Meet Elana Gillespie

Elana’s journey in the financial services industry began in Kansas City, Missouri, back in 1999, where she spent eight years honing her skills in Underwriting. From there, she took on a new challenge in Executive Benefits Investments, where she thrived for 15 years. During this time, Elana gained a wealth of experience across multiple areas, including Case Management, Claims, Technology, Quality Assurance, and Corporate Audit & Compliance.

After a successful career at an A++ rated company, Elana decided to switch gears and joined the Finance Department of a local school district. There, she managed Payroll, Benefits, Retirement, Tax, and Accounting, expanding her experience in yet another direction.

In 2024, Elana joined The Retirement Planning Group (TRPG) as a Tax Coordinator, eager to find a role closer to home. Her passion for helping others and her extensive background in finance make her a perfect fit for the team.

Outside of work, Elana enjoys an active and adventurous lifestyle with her two children, Daniel and Sadie. Whether she’s cooking up a new recipe, hiking, kayaking, horseback riding, or traveling, she loves making the most of her free time with her family.