Award-winning tech founder and former ShearShare CEO inspiring leaders to innovate, scale, and lead with impact.
5.00 of 5
Top rated!5 of 5
"... I don't believe you could have done a better job on this event. I mean, this one was as close to perfection as I've been a part of in a LONG time"
Code42
Courtney Caldwell is an award-winning tech founder, marketing strategist, and industry disruptor dedicated to empowering today’s innovators. As the post-exit co-founder and former CEO of ShearShare the largest salon and barbershop space rental marketplace she redefined flexibility for beauty professionals worldwide. With a career spanning over two decades in global marketing and technology leadership, Courtney brings firsthand expertise in growth, innovation, and resilience. Her keynotes inspire teams, corporate leaders, and entrepreneurs to embrace disruption, scale intelligently, and lead with purpose in an ever-evolving digital world.
Courtney Caldwell’s entrepreneurial journey is one of fearless innovation and purpose-driven leadership. As co-founder and former CEO of ShearShare, she transformed a traditional industry by introducing an on-demand workspace model for salon and barbershop professionals. What began as a simple idea to fill empty chairs became the world’s largest space rental marketplace, connecting licensed professionals with flexible, affordable workspaces in over 1,017 cities. Her ability to blend technology with community impact made ShearShare a pioneering force in the future-of-work movement.
Under her leadership, ShearShare not only revolutionized the beauty and barbering industry but also unlocked new revenue streams for small business owners. Courtney’s vision empowered thousands of independent professionals to work on their own terms democratizing access to opportunity while redefining how service-based businesses operate.
Before launching ShearShare, Courtney spent two decades leading global marketing and growth teams within the technology sector. Her impressive career includes executive roles such as 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.
Her leadership in demand generation and digital strategy directly contributed to RightNow Technologies’ $1.45 billion acquisition a testament to her ability to drive measurable impact at scale. Courtney’s experience bridging technology and marketing gives her a unique perspective on business transformation, leadership, and customer engagement in a digital-first world.
Courtney’s trailblazing impact has earned her numerous prestigious awards. She was named a 2024 EY Women in Innovation, a 2023 Cosmopolitan + Digital Undivided “New C-Suite” Honoree, and a 2022 Hype Hair 30 for 30 recipient. She made history as the first African-American female inducted into the Texas Military Institute Hall of Fame and the first to receive the SMU Cox School of Business Outstanding Young Alumna Award.
Her accolades also include recognition as an Inc. magazine 2019 Female Founder 100, Ada Lovelace Female Tech Founder of the Year, and a Dallas Business Journal Women in Technology honoree. Each achievement reflects her commitment to breaking barriers, championing diversity, and leading with authenticity.
As a speaker, Courtney delivers high-impact keynotes that blend strategy, inspiration, and actionable insights. She speaks on topics such as entrepreneurship, leadership, innovation, digital transformation, and intrapreneurship helping audiences navigate change and harness creativity within their organizations.
Her speaking style is engaging, practical, and deeply human. Whether addressing corporate teams, industry conferences, or startup communities, Courtney empowers audiences to see challenges as opportunities and to lead with courage and clarity. She draws on her own experiences scaling a company, navigating acquisition landscapes, and building inclusive business cultures that foster growth and innovation.
Outside of her professional achievements, Courtney remains dedicated to mentoring fellow founders and supporting emerging leaders. Together with her husband, Dr. Tye Caldwell, she continues to advocate for entrepreneurship, innovation, and family values. The couple are proud parents of an NFL athlete and actively contribute to community-building efforts that align with their shared belief in resilience, education, and empowerment.
Courtney’s story is a testament to the power of vision, perseverance, and leadership grounded in purpose. From corporate boardrooms to startup stages, she continues to inspire individuals and organizations to embrace change, think boldly, and lead with heart.
5 of 5
"... I don't believe you could have done a better job on this event. I mean, this one was as close to perfection as I've been a part of in a LONG time"
Code42
5 of 5
"The way she moved between talking about her marriage, family, work, teams, and values was almost effortless and it showed an incredible amount of EQ in all facets of her life. -- I honestly wished that I had that level of EQ to be able to do that. In addition, most people who have done as much as she is can get a little ego-centric... but she was so far from it. She addressed her mental health habits openly, and disclosed things that were very personal and did so in a way where no one (as best as I could tell) had any discomfort. Her routines such as starting the day with fruit, meditation, and in prayer with gratitude acknowledges hit me the most. She is an incredibly blessed individual that was a born leader."
Code42
5 of 5
"Honestly, she was one of the best speakers I have seen in my career. -- Her story was inspiring, engaging, relevant, and just brought so much joy to me. After hearing her talk, I took to heart some of the things she does and even took a few of them and implemented them in my daily routine. -- I had a banana for breakfast too! Anyhow, this was a fantastic speaker -- Incredible."
Code42
5 of 5
"My team and I are beyond happy that we chose Courtney as our speaker for our Black HERstory month event! From the second we jumped onto our pre-event call, Courtney was so friendly and truly eager to help us achieve our goals. She really took the time to get to know our organization and ensure she had the impact we were looking for. On the day of, Courtney arrived early to ensure that everything was setup properly to deliver a great experience. Her content was informative, and our team truly enjoyed listening to all her stories. We received incredible feedback about our event and how grateful our team was to welcome Courtney for that time. We really appreciated Courtney’s willingness to answer all our questions, her bright and bubbly personality, her incredible insight, and the advice she left our team with at the end of our call. I would highly recommend choosing Courtney as your next speaker!"
Jay Bloch, DEIB Program Specialist Charthop
Keynote by Courtney Caldwell:
Fear is universal—whether you’re scaling a business, raising a family, or climbing a literal mountain. In this powerful keynote, Courtney and Dr. Tye Caldwell share how fear has been a constant companion on their journey—from navigating the build, scale, and successful exit of an award-winning startup to parenting with purpose an NFL athlete to pushing past physical and mental limits on the world’s toughest climbs as they summited Mount Kilimanjaro.
Through real-life stories and hard-earned insights, they challenge the idea that fear is something to avoid. Instead, they show how embracing fear can be the key to achieving audacious goals. Whether you’re launching a startup, stepping into leadership, making a career pivot or life-changing decision, raising the next generation, or tackling a personal challenge that seems insurmountable, the lesson is clear: the greatest breakthroughs happen when you do it scared.
Audiences will rethink fear, reframe risk, and take bold steps toward their biggest goals.
Three Key Objectives:
Reframe fear as fuel: Learn how fear can be a powerful driver for growth, resilience, and success in all areas of life.
Take decisive action: Develop strategies to push through uncertainty, take calculated risks with confidence, and make bold decisions in business, parenting, and personal challenges.
Cultivate a resilient mindset: Gain insights from real-world experiences—scaling companies, raising a family, and conquering mountains—on how to keep moving forward even when the path gets steep.
Intended Audience: Executives, entrepreneurs, founders, tech professionals, parents, and ambitious leaders looking to break through fear-driven limitations and take bold steps toward their next level of success.
Keynote by Courtney Caldwell:
Raising an All-American versus raising venture capital . . . is there a difference? Join award-winning, married startup founders, Dr. Tye and Courtney Caldwell of ShearShare, as they share their firsthand experience winning in the game of life, love, and parenthood.
Gain valuable insights, practical strategies, and endearing anecdotes from this dynamic duo as they share their 25-year journey navigating entrepreneurship while balancing family life. Whether you're a seasoned business owner, aspiring founder, new parent-preneur, or simply curious about the interplay of personal and professional life in the startup realm, this session promises to enlighten and inspire.
Keynote by Courtney Caldwell:
Delve into dynamic approaches for driving inbound leads across both B2C and B2B segments, ensuring a successful product launch and sustained growth. Gain insights into crafting a comprehensive marketing plan that prioritizes inbound lead generation, leveraging data-driven insights, customer personas, and user journey mapping.
Whether you’re a B2C or B2B SaaS, this session offers actionable strategies to effectively introduce your product to the market and achieve long-term success through inbound leads. Don’t miss out on this opportunity to equip yourself with the tools needed to navigate the competitive SaaS landscape confidently.
Watch Courtney Caldwell in action
