August 11

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Female Tech CEO Elizabeth Cholawsky on Growing SaaS-Based Companies

By Mimi MacLean

August 11, 2022


Elizabeth Cholawsky, CEO of HG Insights

Interested in leading or starting a tech company? This is the episode for you! Elizabeth Cholawsky is a seasoned executive with years of experience running tech-based and SaaS companies. She has led and worked with companies to build market-leading offerings, using in-house talent and through partnerships and acquisitions. Elizabeth joined HG Insights as their CEO in 2018 and since has led them to great success through better hiring practices and a focus on solid company culture.

Tune in to learn about her career and C-suite level experience in various companies, how she creates a safe and open company culture, and her top advice for women in tech.

To Find Elizabeth and More About HG Insights:

Episode Contents

Elizabeth’s Journey As A Female Tech CEO

Elizabeth Cholawsky, CEO of HG Insights

Mimi:
Thank you so much, Elizabeth, for coming on today. I really appreciate it. I've been excited to talk to you about your company, that you joined in 2018. So, you've been there for four years or so-

Elizabeth:
Yeah.

Mimi:
-as a CEO of a tech company, which I think is not very common for females to be running a company like that. So, thank you so much for coming on.

Elizabeth:
Oh, my pleasure. I'm looking forward to the conversation.

Mimi:
Yeah. So tell me about… You were also, before this, you were a CEO of a different company as well. It was Support.com, which was a public NASDAQ-traded company, as well. So, I would love for you to just talk about your experiences being a CEO in the tech industry.

Elizabeth:
Yeah. So you're right. It's rare that you run into another female CEO for a technology company. It's gradually getting a little better, but when you're talking a little better, I think the stat's 5% of technology companies are run by women, and it gets worse as you get into the Fortune 100, Fortune 500 companies.

Mimi:
Mm-hmm.

Elizabeth:
So, it is a little different, but I managed my whole career trying to think human being first, and productivity, and impact, and getting the job done, and creating relationships across all different functional areas, and with lots of different kinds of people. So I think when I finally… And I was always ambitious and knew that I wanted to solve bigger and bigger problems. So that led into wanting to do general management work, and then CEO work. But by the time I got into a CEO role, I felt fairly well supported from my network, and from the people that I could bring into the companies to help me build them.

Elizabeth:
So I always say this, that it just for a woman, it just takes a lot longer to get into the role that you want. You're having to prove yourself more. But I think if you do achieve your goal, based on all the foundational work, that I don't think the challenges I've been faced with at the CEO level are particularly different from my male associates.

Mimi:
Right.

Elizabeth:
It's a hard job. Once you get here, it's the same challenges.

What Is An SaaS Based Company and The Benefits of One

Photographer: Hack Capital | Source: Unsplash

Mimi:
Exactly. So HG insights, it's SaaS-based company. So, can you explain to anybody who's listening, who doesn't know what SaaS means?

Elizabeth:
Yeah. So SaaS stands for software as a service, and it's basically the handle that everybody uses for subscription-based products. So, even a Netflix you can think of as a SaaS product. But it was really a sea change in the technology industries, in the mid 2000s, so 2014, '15. Pioneering with salesforce.com, where instead of bringing software onto your premises and running it yourself, it would run in the Cloud and you'd pay for it on a subscription basis, a monthly or yearly subscription. And it's really transformed the technology industry for the better, in my opinion.

Elizabeth:
I was lucky enough, back at that point, I was working for Citrix Online, which if you remember, there was a product called GoToMyPC, and prior to Zoom, there was GoToMeeting. And all of those were some of the very early SaaS-based products. And so I got to learn a lot about both the benefits, and how to manage SaaS-based business based on the pioneering market that Citrix Online did. So.

Mimi:
Right. And SaaS businesses are great because of, like you're saying, the subscription. So for business model purposes, having that recurring repeat income every month…

Elizabeth:
One of the big benefits of it is it's predictable.

Mimi:
Mm-hmm.

Elizabeth:
You can look out to the end of the year. You can look out to a couple of years, and do a much better job at forecasting where your business is going to be. And for the customer that's using it, generally, there's just a lower cost of ownership at the initial stages. So you can get, instead of a business paying a $100,000 to buy a license, they can pay, maybe, $5 a head for the people that are using that on a monthly basis. And so it brings down the ability just get started with a lot of good technology for the customers, and that's a big benefit.

Mimi:
Yeah. And you have some great customers. Like between Oracle and Cisco, I mean, you can't ask for bigger, better. And they're already kind of the kings of the tech industry, anyway. So to have them as customers, that's amazing.

Elizabeth:
Yeah. Yeah. We have 90% of the Fortune 100 technology companies are our customers.

Mimi:
Wow. And so when you joined in 2018, was that the case? Or is that been since you got there?

Elizabeth:
We had a couple of keystone, really great customers, but it's really been the growth of the company in the last four years. So, a little bit about what happened. HG Insights is now 12 years old. Was founded by Craig Harris, great entrepreneur. He really took the first years of the company, and built these deep, deep assets into our AI and our machine learning, to extract insights from the data that we have. But it wasn't so much a go-to-market company, where there was a really great sales team that could spread the word out to people that might use what we have, and really get a broad base of people knowing how to use what we did.

Elizabeth:
So, that's really what happened. It was one of the reasons the board brought me in, as operational development like that for a company is my wheelhouse, as well as creating product. So taking those deep technical assets, packaging them up, and then getting a sales and marketing team to really get it out to people that can use it. That's really what happened over the last four years.

Opting for In-House Sales and Marketing and Her Advice for a Unified Brand Image

HG Insights Home Page

Mimi:
That's great. And so is your sales and marketing, is that in-house, or did you use an outsource?

Elizabeth:
It's in-house. Pretty much 90% of what we do, directly from account executives. And we have a model that is typical for the technology industry, where you have business development reps that, actually, they'll call up companies and do the initial introduction of what we do. Send out content that might be interesting. And then if somebody fits the profile of a good customer for us, they'll work with the account exec then to go in to that prospect, and see if we've got a fit. And if so, do the selling. All of that is in-house.

Elizabeth:
We have offices in Santa Barbara, California, which was where the company was founded. And we also have an office in London. And both those offices have a real core of great sales people that work through North America, and really work throughout the world.

Mimi:
What advice do you have… because I think this would probably be a big part of your business, especially being international, is making sure the message that gets out in your community, and your core values of your company, and what you want spoken out to as they're selling your product. How do you keep that the same? Or how do you create that?

Elizabeth:
Yeah. To me, there's two parts to that question. One's the message about the products that we have, and making sure that everybody is looking at them the same way, which is really important, so that internally you get feedback that's all in the right focused areas. Then you can continue to develop your product. That's really about creating this sales and marketing organization, and having it very cooperative.

Elizabeth:
So lots of times, in a technology company, marketing will say, "Talk about the product this way."

Elizabeth:
And sales is like, "Oh, that doesn't work. I'm going to just go off the reservation and talk about it any way I want."

Elizabeth:
And that might get you one or two sales. But really, to do it properly, there needs to be that back and forth between the two organizations, so that marketing's creating materials, and training, and helping sales to really codify what they know is the interesting things about what we have for the prospects. And then sales, to be able to use those and rely on marketing. So it's a lot about bringing those organizations together, and then making sure that there's good assets in the hands of everybody, so that message can go out globally.

Elizabeth:
But the second part of your question, that I think is interesting, is about culture. We've got a lot of barriers to entry, and our product's great, and I could go on for hours about that. But a lot of times, people buy from other people because of how they feel about working with the company, or with the person. And I believe, from the comments I've gotten from customers, that our values are reflected with how we work with our clients. And that comes all the way down from, we have our top value is we care. We care about customers, our employees, and the business that we do. Really, it comes down to something like one of our sales guys is not going to try to sell something to you that they don't think is really going to benefit your business. We don't force fit that.

Elizabeth:
This goes back to the other comments we had. It's a benefit of a subscription, a SaaS-based business. If you sell something that really doesn't match somebody's need, then they're just going to stop the subscription the next month. That doesn't do anybody any good. So there's kind of a back check on making sure that you have that integrity with the discussion.

Elizabeth:
But also, with things like another one of our values that comes through, is that we give and ask for help. So, if a client is really not, and this happens a lot because we're in the big data area, and its companies are just now really getting sophisticated with using data, if they don't understand even what a data scientist is, or how they should build up their department, or how best to bring in skills to be able to apply what we have into their organization. It's not our job to be a recruiter, but we're happy to sit down and talk to them about best practices because we see them all the time. And if we know people, we'll even help them to build up their teams. But we try to go out of our way to really look at our clients as partners in what we're doing.

Elizabeth:
And we do that based on the values that run the business internally, day after day. To me, that's really important and it's really key to growing a very healthy business.

More Women in STEM and More Female Tech CEO Opportunities

Photographer: CoWomen | Source: Unsplash

Mimi:
That's great. That's great. I know we talked briefly before we got on about diversity in your workforce, which is, I think, tricky also, right? Because there's not as many women that go into STEM when they go into college, but you still had a pretty high percentage of women in your workforce. I think you said it was like the high 20s or 30s.

Elizabeth:
Yeah.

Mimi:
Which I think is pretty high, I would think, for other tech companies as far as… But what have you seen as the trend? Do you see now there's more women going into STEM? Or what are you doing in order to get more women in involved?

Elizabeth:
Yeah, there is. And if you look at the last five or six years, and look at the statistics, there are more women coming into technology. And that's fantastic. We have a local organization called Women in STEM, and our company is a big supporter of that. We've sponsored events at our offices. We provide speakers. And it's programs like that, I think, that have gotten a lot of women thinking, "Oh, yeah. I can do this, too."

Mimi:
Mm-hmm.

Elizabeth:
A lot of women just grow up with this mantra. "I'm not good at math." I mean, where does that come from? It's just-

Mimi:
That's came from when we were little. Right? Ever since elementary school, that's what [inaudible 00:14:09].

Elizabeth:
Exactly. Exactly. I mean, my history I really love, I still do. I love reading. I love arts. I love theater. And so, I just blasted through all the math courses and science courses I could. And then I stopped because you did the graduation requirements. I got to college and realized, "Oh, my God. This is really important for what I want to do as a career," and had to go back and relearn a lot of things. And I think it was just that, as a woman, when I was growing up, I wasn't really pushed into anything to do with math, science, or other parts that would lead you into computer science.

Elizabeth:
But anyway, back to your question. I do think that, now, there's a lot more women coming into the workforce that have a real affinity, and desire, to work in the whole STEM area. And our company does a lot to promote that actively. We try as best we can. It's very hard with recruiting, because recruiting right now is tough, in general.

Mimi:
Yeah.

Elizabeth:
But-

Mimi:
No one wants to work.

Elizabeth:
No one.

Mimi:
Nobody.

Elizabeth:
And if they want to work, they want to work on the timeframe of-

Mimi:
Wherever they are.

Elizabeth:
-wherever they are. And that's really hard, but we've done a lot more with remote working. But we try and make sure all of our hiring managers are well versed with, look at every candidate. And I would love to have the kind of system where it just masks the names on resumes. But-

Mimi:
Yeah.

Elizabeth:
-that's another story, but… But we do everything we can. But the big problem with women in technology is that there's just a large dropout rate. So we've done a really good job over the last five or six years, from the stats that I follow, of bringing more women in at entry and middle manager levels. And then there's a dropout rate.

Mimi:
[inaudible 00:16:01].

Elizabeth:
And there's lots of research about why do we have dropout of more women than men. It's everything from, generally, women are still the primary caretakers, all the way through to, go back to my patience point. Women just have to be more patient.

Mimi:
Mm-hmm.

Elizabeth:
And if they don't see those promotions coming as fast as they think they should… Yeah. There's a lot of things that are easier to do than being a manager in a technology company. So good progress. Good hopeful signs.

Mimi:
Yeah.

Elizabeth:
More work to do.

Never Burn Bridges and Focus On Making Those Key Relationships

Photographer: Tim Swaan | Source: Unsplash

Mimi:
Yeah. Well, that's a good pivot into my next question. And we talked briefly about that earlier, is only 5% of women ever reach CEO status. Not just for tech companies, for any companies across the board, in the United States. And, I guess, that could be up to debate about why. Is there a glass ceiling, or whatever? But I do think there's some ownership and tips that we can provide other women. They may just make the choice that they don't want to be there, and they want to be able to balance a family, or whatever. But I guess my question to you is, any advice that you can give women that would help them make their… If that's their ultimate goal, what can they do to help them along that process? Either to get there faster, or to just get there?

Elizabeth:
And a couple of things [inaudible 00:17:19], and just things that have helped me, right? As a basis, you're all constantly taking in information about your career and what's going on. And I try to coach younger women with this advice. Don't, as a first pass, see everything through a female lens. There's tons of variables, and you've got to be balanced in how you view them. Now, there are circumstances where, at the end of the day, there's still, unfortunately, real discrimination that's out in the workplace, and that you've got to make sure you weed that out. But don't go there as a first choice. Try to analyze the situation, and give everybody the benefit of the doubt, that they're a human being and they're just reacting from their own personalities. So if you've got that as a backdrop, and you're competent, and you're willing to put in the time…

Elizabeth:
The other things, that I found, that can really add that extra key to your career is, I'll call it networking. And I'm going a caveat that, because when I was first said, I used to do more networking. I really resisted that, because I thought it was a waste of time, of going out for coffee with people every couple of days. And it's like, "I have stuff to do, so I'm not going to do that." But networking, what I really came to understand, is really creating those relationships with people that you respect and can learn from, or you can actually do the reverse, and help them with something. But those networks have done me immensely good things throughout my career, and advancing at the right time. And they're not specifically sought out as, "I'm going to connect with this person because it's a really good thing for my career to do," but they come back around.

Elizabeth:
And I'll give you an example. When I was at Citrix, I had a really good colleague. We actually conflicted the first couple of years we were there, and worked really hard at sort of understanding. He was running sales. I was running a line of business, so I wanted more sales devoted to my products. And it was natural conflict. But during that, we learned to respect each other's skills quite a bit, and developed a long term relationship.

Elizabeth:
And then when he got recruited, was from a head hunter, to actually the job that I got at Support.com, he was recruited for it first. And he wasn't interested because the support area in IT was my specialty. That's the line of business I was running. But I was the first person he called, and he said, "Look. I got this recruiter call, but I worked with you now for seven years. This is perfect for you." And gave me a really easy entree into that position, and to be able to be considered for it. And without his help, and without us having worked through differences, and learn how to support each other, and me looking to him to learn a lot about sales and mentor me in that area, I don't think that would have happened. But that's one example of it wasn't a formal mentorship, but I certainly consider him a mentor. And there was a big thing I can point to, that was a benefit.

Mimi:
Yeah. You never want to burn a bridge, right?

Elizabeth:
Never burn a bridge. No, no, no. [inaudible 00:20:39]

Mimi:
Because you never know where that bridge is going to take you. But you bring up a really good point about how when you look to, not mentor, but when you look to network with somebody, don't just look for what can they do for me? Just always be willing to give somebody else something, because then in turn, they're going to be willing to give you something, later on. It's like a give and take.

Elizabeth:
Yeah. And you never know when that give and take is going to happen.

Mimi:
Mm-hmm.

Elizabeth:
There's certainly formal mentorships that are helpful too, because particularly, I think, if you are early in your career, asking somebody to spend time with you periodically to review what your career goals are, and what you're up against, and how you're doing, that can be immensely helpful. And I try to do that with anybody I work with, women included, if they really want to work on something specific. I'll meet with them every couple of months, and we'll just have a little plan, and I'll give them whatever I can from my experience. So, seeking out formal mentors is great too, but this whole idea of networking, and thinking of things in a mentorship way, goes back and forth.

Mimi:
Especially if you can find somebody that's already done, or is where you want to go. That's older, that you can be like, "Okay. What was your career path? How did you get there? What's the way to get there?" No, it's very true. I think there's not enough credit, because as women, I think, we're trying to do too much, right? We're like we got to rush home to our families, or we have to do this or that, and you don't have time to… you just want to get everything off your to-do list. You don't want to take the moment to go get a drink, or go get a coffee, or-

Elizabeth:
Right.

Mimi:
-go play golf or whatever. Wherever it is that you're networking, or going to these random events for your industry, or…

Elizabeth:
Yeah. Yeah. And for some reason, I do think that most men have an easier time with that.

Mimi:
Mm-hmm.

Elizabeth:
They can just carve out and consider that as a good use of time. And it did take me a long while to really teach myself that it's a good use of time, just to have a casual conversation with no end goal or agenda to the conversation, with somebody that I think I can learn from.

Mimi:
Right. Men tend to be… 70% have mentors, or use mentors, where women it's only in the 30s percentile.

Elizabeth:
I bet it would be even lower if you just looked at technology companies because-

Mimi:
Mm-hmm.

Elizabeth:
-most mentors, I think, happen fairly naturally. Right? So, they gravitate to people that they think are going to be coachable, or good coaches, and bond. And it's legitimately difficult in the workplace today, in my opinion, for that to happen between a man and a woman. Just naturally gravitate and get that kind of close bond. There's so many things we have to be careful about, legitimately, both men and women, that the natural friendship bonding. And we are usually not out there playing ultimate Frisbee with the guys. So-

Mimi:
Yeah.

Elizabeth:
-those casual beginnings of mentorship relationships are less available to women. And so, you got to work hard [inaudible 00:23:50].

Mimi:
Yeah. What was the other example you were going to give?

Elizabeth:
We were just talking about mentors, and since I moved to Santa Barbara, gradually got to know a CEO I respect really, really well. A guy named Michael Crandell. He runs Bitwarden. It's a password security company right now.

Elizabeth:
And this was years ago, it had to be 15 years ago, where I was looking at my career and going, "Oh, I don't know whether I'm ever going to get to the CEO role. That's okay. I've done great in my career. It'll be fine." But I reached out to Michael, and I just wanted to find out his perspective on career progression because I saw what he had done over the years. And I guarantee that all CEOs are incredibly busy. But if you ask for help in the right way, most will take the time out of their day.

Elizabeth:
So Michael and I, we did a couple of lunches around that time. Breakfast, actually. He had a favorite place in Santa Barbara, and I was happy to go there. But he is the guy that really taught me that most careers don't take a straight line progression, and that you just need to keep at it. And it gets back to the dropout point we were talking about. Don't drop out out of frustration. Just keep doing the work, and keep building the skills, and good things will happen. Not always, but if you put yourself in the position to get a good opportunity, it generally does happen. And he was right. And I look at those conversations as really giving me the right mindset to continue to do the work. So he is another mentor, extremely important. And that one was a proactive. I need help.

It Is Easy To Get Disconnected From Your Company As It Grows – Don’t Get Discouraged

Mimi:
Oh, that's great, and that's great that he was willing to do it. Now, looking back at your career, especially as a CEO, what would you say was the hardest part that you didn't expect?

Elizabeth:
It's a better job than I ever thought. I got to lead with that. I love this job for so many reasons. At the end of the day, whatever you do, whether it was good or bad, and you can self correct, and it's on your shoulders, and nobody else needs to take responsibility for it. So you can hold yourself, if your [inaudible 00:26:09] revenue, can hold yourself really, really accountable. That's been so true of this role.

Elizabeth:
But I think on the day to day running of things, one of the things that I didn't expect is how hard it is to stay connected to what's going on in the company, particularly as the company gets big. So when I got here at HG, we were around 40 people. The end of this year, we're going to be over 200 people. When we were 40, I knew everybody, and their dog's names, and we're a dog friendly place, and all their kids, and everything. And now I have to work at it to make those connections.

Elizabeth:
And I do try to carve out time. I do things like new hire lunches. So after you're here for a few months, I make sure that I have lunch with you, and hear what you've been experiencing with the company. I always do skip levels. So I've got my executive team, but I always try to randomly set up one-on-one meetings. It's all about hearing what's going on at the company that you don't get from your regular meetings, and executive staff, and KPIs. I try to make sure I go to the fun events. We have lunches outside. Make sure I'm there, and just talk and hear. It doesn't mean that you're going to get the unvarnished truth immediately, but over time, if you make yourself available, you can stay more connected. And I found the culture will gradually understand that coming to you is a safe thing to do and anything. Door's open and you can talk about anything. But that's definitely been harder than, and more time consuming than I thought. I thought, "Hey, everybody wants to talk to the CEO."[inaudible 00:27:54]

Mimi:
Yeah. But everyone's nervous. They don't want to lose their job. That's why Undercover Boss became such a successful TV show because-

Elizabeth:
Yeah.

Mimi:
That's how these companies that were bigger, the CEOs would have to dress up and go ask for people's advice without them knowing that they were the CEO.

Elizabeth:
Yeah. Yeah. Yeah.

The Balance You Set For Yourself Is The One You Will Set For Everyone Else in Your Company

Mimi:
So is there anything else? This has been great, but is there anything else, any insight or advice that you have for other women who want to be CEOs, or are trying to run a tech company?

Elizabeth:
I think it's really important not to be completely… Whatever your work day is, whether it's 7:00 to 10:00, or whatever, you can't be completely driven on that. You've got to figure out a way to maintain your sanity in whatever way you're doing, and have things that are outside of work. Because if you do that, that kind of balance comes back and it sets the tone for everybody else in the company. And it actually keeps you more, I think, open to talking to people, and hearing about their lives. And particularly with how we work today, this whole ability to work remote and to have all our technologies, there is no division between your work life and your life life. It's all intermingled.

Mimi:
Yeah.

Elizabeth:
So, you have to develop techniques to do that. And when I took my first CEO job up at Support.com, the Chairman of the Board… One of my hobbies, and one of the ways I try to stay balanced, is I do triathlons. So…

Mimi:
Good for you.

Elizabeth:
Yeah. So if you're going to do that, you got to have a schedule, otherwise the triathlons are horrible. And the whole point is you want to have some fun. But when I went to Support.com, the Chairman said, "I think one thing you're going to have to give up is you're not going to be able to do triathlons anymore. You're running a public company."

Elizabeth:
And I said to him, I said, "Jim, if I do that, you don't want me to be CEO here."

Mimi:
Wait. Who said that to you? The head of the board?

Elizabeth:
Yeah. And I said, "I think you'll learn that it's more important for me to keep A healthy and mentally balanced, by having time and events that I accomplish goals out that are unwork related, and that it'll make for a better company."

Mimi:
Yeah.

Elizabeth:
And over the course of time, we worked together, he came around. And it's like, "I should have never said that to you."

Mimi:
Well, good if you could do it on the weekends and, yeah, you have to train during the week. But it's not like you're spending four hours a day, right? During the week, running.

Elizabeth:
Yeah. No, no. In fact, I've never done a full Ironman in Hawaii. And that's actually an agreement between my husband and me, that I won't until I retire. Because if you do the full Ironman, you do have to spend four hours every day.

Mimi:
That's a lot. Do you do your swimming training on [inaudible 00:30:41], where you are in Santa Barbara?

Elizabeth:
Since the pandemic, I've been swimming year round in the ocean.

Mimi:
You have? Oh, my gosh. Because there's so many sharks there, aren't you nervous?

Elizabeth:
No, no, no, no, no. [inaudible 00:30:50]. See, and we're a data company. The statistics say that it's more likely that we're going to get hit by lighting than eaten by a shark. So, nope.

Mimi:
Oh, my gosh. I'm know two people, and during the pandemic, surfing in Santa Barbara, that got attacked.

Elizabeth:
Oh, my God. Oh my God. [inaudible 00:31:08].

Mimi:
No. That's why I'm always so nervous.

Elizabeth:
Yeah. So far, so good.

Mimi:
That's good. Anytime you think of that, I'm like, "Aren't you like thinking do-don, do-don, when you're swimming in the ocean?" That's amazing that you do that, though. That's great.

Elizabeth:
Yeah. Thanks. Some people go to yoga, and some people meditate, and I've go out for a run, or swim in the ocean.

Mimi:
That's good. No, but it is true. Balancing it all. Especially if you have a family, because that's the last thing. I mean, I'm guilty of that. Taking care of myself is the first thing I shelf.

Elizabeth:
Yeah. I think we all have a tendency to do that, and maybe women in particular.

Mimi:
Yeah.

Elizabeth:
Don't do that. It won't make you get to a CEO faster, and it's not going to make you a better CEO.

Mimi:
No, it's not going to make you a better person, either, so.

Mimi:
Elizabeth, thank you so much. This has been amazing. I really appreciate it. And I'm very impressed with you having run two tech companies. Thank you very much. I really appreciate your time.

Elizabeth:
My pleasure. Really nice talking to you.

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