What Makes a Great Female Leader, With Allison Hartsoe

Episode 57 Allison Hartsoe, Founder & CEO of Ambition Data, shares her experiences as a female leader in the technology industry. She talks about CEO’s roles and responsibilities, leadership and entrepreneurship reflecting on her journey of founding three different companies. The episode also addresses burning topics like gender biases in workplaces and the pressure women have to choose between their careers and families.

Episode 57

Episode Summary

The role of the CEO.

There is not a straightforward answer to this topic as the CEO’s role changes, like everyone else’s as the company grows and evolves. According to Allison they are the ones in charge on filling in the gaps of the business and finding the next resources to fill in those gaps. This includes knowing the strengths and weaknesses of the team and backing them up with provocative questions and with someone else’s strengths, to help them fill out their skillset. At the same time, CEOs need to realize that people are fitted to their companies in different roles at different times, and they need to build a cultural nut in the business that allows people to come and go whilst the core of the business continues to stand.

Key takeaways from her entrepreneurial journey.

Allison has always had the attitude and mindset of an entrepreneur, and in her journey of building three companies she has learnt a lot and improved both her personal and professional self.

She highlights the importance of having a sense of humour for when things do not go as planned, using inflections as fuel for growth and improvement, while at the same time taking a break when needed to check in on yourself to be able to bring your best self in your executive role. She disagrees with the common vision that entrepreneurs should hustle and grind “every waking moment”, and she stresses the importance of working on your business because you have your heart in it and you believe in its purpose. The business’ purpose should also be conveyed to employees to make sure they are also invested in it and want to be part of the team.

Keeping the conversation going.

As a female leader in a male-dominated industry, Allison is very aware that there are still a lot of discriminations happening and that the conversation around it needs to keep going.

Her experience is unfortunately similar to the ones of other female professionals: from colleagues and other businessmen not recognizing her as an executive, them making comments no one would ever say to a guy, to experiencing the fine line between a business dinner and a date and having to figure out who would take care of the kids and switching roles with her husband. Although nowadays women are also encouraged to climb the corporate ladder, they are still victims of discrimination and gender biases, manifesting in very different ways. Allison also had to learn from these unpleasant experiences, and she made sure to see them as fuel to do an even better job.

To find out more about Allison’s journey and her valuable advice, listen to the full episode on your favorite podcast platform.


This article summarises podcast episode 57 ” What Makes a Great Female Leader" recorded by CX Insider. For more information, listen to the episode or contact Allison on her LinkedIn profile.

Written by Alessia Trabucco



Full episode transcript

Allison: A CEO should never be doing at all, but the role of the CEO changes just like everybody else's role as the company grows. Your role is to fill the gaps and to find the next resource you need to fill those gaps.

Valentina: In today's episode of CX Insider, I speak to Alison Hartsoe, a serial entrepreneur currently CEO at Ambition Data, and we talk about what makes a great female leader in the technology industry. Allison talks about the double standards she has faced as a woman in the workplace.

Allison: Is it a working dinner or is it a date?

Valentina: How she managed to pursue her career as a working mother,

Allison: I actually switched roles with my husband

Valentina: And the sacrifices leaders have to make when they are building a startup company

Allison: What I learned there was not to spend as much time and effort building the culture of a team, and I know that's going to sound like heresy.

Valentina: Enjoy the episode, and don't forget to check out Allison's latest book, The Age of Customer Equity.

Valentina: Is there an indicator that would tell us whether our children have the potential to be successful entrepreneurs? Maybe. Allison certainly was a girl with an entrepreneurial mindset, but as a young adult, she chose a less standard way to achieve her dreams.

Allison: I was the kid that when it snowed, I would make a whole carnival in my front yard and try to get all the kids to come. And, you know, and I didn't try to get them to pay, but I'm just like, "Look, I made a carnival, come here". So, yeah, it was. It was always an attraction. But I but there wasn't really an aggressive start-up space when and there was no entrepreneurial degree you could get when I went to college. So my degree is actually in journalism because I was curious and that was like, that was easy access to almost any subject I wanted to understand. So, when entrepreneurism became a bigger thing, it was just after I graduated from college and I was lucky in that the first company I joined was a start-up. They were looking for people who just wanted to get in and do any number of things. So, I came in doing public relations and drove $2 million of media coverage for this little start-up company by just badgering every journalist I could get hold of to say, "Hey, here's this really cool company". The company got acquired. Buy into it. And then that took us all out to Silicon Valley, and that set the stage for the first one that I founded.

Valentina: From a boardroom to a war room as a serial entrepreneur Allison compares what it was like to lead her first venture-backed company as opposed to leading Ambition Data today.

Allison: I have been on quite an adventure. I've spent many years building different companies. This is my third company and I think it's my love of adventure that always attracted me to start-ups in the first place. The first one was a dot-com company that was venture-backed. The second company was in Colorado, and it was part of an eBay optimization kind of software program or trying to help sellers do the best features. And the third company is Ambition Data, and it pulls across all the others because in the first company, I was operating at the boardroom level and as a venture-backed company, there's a lot of seriousness that happens in the boardroom to make sure that you're returning money to investors. And in the third company, this one, I'm really running it myself and it doesn't have the same structure. We're not a venture-backed play, we're doing it on our own. And so the connection from the boardroom perspective to the tactical war room perspective is a little bit of what I've gained along the way between these different companies, as I’ve worked through. I don't know, maybe with five hundred different Fortune 500 type companies, lots and lots of different pieces of feedback coming in from different companies at different managerial levels. So the one thing I might add here is that Ambition Data when I talk about that connection between the boardroom to the tactical war room that always spins around the customer, everything about ambition data is about the customer. But we're not at war with our customers, there's just not really a good word for the tactical level. And I think one of the unique features and the goal of the company is the way we use data to pull the customer forward and find that really beautiful connection between the financials of a company and the benefit to the customer.

Valentina: So, what does actually make a great leader in Allison's eyes?

Allison: I think there's definitely a lot to be said about resiliency, being resilient, having a lot of grit. I've seen companies that are doing executive programs use that as an advertising tool. Now it's like, this is grit. This is where grit is made, you know? Yeah, OK. But there are many great traits. There's a spectrum. I like to think about these as U-shaped curves just pulling to my analysis side. And what a U-shaped curve is if you don't have any grit, you're not going to get very far. If you have enough grits, you're going to get far. But if you have too much grit, that's also a bad thing. It's as bad as having not enough because you can dig in and not stop when you should rest when you should think about it, is there another alternative? And so I think we're really good at saying, you know, entrepreneurs really have to go after it, they've got to spend every waking moment going for it. I don't agree with that. I really like Arianna Huffington's perspective from Thrive and the sense that you're going for it because you believe in this concept and your heart is in it and that sticks the concept for you. So, for Ambition Data, it's about the customer love and making this bridge between companies' boneheaded perspective sometimes and what the data is telling them in the customer base and what customers really want. So that lights me up internally and I think about, "Oh, this is a bridge, it's something I feel really passionate about". But whatever that bridge is for that person, you can't just hammer it until you are exhausted. So, I would say take a breath, take care of yourself so that you can bring your best into the executive role. The grid is always a big one, and the other one I'll put behind that is having a sense of humor. Again, not every day is an easy day, but the ability to find humor in it and just let things go and make fun of something that happens, good, bad, indifferent is just going to make your day so much better. And I think that's an underestimated trait that, you know, the handy, you know, the offhand quip, the fun of being and it comes through when you have a sense of humor and you can be a little less serious about every cash flow sheet you're looking at, and you know, oh my god, are we going to make it to the next month? Oh, well, I guess we'll find another job. I, you know, whatever it is that that that works for you.

Valentina: In the last couple of years, quite a considerable number of companies and entrepreneurs have relocated from California, for example. You're probably aware of Tesla and Oracle moving to Texas. From Alison's point of view, moving from Silicon Valley to Colorado, how did that affect the company culture?

Allison: We were positioned at a different part of the U.S. geography, and I don't know how much this is an issue today, but I think it's still somewhat of an issue. So first companies in Silicon Valley and in that place, you're saturated with all sorts of people who kind of think like you do, who are pushing the edge, who are adventurous, who are highly talented, very smart, you know, lots and lots of talent all around you. In the second company I moved into the central part of the U.S. into Colorado, and there was definitely a sense of less urgency, people always went home at five, maybe six. Yeah, that just never happened in Silicon Valley, you went to dinner at 7:00 that was early. So, there was a different culture and geographically where the company is based, which I think does reflect the culture that it can execute on. And that also comes, so it comes from the board, it comes from the executives, and it also comes from the location. So, the second company taught me a lot about where the culture is in the business, and then that also translated to "Could I raise funds for that company?" Because in that space, I was coming off a great first round. But the company was based in a location where investors were concerned about military spending and microchips, they weren't concerned about what that company was about, which was about eBay analytics and optimization and essentially SAS before it was SAS. So, the geolocation was a big deal. The third company, I think what I learned there was not to spend as much time and effort building the culture of a team, and I know that's going to sound like heresy, but I think as a CEO, you can bend over backward to build an amazing culture for your team, but in a market where people have a lot of choices and they have a lot of options, everybody else is, you know, doing Friday beers and Wednesday lunches, it's not such a unique differentiator. The one thing you can't get away from, and I think the place where a CEO should focus is in the purpose of the business, do the people believe in the purpose behind it and they want to be part of that, they want to make the world a better place for this angle, this purpose, this approach. I think that is the unique cultural element that really speaks to keeping your team and growing your team. Not, you know, do you have a roadmap for their careers? Have you evaluated them every six months? I mean, you could work yourself to death on all of that, but it won't hold a person unless they really care.

Valentina: Apart from having a hard knowledge of how to run a business, what else would Allison consider to be the most useful skills to have?

Allison: I have to say in my first company, I learned a ton. I often think about it like my, you know, graduate program. The company queued up to go public, we didn't go public, we raised over $70 million in venture capital, lots and lots of pitches, lots and lots of board meetings. I mean, it was a fantastic experience. But what I also learned is I learned a lot about how to read body language. When you're sitting across from investors and they're giving you certain signals like this, which is, I don't believe what you're saying, I'm really skeptical. And you know, when I'm watching my co-founder speak through his hands like this, it's, you know, it's I'm bullshitting you and there's, you know, I don't believe what I'm saying. So, I have found through my career that the ability to read nonverbals carefully pretty well, looking at the whole package of nonverbals that are going on, has helped me a lot to really add more context behind what's going on. And I know a lot of people are always like, "Oh well, I learned more about the financials. I learn more about the product". Yeah, I learned that stuff, too. But what really went the distance was the nonverbals. So, but you know, from an executive perspective, the first company was really good at playing the start-up game, which is talking a big game and then fulfilling it, and that's, you know, that's what you do with investors you represent I'm going to generate x y z amount of revenue, I've got the team to navigate through all these challenges that we know we will. We'll see, but we will be successful anyway. And so that's a start-up as a position of bravado, always, and you have to do that. So, it's a little bit about learning where the B.S. is and learning what's real, especially when it comes to competitors, what you have to be worried about, maybe what you don't have to worry about. So, the signal versus the noise is probably what I find most in the first company, and I use that a lot today.

Valentina: In fast-growing companies, especially start-ups everyone does everything, CEOs are often forced to go above and beyond and do more than what they would normally do because it's their responsibility to make sure that everything goes well. Should it be like this, how should the roles be allocated, and what they should primarily focus on as opposed to doing everything?

Allison: I think it depends on the size of the company. Honestly, when a company is small, there is a lot of involvement from the CEO and there's a lot of setting the core values of the team and what you're really doing, let's say from zero to maybe 1-15 people, maybe your first dozen in that place, you're creating a nut of values and purpose and how do we go about solving problems, where are ethics, where are our values? All of that is getting saturated with your team and you've really got to be checked in. You've really got to be able to provide guidance because it's super easy to let go and say this person is competent and they're executing on this role, but that doesn't mean that they are making ethical decisions or that they are thinking about the financials of the company and thinking about the next step, the CEO's role. And, you know, CEOs have lots of different talents, but I think the role is to take the skills of your team, understand them thoroughly, and then back up their weaknesses with different questions, provocative questions, and perspectives and when needed, partnering them with another person that helps fill out their skill set because there's, you know, it's like a mosaic in every company. People have strengths and weaknesses, and that just is you're never going to find a unicorn. I mean, maybe you're the unicorn because you're the founder, so pulling through all those different threads is important in the very beginning. If you get venture backing or a substantial investment that kicks off this jet fuel, and I remember in my first company when we were hiring 10 new people a month and onboarding them and the company started to grow into the hundreds, I couldn't remember everyone's name. I couldn't remember unique things about them. You know, I would introduce myself more than once to the same people, and that's embarrassing. But you know, I can't remember the names of 200 people, it's so hard. I mean, you know, maybe you can use the memory palace technique and try to pin that altogether if you have that time or you're really skilled with memorization. But at that level, you really rely on your lieutenants. And so, if you've done a good job of setting the core, then you start to plug in additional core executives that change the way the company operates. Now this is tricky, and I think the woman who did the H.R. role from Netflix, wrote a book, I think it's called Powerful, and I can't recall her name off the top of my head, but what I loved about her book is she talks about this concept that your people are fitted to your company in different roles at different times. And what you're going for is you're trying to create as a CEO, you're trying to create this cultural nut that sustained through the original team, but you're also passing off some of their roles, you're expanding, you're translating that into the next team so that people can get on and off the bus and the core of the company continues, because not everyone who starts at the beginning of the company is appropriate for a different stage of the company. So being willing to let that treasured employee number 10 go because you love them and everything they do, but they're not yet right for your company at the two-hundred-person level. And as all the detail comes down and there's more compliance and there's more regulation, maybe they hate that, maybe you hate that, there's a sense of transition that moves on. So, I'd say for CEOs, that's the biggest thing I've picked up is what's appropriate for what stage of the company and a CEO should never be doing at all, but the role of the CEO changes just like everybody else's role as the company grows. Your role is to fill the gaps and to find the next resource you need to fill those gaps.

Valentina: Luckily, in 2021, people openly talk about controversial topics like facing sexism and double standards in the workplace. Alison, as a female leader in a male-dominated industry, was not an exception. Unfortunately, even today, a lot of women are still exposed to these uncomfortable situations. That being said, I do not want to ignore the fact that these things happen to men as well. However, women happen to be targeted disproportionately more than men. Listen to Alison sharing her own stories of becoming a target of these stereotypical attitudes.

Allison: I always listen for things like comparisons to the wife or comparisons to my children, or like certain things that you wouldn't say to a guy. So, you know, if I'm talking, if I'm having a conversation with an older man and he's comparing me to his daughter, I know in his head he is not thinking about me as an executive. He is thinking about me in a different genre that he understands, and I've got to correct that. So there are a lot of activities still happening in this space, I don't think it's cured and I think the conversation needs to continue.

Valentina: Unfortunately, this was not the only experience Alison had.

Allison: When I was between my second and third company, so just before I launched ambition data, I had gone back to working for another company for a while and I really enjoyed that, it was a young company and I felt like I was contributing a lot. That company got acquired and the acquisition was a much, much larger company, it wasn't very comfortable for me, and so I went and started to work for another small company that was in the space. What didn't work about that company had to do with a little bit of the attitude internally, and I didn't really, I kind of sensed it was there. I was uncomfortable and I was like, "Oh, I can do this, I can do this". But I wasn't personally comfortable, and it wasn't until the day that I left that I realized what was going on. And in that conversation, I had the exit interview with the person who was running H.R., and he said, “Oh, what are you going to do next?” And I said, "Well, I'm going to start my next company" and, you know, expecting to get respect on the other side because I had launched two companies and I had a good track record, right? Like, that's obvious. It's a good thing for me to do. And he hauled off with this comment, now this is an HR guy, and like off the cuff, he just said "Or maybe you just want to go have some more babies", and I was so for my mouth like my jaw just floored. I was like, what? I couldn't even think of a good comeback at the moment because it was so inappropriate and off the cuff, but it gave me a certain kind of fuel to piss me off and go push the next company pretty hard. So, I think there are always those, there are always those moments of inflection where something happens and it can be a good thing. It can be a bad thing, but how we use it becomes this fuel that drives us as an entrepreneur because it is not a cakewalk. And you've got to have a fire that pushes you forward. When you're younger that fire will be, I'm going to sleep under my desk, I'm going to do whatever it takes. Sometimes you probably hammer too hard things that you don't actually have to hammer. And when you're older, it's more about working smarter, not harder because you really don't have the choice, you've got a thousand things to balance.

Valentina: And sometimes things can get really blurry and ambiguous

Allison: For young women what I learned and what I would caution them to look for, and I still see this here and there and stories about Silicon Valley is that fine line between is it a working dinner or is it a date? And that is one of those areas that really bugs me, and I experienced that myself, I don't experience that as a married woman with two kids now, not so much anymore, but I think younger women, especially those that are really trying everything to raise funding, they end up in these situations where should I go to dinner with this venture capitalist who wants to talk about my company because it's the only time I can reach them? Or is that not really a professional conversation?

Valentina: What should women do when they are uncomfortable doing something just to fit in the group?

Allison: Early on in my career, after the company had achieved a very substantial joint venture with an international company everybody went to dinner, and then after dinner, the guys lit up cigars. Now, if you've ever been around people smoking cigars, it will make you really sick really fast, right? If you just inhale that cigar smoke and sit there, but yet you can't leave the table, right? So, if you leave the table and be like, OK, I'm done, I'm going to go to bed now you will miss the synergy of the bonding and the conversation. So, what do you do, right? Well, you know, you sit at the table, and you light up a cigar. At that point, because I wasn't willing to leave so that that grit has to kick in at some point, that doesn't mean it's acceptable. So what I like about the conversation that's happening now is it's more of a question of, well, should we light up cigars? And maybe that makes other people not want to stay. Whereas then and this was 20 years ago, that wasn't even a question, it was just, Hey, this is what we're doing and you're the token female and you know, you can hang or not.

Valentina: A lot of women feel like they have to choose between pursuing a career or having a family, although they are encouraged to chase the money and climb the corporate ladder, they are mostly forced to postpone their work life if they want to have a baby.

Allison: It is a challenge. What I did is I actually switched roles with my husband, and I was kind of watching all of these executive men, you know, accelerate through their careers, and they all had wives that just stayed at home and managed all of the velocity of everything that has to do with kids and family, and that is not a small task by any means. And in the beginning, my husband and I both worked, and it was like we were constantly playing ping pong back and forth with the kids. And you can do that, you have to have support around you. If you're going to do that, you're not going to spend your Saturdays cleaning the house. So, if your economic levels are high enough, get the support infrastructures behind you for cooking and for cleaning and other things. Great. You both of you have rock-star careers and you manage to take the things that are not the highest and best use of your time and outsource those. I have had an executive assistant for years that I've also used in that capacity, so I would say cooking, cleaning, executive assistant to handle the minutia stuff that you can't always find time to do yourself. The other avenue is to switch roles with your spouse male, female, whatever it is, I happen to have a husband. And this was an interesting dynamic because it wasn't something I expected, but I was kind of quietly saying, "I wish I had a wife, I wish I had a wife". And so then my husband and I switched roles, and all of a sudden it's him saying to me, "Honey, I really need a break. Why don't you take me on a date?" And it's me healing all the financial pressure, and, you know, I've got to put the bacon on the table and bring home the bacon and, you know, fry it up in a pan. So it wasn't, it surprised me that that role, the way that women feel sometimes with men in the traditional structure still applied that now I was on the other side. So that was helpful. And you know, you have to decide what's right for you. But with my husband, when we switched roles, what happened is all these signs appeared all over the house of what to do and what not to do, and so I just went with it. And if you have that kind of relationship, it can be fun.

Valentina: Thank you for listening to the episode, and we are very much interested in hearing what your thoughts on this topic are. Do you think gender biases in the workplace is a topic that's already talked about enough? What are your personal stories and how do you treat this discussion in the workplace? Let us know on our official LinkedIn Page CX Insider. And if you have a story that you would like to share in the podcast, please let me know in my email or one of my colleagues. Meanwhile, check out Alison's profile provided in the episode description below and her latest book called The Age of Customer Equity. And I will see you next time.