Community First Insurance recently marked a major milestone—10 years of serving the community—with a celebration that truly lived up to its name. The event was held as a community cookout, bringing together clients, friends, family, and supporters for a day of food, fun, and gratitude.
A Celebration of Support
Nearly 300 people came through during the day, some stopping in for a plate of food, some staying to enjoy the atmosphere, and others making it a full-day celebration. No matter how long guests stayed, each person’s presence added to the spirit of the occasion. The turnout was a powerful reminder of the relationships built over a decade of service.
Family at the Heart of the Journey
One of the most special parts of the day was having founder Jessica’s children present. From the very beginning, they were part of the business—helping with envelopes, writing thank-you notes, and cheering on each step of the journey. Their presence at the cookout gave customers a chance to meet the family members so often mentioned with love and pride.
Teamwork Makes the Day Shine
The Community First Insurance team, along with their families, worked tirelessly to make the day smooth and memorable. Special thanks were given to Sarah Smith for her leadership and commitment in planning and executing the event, ensuring every detail was handled with care.
Entertainment and Fun for All Ages
The celebration featured outstanding entertainment and activities that delighted both kids and adults. DJ Donald Holder Jr. of Holder Entertainment kept the energy high with music, while the Kentucky Characters and balloon artist Dave Carney brought smiles all around. Winchester PD made an appearance, and Backyard Bounce KY provided inflatable fun for children to enjoy. Dedicated volunteers, including John and Lori Ballard and Jemella Deraimo, helped keep everything running smoothly throughout the day.
Honoring Long-Time Supporters
The cookout also included awards to honor those who have been an important part of the Community First Insurance story:
- Sally Holting Spencer – Longest-standing customer, supporting the business since day one.
- Moises – Recognized for the most referrals.
- Danny Flinchum – Awarded as the “#1 Medicare Trouble Maker.”
- Lily Dunn – The very first commercial client, who will be celebrating her own 10-year anniversary with the business next year.
Capturing the Memories
Photographer Olivia Durphy of BabaLou Photography beautifully captured the memories of the day, preserving the joy, laughter, and community spirit that made the cookout so special. These snapshots reflect not just an event, but a decade of dedication, relationships, and growth.
Looking Ahead
For Community First Insurance, this anniversary was more than a milestone—it was a chance to pause and reflect on the trust and support of clients, friends, and family who made the journey possible. With 10 years now behind them, the team looks forward to continuing their mission of putting people and community first for many more years to come.
