Co-Founder & CEO of ShearShare; Trailblazing & Award-Winning Tech Entrepreneur & Marketer
Courtney Wiley Biography
Courtney Wiley 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, Wiley 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.
Wiley 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.
Wiley 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, Wiley 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 Wiley and other top speakers and celebrities.
Courtney Wiley Speaking Topics
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Do It Scared
Fear is universal—whether you’re scaling a business, raising a family, navigating uncertainty, or climbing a literal mountain. In this powerful keynote, Courtney Wiley shares how fear has been a constant companion throughout her journey—from building, scaling, and exiting the award-winning startup ShearShare to parenting with purpose as an NFL mom and pushing past physical and mental limits while summiting Mount Kilimanjaro. Through candid stories and hard-earned lessons, Courtney challenges the idea that fear is something to avoid. Instead, she reveals how embracing fear can become the catalyst for extraordinary growth, resilience, and breakthrough success. Whether you’re launching a business, stepping into leadership, making a bold life transition, raising the next generation, or pursuing a goal that feels bigger than you, this keynote delivers a powerful reminder: the greatest accomplishments often happen when you choose to do it scared.
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Fortified Founders: How Partnership & Parenthood Strengthen the Startup Journey
What does raising an All-American have in common with raising venture capital? More than you think. Join Courtney Wiley — award-winning entrepreneur, startup founder, venture-backed CEO, and NFL mom — as she shares firsthand lessons from building a high-growth company while raising a high-performing son. Through candid stories, practical strategies, and hard-earned wisdom from her journey as cofounder of ShearShare, Courtney explores the parallels between entrepreneurship and motherhood: resilience, discipline, sacrifice, leadership, and believing in potential before the world sees it. Whether you’re a founder, executive, parent-preneur, or someone striving to build both a meaningful career and family legacy, this session will leave you inspired, empowered, and equipped to pursue success without losing what matters most.
Courtney Wiley 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 Wiley to speak at my event?
Our experienced booking agents have successfully helped clients around the world secure speakers like Courtney Wiley 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 Wiley, 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 Wiley or any other speaker of your choice. -
What are the speaker fees for Courtney Wiley
Speaking fees for Courtney Wiley, 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 Wiley are under $10,000 for live events and under $10,000 for virtual events. For the most current speaking fee to hire Courtney Wiley, 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 Wiley speak about?
Courtney Wiley 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 Wiley travel from?
Courtney Wiley generally travels from Dallas, TX, 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 Wiley’s agent?
AAE Speakers Bureau has successfully booked keynote speakers like Courtney Wiley 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 Wiley for your next private or corporate function. -
What is a full-service speaker booking agency?
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 Wiley 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. -
Why is AAE Speakers Bureau different from other booking agencies?
If you’re looking for the best, unbiased speaker recommendations, paired with a top-notch customer service experience, you’re in the right place. At AAE Speakers Bureau, we exclusively represent the interests of our clients - professional organizations, companies, universities, and associations. We intentionally do not represent the speakers we feature or book. That is so we can present our clients with the broadest and best performing set of speaker options in the market today, and we can make these recommendations without any obligation to promote a specific speaker over another. This is why when our agents suggest a speaker for your event, you can be assured that they are of the highest quality with a history of proven success with our other clients.
Courtney Wiley 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, Breaking Barriers, Building Bridges: Thriving as a Woman in Tech, Unveiling Effective Marketing Strategies for Introducing Your New SaaS Product, Future of Work: The Experience Economy and The “Silver Rule”: How to Build & Manage Successful Remote Teams. The estimated speaking fee range to book Courtney Wiley for your event is available upon request. Courtney Wiley generally travels from Dallas, TX, USA and can be booked for (private) corporate events, personal appearances, keynote speeches, or other performances. Similar motivational celebrity speakers are Dr. Tye Caldwell, Jasmine Crowe-Houston, Aniyia Williams, Nicole Yeary and Viola Llewellyn. Contact All American Speakers for ratings, reviews, videos and information on scheduling Courtney Wiley for an upcoming live or virtual event.
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