Courtney Caldwell

Courtney Caldwell is an award-winning tech founder, marketing strategist, and industry disruptor dedicated to empowering corporate intrapreneurs, solopreneurs, and small business owners. As the post-exit co-founder and former CEO of ShearShare, the largest salon and barbershop space rental marketplace, she helped transform the beauty and barbering industry by introducing flexible, on-demand workspace solutions. Under her leadership, ShearShare scaled to over 1,017 cities, matching licensed professionals with unused salon space and creating new revenue opportunities for business owners.

Before pioneering ShearShare, Caldwell spent two decades leading high-growth marketing teams in the technology sector. She held executive positions at major tech firms, including Vice President of Marketing at Marketing Advocate, Global Director of Oracle’s Worldwide Digital Marketing Strategy & Innovations Group, and Head of Digital Demand Generation and JAPAC Field Marketing at RightNow Technologies, where her leadership in demand and revenue generation played a pivotal role in the company’s $1.45B acquisition.

Caldwell was named a 2024 EY Women in Innovation, a 2023 Cosmopolitan + Digital Undivided “New C-Suite” Honoree, a 2022 Hype Hair magazine 30 for 30, first African-American female to be inducted into the 2021 Texas Military Institute Hall of Fame, Inc. magazine 2019 Female Founders 100 list, is the first African-American female to be named the SMU Cox School of Business Outstanding Young Alumna, the 2019 Ada Lovelace Female Tech Founder of the Year, is a 2018 Dallas Business Journal Women in Technology, and the 2017 L’Oreal Women in Digital NEXT Generation Award winner.

Caldwell is also the first African-American female to be inducted into the Texas Military Institute Hall of Fame and to receive the SMU Cox School of Business Outstanding Young Alumna award.

Beyond tech and entrepreneurship, Courtney is passionate about mentoring fellow founders, fostering innovation, and sharing insights on leadership, business strategy, and digital transformation. She and her husband, Dr. Tye Caldwell, are also proud parents of an NFL athlete, balancing their careers with a deep commitment to family and community.