The Penny Insurance Team

Meet Our Team

We are a third-generation family-owned business serving the insurance needs of Western North Carolina and Upstate South Carolina for nearly a century. We are licensed insurance professionals, many of whom have been in the insurance business for more than 25 years. We treat clients as individuals, not numbers. We work diligently on your behalf to meet your needs today and in the future. Our goal is to exceed your expectations and create a life-long client, and friend.

 

William Penny Jr

CAPI, President

will@pennyinsuranceagency.com
(828) 692-9171

Will Penny is a Henderson County native and the proud third-generation president of Penny Insurance Agency. He is a graduate of Wofford College and holds a Certified Advisor of Personal Insurance (CAPI) designation from the Aresty Institute of Executive Education at the Wharton School of the University of Pennsylvania and Chubb Insurance. He has been working with Penny Insurance for 30+ years. Will has also been married to Lynn Penny for 30+ years, and is the proud father of four beautiful daughters. He is an avid outdoorsman, enjoying hunting, fishing and golf in his North Carolina home, and is honored to be leading this established boutique family agency as it nears its 100th anniversary.

Lynn L Penny

VP of Business Development

Lynn Llewelyn Penny serves as Vice President of Business Development for Penny Insurance Agency, leading strategic growth initiatives across the Carolinas, cultivating new partnerships, expanding markets, and strengthening long-standing client relationships while helping guide the next chapter of the agency’s nearly 100 year-old legacy.

With a career spanning business development, corporate partnerships, marketing, and nonprofit advancement, Lynn has built a reputation for creating meaningful collaborations that drive revenue and community impact, serving in leadership roles in the sports, entertainment, and nonprofit sectors, in which she has successfully developed sponsorship programs, launched strategic initiatives, and led major fundraising and marketing efforts.  A passionate community advocate, Lynn serves on several nonprofit boards and remains actively involved in arts, athletics, and philanthropic initiatives throughout the region. She is a graduate of Southern Methodist University, proud wife of 30+ years to Will Penny, and mom to four amazing daughters!

Mackenzie Graham

CISR, Commercial Insurance Advisor

Mackenzie Graham recently moved to Hendersonville, after living in Asheville for more than nearly 20 years. MacKenzie studied Criminal Justice at Asheville-Buncombe Technical College and joined the Penny Insurance team in the summer of 2014. MacKenzie is a notary public, licensed in property and casualty insurance, and focuses primarily on commercial lines insurance.

Stacey Allison

Commercial Insurance Advisor

Stacey Allison is a proud Hendersonville native and the mother of two beautiful children. Stacey has been with Penny Insurance for more than 27 years as a commercial lines agent. She has a CISR designation and is licensed in property and casualty insurance. In her free time, Stacey enjoys spending time with her family and being outdoors. 

Cherrie McCoy

Personal Insurance Advisor

Cherrie McCoy joined the Penny Insurance Agency team in the summer of 2017, coming from Nationwide Insurance. She specializes in property and casualty insurance for the Carolinas. Outside of the office, Cherrie enjoys relaxing on the river with friends and family. Residing in Tryon, North Carolina, Cherrie lives with two of her children, Bryna and Satchel, and has a total of four children, two grandchildren and one grand-dog.

Bob Howard

CPCU, ARM, Insurance Advisor

Bob Howard graduated from the University of West Florida and obtained certification from the Associates Institute of America in the areas of risk management, risk management for public entities, commercial underwriting and information technology. Previously, Bob served as the Rutherford County Airport Authority Chairman for two years. In his free time, Bob trains pilots as a licensed FAA flight instructor.

John Gillie

Insurance Advisor

John Gillie attended Brevard College and Appalachian State University. A native of Polk County and father of two daughters, John has been in the insurance industry for 25 years, working at Penny Insurance for 20 years. John is licensed in property and casualty. In his free time, he enjoys biking, running and swimming.

Katie Strickland

Personal Insurance Advisor

Katie Strickland is a Personal Lines Agent at Penny Insurance Agency’s Hendersonville location, specializing in home and auto coverage. Before joining the team, Katie served as a Registrar in the Henderson County School System and brings that same people-first dedication to her clients. She is licensed in North Carolina and is passionate about taking the stress out of insurance by listening closely to each client’s needs and finding the right answers to protect their lifestyle, assets, and loved ones. Outside the office, Katie lives on a small horse farm, is training for the Make-A-Wish Trail Blaze Challenge, and is always up for her next adventure – from scuba diving to dog sledding in the Arctic Circle.