Courtney Caldwell
PROFILE
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, Courtney 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.
Courtney 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.
Courtney 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.
SPEAKING TOPICS
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.
Unveiling Effective Marketing Strategies for Introducing Your New SaaS Product
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.
Future Of Work: The Experience Economy
The "Silver Rule": How To Build & Manage Successful Remote Teams
Digital Marketing: How To Take Digital Demand Generation By The Horns & Win
