Interviews, North America

Courtney Caldwell – Cofounder & COO at ShearShare

Make sure you are eating well, sleeping well, hydrating well, moving well and socializing well. If you make sure you are doing those basic five things well, you will be surprised how you can push the ball up the hill when it comes to your startup.

Courtney Caldwell is the Cofounder & COO of beauty-tech startup, ShearShare, the largest provider of on-demand salon and barbershop space rentals. The ShearShare app gives licensed beauty and barbering professionals the freedom and flexibility to rent workspace by the day in cities all over the world, while salon and barbershop owners make money on unused space.

Prior to cofounding ShearShare, Inc., Google Demo Day winner 2018, Tech. Co’s Startup of the Year, and a YC Fellowship and 500 Startups alum, Courtney managed an award-winning salon with her husband and cofounder, which was the genesis behind ShearShare. Before that, Courtney ran a boutique consulting firm where she fast-tracked international sales and marketing success for brands such as Zendesk, Zenefits, and Qualtrics. 

Courtney spent nearly two decades building winning teams in tech marketing and has held leadership positions in both early-stage and late-stage technology organizations: vice president of marketing for Marketing Advocate, global director of Oracle’s worldwide digital marketing strategy and innovations group, head of digital demand generation and JAPAC field marketing at RightNow Technologies. Her leadership in demand and revenue generation at RightNow Technologies was instrumental in the $1.45B acquisition of the company.

Courtney recently received an honorary doctorate degree from Miracle University and is the 33rd African-American female to raise $1 million in venture funding. She was named to the 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.

She volunteers with various children’s, education, and civic organizations, and serves on the Advisory Board for Ogle Cosmetology School, the Alumni Board for Southern Methodist University, the President’s Council at SMU, the Board of Trustees for Texas Military Institute, and the Board of Directors for the UT-Dallas Entrepreneurship Council.

Courtney lives in McKinney, Texas, with her cofounder husband, Dr. Tye Caldwell, and is mom to their 19-year-old son, Trey, a cadet and football player at the United States Air Force Academy.

In a nutshell: Tell us a bit about jor job and what role technology plays in it?

As a startup founder in the earliest days, you are everything to every part of the business. Every vision, every strategy, every tactic—from the biggest decision down to the smallest—requires your mindshare. And so that means that my Monday mornings can look completely different from my Tuesday afternoons. I may be fielding a partnership call one hour, reviewing resumes the next, to approving marketing campaigns and meeting with our investors. No day, no two hours look the same. 

At the most basic level, I serve as Co-Founder and COO of beauty-tech startup ShearShare, the first mobile app that lets stylists rent empty salon and barbershop space by the day in cities all over the world. 

Today I can’t imagine doing anything else, but I never thought I would be a startup founder. 

Where did your professional journey start and how did you get to where you are now?

I earned my Bachelors degree from Southern Methodist University in Marketing and International Studies and ended up working in corporate America for 20+ years. I absolutely loved it and honestly thought that I would retire from the corporate world. I worked my way up to running global marketing innovation projects across five continents. 

But one day my husband, Dr. Tye, came home and mentioned a phone call he received about renting out a suite at our salon for a couple of days. Three years later we found ourselves manually matching stylists to empty salon spaces. So when Dr. Tye said, ’Hey, I think this needs to be an app,’ my corporate America hat immediately transitioned to a startup founder.

How did you become a tech startup founder considering the fact you don’t have a tech background? How did you manage that transition from corporate to startup and then tech?

I still ask myself that question. I had grown my career in B2B technology marketing and always worked for companies that were tech-enabled. One of my last 9-to-5s was working at Oracle; before that, I worked at a company that developed customer experience software; before that, online community blogs and forums for different city and state municipalities. I was in full-time ministry for several years and also worked for a company that created online social networks before they were even a thing. 

I’ve always been around innovation and have had a knack for figuring out how to move the needle. So when we started ShearShare, we were truthfully working to first solve our own problem.

I’ve always been around innovation and have had a knack for figuring out how to move the needle. So when we started ShearShare, we were truthfully working to first solve our own problem. When you layer in the advent of Airbnb and the general public learning more about the sharing economy, we knew that whatever we created had to have a tech layer and required automation. Back in 2012, there was no app for monetizing empty salon and barbershop space; we just knew we had to create it. 

We started asking questions and talking to people who knew how to code, people like old CTOs I used to work with, engineers who were clients at the salon, anyone who knew anything about developing a mobile app or building a technology company.

What I’ve learned over the years—and what my husband has always known as an entrepreneur—is that relationships matter. So we started ShearShare by first building on our established relationships.

What skills do you need for a successful career, what is crucial (aside from the tech skills)?

Now that I’m on the other side, I realized that as a young marketer, I wasn’t vocal enough when entering a room or meeting. At one job, I trained four or five of my managers before eventually realizing that I was the secret sauce. 

The advice I would give to another female entrepreneur is actually nothing about running the day-to-day operations of her company. I would want to make sure she was disciplined in her thinking and in how she sets priorities. You also have to be ok doing the non-sexy things first in order to get to the place where you can transition in your business. 

Around year 2 of ShearShare, I had a wonderful female coach named Robyn Ward, and the best advice that she ever gave me is to make sure you are doing five things well every day. And the same advice is one of the first things I would share with the next female entrepreneur. Your days are going to go up and down like a rollercoaster, but no matter what, make sure you are (1) eating well, (2) sleeping well, (3) hydrating well, (4) moving well, and (5) socializing well. If you make sure you are doing those basic five things well, you will be surprised how you’ll be able to push the ball up the hill when it comes to your startup. But you have to feed yourself first, because your business is only as healthy as you are. 

What is the greatest transformation in technology you’ve witnessed in your career?

My mind immediately goes to one thing: mobile transactions. ShearShare wouldn’t be what it is today if that functionality didn’t exist.

While we were going through one of the top accelerator programs in the world—500 Startups out in Silicon Valley—we decided to cold email Joe Gebbia, one of the original founders of Airbnb, and ask for a meeting. He said he would give us 20 minutes of his time and to come on out to headquarters.

To make a long story short, we ended up meeting with him for an hour. In that conversation, Joe said, ‘Honestly, don’t think of Airbnb as the “shared economy godfathers” because Airbnb wouldn’t be here if it hadn’t been for eBay.’ 

See, eBay was one of the first, if not the first, to support money transactions through a mobile device—essentially allowing people to sell and transact products or services without having to be in person.

So beyond the proliferation of the sharing economy, I’d have to say that the most innovative, forward-thinking tech . . . in my opinion . . . has been the ability to transact through a mobile device.

When you think about ‘women’ and ‘technology’, what comes to your mind first?

Not. Enough. I wish that there had been more role models when we first started ShearShare and definitely when I was in school. Had I seen and talked to and witnessed more Black couples building tech companies, I would have nurtured that vision in the recesses of my mind. That’s the key reason why my husband and I are adamant about speaking at career days or taking part in public relations’ opportunities where the rising generation will be the audience. It’s important to be a part of those groups because I never knew a Black Mark Zuckerberg, or a female Bill Gates. The more the next generation can see themselves in you, the better. 

Besides, there is tons of research now that says companies with female cofounders are more successful than when there is an all-male leadership team. So there’s that.

We always hear there are not enough women working in tech. What needs to happen to change that?

The more people see themselves in someone or in a startup founder and a female founder in tech, the better.

Again, it’s modeling. It is so important to serve as an example to young entrepreneurs so that they can see the possibilities.  I especially love what we do at ShearShare because we take something that people naturally gravitate towards—beauty, hair, makeup—and marry it to tech. There haven’t always been a lot of platforms that put those things together. 

And that’s exactly what we are. So we’re able to model for others that whatever you love innately, you don’t have to dismiss it as a career because it doesn’t yet exist in the world. My husband and I are prime examples of people who just followed their hearts and came out on the other side as tech founders.

Who is your tech role model?

My tech role models are venture capitalists Arlan Hamilton and TD Lowe. Both of these women are amazing. They each walked a very tenuous road from their upbringing to Silicon Valley and just figured it out along the way. 

Collectively, they’ve each invested in hundreds of companies that are run by women, LGBTQ, and minority founders. Just spending 10 minutes with them is beyond encouraging.

If you could host a dinner party with three influential people in tech, who would you invite and why?

I’d have to add a +1 and invite four women. I’d love to host a dinner party with Arlan, TD, Serena Williams, and Beyonce. 

For each of these women, excellence is their standard, so I know the conversation would be second-to-none. Plus, Beyonce is from Texas and her mom used to own a hair salon—there’s a lot we could discuss. 

If you could go back in time, what advice would you give to your 14-year-old self?

I would tell 14-year-old myself to keep going – you are doing what you are supposed to be doing.

I would tell myself to keep doing then what I’m doing now—and that’s lead. When I was in high school I attended a military school and came to the realization at a young age that there are a lot more followers in the world than leaders. And that if you just stand up and lead, people will follow. So I would tell 14-year-old self to just keep going – you are doing what you’re supposed to be doing. 

Courtney Caldwell is the Cofounder & COO of beauty-tech startup, ShearShare, the largest provider of on-demand salon and barbershop space rentals. The ShearShare app gives licensed beauty and barbering professionals the freedom and flexibility to rent workspace by the day in cities all over the world, while salon and barbershop owners make money on unused space.

Prior to cofounding ShearShare, Inc., Google Demo Day winner 2018, Tech. Co’s Startup of the Year, and a YC Fellowship and 500 Startups alum, Courtney managed an award-winning salon with her husband and cofounder, which was the genesis behind ShearShare. Before that, Courtney ran a boutique consulting firm where she fast-tracked international sales and marketing success for brands such as Zendesk, Zenefits, and Qualtrics. 

Courtney spent nearly two decades building winning teams in tech marketing and has held leadership positions in both early-stage and late-stage technology organizations: vice president of marketing for Marketing Advocate, global director of Oracle’s worldwide digital marketing strategy and innovations group, head of digital demand generation and JAPAC field marketing at RightNow Technologies. Her leadership in demand and revenue generation at RightNow Technologies was instrumental in the $1.45B acquisition of the company.

Courtney recently received an honorary doctorate degree from Miracle University and is the 33rd African-American female to raise $1 million in venture funding. She was named to the 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.

She volunteers with various children’s, education, and civic organizations, and serves on the Advisory Board for Ogle Cosmetology School, the Alumni Board for Southern Methodist University, the President’s Council at SMU, the Board of Trustees for Texas Military Institute, and the Board of Directors for the UT-Dallas Entrepreneurship Council.

Courtney lives in McKinney, Texas, with her cofounder husband, Dr. Tye Caldwell, and is mom to their 19-year-old son, Trey, a cadet and football player at the United States Air Force Academy.

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