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Servant leader. Board Member. Philanthropist. Unicorn.
A director and counsel at Kyndryl, Malaika Caldwell is the sole benefits and compensation attorney in her company of around 80,000.
Just a month after accepting a role at the global tech company and knowing only a few people in the firm, the Employee Retirement Income Security Act (ERISA) lawyer volunteered to found and colead the company’s Black employee resource group (known as KINs), BeKIN.
“I wanted to be a connector and help foster and create programming and career and professional development opportunities for other employees of color,” Caldwell explains. “It was a passion project that I truly love.” She now jokingly calls BeKIN her “night job.”
Caldwell’s drive to advocate for colleagues she had yet to meet or work alongside makes her a natural servant leader. Even when she was familiarizing herself with the newness of Kyndryl, she found time and space to serve others.
“Do not try to give yourself to a bunch of different causes. You will burn out. Be true to yourself, and you will figure out what service means to you.”
Malaika Caldwell
Months later, still in the early days of her job, Kyndryl selected Caldwell as the young company’s first fellow for the Leadership Council on Legal Diversity (LCLD), an experience Caldwell describes as “incredible.” And when reporting back to leadership at Kyndryl, she saw it as an opportunity to advocate for Kyndryl’s continued investment in opportunities like LCLD for other members of Kyndryl.
Caldwell is a Black female attorney with deep ERISA and global benefits expertise. She rarely sees anyone who looks like her in meetings, especially in an area of the law that rarely attracts women or attorneys of color, and it has been that way throughout her career. It’s why the lawyer is so passionate about advancing the careers of other employees of color and providing them with meaningful opportunities to grow their skill sets.
Caldwell’s service to Kyndryl has not gone unnoticed. Recently, she was selected to receive the prestigious inaugural Heart of Kyndryl Award. She was recognized along with her fellow recipients at a global ceremony in September 2024 in Portugal.
“It’s really rewarding to work with Malaika because she is smart, with good practical judgment, and has strong technical knowledge,” says outside employee benefits counsel to Kyndryl, Spencer Walters at Ivins, Phillips & Barker, Chtd. “It is also very impressive that Malaika has quickly earned the trust of her internal clients at Kyndryl and immediately contributed to such a positive workplace culture, which is not always easy, particularly at a corporate spin-off like Kyndryl.”
Unsurprisingly, Caldwell’s advocacy for colleagues is just a fraction of Caldwell’s service to others. She served on the board of directors for BUILD Chicago, a nonprofit dedicated to gang intervention, violence prevention, and youth development, from 2016 to 2023. She is now joining the board for Chicago Arts Partnership in Education, an organization that helps reach students in Chicago Public Schools through the arts. Caldwell is also a member of the Association of Corporate Counsel Street Law Program, which introduces high school students from underrepresented backgrounds to careers in law.
Caldwell advises younger attorneys who want to give back to seek out associate boards and nonprofits that can benefit from their expertise. The most important qualification? A passion for the cause.
“If you care about the work that you do, you will find time for it,” Caldwell says. “Do not try to give yourself to a bunch of different causes. You will burn out. Be true to yourself, and you will figure out what service means to you.”
In that sense, Caldwell’s community service is incredibly personal. Caldwell grew up on Chicago’s West Side. While her parents raised their daughter to pursue her dreams, her older brothers had trouble seeing past the neighborhood. Though they were all intelligent young men with great potential, they were drawn into gang life and trouble with the law.
Caldwell says community centers and books were her way out of economically impoverished, violent surroundings. Also, Caldwell’s mother was her cheerleader, pushing her to excel in school and seize her dreams.
“My parents did not pursue higher education,” Caldwell says “but they were both so encouraging and instilled confidence in me to always dream big. They would figure out a way to buy me any book that I wanted or needed. That opened up new worlds for me.”
Caldwell still lives on Chicago’s West Side. It’s where she’s from, and it’s the community she wants to empower. She knows firsthand how hope can drive change in underserved and underrepresented communities, and she wants to be part of that change. She says her service work is an obligation. She accessed resources in her community to help her achieve her dreams, and she wants to ensure more people have those same opportunities.
Caldwell’s professional excellence in a male-dominated niche area of the law, coupled with her servant leadership and philanthropic endeavors, makes her a true unicorn. And she works hard to ensure that talented unicorns won’t be so rare in the future.
