Know Who We Are

We are dedicated to enhancing organizational well-being through comprehensive business solutions and wellness programs.

Our partnerships with industry leaders enable us to offer innovative services tailored to diverse needs.

With a commitment to excellence, we strive to support businesses, governments, cities, schools, and universities in achieving optimal health and productivity.

President • 757-285-4540 • chris@custombenefitsolutions.net

Chris Caldwell was born in 1968 in Blacksburg, Virginia. He graduated from Tabb High School in 1986 and from Christopher Newport College in 1990 with a BA in Business Administration. From 1990 to 1996 he held a management position with Food Lion, leading and growing it into one of the top locations in Hampton Roads.

In 1996 he obtained his insurance license and built a Farmers Insurance agency, which he sold in 2000 to build his own independent agencies, Cardinal Associates and All American Auto Independent Agency. He built both into successful agencies and sold them in 2007, then proceeded to build another independent agency, Cardinal Agency, which he grew and sold before retiring in 2021. His independent agencies represented 50 or more carriers and were highly profitable every year, with millions in premium across multiple companies.

In 2018, Chris began transitioning into a field where he could help others in a different way, becoming a dealer with Action Trackchairs — all-terrain wheelchairs for veterans and the disabled — with a territory spanning five states. These chairs bring independence and normalcy back to people’s lives, enabling them to fish, hunt, and enjoy the outdoors with their families.

After seeing and experiencing the need for better health and wellness options, Chris came out of retirement to join the health and wellness industry — to make a difference by developing a proactive, rather than reactive, approach to health.

Vice President • 757-535-4000 • stacey@custombenefitsolutions.net

Stacey Bennis, born in 1966 in Virginia Beach, VA, is a successful, passionate, and driven businesswoman well known in the Hampton Roads community, with proven success as an executive leader in the automotive finance & insurance industry.

She began her 45-year career in the automotive industry at age 14½, following in the steps of her parents, who owned their own business. Starting as a receptionist/title clerk and later returning to work as an administrative assistant at Checkered Flag, she advanced over the next ten years to General Sales Manager of a successful multi-franchise dealership, earning many awards and accolades along the way. She then accepted an Executive Director position with Priority Automotive Group, where she taught, led, and directed a large sales and finance department at a high-volume Honda store to a position in the top 5% in the country.

Throughout her career she has helped many dealerships develop top performers who advanced to leading positions, and she is highly regarded and sought out by local companies for her expertise in the finance & insurance industry.

After taking two years off to care for her terminally ill husband, Kevin, and to help her granddaughter work through challenges, Stacey changed her career path and obtained her Life, Annuities & Health license. Her venture into the life and health field came from personal experience with her family and the need for better health and mental care options for everyone. Her passion has always been to help others — family, clients, and friends — by teaching people how to be proactive about their health and wellness. She lives by the words she instills in her children and grandchildren: “be the change you wish to see in others.”

Chief Commercial Officer • 919-214-2978 • scott@custombenefitsolutions.net

Scott Little is a distinguished international business executive with over three decades of success in driving high-level sales and marketing initiatives. Since beginning his professional career in 1992, Scott has established a reputation as a versatile leader capable of navigating the complexities of global markets, from Fortune 500 corporations to agile, family-owned enterprises and startups.

Throughout his 30-year tenure, Scott has been instrumental in cultivating and managing cornerstone accounts for some of the world’s most recognizable brands. His portfolio includes strategic partnerships with industry leaders such as Nestle, PepsiCo, Starbucks, Del Monte Foods, Colgate, Reckitt Benckiser, Clorox, Church & Dwight, Novartis, Abbott and BASF.

A seasoned strategist, Scott is recognized for his expertise in new account penetration and his ability to scale business growth on a global level. His leadership extends beyond the boardroom; he is an expert in developing high performing sales teams and leading multi-disciplinary product development projects. His reach is truly global, having spearheaded major initiatives across China, Singapore, Thailand, Malaysia, Indonesia, Vietnam, India, EU and throughout South America.

Scott attributes his enduring success to a collaborative philosophy, effectively aligning diverse stakeholders, from upper management and procurement to engineering and brand marketing, to achieve unified commercial goals. His commitment to global expansion is further evidenced by his extensive international footprint, having logged over three million airline miles in pursuit of business excellence.

Scott holds a B.A. in Business Management & Economics with a minor in Marketing from North Carolina State University.

Chief Officer Private AI • 919-704-6584 • thompson@custombenefitsolutions.net

Based in Raleigh, North Carolina, Thompson Little is passionate about helping organizations leverage AI and emerging technologies to solve real-world business challenges. He earned his Bachelor’s degree in Marketing from North Carolina State University in 2023, where he gained early professional experience through an internship with NC State Campus Enterprises.

After graduation, Thompson joined an AI startup, where he developed experience working with cutting-edge artificial intelligence solutions before transitioning into marketing at IAT Insurance. He later joined Custom Benefit Solutions, where he combines his background in technology, marketing, and business development to help employers identify innovative strategies that enhance employee benefits and improve organizational outcomes.

Thompson is also a licensed North Carolina Life and Health Insurance Agent, bringing a unique perspective that bridges emerging technology with practical business solutions.

In addition to his professional role, Thompson serves as the Chief Technology Officer for the American Marketing Association Triangle Chapter, where he helps drive technology initiatives and supports the chapter’s digital strategy.