About

On a mission to change the world by empowering individuals and organizations to discover fulfilling ways to work and live.

Highlights

Kelly is an accomplished leader and serial entrepreneur with extensive experience leading transformative growth, orchestrating mergers and acquisitions, and executing strategic investment initiatives for over 15 businesses across highly diverse sectors. 

  • Growing 15 diverse businesses

  • 3 acquisitions & mergers, 2 restructures

  • Private equity acquisition of over $300m

  • Investment returns of over 400%

  • Guided hundreds of leaders and executives

  • Worked across over 10 different industries

My Story

Kelly Ryan Bailey is an entrepreneur, speaker, advisor, investor, model, and mama of three.

In 2016, Kelly experienced a debilitating burnout. She had been working 80 hour weeks, traveling 3 days a week, and trying to parent three children. At the same time her five-year-old was diagnosed with dyslexia, ADHD, and high anxiety. 

Prior to this burnout experience, she had spent her professional career facilitating skills-based hiring and learning through data and emerging technology. The focus was always on financial success, best return on your educational investment, and moving up the career ladder. No one ever talked about what makes you happy in life.

Determined to help her daughter find her happy and become a positive influence in her life, she quit her job and embarked upon a long journey of self-help, personal discovery, and therapy that led her to discover growth mindset.

Funny enough, the belief that we can grow and change over time not only helps you navigate all life throws at you, but, as she had already discovered in her work, also cultivates the same skills that employers most struggle to find in any industry, in any job, at any level. Traditionally dubbed ‘soft skills’, these life skills include: emotional intelligence, communication in all forms, creative problem solving, resilience, and empathy.

So Kelly decided to reinvent herself with the commitment to empower individuals and companies with the life skills to discover fulfilling ways to work and live.

Bio

Kelly Ryan Bailey aspires to change the world by empowering individuals and organizations to discover fulfilling ways to work and live through her leadership development workshops, consulting, advising, and evangelist activities.

Kelly is an accomplished leader and serial entre/intre-preneur with extensive experience leading transformative growth, orchestrating mergers and acquisitions, and executing strategic investment initiatives for over 15 businesses across highly diverse sectors.

She played a pivotal role in shaping the skills economy by pioneering the first data and AI technologies to facilitate skills-based hiring and learning, including the first open-source skills taxonomy. 


Kelly’s portfolio-style career also includes angel investing, real-estate, modeling and acting, professional speaking, and her family businesses, The Scone Pony Bake Shoppe, Ferns Restaurant, and The Belfry.

Kelly is the Founder and CEO of Kalimera Future, a global innovation agency dedicated to empowering leaders and organizations of the future. Her additional roles as Fractional Chief AI Strategist at Bast AI, as well as, Braintrust Member and Entrepreneur-in-Residence Mentor at Innovation Foundation powered by the Adecco Group, allow Kelly to further work towards her goals by pioneering innovative solutions and fostering ethical technology use across a multitude of societal challenges.