Co-Founder & CEO of ShearShare; Trailblazing & Award-Winning Tech Entrepreneur & Marketer
Courtney Caldwell Biography
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.
Contact a speaker booking agent to check availability on Courtney Caldwell and other top speakers and celebrities.
Courtney Caldwell Speaking Topics
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Do It Scared
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.
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Fortified Founders: How Partnership & Parenthood Strengthen the Startup Journey
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.
Courtney Caldwell Videos
The Key to a Successful Co-Founder Relationship
ShearShare co-founders Dr. Tye and Courtney Caldwell are married co-founders who have found success in both business and their relationship. From...
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How do I book Courtney Caldwell to speak at my event?
Our experienced booking agents have successfully helped clients around the world secure speakers like Courtney Caldwell for speaking engagements, personal appearances, product endorsements, or corporate entertainment since 2002. Click the Check Availability button above and complete the form on this page to check availability for Courtney Caldwell, or call our office at 1.800.698.2536 to discuss your upcoming event. One of our experienced agents will be happy to help you get speaking fee information and check availability for Courtney Caldwell or any other speaker of your choice. -
What are the speaker fees for Courtney Caldwell
Speaking fees for Courtney Caldwell, or any other speakers and celebrities, are determined based on a number of factors and may change without notice. The estimated fees to book Courtney Caldwell are under $10,000 for live events and under $10,000 for virtual events. For the most current speaking fee to hire Courtney Caldwell, click the Check Availability button above and complete the form on this page, or call our office at 1.800.698.2536 to speak directly with an experienced booking agent. -
What topics does Courtney Caldwell speak about?
Courtney Caldwell is a keynote speaker and industry expert whose speaking topics include Black Heritage, Black History Month, Business, Children's Authors, Disruptive Thinking, E-Commerce, Entrepreneurship, Family & Parenting, Future of Work, Futurism, Health & Wellness, Human Resources, Innovation, Leadership, Marketing, Motivational, Spirituality, Teamwork & Teambuilding, Technology, Women in Tech, Work-Life Balance -
Where does Courtney Caldwell travel from?
Courtney Caldwell generally travels from Buffalo, NY, USA, but can be booked for private corporate events, personal appearances, keynote speeches, or other performances. For more details, please contact an AAE Booking agent. -
Who is Courtney Caldwell’s agent?
AAE Speakers Bureau has successfully booked keynote speakers like Courtney Caldwell for clients worldwide since 2002. As a full-service speaker booking agency, we have access to virtually any speaker or celebrity in the world. Our agents are happy and able to submit an offer to the speaker or celebrity of your choice, letting you benefit from our reputation and long-standing relationships in the industry. Please click the Check Availability button above and complete the form on this page including the details of your event, or call our office at 1.800.698.2536, and one of our agents will assist you to book Courtney Caldwell for your next private or corporate function. -
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AAE Speakers Bureau is a full-service speaker booking agency, meaning we can completely manage the speaker’s or celebrity’s engagement with your organization from the time of booking your speaker through the event’s completion. We provide all of the services you need to host Courtney Caldwell or any other speaker of your choice, including offer negotiation, contractual assistance, accounting and billing, and event speaker travel and logistics services. When you book a speaker with us, we manage the process of hosting a speaker for you as an extension of your team. Our goal is to give our clients peace of mind and a best-in-class service experience when booking a speaker with us. -
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Courtney Caldwell is a keynote speaker and industry expert who speaks on a wide range of topics such as Do It Scared, Fortified Founders: How Partnership & Parenthood Strengthen the Startup Journey, Unveiling Effective Marketing Strategies for Introducing Your New SaaS Product, Digital Marketing: How to Take Digital Demand Generations by the Horns & Win, The Riches are the Niches: How Solving Your Own Problem Leads to New Innovation and Unlimited Leadership: How Working in Full-Time Ministry and Being an Army Brat Prepared Me for Entrepreneurship. The estimated speaking fee range to book Courtney Caldwell for your event is available upon request. Courtney Caldwell generally travels from Buffalo, NY, USA and can be booked for (private) corporate events, personal appearances, keynote speeches, or other performances. Similar motivational celebrity speakers are Dawn Dickson, Leah Solivan, Nicole Yeary, Erik Qualman and Tonya M. Evans. Contact All American Speakers for ratings, reviews, videos and information on scheduling Courtney Caldwell for an upcoming live or virtual event.
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