Our Story
Our story

Trailhead Financial Group was founded in 2024 by Michael Jay Raymond, whose journey in financial services began when he joined the industry in 2018. After establishing a practice in Western North Carolina and Central Florida, and leading a successful team for several years, Michael launched Trailhead Financial Group to provide a fresh approach to financial services. 

 

At Trailhead Financial Group, we see financial planning as a journey—one that’s unique to each individual. Our goal is to empower clients and help them grow in financial confidence, so they have the freedom to pursue their own purpose and passions. We listen intently and seek to understand each client’s unique circumstances before offering comprehensive, transparent and holistic financial advice. 

 

Whether you’re taking your first steps toward financial independence, growing a family, preparing for retirement or enjoying your well-earned golden years, we’re here to guide you. We also specialize in empowering women and supporting business owners on their financial journey. In addition, we are proud to serve the Spanish-speaking community.

Trailhead Financial Group is equipped to meet you wherever you are on your financial path and help you each step of the way. Let us be your guide on this journey.

Trailhead Financial Group our story image 1
Michael Raymond
Michael RaymondWealth AdvisorChFC®, FIC, CEPA®

Michael joined Thrivent in 2018 and is the founding member of Trailhead Financial Group. He is responsible for portfolio management and investment services. He also helps our clients plan for retirement, develop wealth transfer strategies and address complex business structuring.   

  

Prior to joining Thrivent, Michael served in the U.S. Army as an airborne infantryman. After attending the Special Forces Assessment and Selection and the Special Forces Qualification Course, he served as a senior medic until he retired.  

 

Michael earned his bachelor’s degrees in philosophy and Spanish from the University of North Carolina – Asheville and graduated magna cum laude. He now serves on the UNC Asheville Foundation Board of Directors and the Alumni Board of Directors and is the Philanthropy Committee Chair.   

 

Outside of work, Michael loves spending time with his beautiful wife, Vicky, their two sons, Oliver and Benjamin, and their dog, Georgie. His hobbies include hiking, camping and volunteering. He currently volunteers for the Boys and Girls Club of Henderson County. In addition, he is working toward his MBA at the UNC Kenan-Flagler School of Business.  

 

Brittany Killeen
Brittany KilleenExecutive Assistant

Brittany joined Thrivent in 2026 as an Executive Assistant to Michael Jay Raymond. She’s passionate about making a meaningful difference in people’s lives—even in the small, everyday moments. She was drawn to Thrivent’s client first approach and Trailhead’s focus on clear, actionable next steps. She loves helping clients feel cared for, informed, and confident before and after every meeting.

Before joining Trailhead, Brittany spent five years as a realtor and broker serving Western North Carolina, guiding individuals and families through important decisions with clarity and compassion. She also brings two years of experience as a legal assistant, strengthening her background in documentation, organization, and client communication. She supports the Trailhead team with scheduling, workflow coordination, and Salesforce documentation, and is currently pursuing her Bachelor of Science in Health Science.

Outside of work, Brittany finds the most joy in spending time with her two children, Eli and Olive. Whether they’re hiking local trails, discovering hidden scenic spots, or simply soaking in Asheville’s natural beauty, time outside is where she feels most grounded. She’s also passionate about health and fitness and enjoys staying active, traveling, and finding new adventures to share with her kids.

Vicky Raymond
Vicky RaymondInsurance Associate

Vicky joined Thrivent in 2019 as an office professional supporting Michael’s growing practice. In 2024, she earned her Life and Health insurance licenses and now serves as an Insurance Associate for Trailhead Financial Group. She specializes in serving young families, single mothers, business owners, and nonprofits within the Hispanic and Latino communities through financial education and the implementation of insurance strategies.

Vicky previously worked as a Spanish language interpreter in medical and community settings, ensuring meaningful access for Hispanic individuals during appointments, community events, and educational interactions. She also served Buncombe County Schools as both an interpreter and coordinator of the Language Services Office, supporting effective communication among families, students, and school staff.

She earned her bachelor’s degree in modern Languages teaching English as a Foreign Language in Colombia. Vicky later completed a master’s degree in Audiovisual Translation from the University of Cádiz in Spain and has worked as a freelance translator for nine years.

Outside of work, Vicky enjoys spending time outdoors with her sons, Oliver and Benjamin, her husband Michael, and their dog Georgie. She volunteers in her church’s kids’ ministry, assists Hispanic community members navigating school and healthcare systems, and enjoys reading and watching documentaries about fashion history and design.

Gary Everhart, Jr.
Gary Everhart, Jr.Financial Advisor

Gary joined Thrivent in 2015 after over two decades as an independent financial advisor. He is responsible for retirement planning solutions, insurance planning, and risk management tailored to each client’s needs – expertise reflected in his Certification for Long-Term Care (CLTC) and Retirement Income Certified Professional (RICP) designations.

Gary began his career in 1993 with life, health and senior planning specialty firm Family Security Corporation in North Carolina’s Triad region after graduating from the University of North Carolina at Chapel Hill.

Gary has led a life of service through Jaycees and Rotary, and has served alongside his team through Thrivent Action Teams for over a decade. He has been a church deacon, Rotary District Chair for Coins for Alzheimer’s Research Trust (CART) Fund, and currently serves on the board of the Triad Fellowship of Christian Athletes.

Outside of work, Gary loves spending quality time with his bride Carrie and their children, Emerson and Oliver. He enjoys following his kids’ sports – tennis, soccer, swimming, golf, and basketball. Gary and Carrie are avid travelers, and look forward to their ever-expanding list of adventures together.

Walker Hart
Walker HartFinancial Advisor

Walker joined Thrivent in 2026, bringing 17 years of experience in insurance planning and financial services. A diverse professional background that includes business ownership in construction and technology informs a grounded, real‑world perspective when guiding clients through retirement planning decisions. Walker has served hundreds of clients and holds securities registrations and insurance licenses across multiple states throughout the Southeast. With advanced securities licensing, Walker provides comprehensive retirement planning built on clarity, trust, and long‑term focus.

Outside of work, Walker and spouse Angie enjoy spending time outdoors, especially fishing and boating in the mountains of Western North Carolina and along the South Carolina coast. Family is central to life, with time spent enjoying children and grandchildren. Personal interests include following aviation pursuits, supporting a youngest son while touring with the bluegrass gospel group The King James Boys, and sharing a love of Atlanta Braves baseball.

Corey Sturdivant
Corey SturdivantEngagement Leader

Corey Sturdivant joined Thrivent in 2018 and brings a rare combination of hands-on community experience to his partnership with Trailhead Financial Group. He understands how mission-driven organizations create lasting impact and brings that same philosophy to everything he does alongside our team.

His background in nonprofit work, higher education, and faith-based ministry gives him a unique lens for understanding what genuinely moves people toward action and trust. Whether it is developing community partnerships, creating engagement opportunities, or helping our team show up well at local events, Corey is a connector who makes our presence in the community more meaningful and more memorable.

When he is not serving advisors and their communities, Corey enjoys cooking, playing tennis, and traveling.

Although Corey is not a member of Trailhead Financial Group he partners with the team to develop community partnerships and create engagement opportunities.

Field Practice Solutions (FPS)
Field Practice Solutions (FPS)Strategic Operational Partnerships

At Trailhead Financial Group, we believe our clients deserve both meaningful relationships and exceptional service. To help ensure every detail is handled with care, we partner with Thrivent's Field Practice Solutions (FPS) team, a dedicated group of professionals who support our advisors and staff behind the scenes.

 

Serving as an extension of our practice, the FPS team assists with account servicing, appointment preparation, paperwork processing, client follow-up activities, marketing support, and a variety of administrative and operational tasks. Their partnership allows our advisors to spend more time focused on what matters most: building relationships, understanding your goals, and helping you make confident financial decisions.

 

Together, our local Trailhead team and the FPS team work to provide a seamless experience, combining personal service with the operational support needed to serve clients efficiently and effectively.

Ready to connect?

We'd love to answer any questions you may have and start learning about your goals. We can meet however you're most comfortable—phone, virtual or in person.

Or call us directly: 877-958-6603

Licensing is available through your State Insurance Department’s website, which can be located through the National Association of Insurance Commissioners website.

Thrivent financial advisors and professionals have general knowledge of the Social Security tenets. For complete details on your situation, contact the Social Security Administration.

Not all team members may provide all products, programs and services in all states.

Not all team members may office at the locations listed.

* as of December 31, 2024

** Thrivent and its financial advisors and professionals do not provide legal, accounting or tax advice. Consult your attorney or tax professional.

Rating is based on Thrivent’s financial strength and claims-paying ability. Does not apply to investment product performance. For information on this rating, visit the rating agency's website.

Designations
For additional information on professional designations and the requirements to earn them, visit https://www.thrivent.com/designations