As a part of our interview series called “Women Of The C-Suite,” we had the pleasure of interviewing Elizabeth Cholawsky.
Elizabeth is an established executive leader in the technology industry with a strong focus on growing successful SaaS-based businesses.
Prior to joining HG Insights, Elizabeth was the CEO of Support.com (SPRT), where she transformed the business from relying solely on outsourced services revenue to selling its own SaaS product that efficiently ran large contact centers.
Elizabeth has also held executive positions at Citrix (CTXS), Valueclick, and other innovative technology companies, in leadership roles spanning general management, marketing, product management, global client services, and contact centers.
Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?
I grew up ambitious. My first career goal was to be the president of the US, but I was told that girls weren’t allowed to be president. So, I decided to be president of a company.
My interests quickly led me to analyzing data, specifically using quantitative measures to assess social phenomena. That led me into a career in computer modelling and statistics… a skill set that did lead me to work for the government, though not how I pictured it.
I was hired by the CIA as a “quantitative methodologist,” one of the only titles I’ve had I like as much as CEO.
The rest is classified….
Can you share the most interesting story that happened to you since you began leading your company?
As a CEO, everyday is interesting. You are constantly presented with new circumstances and situations to manage that you have to lead through. It’s one of my favorite things about the job.
After my years of experience, I thought that there were few challenges left I hadn’t already seen yet.
Then came March 16, 2020. Even though the lockdown was announced, I thought we’d be back to the office in a couple of weeks….
As a CEO, it put me in a position to address my 100+ employee’s concerns, both personal and professional, in an uncertain time. I was also responsible for overseeing the change from a 100% in-office work culture to a dispersed remote team, and keeping HG’s culture going strong through the pandemic.
It required me to use different muscles that I hadn’t used in a long time, and it made me a better leader.
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
When I started at HG Insights I made a funny mistake, one that taught me a valuable lesson.
I was holding the first Town Hall meeting, a monthly event that keeps the team up to date with everything that’s happening, and I noticed the room was filled with dogs. Because we have a dog-friendly office, I joked that we should give equal opportunities for cats to come in. We laughed and began with the meeting, but people actually believed me! It made for quite a day.
The joke didn’t work out well, but the laughs continue. Now we have a conference room named after the local island, Catalina, that’s covered in photos of the team’s cats! And I learned that:
People put a lot of weight on what you say as a CEO, even if it’s a joke!
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
Lots of people have helped me, it’s humbling to think about. But one person who stands out is a man named Michael Crandell.
When I just started as an executive, early on, he would take the time to occasionally meet me and answer questions about how I could achieve my career goal of being a CEO. It wasn’t the typical ‘intro for a job’ relationship, and it was really generous to meet with me and talk about what he was doing. Long before I was a CEO, as my career progressed, he was somebody I watched to learn from.
At one point in my career I didn’t feel like I was on the right path. I felt I was getting stalled in my goal of rising to the top. To teach me, he went into detail of his own path, and shared his persistence, which showed me that a career path is never a linear trajectory. And just because I didn’t see a straight path forward didn’t mean I should give up.
He was unique with his openness and generosity with time — he shared the stuff you can’t get out of a book. I hope to pay that forward some day.
In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high stakes meeting, talk, or decision? Can you share a story or some examples?
Exercise! I am a huge proponent of getting out there and moving! Personally, I love triathlons. Here in Santa Barbara, HG Insights sponsors some local organizations that hold fun swim or run exercises, followed by food and drink. Our whole team is invited to come out and have fun, get some exercise in, and get to know each other outside of the office.
As you know, the United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?
Diversity is important for so many different reasons — inclusion is everything. For me, diversity of thought is really important — you need to have an open attitude to ideas and different perspectives.
As a female CEO, I try to talk about all aspects of diversity, not from just a female perspective. My commitment is to every type of diversity. It comes in many different forms, and everyone has something special to contribute, you just have to be able to see it. Everyone has an opinion to share, and everyone needs a seat at the table.
As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example for each.
Great question. I’ve always been a firm believer that communication is everything. Whether that means stomping out bad vocabulary — antiquated terms like “girl” or “son,” right when you hear them — or calling people out. Just like I said, this has to be an open conversation. This conversation is not a siloed, segmented event, you have to address the whole society.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?
To me, one of the most important responsibilities of a CEO is to be able to make decisions completely independently. Success is a team effort, and I’m only successful with my team, but the expression “lonely at the top” is real. You can’t wear your anxieties on your sleeve and worry others, it doesn’t do the organization, or your team any good to go out and share that.
You’ve got to make it look easy. It’s your job to come up with the strategy, to get to the end result. You’re in the position to share your experience, the company is on your shoulders.
Like climbing a Mountain, the air gets thinner the higher you go.
What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?
One of the biggest myths might come as a surprise, but it’s that what you say might not actually be done!
Like we just said, a CEO has to take the time to make the right decisions all by themselves, even when consulting others, but the execution is really what matters. And executing a CEO’s decision is not always what happens.
When I was working for The Agency an example we sometimes used was the Cuban missile crisis. In this instance of political horse trading, President Kennedy promised that the U.S. “would not participate or support the invasion,” yet his hawkish military brass did take a direct role in the invasion, and bungled it.
One of the biggest lessons Kennedy learned from this episode was the need to consult both industry insiders, and outsiders, to get a balanced, detached view of any situation. He also learned that he needed to pay close attention to what was happening on the ground, constantly monitor it, and make sure it reflected his decisions.
We’ll come back to this later.
In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?
Looking back, one of the biggest realizations I’ve had about being a female executive is the length of time it takes to get to the top. In my experience, women just have to prove themselves so much more… unless you get lucky. My advice is:
- Don’t resist the climb
It’s the reality of the world. Do the work, be persistent and don’t give up
- Seek out mentors
In many corporate settings, where the majority of the team is men, they can sometimes get mentors by proximity. As a female executive you’re not going to go to the loo with the rest of the team, so you will need to seek out other ways to bond with your colleagues
- Get your seat at the table
Participate in company events and outings. Getting time face-to-face with the higher ups is an important part of advancing your career
What is the most striking difference between your actual job and how you thought the job would be?
I’m not sure all CEOs would agree with me, but the role of CEO is way better than I thought.
Even though it’s stressful, it’s rewarding to live and die by your decisions and actions. Everyday, you’re on trial and you get feedback — from your customers, your Board of Directors, executive team, employees, or shareholders — about whether you’re making the right choices. When it comes to a CEO, at the end of the day it is black and white. You made the right decision or you didn’t, and hopefully you learn from it.
To me, it’s liberating. I wish I was able to achieve this level a while ago. I thrive by achieving goals, and I love the act of trying to process a lot of information to make a good decision. It’s exciting.
Do you think everyone is cut out to be an executive? In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?
I think everybody is cut out to be the executive of something, whether it’s their own business making salt cellars on Etsy, or the CEO of Walgreens. It’s important to know yourself, you can stoke any of your own personal character traits and leverage them to work for you. Some of the traits that helped me get to, and excel at this level, is ambitiousness, composure under high-levels or pressure, and diplomacy, thanks to my background in politics and working for The Agency.
If the question is about whether everyone is cut out to be a CEO at a tech company and lead hundreds of people, then the answer is probably no. If you have difficulty making decisions under pressure and/or scrutiny, or find yourself procrastinating having difficult conversations with people, the role of CEO is likely not for you.
What advice would you give to other women leaders to help their team to thrive?
This is a great question, and one that I am frequently asked. Every time, my advice is to try not to see everything through the “woman” lens. It’s important to consider some things through this lens, of course, but it’s also important to remember that every single person is different. We are all diverse in some way, and we all have something to bring — this echoes JFK’s advice we talked about earlier.
If you don’t immediately categorize people and sort them into boxes you’ll find you have a broader influence on people in general, and it helps teams thrive.
How have you used your success to make the world a better place?
Personally, I try to use my wealth to fund charities that are near and dear to my heart. This is the same at HG Insights, where we sponsor events that align with our core values and mission.
For me, I’ve been involved with an organization called Exceeding Expectations. We help at-risk kids to move their lives in a positive direction through triathlons. It is an admirable mission, and it is humbling to see kinds learn goal setting by training for and competing in triathlons. If the students get good grades, meet their training goals, and go to college, Exceeding Expectations covers the cost of their education. We have already graduated 12 students, and now receive more applications than we can take on — starting at 8 years old!
But more importantly, I try to be generous with my time and my connections when someone asks for help, something I learned from my own mentor when I was working to become a CEO.
What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)
- Don’t get hung up on titles
I’ve seen executives pass on jobs that could be a huge stepping stone just because the title isn’t what they consider “the right title” for their progress and professional growth.
For example, I was working for a speech recognition as a vice president, but I wanted to get into a bigger company with better recognition in the market. Digital Sound offered me a director of product role, and even though on paper it looked like a step back, it didn’t hurt my career — actually it helped me because it was a broader role, and it proved a broader set of skills.
Career paths aren’t always linear. If you’re hung up or feeling stuck, don’t constrain yourself by looking for “the right title.” There’s no such thing.
2. A broad range of experience is good
Don’t worry about having too many interests or making changes in your career.
For example, going from the CIA, to programmer, to customer success and digital marketing roles, my career path would not be considered “typical” for many CEOs. I did worry about jumping around a lot, but over years, following my interests as they developed organically, I gained lots of substantive knowledge and built up skills that served me well.
Many professionals excel at what they do — whether that’s a firmware designer or data analyst, but you need to cultivate a lot of things. Especially if you want to be a CEO.
3. Not all companies, big or small, are created equally
Even if they are profitable, some companies just aren’t well run.
For example, I’ve seen executives take “prestige jobs” because it looks like a step in the right direction, but that’s not necessarily right for everyone. I learned this the hard way. I’ve worked at a few large public companies, and it was nuts. After working at Move.com. I vowed never to work at a public company again, but then I got recruited by Citrix, another enterprise-level outfit. It was a great offer, and they twisted my arm, so I went to work for them. I was relieved that the experience was entirely different than how I thought it would be, I shed my preconceived notions and got to work!
4. Get fired … at least once …
At certain times in your career, it’s important to push the envelope and see where it breaks. There’s a caveat here: You should only get fired for the right reason.
For example, when I was a young executive at ValueClick, I had a lot of conviction. ValueClick grew by acquisition, and absorbed lots of companies in the media space. I felt strongly that ValueClick could be a major force by consolidating the brands, and as the VP of marketing I was adamant that we had to do this. I was given enough leash to have control over multiple entities and I gradually brought the power of the brands together. Unfortunately for me, it made the CEO uncomfortable because he felt the individual logo’s CEOs were changing loyalties to the conglomerate rather than himself, the overall CEO. And I got fired!
It was a valuable experience in my career. Too often, people are timid or ashamed, so they don’t vocalize what they have learned in their experience. Getting fired shouldn’t be something to hide in the closet, it can be a formative event that shapes the future of your career.
5. Ask for help!
There’s always somebody you can discuss important decisions with, even if you have to make the decision yourself. Whether I’ve sought out advice throughout my career, or haven’t, it’s made a difference.
For example, I was working for a Boston-based company called AI Corp that merged with a company on the west coast. I wasn’t happy about the merger, but instead of asking anybody for help, I made the decision to leave for a small company called Open Books. I didn’t take a step back for any due diligence. Open Books ended up being a flash in the pan, while AI Corp still had lots of opportunity ahead of it. If I had consulted my network, I don’t think I would have made this decision.
Remember: When you’re named a CEO, everybody wants you to succeed. People really do want you to succeed, so don’t be afraid to use them for help!
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
That’s a big question! In my mind, a movement that could bring the most amount of good for the greatest number of people is literacy. Reading and writing is so important because it empowers you to take your education into your own hands, it allows you to learn all by yourself. If we could get everybody to an intermediate reading level I feel like the world would be much better off.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
Winston Churchill has some of the best quotes for life lessons — my favorites have to do with perseverance — for example:
- “Never give up on something that you can’t go a day without thinking about.”
- “Never give in — never, never, never, never, in nothing great or small, large or petty, never give in except to convictions of honor and good sense.”
- And, my favorite, simply: “Never, never, never give up.”
Throughout my career I have faced many challenges and setbacks. No matter what industry I was working in, what title I held or company I was working for, the way I got to where I am today is by pushing myself. Even with the help of mentors and a broad range of advisors, it’s up to you to constantly push through. Especially as a female CEO in the tech industry.
We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them
This is an easy one! Billie Jean King. She has been categorized as a sports star, but really she’s a fighter of equality for all women, and she paved the way for many of us. For example, tennis is one of few sports that females are paid equally, and she is credited with this.
King spent years and years working on pay parity, and is credited with this accomplishment that still has yet to be replicated in other sports. Even today this battle is still fought on many fronts, we are seeing it now in women’s soccer, for example.
If the world had more Billie Jeans we might have more gender equality in executive positions.