.
  • Design and lead sales compensation and commission strategy
  • Direct benefits programs, including health, retirement, wellness, and other employee support offerings, ensuring competitiveness and compliance.
  • Partner with HR, finance, and leadership teams to ensure alignment of total rewards strategies with workforce planning and financial goals.
  • Ensure compliance with applicable local, state, federal, and international regulations related to compensation and benefits.
  • Oversee the administration and governance of retirement programs, 401K including compliance, audits, and plan communications.
  • Drive communication strategies to ensure employees understand and value the rewards programs.
  • Lead, mentor, and develop a high-performing Total Rewards team, fostering professional growth and a culture of innovation.
Personal / Professional Attributes
  • Excellent analytical, communication, and leadership skills.
  • Strong strategic thinking and project management capabilities.
  • Excellent communication and stakeholder management skills.


Key Competencies
  • Analytical and Financial Acumen
  • Strong people leadership and engagement
  • Ability to analyze and interpret complex data to inform decision-making.
  • Strong operator in building process and programs

Qualifications
  • Bachelor’s degree in Human Resources, Business Administration, or a related field; advanced degree or certifications (e.g., CCP, CBP, or SPHR) preferred.
  • 10 years of progressive experience in compensation and benefits, including leadership roles.
  • Expertise in compensation and benefits strategy design and implementation.
  • Demonstrated success operating in a fast pace, high growth, matrixed environment
  • Strong knowledge of regulatory requirements and compliance standards related to compensation and benefits.
  • Experience with HR technology platforms and data analysis tools.
  • Expertise in 401(k) administration and governance and familiarity with fiduciary responsibilities.
  • Proven experience in job architecture design and deployment for complex organizations.
  • Preferred with UKG (Ultimate Kronos Group) systems

Equal Employment Opportunity
At World Insurance Associates (WIA), we celebrate and support our differences. We know employing a team rich in diverse thoughts, experiences, and opinions allows our employees, our products, and our community to flourish. WIA is honored to be an equal opportunity workplace. We are dedicated to equal employment opportunities regardless of race, color, ancestry, religion, sex, national orientation, age, citizenship, marital status, disability, gender identity, sexual orientation, or Veteran status. In addition, WIA makes reasonable accommodations to known physical or mental limitations of an otherwise qualified applicant or employee with a disability, unless the accommodation would impose an undue hardship on the operation of our business.

Salary.com Estimation for Head of Total Rewards in Chicago, IL
$259,321 to $337,595
If your compensation planning software is too rigid to deploy winning incentive strategies, it’s time to find an adaptable solution. Compensation Planning
Enhance your organization's compensation strategy with salary data sets that HR and team managers can use to pay your staff right. Surveys & Data Sets

What is the career path for a Head of Total Rewards?

Sign up to receive alerts about other jobs on the Head of Total Rewards career path by checking the boxes next to the positions that interest you.
Income Estimation: 
$76,679 - $94,266
Income Estimation: 
$96,119 - $121,238
Income Estimation: 
$96,119 - $121,238
Income Estimation: 
$120,881 - $156,227
Income Estimation: 
$179,661 - $237,967
Income Estimation: 
$208,288 - $283,280
This job has expired.
Employees: Get a Salary Increase
View Core, Job Family, and Industry Job Skills and Competency Data for more than 15,000 Job Titles Skills Library

Job openings at World Insurance Associates, LLC.

  • World Insurance Associates, LLC. Warwick, RI
  • Summary World Insurance Associates is a unique insurance organization offering top products and services from major providers, combined with attentive serv... more
  • 1 Day Ago

  • World Insurance Associates, LLC. Indianapolis, IN
  • Company Overview World Insurance Associates (“World”) is a unique financial services organization with a global network of brokers and specialists who empo... more
  • 1 Day Ago

  • World Insurance Associates, LLC. Iselin, NJ
  • Company Overview World Insurance Associates (“World”) is a unique financial services organization with a global network of brokers and specialists who empo... more
  • 1 Day Ago

  • World Insurance Associates, LLC. Needham, MA
  • Company Overview World Insurance Associates (“World”) is a unique financial services organization with a global network of brokers and specialists who empo... more
  • 1 Day Ago


Not the job you're looking for? Here are some other Head of Total Rewards jobs in the Chicago, IL area that may be a better fit.

  • IAT Insurance Group Rolling Meadows, IL
  • IAT Insurance Group has an immediate opening for the Head of Total Rewards that can be located in our Raleigh, North Carolina, Cheshire, Connecticut, Naper... more
  • 9 Days Ago

  • IAT Insurance Group Naperville, IL
  • IAT Insurance Group has an immediate opening for the Head of Total Rewards that can be located in our Raleigh, North Carolina, Cheshire, Connecticut, Naper... more
  • 9 Days Ago

AI Assistant is available now!

Feel free to start your new journey!