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Jessie Stirling

Investment Analyst
Wealth Advisor


Jessie is a Careful Analyzer, Quick-Witted Confidant, Compassionate Friend and Wife, Avid Hockey Fan, and Believer in Making Numbers Fun

Jessie is an Investment Analyst and Wealth Advisor with Stephens Wealth Management Group (SWMG). She utilizes her analytical background as a member of our Investment Committee and overseeing trading and model portfolios for the team. She also helps her clients envision and achieve their financial goals by providing an approachable strategy to holistic wealth management.

Before joining SWMG in 2021, Jessie worked as a Private Wealth Financial Consultant with Wells Fargo Advisors for six years where she honed her portfolio management and advisory skills. She also previously worked at Bank of Ann Arbor in their mortgage and consumer departments. She completed Level I of the Chartered Financial Analyst (CFA®) Program in December 2019 and is a Level II Candidate.

Service & Leadership

Jessie spends her time volunteering in both Washtenaw and Oakland Counties, namely in the Ann Arbor community where she is a member of Women’s Exchange of Washtenaw and the Huron Valley Alumnae Chapter of Alpha Gamma Delta. She is also active in United Way of Washtenaw County’s Emerging Philanthropists group, where she previously served as Committee Chair and received UWWC’s Volunteer of the Year award in 2018. She volunteers as the Social Media Manager for both the Oakland University DIII and Birmingham Unified Hockey teams.

Jessie's Money Story

From a young age, my family instilled in me both a comfortable and cautious approach to money.  We valued earning our way and understanding the balance between affording the things you want and saving for the future. One of the people who advocated for this most was my Grandpa Charlie, who first encouraged us to open savings accounts and taught us the value of compound interest. I remember him explaining, in simple terms, what a stock was and how to allow your investments to grow—childhood me thought it was so cool that you could own a (very small) part of companies like McDonald’s.

He also valued education.  When I became interested in math and finance, he encouraged me to deepen my knowledge and pursue my goals. Throughout college I thought I wanted to be an actuary, but quickly learned that I not only preferred my finance classes, but also I needed a job where I could work with people.  I pivoted my job search toward either a Financial Analyst or Advisor role and soon connected with a team at Wells Fargo Advisors, where I was able to work with both the logical and personable sides of my brain. Grandpa Charlie made sure I started contributing to my retirement plan as soon as possible.

From him, as well as my entire family, I learned how important it is to start these conversations early to instill confidence and awareness around money, which is so often a daunting and uncomfortable subject. As my career develops with SWMG, I hope to continue to share these values with my friends, clients, and their families.

Jessie Stirling

Education and Designations

Bachelor of Science, Actuarial Mathematics and Mathematics of Finance and Risk Management, University of Michigan

Chartered Financial Analyst (CFA®) Program Level II Candidate

Life, Accident and Health Insurance Resident Producer - Michigan

Outside of the Office

Originally from Dexter, Jessie currently lives in South Lyon with her husband Matt and dog Memphis. In her free time, she enjoys playing golf, crafting, and spending time with family. She loves to go Up North and to travel whenever possible. She can often be found in a hockey rink or at Michigan sports games.

Investment advisory services offered through Stephens Consulting, LLC, a SEC registered investment adviser, doing business as Stephens Wealth Management Group (SWMG).


5206 Gateway Centre, Suite 300
Flint, MI 48507
Phone: 810.732.7411
Fax: 810.732.8190
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712 S. Oregon Avenue
Tampa, FL 33606
Phone: 813.251.1879
Fax: 813.251.1716
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Investment advisory services offered through Stephens Consulting, LLC, a SEC registered investment adviser doing business as Stephens Wealth Management Group (SWMG).  SWMG is not a registered broker/dealer.  SWMG investment adviser representatives may only conduct business with residents of the states and/or jurisdictions for which they are properly registered. Therefore, a response to a request for information may be delayed. Please note that not all the investments and services mentioned are available in every state. Investors outside of the United States are subject to securities and tax regulations within their applicable jurisdictions that are not addressed on this site. Contact our office for information and availability.

Links are being provided for information purposes only. SWMG is not affiliated with and does not endorse, authorize, or sponsor any of the listed websites or their respective sponsors. SWMG is not responsible for the content of any website or the collection or use of information regarding any website's users and/or members.  Important Disclosure