Xiomara Leslie’s professional path has been marked by a series of transformative milestones, each building upon her scientific foundation and her steadfast commitment to serving others. Since 2018, she has found success as the principal at Chesapeake Benefits Group Inc., where she leads a team of 30 agents. In this capacity, she focuses on training agents to replicate her skills and knowledge, managing teams effectively and recruiting new talent to strengthen the organization. Ms. Leslie’s expertise in life insurance, health insurance and Medicare planning has cemented her reputation as a leader in helping individuals achieve better lives through informed decision-making and comprehensive coverage solutions.
Prior to her present position, Ms. Leslie entered the insurance industry after an accomplished tenure in corporate America. She partnered with MassMutual, undergoing intensive training that laid the groundwork for her future endeavors. A temporary assignment with Cigna followed, during which she surpassed expectations by achieving 300 percent of her sales target. This exceptional performance led to an apprenticeship with Cigna, where she learned the fundamentals of running an insurance company and benefited from mentorship, office resources and hands-on experience. These formative years equipped Ms. Leslie with the skills necessary to launch her own insurance agency and pursue partnerships such as her collaboration with Integrity through Tony Holland.
Earlier in her career, Ms. Leslie excelled over the course of a decade at Pitney Bowes, initially recruited for what was intended as a temporary opportunity that quickly evolved into a long-term commitment. During this time, she earned national recognition, including six President’s Club Awards with three as a top agent and three as a manager, demonstrating her ability to excel in both individual and leadership roles. The 2010 recession prompted her transition from corporate sales to entrepreneurship, motivating her to build something lasting while supporting businesses and families alike.
Ms. Leslie’s career began in science as a chemist by trade, working as a scientist with the Environmental Protection Agency before conducting research for the National Cancer Institute on rare stage-four diseases. For seven years, she was active as a government contractor until federal shutdowns highlighted the instability of government employment, prompting her eventual shift into the private sector. Ms. Leslie is also noted for her involvement in professional organizations, including her lifetime membership in Alpha Chi Sigma Fraternity. Her commitment to civic service is evident through ongoing support for local senior provider networks, church initiatives and food pantries.
Ms. Leslie’s dedication extends beyond business achievements into meaningful community engagement. During the first recession, she devoted herself to volunteer work that remains one of her proudest accomplishments. She served as education chair for the NAACP and was appointed as a parent guide, traveling throughout her county to recruit teachers and working with MassMutual to provide financial literacy education to middle school students. These roles proved deeply rewarding and ultimately prepared her for leadership in training agents within the insurance field.
Throughout her career, Ms. Leslie has been honored with numerous accolades reflecting her excellence across multiple sectors, including an Outstanding Achievement Award from Johns Hopkins University. She further obtained awards from Aetna Inc., Capitol Office Solutions (Xerox Corporation), Konica Minolta Inc., Pitney Bowes Inc., CareFirst, as well as Top Sales Awards from Delmarva Benefit Group and United HealthCare Services Inc. Ms. Leslie attributes much of her success to self-awareness and personal growth, emphasizing the importance of recognizing flaws and accepting constructive criticism from staff and colleagues as essential elements of continuous improvement.
To support her professional ambitions, Ms. Leslie pursued a formal education, graduating with a Bachelor of Science in chemistry, a credential that has provided a rigorous analytical framework for every stage of her career. She completed graduate coursework with aspirations to become a doctor before discovering her aversion to blood redirected her path toward other scientific pursuits. Later earning another undergraduate degree in massage therapy, Ms. Leslie integrates this knowledge into her approach with clients by combining scientific understanding with wellness principles.
Born in Washington, Ms. Leslie values family above all else. She cherishes large family gatherings filled with laughter, warmth and great food—moments where she feels most at home and appreciated. In addition to spending time with loved ones, Ms. Leslie enjoys decorating spaces, creating art, hosting Sip and Paint events at senior citizen centers, playing bingo and organizing family activities with clients.
Looking toward the future, Ms. Leslie is focused on expanding the impact of Chesapeake Benefits Group Inc., striving for significant business growth while empowering agents to become leaders within their communities. She encourages those around her not to fear their own identities as they embrace business ownership, reminding them that true strength comes from self-acceptance and learning from one’s own choices along the way.