Welcome To
Retirement Renegade
Meet the Retirement Renegade Team
The Retirement Renegade team includes the people who help support client education, communication, planning coordination, and day-to-day service. Each team member plays a different role in helping create a clear and professional experience for retirees and pre-retirees.
Based in Franklin, Tennessee, our team works together to support Retirement Renegade’s education-first approach and client-focused service.
Caleb Staggs launched his career at Aetna, where he specialized in helping Medicare recipients navigate the complexities of their coverage options. With a strong passion for education, Caleb is dedicated to empowering individuals to make informed decisions about their healthcare needs. His primary goal is to ensure that clients are well-protected and confident in accessing the services they require.
Having assisted Medicare recipients nationwide, Caleb is thrilled to bring his expertise to the Middle Tennessee area. He understands that each person’s situation is unique, which is why he believes in the importance of personalized consultations. By taking the time to assess individual needs, he ensures that every client receives the coverage and strategies that best suit their circumstances.
As a Certified Financial Fiduciary®, Caleb also specializes in making sure people are protected for retirement as well. He has expertise in making sure that people have all the pieces of the puzzle taken care of, such as tax planning, long-term care planning, Social Security optimization, proper income planning, growth strategies, and expert financial advising. He believes that people who have worked hard their entire lives should have proper planning in place to make sure they can live the retirement of their dreams and not run out of money before they run out of life.
Caleb meticulously reviews all available options for his clients, selecting those that he believes will provide the best protection for his clients in the future. His commitment to outstanding service and support makes him a trusted resource for those seeking to improve their retirement and healthcare experiences.
When he’s not working, Caleb loves cheering on the Tennessee Vols, spending quality time with his wonderful wife and their three energetic dogs, and perfecting his skills on the smoker. There’s nothing quite like the joy of a game day, the companionship of his furry friends, and the satisfaction of delicious, smoked meats.
Dennis possesses a comprehensive background in the field of agri-business, which has served as a solid foundation for his subsequent foray into the financial services industry. He engaged in a fruitful partnership with Tosh Farms, a prominent agri-business entity situated in West Tennessee, focusing on the efficient production of over one million market hogs on an annual basis. Concurrently, Dennis contributed his expertise to the premier producer of Pasture Raised Eggs, Vital Farms, a publicly traded company listed on the Nasdaq exchange (VITL). Remarkably, during his tenure at Vital Farms, Dennis helped facilitate the substantial growth, expanding its egg production capacity from 500,000 hens to a staggering 1.5 million hens, effectively establishing a presence in over 12,000 stores nationwide.
Kelley Rutledge is the Director on First Impressions at Retirement Renegade. Kelley has two decades of experience as a health and wellness professional. Prior to working with Retirement Renegade, she spent a few years designing and implementing fitness programs for individuals and groups of all ages. Throughout the last few years as a wellness coach her focus has been on gaining knowledge in chronic pain and injury prevention. She enjoys educating and encouraging people to live a pain free lifestyle. Kelley’s passions include outdoor adventures and cooking. She lives in Franklin with her husband and has two children. Kelley understands what our clients need and her focus is ensuring quality interactions and excellent customer service.
Eddie Sisneros is the Chief AI & Creative Systems Officer at Retirement Renegade, where he leads the company’s AI Integration Initiative and drives innovation across operations, workflow efficiency, and creative communication.
Combining his background in operations, automation, and content production, Eddie designs and implements AI-powered systems that help the team operate faster, smarter, and with greater clarity. He works cross-departmentally to modernize internal processes, streamline event execution, improve data flows, and support Retirement Renegade’s mission of helping Americans thrive in the retirement red-zone.
Eddie is a graduate of the Generative AI Mastermind program by Outskill founder Vaibhav Sisinty, further strengthening his expertise in applied artificial intelligence, automation strategy, and workflow design.
He also serves as a key creative force behind Retirement Renegade’s educational content, including YouTube, social media, in-office media production, and client experience tools — helping the company communicate complex financial topics with simplicity, clarity, and impact.
Driven by a belief that AI should empower people rather than replace them, Eddie’s mission is simple:
build smarter systems that free teams to do their best work and elevate the client experience.
Jessica Winnett serves as Retirement Renegade’s Director of Marketing. Jessica has an extensive background in digital marketing. She has had the privilege of helping businesses in several sectors achieve geometric results. She thoroughly enjoys serving the women in our community by spreading the message and mission of Retirement Renegade. She is married to Andrew (our President) and homeschools their 4 children. Jessica’s passions include eating great food and trying new Nashville area restaurants, as well as being outdoors with the family.
Danae Dalbey serves as our Administrative Assistant and is an essential part of keeping our office running smoothly. Known for her incredible organization and helpful attitude, Danae is often seen buzzing around the office making sure every client experience is seamless from start to finish.
With an extensive administrative background, Danae brings a high level of efficiency and care to everything she does. She is always ready to step in wherever needed to serve our clients and guests well.
Danae is also a beloved part of the Winnett family. She often helps with the Winnett kiddos and has become like another aunt to them. Her servant-hearted nature, reliability, and warmth make her a valued support to both our team and the families we serve.
Eliana Girdler is our Office Coordinator and the bright, welcoming face you will see when you first walk into our office. She takes great pride in creating a warm and comfortable environment for every client and guest.
Originally from England, Eliana brings years of experience in high-end client service and hospitality. Her background has shaped her attention to detail and her natural ability to make people feel cared for and valued.
Eliana greets visitors with a smile and makes sure everyone feels at home, often offering a drink or refreshment while they wait. From managing the front office to helping ensure appointments run smoothly, she plays an important role in creating the exceptional client experience our firm is known for.
Who is on the Retirement Renegade team?
The Retirement Renegade team includes professionals who support client service, education, operations, marketing, and retirement planning coordination. Team members may have different specialties based on their role and background.
What does the Retirement Renegade team help with?
The team helps support the client experience through communication, education, scheduling, content, planning support, and ongoing service across Retirement Renegade’s processes.
Is the Retirement Renegade team based in Franklin, TN?
Retirement Renegade is based in Franklin, Tennessee, and the team supports clients locally and beyond the local area.
Can I learn about each Retirement Renegade team member?
Yes. This page provides background information for Retirement Renegade team members, including their role and how they support the client experience.
How do I contact the Retirement Renegade team?
You can contact the Retirement Renegade team through the company’s website to schedule a conversation or connect with the appropriate person.
Does the team page replace financial, legal, or tax advice?
No. The team page is provided for informational purposes only and is intended to introduce the people and roles that support Retirement Renegade’s client experience.