Her Story
About Caitlin
Caitlin McMillan is the Training and Development Manager at Kinsale Insurance, bringing more than 14 years of experience in the excess and surplus lines insurance industry to her work developing talent across the organization. She began her career in underwriting, spending roughly eight and a half years building technical insurance expertise before pivoting to training and development in May 2021. That foundation now informs her approach to teaching, giving her genuine insight into the day-to-day realities of the professionals she trains. In her current role, she leads training sessions and builds and refines the educational resources that help employees strengthen their skills and advance their careers.
Beyond her core responsibilities, Caitlin stays engaged with the broader insurance and HR community through active involvement in several professional organizations. She recently earned a seat on the Richmond Chapter Board of VCIC, an achievement she counts among her proudest, and she continues to participate in the Richmond chapters of the CPCU Society and SHRM. These affiliations keep her connected to industry peers, sharpen her leadership skills, and create space for her to give back to the field that shaped her career.
Mentorship has been a defining thread throughout Caitlin's professional journey, and she credits much of her growth to the guidance of her manager, Amber Sheraton, along with the many underwriting and claims colleagues who shared their knowledge along the way. That experience has become central to how she leads today: she's a strong believer that women in insurance, HR, and training should champion one another rather than compete, and she carries that philosophy into her daily work. As artificial intelligence reshapes how training is delivered and information is accessed, Caitlin sees an opportunity to embrace new tools without losing sight of the human connection that makes learning meaningful. Outside the office, she recharges through stand-up paddleboarding, hiking, camping, and time with her family.
Her Interview
Ten minutes with Caitlin
01What do you attribute your success to?
I attribute my success to the people around me, particularly the knowledgeable colleagues in underwriting and claims leadership at Kinsale who have generously shared their expertise. Working alongside professionals with such diverse insurance backgrounds has broadened my understanding of the business, and I've benefited greatly from mentors who invested their time in helping me grow, especially as I transitioned from underwriting into training and development.
02What’s the best career advice you’ve ever received?
The most influential guidance I've received has come from my current boss, Amber Sheraton, who has mentored me over the past five to six years and played a key role in helping me move from an underwriting-focused position into training and development. I've also learned a great deal from colleagues across underwriting and claims leadership, whose support has helped shape the leader I'm becoming.
03What advice would you give to young women entering your industry?
I encourage women entering insurance, training, or human resources to support one another and actively uplift the women around them. I believe we should focus on developing ourselves while also helping others grow, because we rise together when we share the same goals. My own career shows how important it is to stay open to new directions—skills built in one role can open doors in another, and trusted mentors can help you see possibilities you might not recognize on your own.
04What are the biggest challenges or opportunities in your field right now?
One of the biggest developments I see affecting insurance, HR, and learning and development is the growing influence of artificial intelligence. It has changed so much of the landscape from both an insurance and an HR perspective, and I see it as both a challenge and an opportunity at the same time. For training professionals like myself, it's pushing us to create more efficient and accessible learning experiences while still prioritizing the personal interaction and connection that I value most in my work.
05What values are most important to you in your work and personal life?
Collaboration, professional growth, mentorship, connection, and continuous learning are the values that guide me most. I strongly believe that women should support and uplift one another rather than treating each other's success as competition. I also place a lot of value on professional relationships—my own career has grown because colleagues and mentors were willing to share their expertise with me, and I hope to offer that same encouragement and support to others.
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