Leaving something you love isn't a betrayal. Holding both the love and the cost taught me it can be the clearest sign of how much you've grown.
Kimberly Isley-Pesto, MATD · In Her Own Words
Her Story
About Kimberly
Kimberly Isley-Pesto, MATD, is Director of Inflight Learning and Compliance at Endeavor Air, a Delta Connection carrier. She leads the Minneapolis-based inflight function, overseeing inflight training, auditing, and compliance with FAA regulations. Drawing extensive experience at the intersection of learning and development, regulatory compliance, and aviation, she guides instructional design updates and advances the audit and regulatory readiness programs that strengthen both safety protocols and the customer experience for flight attendants.
With close to a decade of experience in aviation and a broader career spanning safety, talent development, and capability building, Isley-Pesto has held key leadership roles at organizations including United Airlines and MV Transportation, where she directed large-scale training and safety strategies across national and global operations. Her work consistently centers on aligning learning initiatives with organizational vision, regulatory standards, and measurable performance outcomes.
She holds a bachelor's degree in Business Administration from Fontbonne University and a Master of Arts in Training and Development from Roosevelt University. Her credentials include certifications in facilitation from Development Dimensions International, e-learning instructional design, and evaluative measures for learning. Among her recognitions, she has received United Airlines' prestigious United 100 Award, the company's top recognition, and the National Express Group Values Award for Innovation Excellence.
Isley-Pesto maintains active involvement in the Association for Talent Development at both the national and Chicago chapter levels, the American Society for Training and Development, and the National Safety Council, reflecting her ongoing commitment to advancing the training and development profession.
Her leadership philosophy is rooted in servant leadership, authenticity, and genuine human connection. "I truly believe that when we cross paths with another person, we should leave them either the same or better than we found them," she says. This philosophy extends to her volunteer work as well. For over a decade, she served as a Corporate Fundraiser for Special Olympics Illinois, developing fundraising strategies and engaging corporate donors in support of the organization's mission.
Isley-Pesto attributes her success to a continual hunger for learning and an unshakable belief that she can always keep growing. She follows what she calls the KIP philosophy: Keep Improving Performance. "As I improve, I try to help others improve alongside me," she explains. Her advice to young women entering the field: "Be deeply confident in what you bring to the table, even if that means being willing to stand alone until you find the right opportunity." The best career advice she has received, and now shares, is to know your worth and never be afraid to ask for it.
Her Interview
Ten minutes with Kimberly
01What do you attribute your success to?
I attribute my success to a continual hunger for learning and an unshakable belief that I can always keep growing and improving. There's a saying that it's never too late to become who you were meant to be, and I live by that idea — I'm always evolving, always asking myself what the next chapter looks like and how I can get better at what I do. As I improve, I try to help others improve alongside me. I call this philosophy KIP: Keep Improving Performance.
02What’s the best career advice you’ve ever received?
The best advice I've ever received is to know my worth — and to never be afraid to ask for it.
03What advice would you give to young women entering your industry?
I'd tell young women to be deeply confident in what they bring to the table, even if that means being willing to stand alone until they find the right opportunity. It's okay to go it alone sometimes, because the courage to walk out on your own path is often exactly what carries you to the next step in your career.
04What are the biggest challenges or opportunities in your field right now?
The challenge I've seen repeatedly over the last five years is that many organizations aren't willing to give employees the autonomy to make decisions and move work forward on their own. We talk about "failing fast," but I don't think organizations truly want people to fail — so instead, they become afraid of mistakes altogether. I believe that unless a mistake could cause real harm, it's important to let people stumble, learn from it, and grow, as long as they don't repeat the same error.
05What values are most important to you in your work and personal life?
Servant leadership is the value that comes to mind first for me. As a leader, I believe it's important to put myself in others' shoes so I can genuinely support them — and that support has to come from a place of authenticity. Connecting with people on a real, honest level matters deeply to me, and honestly, the line between my personal and professional life blurs here, because meaningful connection matters everywhere. I truly believe that when we cross paths with another person, we should leave them either the same or better than we found them. That genuine human connectedness is at the core of what's important to me.
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