Kelly Gillman: A Strategic Powerhouse in Workers’ Compensation and Risk Management 

When it comes to redefining success in the workers' compensation and insurance industries, Kelly Gillman is a name to remember. A powerhouse of strategic networking, collaboration, and innovation, Kelly transforms challenges into opportunities. Her recently earned promotion to Vice President at Captive Resources showcases her relentless drive, brilliance, and ability to bring people together to create meaningful change. 

Kelly’s career has been anything but conventional, and that is precisely what makes her impact so remarkable. She sees beyond obstacles—only options for success. Through creative problem-solving, relationship-building, and an innate ability to see beyond the immediate problem, she has continuously driven results that benefit her organization and elevate the entire industry. 

An Unexpected Path to Impact 

If you had told Kelly in her early years that she would be a leader in risk management, she likely would have laughed. After all, she did not exactly grow up dreaming about workplace safety and insurance policies. But looking back, the seeds of her career were planted much earlier than she realized. 

While studying psychology and biology in college, Kelly worked in a campus hospital. This hospital experience opened her eyes to the preventable injuries that landed patients in the emergency room. Instead of just accepting these situations as inevitable, Kelly found herself asking deeper questions: Why did this happen? How could it have been avoided? What systems failed these individuals? 

That curiosity and desire to create meaningful change ultimately led her to the world of workplace safety. She saw an opportunity to build a career and solve real problems, make a lasting impact, and help organizations foster safer, healthier work environments. 

And from that moment on, Kelly was all in. 

A Defining Moment in Resilience 

Kelly’s path has been shaped by pivotal moments, none more impactful than the experience of being furloughed during the COVID-19 pandemic. 

At the time, she worked for a childcare company that saw its business grind to a halt almost overnight. The financial uncertainty forced the company to furlough 85% of its corporate office, and Kelly, despite her track record of success, found herself among them. 

But in true Kelly fashion, she did not dwell on the setback—she strategized. 

Instead of waiting for a return to normal, she decided that she would never put herself in a position where she could be easily sidelined again. She leveraged the time to network, expand her skills, and build new opportunities. In less than 60 days, she was back—with a promotion. 

But that experience left a lasting mark. 

It reinforced the importance of adaptability, the power of relationships, and the necessity of positioning oneself as indispensable. Just six months later, Kelly's proactive approach paid off when Captive Resources came calling with an opportunity that would shift her career in an entirely new direction. 

The Drive to Succeed: A Competitive Edge 

Ask Kelly what fuels her success, and she will give an honest answer—one that might not be what people expect. 

Fear of failure. 

As an athlete and an intensely competitive person (seriously, don’t challenge her to a board game unless you’re ready for a battle), Kelly thrives on pushing herself beyond limits. She never wants to fail her company, her family, or herself. 

That relentless drive, along with an innate curiosity and passion for problem-solving, has made her a impressive force in the industry. 

Her biggest motivation? Her family. Providing them with a life filled with stability, opportunity, and joy fuels her to strive for excellence constantly. But beyond that, she is driven by a deep sense of responsibility—to her colleagues, clients, and the organizations she serves. 

Building Bridges, Creating Solutions 

One of Kelly’s greatest strengths is her ability to bring people together. She understands that real innovation doesn’t happen in silos—it happens through collaboration, shared knowledge, and a willingness to think differently. 

Throughout her career, she has built a reputation for being a connector and someone who envisions solutions. Whether navigating complex corporate structures, developing new risk management strategies, or mentoring the next generation of professionals, Kelly is always thinking several steps ahead. 

Her ability to foster relationships and build strategic partnerships is a skill she honed under one of her biggest career influences, Toni O'Grady. Watching Toni masterfully balance technical expertise with relationship-building showed Kelly firsthand what it takes to lead effectively in a dynamic industry. 

Leading with Compassion and Vision 

Leadership, for Kelly, is all about impact. 

She defines leadership as a balance of compassion, integrity, influence, vision, and continuous growth. Whether leading a team, mentoring peers, or guiding clients, she approaches every interaction with a deep understanding of the people involved. 

Her philosophy? Meet people where they are, not where you want them to be. 

This approach has not only allowed her to develop strong teams. Still, it has also positioned her as a trusted leader within her industry. She knows leadership has never been about dictating direction but about empowering people to succeed. And that, she believes, is one of the most rewarding parts of her career. 

Lessons That Last a Lifetime 

Through every challenge, every success, and every unexpected twist in her journey, one lesson stands out: 

You cannot make sound decisions without fully considering those affected. 

Early in her career, she made a decision with the best intentions, only to realize later that it had unintended consequences. That experience reinforced the importance of listening, seeking understanding, and ensuring that change is implemented with thoughtfulness and foresight. 

Whether Kelly shapes risk management strategies or makes high-level business decisions, she carries that lesson. She always ensures that the human element remains at the center of her work. 

Advice for Women in the Industry: Own Your Superpowers 

For women entering the workers’ compensation and insurance space, Kelly has one key piece of advice: 

Know your superpowers—and use them. 

Too often, she says, women downplay their strengths or wait for permission to reach their potential. But the truth is, everyone brings something valuable to the table. The key is recognizing those strengths and using them to propel yourself forward—regardless of the room you are in or the experience level you have. 

For Kelly, that meant learning to embrace her competitive nature, leveraging her curiosity, and leaning into her ability to connect and build relationships. Those qualities, paired with an unwavering drive, have positioned her as a leader in her field and a true innovator in the industry. 

The Future is Bright 

With her new role as Vice President at Captive Resources, Kelly is poised to make an even bigger impact that will shape the future of risk management and workers' compensation. 

Kelly proves that success encompasses strategy, adaptability, and an unwavering belief in what IS possible. She is a leader who builds bridges, challenges the status quo, and refuses to accept limitations. 

And she does it all with humor, humility, and a fearless determination that makes her a true powerhouse in every sense of the word. 

Kelly Gillman: a name to know, a leader to watch, and a woman whose impact is only just beginning. 

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