Jessica Cannella
Co-Founder and President
Jessica Cannella is the Co-Founder and President of Oak Harvest Financial Group, where she has spent more than two decades helping individuals, families, and business owners make confident financial decisions and build lasting wealth.
Throughout her career, Jessica noticed a pattern. While many women were becoming financially successful, they were quietly asking a different question: Now what? They wanted more than financial security—they wanted meaningful friendships, renewed purpose, greater confidence, new adventures, and a life that felt deeply aligned with who they had become.
That realization inspired Jessica to found GoGo Sisterhood, a community designed for women 40+ who are ready to embrace the next chapter with intention. Built around connection, personal growth, wellness, education, philanthropy, and unforgettable shared experiences, GoGo Sisterhood empowers women to create lives that are rich not only in wealth, but in meaning.
As a speaker, entrepreneur, and community builder, Jessica is passionate about helping women redefine what is possible in the second half of life. She believes financial confidence is only one part of a fulfilling life; true success is having the freedom, relationships, purpose, and courage to design a life you genuinely love.
Her message is simple: The best years are not behind you —they’re waiting to be created. Because the second half of life isn’t about winding down. It’s about becoming the fullest version of yourself
At home, Jessica enjoys spending quality time with her toddler, Sebastian, and biking on the scenic trails of the many parks in the Houston area.
Featured Content & Resources from Jessica
Getting to Know Jessica Cannella and the Story of How Oak Harvest Financial Group Began
4 Most Important Things to Consider When Estimating Retirement Expenses
Women & Wealth: The Power of Financial Planning in Retirement
Webinar: Retirement Transitions
