Financial Planning That Puts You First
At Sears Group, we combine time-tested financial strategies with a deeply personal approach. We help professionals and retirees in St. Petersburg and the greater Tampa Bay area, Virginia Beach and surrounding areas, and nationwide feel confident about their financial future - so they can spend their energy today on the people and moments that matter most.
"Our mission is to educate, guide, and inspire our clients to make confident decisions with respect to the utilization, preservation, and transfer of their life's work."
More Than a Financial Firm—A Lifelong Partner
We believe the best financial plans are built on real relationships—not transactions. Here's what sets Sears Group apart.
Personal by Design
Sears Group was founded on a simple belief: financial planning should be personal. Not transactional. Not product-driven. Personal. We take the time to understand your life—your goals, your family, your values—and build strategies that reflect who you are and where you want to go.
Rooted in Community
What began as a vision to provide thoughtful, client-centered guidance has grown into a trusted practice serving professionals and retirees in St. Petersburg and the greater Tampa Bay area, Virginia Beach and surrounding areas, and nationwide. Our clients come to us at pivotal moments—preparing for retirement, navigating social security and retirement income, simplifying portfolios, planning their legacy—and they stay because we treat every conversation like it matters. Because it does.
Built to Adapt
We don't believe in one-size-fits-all solutions. We believe in listening first, understanding deeply, and building plans that adapt as your life evolves. That's the Sears Group difference—and it's why our clients trust us with their most important financial decisions.
How We Got Here—and Where We're Headed
From our founding to today, every milestone has shaped how we serve our clients.
1995
Sears Group Is Founded
Michael Sears launches an independent financial planning practice with a mission to educate, guide, and inspire clients to make confident decisions about their financial future.
2018
Rachel Sears Joins the Team Rachel brings fresh perspective and a background in accounting and auditing to the practice, focusing on personalized planning for the next generation of clients.
2020
Expanded Services & Reach
Sears Group expands its service offerings and deepens its focus on behavioral finance—helping clients make better decisions by understanding importance of aligning their emotions and values with their financial plan and decisions.
2023
Rachel Assumes Leadership
Rachel Sears takes over as Owner, bringing renewed energy and a commitment to serving clients in St. Petersburg and the greater Tampa Bay area, Virginia Beach and surrounding areas, and nationwide with the same values the firm was built on. Carly also joins the team.
2026
A New Chapter Begins
With a refreshed brand and continued focus on trust, clarity, and real relationships, Sears Group looks ahead to serving the next generation of clients and families.
Meet the People Behind Sears Group
We're a small team with a big commitment: helping you build clarity and confidence at every phase of your financial journey.
Rachel Sears is the Owner and lead Financial Advisor at Sears Group. With a background in accounting from the University of North Carolina Wilmington and early career experience at KPMG, Rachel brings analytical rigor and a genuine passion for helping people navigate life's financial decisions.
Rachel believes financial planning should feel empowering—not overwhelming. She specializes in working with dual-income families, pre-retirees, and military households, helping them build clarity around retirement, investments, and legacy planning. Her approach combines traditional financial strategies with behavioral insights, ensuring clients not only have a plan—but feel confident executing it.
When she's not working with clients, Rachel enjoys spending time with her family, exploring her new home in St. Pete!, and supporting local community organizations.
Carly Crockett serves as the Office Manager at Sears Group, where she supports the team in delivering a seamless client experience. From preparing meeting materials to coordinating client communications, Carly helps ensure every detail is handled with care and professionalism.
A finance graduate of ODU, she has a passion for organization and a genuine interest in helping others, playing a key role in keeping the planning process running smoothly. She enjoys building relationships with clients and takes pride in making their experience with Sears Group as stress-free as possible.
Outside of work, Carly enjoys spending time with her family, exploring the Virginia Beach area, and staying active in her community.
How We Think, Work, and Serve
Our values aren't just words on a wall—they guide every conversation, every recommendation, and every relationship we build.
Trust
Everything we do is built on trust. As an independent fiduciary, we're legally and ethically obligated to act in your best interest—always. No hidden agendas, no conflicts of interest.
Clarity
Financial planning doesn't have to be confusing. We translate complex concepts into plain language and help you see clearly—so you can make decisions with confidence.
Partnership
We work with you, not just for you. We take the time to understand your life, your goals, and your concerns—and we walk alongside you at every step.
Adaptability
Life changes. Your plan should too. We build strategies that evolve with you—through career moves, market shifts, family transitions, and everything in between.
Let's Talk About What Matters Most to You
Whether you're preparing for retirement, navigating a financial transition, or just want a second opinion—we're here to help. Schedule a complimentary conversation and see if we're the right fit.
