Our CEO, Elizabeth Cholawsky, was recently featured on the MarTech Podcast, a podcast that shares the stories of word-class innovators and industry leaders that use marketing and technology to drive business growth and achieve career success. Elizabeth has taken huge leaps throughout her career, using Big Data to solve complex problems all along the way. 

Tune in to the podcast to learn how she:

  • Used her academic background in government, political science and econometrics, to solve core problems related to politics and international relations via conflict analysis and computer modeling.
  • Applied data to her early marketing roles, as the marketing discipline transitioned from an art to a data-driven science. 
  • Navigated the changes involved in transitioning from an individual contributor, a manager, a president and eventually a CEO.
  • Adapted her leadership style from command/control to convince/cajole to lead and direct cross-functional senior teams.
  •  Overcame the challenges involved in being a female executive in a male dominated industry. 
  • Found her fit at HG Insights where her background in Big Data perfectly complemented the company’s core IP of technology intelligence. 

Listen to the MarTech Podcast Episode

Prominent Female Tech Exec’s Approach to Mastering Big Data

Episode Transcript

Benjamin: Welcome to career day on the MarTech podcast. Today we’re going to learn about the skills accumulated and lessons learned from a great marketer throughout the various stops on her career. Joining us for career day is one of the most prominent marketers in the MarTech space.

Elizabeth Cholawsky is the CEO at HG Insights, which is a platform that uses advanced data science methodologies to process billions of unstructured digital documents to produce the world’s best technology installation information for IT spend and contract intelligence to accelerate companies, sales, marketing and strategy efforts. Prior to her role leading the HG Insights team, Elizabeth held executive roles as the president and CEO of support.com, and she was also the general manager at Citrix.     

Okay. Here is my interview with CEO of HG Insights, Elizabeth Cholawsky. Elizabeth, welcome to the MarTech podcast.

Elizabeth: Thanks, Ben. I’m happy to be here. Thanks for the opportunity.

Benjamin: It’s an honor and a privilege to have you here. My only regret is we didn’t have you on  the show for women in MarTech week. We didn’t get introduced until after I had already produced that series, but it’s an honor to have such a wonderful representation of the executive MarTech space from a female perspective. I’m really excited to hear about your career. Let’s start off from the top. How did you get into marketing?

Elizabeth: So I’ll go all the way back and at the very beginning, my background is really technical, so I started as a programmer on list machines in sort of the first wave of AI. But very quickly with that experience, I got really interested in applications and how technology really helps improve what we do across the board in so many different ways now.

So as I got more interested in developing applications and really matching that up with problems that we could solve, the big problem you have once you have a great application, how do you actually get people to use it? So that led to really getting a specialization around all the go to market techniques that we’ve got.                     

So it was a progression from technical, you get interested in applications, and then you match up requirements with use cases and get excited about that, then you want as many people to use them as you possibly can, and marketing. So, there you have it.

Benjamin: So you started off in your career, I’m just looking at your educational experience, you have a BA in government from Franklin and Marshall College. You have a PhD in political science with a concentration in econometrics, and you also had a director’s college degree from Stanford. None of those are necessarily technical, and yet your early experience was in artificial intelligence and building applications.                    

Help me bridge the gap there. You started off on a very sort of liberal arts focus and focused on the government and got into technology and a lot of the adoption of data that led you into marketing. Before we get too much into the marketing weeds, how does that story unfold?

Elizabeth: Yeah, on paper it doesn’t look normal, does it?

Benjamin: No one’s resume looks normal on paper.

Elizabeth: I think that’s true. When I first went to F and M, my ambition was to become president  of US. So what I quickly learned was that I was more interested in really analyzing the problems than being a lawyer and going into politics. So the problems that we have in politics and international relations, to me, are solvable objectively if you understand them. So I got into, very early on, analysis and data. So the cover story of international relations and political science, if you scratch the surface of that, what I did was a lot of computer modeling of things like conflict analysis, so just the buildup of weapons technology and spending on conflict analysis and creating models and analyzing what’s at the core of the causes of things that make the world go round politically. So the PhD work I did was a lot about weapons acquisition and escalation. All of that was technical.                     

And then my first leap was into the government where I was helping the US government foreign policy, trying to solve some of those with computer models. So the technology was never far from what I was doing.

Benjamin: Fascinating. So what looks like more of a liberal arts focus, you know, you think of  government and political science, actually is very much rooted in data analysis and the use of technology. You start working in the government, eventually you transition to the private sector. Tell me about some of the roles and responsibilities you had early in your career when you decide to go into the corporate environment. What was your individual contributor and early career like?

Elizabeth: As you mentioned, that was sort of the first wave of AI when we were really trying to do a lot of expert systems and rule-based processing to take what’s kind of up here with experts and get it into systems that are usable and can make all of us smart. So that was kind of in the mid-80s. So I was part of several teams. One interesting example is in the insurance industry with adjusters where, instead of sending adjusters out to a natural disaster area to really figure out how much of an insurance payout they should do on a house or a car or whatever, we could just take the data that a human being would be looking at, put that into an expert system and come out with the same answer, or a very good answer.                    

So we were doing some of the early automation that was really helping to take expertise and put it into much broader hands. That example was the insurance industry, but we were also working with financial industries, and one really interesting one was I did a bunch of work with the food services industries to cut down on food waste. And that was, again, trying to take the experts’ knowledge and get that into systems that could take in data and create the same kind of adjustments or new rules or set asides in kitchens.

Benjamin: So there’s a pattern here where you’re taking these big datasets, you’re working in industries that are large and complex and you are building systems and algorithms and technologies to interpret what would be a manual process in your individual contributor and the early phase of your career. What lessons did you take out of the experience of looking at those large industries and trying to solve those complex problems yourself that you’re using today as an executive?

Elizabeth: I think there are a couple of things. One, you know, I look at that early phase of  automation and really using computers to make us all smarter. And every phase that I’ve been in with data and automation, people think it’s new and we’re going to get attacked by the robots. And this is like the last wave-

Benjamin: we’ve all seen Terminator, it’s Skynet.

Elizabeth: Exactly. What we’re doing today is going to be standard operating process in the future.  And there’ll be some other really interesting technical invention that allows us to do even more in the future. So just because something is called AI today, it’s not what’s going to be called AI tomorrow. So a lesson is to not rest on the laurels of how we’re doing something today because it’s going to be standard and there’s going to be something better to do even more in depth, interesting work in the future.

Benjamin: So early in your career, building out some of these complex models and ways to evaluate  complex situations, you had the realization that the technology is going to keep growing. As you moved beyond your individual contributor roles into some of the management roles you have, I see that you worked as a VP of marketing for Clarit, for ValueClick. Talk to me about the transition to being a manager, sort of that middle management role, and how did the lessons you learned as an IC help you succeed in management?

Elizabeth: I really enjoyed that transition from just being the contributor, which is great. I still get  instant gratification from a little bit of technical work I get  to dabble into. But moving into a management role, you just get to solve bigger problems, and that’s what really drew me into first middle management and then keep going with it because you’re presented with even more complex ecosystems that you have to solve, other things that you have to gain expertise in.                

As I mentioned, one of the ways I got into marketing is you can create a great application, but if nobody’s using it, it’s not very satisfying. And getting those skills and solving those problems as a manager really kept me intellectually challenged, and also the gratification of a job well done gets bigger and bigger because you’re influencing more people, you’re helping more people do good work, and hopefully, you’re creating better technology out in the marketplace.

Benjamin: It seems like the picture you’re painting where, as an IC, the ability to leverage data  and build systems and use data to solve complex problems is a natural fit for digital marketing. All of the inputs that we’re getting from website interactions, all of the activity you get from your marketing data, it can be overwhelming, right?

Elizabeth: Yeah.

Benjamin: You get so many signals and so much noise and it’s hard to figure out what is actually the  actionable data. I see that you worked at ValueClick. It was a company that owned Commission Junction, the affiliate marketing platform. Talk to me a little bit about that experience, and it seems like that was one of your first marketing specific roles. What were you doing at ValueClick? What did you learn from that experience?

Elizabeth: ValueClick was really fun, and Commission Junction, which is still around a CJ Affiliates today, was just a great startup to be involved with. Moving into the marketing role at Commission Junction, under marketing, and this is true I think of a lot of companies, there was product management in product marketing, which I love and still gravitate to to this day, and then all the other marketing functions also were combined into that organization. But I learned a lot about the application of data into the marketing function in that role in particular. I think prior to that, the industry was more about, thought of marketing as brand marketing and it was an art, not a science, but with the advent of internet advertising and Google ad words and all that, marketing I think became much more of a numerically data-driven discipline, which attracted me. That’s one of the big things that got me excited about the change in marketing and why I thought it could be so important. CJ, in particular, had about 5000 sellers, vendors, but then we had tens of thousands of publishers that were out, and at the time, these were guys sitting in their pajamas in the garage getting 5 cents off of every link.

Benjamin: Very likely still in their pajamas, just a bigger garage.

Elizabeth: Yeah, exactly. But you know, it was the first company that I was at where we just had  these massive amounts of data to mine, and we ended up getting, and they weren’t called data scientists at the time, but they’d come in and they’d have real analyst skills and it helped us to grow that network and really get the products for ValueClick and for the early ad networks to be really performing well for the people that used them. And it was all data-driven. But as I said, that really drew me to the marketing discipline, is it was changing to be more of a science rather than an art.

Benjamin: So as you depart from working at ValueClick and on Commission Junction, you really get into a set of executive roles. You were the SVP of consumer experience and product at Move. You were the VP and GM of IT support and access line business at Citrix, and the president and CEO of support.com prior to your current role at HG. Talk to me about becoming an executive. What were some of the challenges you faced? You have a very specific data-driven approach, but now you’re getting into these executive and general management and even, you know, the head honcho, the president and CEO roles. From a career perspective, from you know, an interpersonal, managing the team perspective, what were some of the challenges you faced going from being sort of vertically siloed in marketing to a broader focus?

Elizabeth: Well, I’ll just start out and say it wasn’t easy. It was a big change, I think, to be from a  functional leader to then having to lead and interact with a cross functional group of equally astute and knowledgeable people in their own right, and then having to lead that kind of group. One of the key skills I had to learn was how the convince and cajole instead of do command and control.                     

You know, when you’re a functional leader, you can just sit down and kind of, “here are our priorities this week and let’s go get them done.” When you’re a leader of a cross functional senior team, it’s much more about getting people on board with how you’re thinking about driving the company, and really nudging them into the right disciplines, and then you just see things happen with the team.                     

I think that was one of the bigger things that I really had to learn. I mean, coming from the east coast, there’s a lot of Philadelphia command in me, and toning that down, I think, gets the best out of people and lets them blossom with their creativity.

Benjamin: So I feel like I’d be remiss if I didn’t ask a gender-related question, because you’re an  experienced executive, you’ve been working in marketing and technology for a long time and you’re a woman. How do you think being a woman played a role as you became an executive? How did it help you and did you face any challenges as a woman in technology?

Elizabeth: Yeah, I’m not sure it helped. It seems to sometimes take longer to get recognized as a  female. You have to be more confident and more persistent sometimes than other people in the business, because, and I don’t think this is anything that we’re going to overcome anytime soon, we have impressions of how people fit into certain slots and we grow up with lots of social norms. And so, overcoming that so that you’re just treated as kind of part of the team and people don’t see your gender, just takes a lot of persistence. And I think that’s kind of the biggest thing to overcome.

Benjamin: Well, you mentioned that the challenge of transitioning from being a functional area  manager to an executive was moving from, I think your words were, essentially, commanding to cajoling. To me, when I think of the challenges women face in the workplace, is that a lot of them feel like, and this is just from, not my personal views, but from some of the interviews that we’ve done here on the MarTech podcast, and I’m obviously trying to walk the line here as a man working in technology, I hope don’t offend anybody, but some women feel uncomfortable being in a position of command or feel like they are going to be viewed as pushy if they are commanding.

And your transition seems interesting to me because you’re saying, “I was commanding and I had to learn to cajole, and I had to learn to influence with more of the velvet glove than the hammer.” You know, those things seem to be a little different to me, and I don’t want to make this whole conversation about gender dynamics, but talk to me a little bit about that. You know, why was it more commanding at first and how did you feel people viewed you making the transition as an executive?

Elizabeth:  I think it’s a really important topic. You know, hope women are people too, and there’s  this whole spectrum-

Benjamin: Women are more than 50% of all people and they birth all of the babies and they work…  Yeah, we don’t have to explain how wonderful women are.

Elizabeth: Yeah. But it happens. But there’s a whole spectrum of leadership styles on both males  and females. I think there’s a lot of women who have been taught over their career that it’s better to just keep their mouths shut, or they’re a little hesitant to jump into the conversation, and that can, at times, be interpreted as weakness and not having a commanding personality. So they are told to speak up more. And I’ve seen a lot of missteps with that because speaking up more, they follow the spectrum of men where they’re very dictatorial, and it can get you in trouble at times.

So I think we’re still in this very much a transition stage of taking the norms of female behavior, I’ll call them. I mean, there’s been lots of studies, there’s some great studies that talk about just the natural tendency for women to not raise their hand in a group setting to ask a question. That doesn’t necessarily mean they’re not dictatorial when it comes to management, just that they aren’t comfortable speaking out in public. So I think learning the skills of being able to be cooperative and, as I said, cajoling, convincing, is important, even if you’re more of an introverted female.                     

For me, part of it was, as I mentioned, the east coast. There is a difference in leadership style and companies on the east coast and people on the East coast and California. I lived half my life in Philadelphia, and California has a much more open way of talking about things. You know, my VP of channel, we call him the masshole.

Benjamin: I went to Boston University. It’s not the first time that I’ve heard the term masshole.

Elizabeth: Yeah, I mean endearingly. You know, there’s a lot of these vectors. There’s East coast,  West coast, there’s the female’s day to day persona versus what she thinks her leadership style needs to be. So it’s not a one size fits all, it’s a constant progress and tenacity of working at it so that you can take in what you’re doing well, modify your behavior, and learn from people that you admire. And that’s what I meant about maybe it taking a little bit longer for females because we don’t have as many success stories to look at.

Benjamin: It’s one of the reasons why I specifically wanted to call out women in MarTech week, and  I would have loved to have had you as a speaker on that segment.

Elizabeth: Yeah, I would have loved that.

Benjamin: If you go back to the Mad Men era of marketing, there are lots of male role  models to follow. There are not a ton of female executives that have 20, 30, 40 years of marketing experience. And so, when we find someone like yourself who has a long and distinguished career, I always feel that it’s important to a) highlight, someone like you as a great role model for other women in marketing and technology, but it’s also interesting to hear some of the trials and tribulations and the way that you’ve found your voice.                     

I do you want to get back to talking about your career path. You had all these executive roles and you’re getting this executive experience. You went from being the president and CEO of support.com to starting your own agency prior to taking your current role at HG Insights. Talk to me a little bit about why you made the transition from working at publicly traded companies as a lead executive to your own consulting firm, and what was that experience like?

Elizabeth: First of all, I loved the experience at support.com. I mean, running a public company is a  unique experience with unique guidelines. At that company, I was taking it from being a service-based revenue stream to creating a product and getting it to market, so that was kind of in my sweet spot. But when that ended, and we can do a whole podcast on this, with the activist investors taking over the company, and there’s lots of interesting stories there-

Benjamin: Sounds dramatic.

Elizabeth: Oh, it was very dramatic. So, as I said, could do a whole podcast on it. But at that point, I  looked at what I had done in my career and thought, “You know, I’ve got a lot of different areas that I could help other companies with in terms of getting their product market fit right and then taking it to market with kind of the newest kinds of go to market techniques.” So I wanted to jump in and, with an associate who was working with me at both Citrix and support.com, we went into that to just get out to more companies and apply our experience and do some more interesting things.

Benjamin: It seems like as you get farther along in your career, finding the right role is more  challenging. Early in your career, you’d take a job because it’s what’s available, right? Or you can job hop a little. When you are more expensive and you have more leadership skills and you’re going to influence the organization more, it takes a longer time to find that match. And so what I’ve seen is lots of executives will become a consultant because they need a year to date other companies and figure out what’s the right fit. Eventually, you land at HG Insights. Talk to me about why you decided to take the role at HG Insights and tell me a little bit about what you’re doing at the company.

Elizabeth: So I’ve gone back and forth between Santa Barbara and the Bay area since I moved to  California in the 90s, so I had some connections to Santa Barbara, one of them that is a board member at HG. So when he found out that I was doing some consulting, he said, “Do you know the company?” And I actually didn’t, shame on me. And he said, “I think they are kind of at the right part in their growth where they can really use your help.” And I said, Oh yeah? Why?” And he said, “Well, they’ve been spending seven, eight years really developing this deep IP around using big data to mine technology installs, and they’re really at the point where they could get that out to market in a much bigger way with the right kind of help and skills in the company.”                     

So I started there about six months before I took over the role of CEO. I started talking to Craig Harris, the founder, and just got really intrigued by what HG Insights was able to do and had been able to do over the course of their early years to come up with some very unique information that helps accelerate in all sorts of ways at companies, not just marketing, but sales and corporate planning, and it’s just applied in so many different use cases. And I saw a potential there that the company had only just tapped into.

Benjamin: So you have this background in data and analytics and building systems. You get  executive experience, you land at HG at a time where big data is becoming a) not only a popular term and potentially even a buzzword, but it’s also a major focus in marketing and outside in other industries. Tell me a little bit about what HG does, what this core IP is and what are some of the applications as they relate to marketing?

Elizabeth: What we do is mine literally billions of free form documents that are publicly available to  then be able to tell you, for a company, what technologies that company’s using and a number of other attributes about those technologies, as well as tell you their IT budgets and give you the contract information for many of those companies.                     

But the core VIP is around the technology installations. So it’s a big data play where we use AI and machine learning, natural language processing and rule-based algorithms to take those every month, 13 billion documents, and cull it down to our customers’ use, which is the ability for basically any company globally to say that they’re using this particular Cisco router and Salesforce CRM and Microsoft-backed Office products.

Benjamin: It enables companies to understand what IT and systems are being installed by their  competition and even their potential customers.

Elizabeth: Yeah, and it’s mainly used for technology companies that are selling their products and  wanting to understand the markets and the customers that they’re selling to.                     

So let me give you a typical use case. For a marketing organization, one of our customers knows that there are certain partner products that, if they exist at a company, are going to make it very easy to sell their own technology into that technical landscape. So we can tell them that. We can tell them that the stack and whether there’s a gap for their own product, and a marketer can take that and put that right into their lead scoring, whether it’s in a system that they’ve got or in Marketo, or if they do their lead scoring in Salesforce. And the kind of ROI statements they get are amazing, a 30, 40% increase in the ability to appropriately target a company and that saves tons of money and time.                     

So that’s just one use case and it goes from there to things like territory analysis and white space analysis, and then all the way up to being able to get the size and shape of markets and do total addressable market analysis. There’s lots of ways to use it.

Benjamin: What’s interesting to me as I think about your career as a whole, you’ve gone from a  focus on government for your education, working in government systems, applications, worked in the marketing industry specifically, and now on a technology that helps all sorts of organizations get access to data and intel, and I would say primarily focused on probably B2B SaaS companies. As you look back on your career, you know, what advice do you have for people that want to be an executive that have a similar skillset to you with a focus on analytics, data and technology, and how can they take advantage of the current landscape in marketing?

Elizabeth: I’ve said this earlier in the conversation, and one thing is tenacity and persistence. I  think that never, never, never give up statement applies to getting to the point. If you want to leave, you want to leave the group. If you want to work on bigger problems, which is what drove me through to the CEO role, then keeping at it and not getting tired of what you’re doing, so making sure that you’re getting enough creative problems to keep your own brain going, that’s absolutely critical. On the data side, I really do think it helped me that I could always go back to being very fact-driven. Because getting your hands dirty on the data and actually knowing whether it’s the data of your product or the usage of your customers using it, you can be the expert in the room if you keep hands on with the data that your products and markets have available for you to be able to do better in your job.                     

So I think that’s two prongs, you know, be persistent and never think you’re above actually getting your hands dirty with the actual facts and data that apply to your business.

Benjamin: One of the things that I appreciate so much about your story is a clear understanding of  what your approach and what your core talents are. Obviously you’ve developed management skills outside of just the technical understanding and the data-centric approach, but there’s a clear theme throughout your entire career of a way of looking at solving problems using data and you’ve found roles in organizations that appreciate that. And I think that, you know, to me, that’s one of the biggest lessons is understanding who you are, what your approach is and what you’re good at, and finding places where you’ll be successful is a path that other people can follow as well.

Elizabeth: Yeah, really good observation. I think it’s probably one of the reasons I’m so thrilled to  be at HG because it brings it all together.

Benjamin: I appreciate it and congratulations on all your success. It’s an honor to have you as a  guest on the show and appreciate you being here.

Elizabeth: Thank you very much, Ben. Thank you for the opportunity.

Benjamin: Okay, and that wraps up this episode of the MarTech podcast. Thanks to  Elizabeth Cholawsky, CEO at HG Insights, for joining us. If you’d like to learn more about Elizabeth, you can click on the link to her LinkedIn profile in our show notes. You can send her a tweet @echolawsky, or you can visit her company’s website, which is HG Insights.