Kelley C. Pyles

Certified Financial Planner®

Kelley C. Pyles is a CERTIFIED FINANCIAL PLANNER®Certified Long Term Care Specialist, Independent Investment Adviser Representative, and insurance professional. Kelley’s number one priority is ensuring that clients can live their lives to the fullest and make the most of their hard-earned money.

Kelley began her 30-year career in financial services with Allstate Insurance. There she developed a passion for helping others with their finances. She began to focus solely on the financial services industry and retirement planning. She then obtained her CFP® certification, and is proud to serve as a fiduciary adviser acting in the best interest of her clients in every part of her practice.

Kelley’s specialties include income and legacy planning, investment advice, analyzing the proper balance of risk and safety, long term care planning, and tax minimization strategies. She passed the Series 65 securities exam and holds her life and health insurance licenses. 

My Story

She earned her bachelor’s degree from the University of Florida and is an avid Gator fan. In her free time, Kelley enjoys cooking, reading, and spending time with her family and friends. She and her husband, Jim, have two children, William and Katie. Katie is starting her career in the hospitality industry and William is currently serving in the Marine Corps as a crew chief on the CH-53K helicopter.

Kelley has lived in Lake County, Florida since she was a child, and her husband is a Florida native. She has watched The Villages and surrounding retirement communities blossom, and she is proud to help her clients pursue their dreams.

Professional Achievements

Founder's Club Award

2024: $100+ Million in Assets Under Management

Certified Financial Planner

Since 2014

Certified Long Term Care Specialist

Since 2018

Gallagher Life & Annuity

Top 25 Producer: 2021, 2022 & 2023

Association of Financial Educators

Since 2025

Allianz Life & Annuity

A List Producer: 2016 – 2022