Alyssa Bailey on Confidence, Clarity, and Career Growth

In this episode of Founders Future with host Olivia Sammons, we sit down with Alyssa Bailey, founder of Rise Up Career Coaching. Alyssa shares her journey from spending 15+ years climbing the corporate ladder in retail and marketing technology to launching a coaching practice for ambitious professionals who feel overlooked, underpaid, or stuck—despite doing everything “right.”Drawing from her corporate experience, Alyssa breaks down her CLEAR framework, designed to help mid-career professionals gain clarity, build confidence, and advocate for themselves without playing office politics. She also discusses overcoming imposter syndrome, growing a coaching business organically through LinkedIn, and balancing entrepreneurship with motherhood—making this an encouraging conversation for anyone ready to stop waiting to be chosen and start choosing themselves.