Courtney Caldwell
Building a marketplace from zero is a different discipline from running marketing inside a mature business. Leaders who have only operated inside the enterprise tend to under-invest in supply-side acquisition and over-invest in demand-side spend. The question is how to apply enterprise marketing rigour to early-stage growth without losing the founder economics that make scale-up possible.
Courtney Caldwell is the cofounder and former CEO of ShearShare, the salon and barbershop booth rental marketplace acquired in 2024, who helps commercial leaders apply enterprise demand-generation discipline to early-stage growth and marketplace scale.
Full Profile
Why organisations work with Courtney Caldwell
- She has run demand generation at both ends of the company lifecycle: inside Oracle’s worldwide digital marketing group and at RightNow Technologies before its $1.45B sale, and again from zero at ShearShare. Few speakers can argue commercial strategy with that lived range.
- She built and exited a two-sided marketplace in a $500B services category that most enterprise marketers never touch. Beauty and barbering is not adjacent to enterprise SaaS, and her cross-vertical fluency makes her useful to leaders whose growth playbook is too narrow.
- She is a credible voice on founder economics from the inside, including raising venture capital as a Black woman, scaling through Google Demo Day, YC Fellowship and 500 Startups, and selling under financial pressure. The exit was not a clean Silicon Valley story.
- One of a small number of speakers who can move a room from enterprise SaaS marketing to gig-economy workforce dynamics in the same talk, because she has operated in both.
Biography highlights
- Cofounder and former CEO of ShearShare, acquired in November 2024 after scaling to over 1,000 cities.
- Former global director of Oracle’s Worldwide Digital Marketing Strategy & Innovations Group.
- Former head of digital demand generation and JAPAC field marketing at RightNow Technologies, acquired by Oracle for $1.45B.
- Inc. magazine 2019 Female Founders 100 honoree; 2019 Ada Lovelace Female Tech Founder of the Year; 2017 L’Oreal USA Women in Digital NEXT Generation Award finalist.
- 2024 EY Entrepreneurs Access Network cohort member.
- BBA, SMU Cox School of Business; MBA in Marketing, UT Dallas.
Biography
Most enterprise marketers have never had to build supply. Inside a mature SaaS business, the funnel exists, the segments are mapped, and the work is to compound what is already there. Building a two-sided marketplace from zero asks for a different skill: acquiring two customers at once, in different verticals, with different motivations, before either side trusts the platform.
Courtney Caldwell has done both. At Oracle she was global director of the Worldwide Digital Marketing Strategy and Innovations Group. Before that, she ran digital demand generation and JAPAC field marketing at RightNow Technologies in the run-up to its $1.45B acquisition by Oracle. The discipline she carried out of enterprise software was demand-gen rigour at scale: segmentation, attribution, funnel ownership.
She then applied that discipline to a $500B services category that enterprise marketing usually ignores. ShearShare, the salon and barbershop booth rental marketplace she cofounded with Dr. Tye Caldwell, reached more than 1,000 cities and over 70,000 small businesses before being acquired in November 2024. The platform was a Google Demo Day winner, a YC Fellowship and 500 Startups alum, and a 2022 Fast Company World-Changing Ideas honoree.
The exit was not the textbook version. ShearShare was sold to a strategic buyer under financial pressure during a dispute with M&T Bank. Caldwell speaks publicly about both halves of the journey, the recognition lists (Inc. Female Founders 100, Ada Lovelace Founder of the Year, L’Oreal Women in Digital, EY Entrepreneurs Access Network) and the harder economics underneath. That candour, paired with a Fortune 500 marketing pedigree, is the unusual combination she brings to a room.
Key speaking topics
- Marketplace growth and two-sided customer acquisition
- Demand generation and digital marketing at scale
- Founder economics and venture-backed scale-up
- Future of work in the experience and gig economy
- Black women in technology and founder mental health
- Local startup ecosystems outside Silicon Valley
- Partnership, parenthood and entrepreneurship
Ideal for
- CMOs and heads of growth at SaaS and consumer platforms reassessing demand-generation discipline.
- Founders, CEOs and operating partners building or backing two-sided marketplaces and scale-ups.
- Corporate innovation leads exploring services-vertical platform opportunities outside core tech.
- Diversity, leadership and ERG programmes commissioning substantive Black-women-in-tech content rather than generic representation talks.
Audience outcomes
- A clearer view of where enterprise demand-gen discipline applies to early-stage marketplace growth, and where it does not.
- Specific tactics from inside Google Demo Day, YC Fellowship and 500 Startups that translate to corporate venture and intrapreneurship programmes.
- A frank account of what scaling and exiting a marketplace looks like when the cap table and operating economics are under pressure.
- A sharper read on the gig and experience economy from someone who operated a platform inside it, not just analysed it.
Talks
How on-demand platforms are restructuring service work and what that means for corporate workforce strategy.
Key takeaways:
- The economics of converting underused physical assets into supply for a platform business.
- Where the experience-economy thesis holds in services categories and where it breaks.
- Implications for corporate HR, real estate and procurement functions that buy from gig platforms.
Why category-specific marketplaces outperform horizontal platforms in services verticals.
Key takeaways:
- How to size a vertical that horizontal players have ignored.
- Two-sided acquisition tactics for supply-constrained categories.
- The signal that tells a founder when to stay narrow versus expand.
Building a venture-backed company while running it as a married cofounder team with a family.
Key takeaways:
- Governance and decision rights inside a spousal cofounder team.
- Founder mental health and the cost of scaling under pressure.
- What investors look for, and miss, in family-led startups.