Her Story
About Chelsey
Chelsey Watson is an experienced insurance sales professional currently serving as an Account Executive at Gallagher, where she specializes in professional liability insurance and executive management coverage for accounting firms. With approximately eight years of experience in the insurance industry and more than 20 years of prior sales experience, she brings extensive expertise in client relationship management, business development, and insurance solutions tailored to professional organizations. In her current role, she focuses on supporting accounting firms through specialized insurance products, helping clients understand their coverage needs and protect their businesses against professional risks.
Throughout her career, Chelsey has held several positions in commercial and professional insurance, including roles at Goodman Gravley Insurance Source, Bukaty Companies, Copeland Insurance Agency, and Pearl Insurance. During her nearly five years at Pearl Insurance, she consistently exceeded sales goals and earned membership in the Executive Chairman's Club for four consecutive years. Her professional background includes experience with professional malpractice, property and casualty insurance, commercial insurance, and business-to-business sales. At Gallagher, she continues to build on this experience by developing insurance solutions for accounting professionals and strengthening relationships with clients and industry partners.
Chelsey's professional approach is grounded in relationship building, honesty, ethics, and integrity. She believes in providing thoughtful guidance rather than relying on aggressive sales tactics, prioritizing trust and long-term client relationships. Her strong work ethic and commitment to excellence have been important drivers of her success, while her role as a mother motivates her to lead by example and demonstrate the value of dedication and perseverance. She studied at Washburn University and holds a background in paralegal and legal studies. She is also pursuing the Registered Professional Liability Underwriter (RPLU) designation through PLUS University to further strengthen her expertise in professional liability insurance.
Her Interview
Ten minutes with Chelsey
01What do you attribute your success to?
I attribute my success to my strong work ethic. I've always been a go-go-go type person who worked multiple jobs when younger. My kids have always been my purpose and motivation because I want to show them the value of hard work. I'm also a bit of a perfectionist who likes to be the best at what I do.
02What’s the best career advice you’ve ever received?
The best career advice is to focus on relationship building rather than aggressive selling. Treat clients like humans and neighbors, not transactions. Note personal details they share, know your policies thoroughly, be responsive, answer calls and emails promptly, and provide genuine customer service. This leads to referrals and winning business even when quotes aren't the most competitive.
03What advice would you give to young women entering your industry?
Insurance is a male-dominated industry often called the Boys Club. Young women need to work a little bit harder to advance. Establish yourself by working hard and being knowledgeable. Find people in executive roles make friends with them and keep them close because they will help you move within the industry when opportunities arise.
04What are the biggest challenges or opportunities in your field right now?
Biggest challenges include competing with AI and ChatGPT when clients quote inaccurate information from it, dealing with difficult argumentative customers who nitpick, strict underwriting guidelines especially for older buildings in property insurance, finding carriers willing to insure in certain markets nationally, and convincing long-term clients to switch carriers even when better rates are available. The market is shifting from hard to soft which presents opportunities.
05What values are most important to you in your work and personal life?
Ethics honesty and integrity are most important. I have a paralegal legal studies degree and believe in doing things the right way. I am honest with clients even if it means telling them to stay with their current carrier. Nothing is worth losing my license over so I refuse any extra compensation outside commissions. Being genuine and authentic with people builds trust.
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