A Discussion with Vanessa Ogle, Founder, Enseo and Founder of HigherHill Studios

Emily Chang: Hi. I’m Emily Chang. Author of Brotopia. Welcome to the SHEconomics series honoring women who are blazing trails as CEOs and founders. Today I am joined by Vanessa Ogle, founder and chair of Enseo, a company that powers digital media for the hospitality industry, education, senior living communities and more.

Vanessa, it's so great to have you here. Thank you so much for joining us.

Vanessa Ogle: Thank you for having me.

Emily: So you actually sold Enseo in the last year and started a new thing. First, tell us, how did you make the decision to sell the company?

Vanessa: Well, we had retained a banker to try to buy some other companies because we actually did very well through the difficulty of the COVID crisis and the hospitality industry, and I knew that some of our competition wasn't doing as well, so I was gonna buy some other companies. And because we had done so well, a couple of the big PE firms came in and they made me an offer I couldn't refuse.

Emily: What was it like—kind of letting go?

Vanessa: You know, it's hard. There's no doubt that it's hard, but everybody says, your company is your baby. And I founded it and I bootstrapped it for 22 years but it's not my baby. I have children.

So, having gone through the last two years has, I think, uniquely put me in a position and a mind-frame to be able to prioritize my family in a way that... I always think the company will do better. I always think that the value's gonna go up. I think every entrepreneur does. So recognizing where my priorities were and that what was enough, that, this last two years put me in the place to be able to make that decision and do it with a clear conscience.

Emily: It's interesting that the company was doing well because powering digital media for the hospitality industry in the middle of a pandemic with everybody stuck at home, nobody traveling, it sounds like it would've been the opposite. Talk to me about how COVID impacted the business and how you navigated that as a CEO and a mom.

Vanessa: Well, it was terrifying. The business really... the bottom of the business dropped out completely from under us. But having been doing this for two decades, we've seen other crises before and the one thing I knew is that we had to act quickly. And we did, we acted decisively and quickly and made some really hard decisions to put people on furloughs and layoffs and to change salaries for team members. And then we were lucky enough to get a PPP loan, which really bred life back into the business.

I hired my entire team back, which a lot of companies didn't do. And we immediately went to work doing what we always do, which is innovating. So we're really good at doing new things and I said, we have to take everything that we've done before, scrap it and design all new products that are gonna help the market come back. And we did. And we delivered new products to help people come back and be able to travel, touchless technology, temperature technology, IOT safe technology, and that was very well received by our customer base. And so we were able to really use innovation and corporate culture to pull through and to have a very successful year.

Emily: You also, as I understand, were the first to bring Netflix to hotel rooms. Talk to me about the initial innovations.

Vanessa: Well, the Netflix story is a great one because, being a woman in business, you know, being in front of things isn't always easy. And I remember being well very close to this office right now, at the Netflix headquarters, and trying to get the Netflix team to convince... to allow us to have access to their technology. And they were really big supporters of ours.

It took a while, but once they said, yes, they put their power behind us—let us give it a shot. And when we made the technology work, they celebrated us and supported us ever since. And now it's, you know, a hundred million guests a year get to use our technology to watch Netflix in their hotel rooms.

Emily: Your technology is also being used to help keep kids safe at school, keep women safe at work. Can you explain that to me? How does it work?

Vanessa: Yeah, so that's my favorite technology that we've launched. We took the same infrastructure that we put in hotels, in schools, that was a digital entertainment infrastructure, and we added other pieces of IOT technology to that so that we could help geolocate where someone was when they were in distress.

And so, we created these buttons, like a panic button, but a don't panic button so that a teacher in a classroom can focus on teaching in the classroom. Because if there is an event that's an emergency, they can push that button and immediately first responders know where they are, who they are, and they need help and they know that first responders are on their way. And the same technology is used for housekeepers in hotel rooms across the country.

Emily: How did you make the decision? I know you spent some time in corporate America running billion-dollar public... you know, publicly traded businesses. How did you make the decision to leave and start your own thing?

Vanessa: Well, I was running a division of a big publicly traded company and the division that I was running was kind of the James Bond division, as it were, right? Like we didn't sell a lot of things, but we sold to the financial industry; we sold to the hospitality industry. So it was low volume, but very, very, very high end solutions. And the new publicly traded company that had come in and bought our organization, they wanted to be a media company more than a technology company.

And so, I went to the board and convinced them that I could do better for them if they loaned me the money personally, for me to start a new company and then I would buy the assets and run it as an independent entrepreneurial venture. And they trusted me enough to do it and funded me with some loans and I was off to the races.

Emily: Talk to us about your evolution as a founder and a CEO—you know, running a new company and in this new role where the buck stops with you.

Vanessa: Evolution as a founder and CEO is... it's been the most amazing journey. It's just been a spectacular journey. At first, I was so worried that I didn't deserve to be the CEO, that I, second... I was my worst critic. I was my biggest second guesser and I was defensive all the time about what I should do; what I shouldn't do.

And over the years, over living through crises and innovating and winning business and growing businesses, I learned that I actually have my job for a reason. And the most important thing I did was I built a great team. And I built the best leadership team that I could find and got people that I had no business having at a company my size. They way outclassed the business, but because of the culture that we offered them and the freedom that I offered them to do their job their way, I brought in some amazing talent and that allowed the company to grow even more.

Emily: So how do you think you're different today than the day you started the company?

Vanessa: I'm very different. I am very different. I'm much more confident. But I would say I'm much more quietly confident now than I was then. So when I started the business, I wasn't even 30 years old. I looked like I was about 15. I was just like big fluffy hair and big eyes and that was it. And I was so busy trying to prove that I was good enough to do it, that I missed a lot.

And I missed a lot of the subtlety of, you know, there's a quiet confidence of just knowing that you know things and knowing that you are leading in the right direction that lends the people around you confidence. And that inspires them to do even more than they would have otherwise.

And so, I think wisdom of several decades of doing this, I think I have more confidence to trust my team, to delegate to my team, to understand that entrepreneurial intuition is real and it matters and to listen to that, which makes us move faster and do things that other people wouldn't think of doing. And that's okay.

Emily: You also have a hundred patents, a hundred patents.

Vanessa: I do.

Emily: I wanna say that again, you have a hundred patents. How is that even possible?

Vanessa: I don't know.

Emily: But seriously, you're developing really innovative technology that no one has developed before. I mean, that's the point.

Vanessa: We are. And I have a brain that is always thinking of new things. And by bringing the team around me that I brought around me, I had an idea for something and they were able to take that idea and use the Lego blocks of technology that was available in the market to create a product that actually worked and to bring service professionals around us to be able to support that in the field.

There's a lot of people who have good ideas, but to have the determination to stick with it, to write it up as a patent... But really the more impressive part of the business is the fact that the technology team that I have created real products that serve real people day in and day out. So I'm thrilled for the patents because it's fun, but being able to serve almost a hundred million people a year with our technology and keep women safe at work and keep children safe in the classrooms.

Emily: Tech is a male-dominated industry.

Vanessa: Really?

Emily: Majority of founders and CEOs are men. Investors are mostly men. What was it like being a woman navigating this industry? Did you feel like an outsider? Did you feel like you were at a disadvantage?

Vanessa: I think it depends on the moment. So for sure, I think that not only... There were moments where I was at a disadvantage, but my team was at a disadvantage. Working for me was harder than working for the male CEO next door.

My team had to hear awful things being said when we won and the other guys lost. They would turn it into character assassination kind of statements. We didn't let it stop us. We just kept going. But, you know, when someone cares about their job and they have to hear that kind of thing at work, it's hard on them to do that.

I think it was never a part of our daily job. Like we never... I never woke up in the morning and said, "Oh, I'm a woman CEO. What am I gonna do today?" Like that never even would've occurred to me. I just did my job. Now, I may have thought, oh, I've gotta juggle and stop this meeting so that I can go breastfeed the baby. That was a feeling that was real that I had, but it wasn't ever about the difference between me or the CEO next door.

Emily: So how did you overcome that? Especially, you know, the skepticism from competitors or... it's sexism, that's what it is.

Vannessa: It's blatant sexism and it's blatant... And we had customers who said things that were outrageous things like, "Well now that we've tried, you know, your cooking, we'll see if your competitors... we're gonna give them your recipe and see if they can make it as good as you do."

Emily: Do you say something in that moment or do you stay silent?

Vanessa: I spoke up. To my detriment, I think, I spoke up. And there were many relationships in business that were difficult for us because I couldn't help myself but be outspoken. And I said, "No, no, that's intellectual property theft. You can't take it. It's mine." "Well, you didn't invent it." I'm like, "I did invent it." "You didn't invent Netflix in hotel rooms." I was like, "Actually, I did. I have a patent. I have the patent, that actually means I invented it, like legally. You can't do that," but they would do it.

The moment the gentleman looked at me and said, "Why won't you just shut up and be obedient?"

Emily: Wow.

Vanessa: "The guy CEOs don't gimme this kind of shit. Why would you do this to me?" And to speak in that language and in that way and that aggressively—there's a time when you ignore it... a lot of time when you ignore it and there's a time when you realize that it's just enough. And I think the last five years of my career were very different than the first 20.

Emily: How?

Vanessa: Well, the last five years, I was established and I had a company that was a successful company. And I didn't doubt myself and I didn't have to prove to anyone who I was. And so, when someone acted out in a way that was inappropriate, that was sexism, that was racism, I would be able to very clearly just speak out and say, "No, you don't get to say that. That's not okay."

And the thing that really changed it for me was realizing that I have other members of my team that would be out there, that wouldn't have the same strength or poise or reputation that they could speak out and survive speaking out, their reputation would take a hit.

I had reached a plateau in my career where, not that I was unassailable, but that I had a reputation that was already there and established. And I feel like I have an obligation to speak out—an obligation to speak up and to speak the truth so that it paves the way for the people that are coming.

Emily: So let's talk about the people that are coming. What is your advice to them? Because there's a lot of women out there who are wondering if they should speak up, when they should speak up. What would you tell them?

Vanessa: You know, I would tell them to trust their instincts because... It's not an easy answer. I think that there are a lot of people on both sides of the spectrum that would say you have to speak up every time, no matter what. I don't think that's what you have to do.

And each person, be it a woman, be it a person of color, they have to trust their own inner instincts of, is this the time where they have enough support in their company, in their industry, in their position where they are, that they have the safety to speak up and to speak out. And they will know and when they do, they should do it and do it boldly. But if it's not the time, that's okay. That's not a bad thing. They just need to trust themselves that there will be a time and they will take the opportunity when it's their opportunity to speak the truth.

Emily: There's a lot of concern that women are backsliding in the pandemic. Women are leaving the workforce. They've had to take care of their families, school their children at home. It's hard to get back in. Are you concerned about that?

Vanessa: I am. I am so concerned about that. There are several young women that I am mentoring and they've had to stop. You know, they've had to stop their careers and they've had to... they've not had to, they've chosen to put their priorities where their children are their first priority and where they are taking care of their children first. And I applaud that.

Emily: Well, and it's hard because you shouldn't have to choose.

Vanessa: You shouldn't have to choose.

Emily: You should have more support in corporate America to not have to make that choice, right?

Vanessa: Well, there should be. And so, I think one of the things that I would love to see happen... We tried to set an example for how you can create a corporate environment where you don't have to choose.

One of the things we did in the pandemic is we created family spaces at our office so that any person who had a family, who had a child that maybe couldn't go to school that day, that they could use one of our family spaces. They could bring their child to work and they could take care of their child at the office in one of our family spaces.

You know, making sure that we were flexible about working from home, making sure that we were flexible about, you know... I was the first one that had children in the background or the foreground of our video calls or even meetings in person. And so, we had a corporate culture that was embracing the family, being part of the office from day one. So we had a little bit of a leg up on other companies to do that. But now is a great opportunity to really take where we are with that and run with it.

Emily: So what's your advice to these women who are at kind of a crossroads?

Vanessa: Well, I think that an important piece for any woman who is trying to balance her family and her career is to choose what priorities make the best sense and to reach out and to take the offers of support that are around her.

I find too often that women are trying to do everything perfectly by themselves. We don't have to do it by ourselves, we can lean on our partners to do more. We can lean on our community to do more. We can lean on our companies to do more.

And I think if you have an opportunity to walk in and to tell your team at work what you need and how you need something to be successful for you and your family, if you speak up and ask for what you need, there's a really good chance you might get it.

Emily: Yeah. So you are not only an inventor, founder, you know, chair, you are also a musician, and that is part of your next act. Tell us... you know, you sold the company, you're starting something new. It has to do with music. Tell us more.

Vanessa: Well, during COVID, we obviously had a lot of time at home and like most people we had a COVID project. My husband and I, we were each in bands so we had several things of music that were always happening anyway. We had corporate bands. We had private bands. But we started writing music. And in the process of writing music, some producers, actually really great producers, picked up our music and wanted to bring it to market.

Emily: What do you play?

Vanessa: I play the guitar and I play the ukelele.

Emily: Ukulele. I'm from Hawaii. I heard them all through the years growing up.

Vanessa: Yeah. And, of course, the tambourine which is an instrument that you... everybody needs tambourine. And my husband plays the guitar viciously. He's really amazing. And he makes guitars.

Emily: So what's your dream for this sort of next phase of your life?

Vanessa: Well, I think, you know, us bringing our music to life wasn't about that. It was really the opportunity to work with musicians, to work with producers, to understand more about the music business. I was most excited when we talked about blending these things, that there was a lullaby I had written for my kids.

And I thought, oh, if we could get this produced, it would be so nice that no matter what happens to me, my children get to hear me sing them a lullaby. That's fun. That's sweet. But being in that business, I realize that even more than technology, the music business is a white male-dominated business. I mean, dramatically so.

And so, I started thinking about... you know, there's a lot of people supporting tech teams and being able to have the tools to learn how to grow a tech business, how to think about bringing technology businesses to market. And we call them incubators, right? We have technology incubators. There aren't music incubators.

And so, my concept on this is that we'll have a music incubator so that we'll allow for more women and people of color and with gender diversity that are both the artist as well as the people supporting those artists, to kind of lift up both of those teams, to let them have an opportunity that they wouldn't have had otherwise.

Emily: So what is your hope for what you will accomplish in this next phase and bring what you learned as a woman CEO, founder, chair, to this new industry?

Vanessa: Yeah, so the new phase of me, I think, is just realizing the place that I have in our industries and our society, which is, I made it, like I actually... I made it. It happens so rarely. I mean, I'm Latina. I'm a mom. I was a single mom for a lot of years. I was a bootstrapped entrepreneur. The fact that I actually was able to balance and make it happen and make that... and achieve that reality, I wanna make sure that I'm sharing those stories. And I wanna make sure that not only am I sharing my stories, but I am lifting up as an opportunity, the opportunity for other women, people of color, people of different genders, to have their stories heard and their voice is heard whether that's in technology or music or otherwise.

Emily: Well, that is a wonderful optimistic note to end on. Congrats on making it and thank you for paying it forward.

Vanessa: Thank you.

Emily: And bringing your learnings to the people coming next.

Vanessa: I can't wait for what's to learn next well.

Emily: We'll be watching. Vanessa, thank you so much for joining us. It was really great to have you here today.

Vanessa: Thank you for having me, Emily.