Meet Malaika K. Caldwell, Esq., LL.M.

Strategic Legal Executive | ERISA Expert | Founder & Principal | Kellogg MBA Candidate ‘27

Malaika K. Caldwell is a strategic legal executive with more than 15 years of experience at the intersection of ERISA, global benefits, executive compensation, and inclusion. She founded ExecuComp Consulting™ to bring that same executive-level counsel directly to individuals and organizations who need it most.

Called a “unicorn” by peers and recognized in Modern Counsel Magazine, Malaika is one of a rare few Black female attorneys in the country with a deep ERISA expertise. She began her career as a Total Rewards leader and then as an Investigator with the U.S. Department of Labor’s Employee Benefits Security Administration. She then built her private practice at AM Law 200 firms — including Ice Miller and Faegre Drinker — advising Fortune 100 clients. In 2022, she joined Kyndryl, the world’s largest IT infrastructure services company, where she serves as Director & Senior Counsel.

A proud West Side Chicago native, Malaika is also a Kellogg MBA Candidate ‘27, LCLD Fellow, and Board Member committed to community and servant leadership. She authors “The Servant Counsel’ newsletter on LinkedIn — a biweekly exploration weaving together business, culture, and the moments that remind us why leadership matters.

Credentials & Recognition

  • J.D., UIC School of Law, 2011

  • LL.M. in Employee Benefits Law, UIC School of Law, 2012

  • Kellogg School of Management, MBA Candidate ‘27

  • LCLD Fellow, 2023

  • Illinois Super Lawyers Rising Star, 2019 & 2020

  • Heart of Kyndryl Award, 2024

  • Featured in Modern Counsel Magazine

  • Former U.S. Department of Labor, EBSA Investigator

Let’s Work Together

Ready to get expert guidance on your compensation, benefits, or career strategy? Reach out and we’ll be in touch shortly.