April 4, 2023

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C-Level Leader Abby Kearns Shares Insights into Tech Roles that Build Leadership Judgment and What We All Need to Know about Risk

Abby Kearns, advisor & investor

Abby Kearns, advisor & investor

In this installment of our Women in Tech Series, Kenning Partner Cathy Boeckmann talks with Abby Kearns. Abby is a C-level business and technology executive who has held top roles at Puppet, Cloud Foundry Foundation, and Pivotal Software, to name just a few of the influential organizations she’s been a part of. She talks about how two roles – project manager and product manager – opened her eyes to the world of tech and inspired her strategic style as a leader. She shares her passion for enterprise infrastructure and for being a part of the open-source movement. Focused on the challenges of scale and complexity, Abby offers an inspiring take on how all of us, and women in particular, can look for ways to get more comfortable with risk.

Anyone contemplating a career in tech, potential founders who want to understand how investors think, or rising leaders who are curious about what top tech executives focus on will find something of value in this conversation.



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Cathy: I’m Cathy Boeckmann, managing partner of Kenning Associates. Welcome to the Knowing Kenning podcast.

This episode is another installment in our Women in Tech series where we spotlight guests who have an interesting story to tell about their involvement with the tech world. We also shine a lens on the arc of each guest’s leadership development journey. Today I have the unique pleasure of speaking to Abby Kearns.

Abby is a C-level business and technology executive, investor, and board member. She’s held top roles at companies like Puppet Cloud, Foundry Foundation, Pivotal Software, Verizon, and Totality. I hope you enjoy listening in on our conversation, which touches on some of the tech roles Abby has held, what she’s learned from them, and the passionate interests that have shaped her career.

Next up my conversation with Abby Kearns. 


I’m thrilled to be speaking with Abby because she has had a particularly interesting career. She has progressed through a variety of technology roles as she’s marked out a path from product management to angel investing. Her career focus throughout has been on enterprise infrastructure, a lens that she brings to her current work, serving on boards and doing early investing. Welcome, Abby.

Abby: Thank you for having me. I’m so excited to be here.

Cathy: I find your career so interesting that I think that’s probably where I’d like to start, getting a sense of where your first roles were and how you progressed through them. So let’s start right at the beginning. How did you get your start in technology?

Abby: Well, going way back to the beginning in the way-back machine, I did major in Comp Sci in college, so I did have some intentionality on this thing called tech. But I will say that when I was in college, not to date myself too much, but it was in the nineties, so tech was an emerging thing, but it wasn’t necessarily a career path that most people aspired to.

But I had a vague notion of interest in computers and the opportunity that technology could bring to bear. And so I decided to major in it. And my first job out of school was working for this little company called Sabre. Sabre, if you’re not familiar with how flights happen, is how the magic happens as we fly across the continental United States or even beyond.

American Airlines had a technology division that they spun out into this company called Sabre. And Sabre does a lot of the backend reservation systems and still does to this day. And at the time, I took the first job that would hire me, as you are want to do, out of college. And so you’re like, great, I can do this.

And so I got a job as a project manager. That was my first job in tech, and I landed in the global infrastructure division at Sabre, and I’ve stated in infrastructure ever since. It’s one of those things where I didn’t have intentionality with going into infrastructure. I fell into it and loved it. Infrastructure is part of everything. It is the underpinnings of everything that we think of today as technology. 

And so my first job was project management, like I said. I’d be a little biased here, but I do think everyone should have to do a little stint as a project manager and product manager too. I’ll say that for any job in tech, just to give you an appreciation for how things come together. 

I would say having my first job as project manager on infrastructure, and actually thinking deeply about data centers and hardware, gave me a strong appreciation for where we are today from a technology standpoint, but it also gave me a love for all things technology. How does something come together? How does a product come together? How does it go to market? How does it work? How do all of the teams and a company come together to create something that is so unique or differentiated? That first job really kicked off a lot of my loves that I still carry on through everything that I do today.

Cathy: So it sounds like you’ve been both a product manager and a project manager. Can you help us understand the difference between those two roles and why you find them so foundational?

Abby: Project manager is really someone that looks at the entirety of a project. So all of the things that come together, it could be multiple products, it could be multiple work streams, but as someone that looks at the entirety of that outcome and understands how to pull a team of people, usually cross-functional team of people, together to really collaborate and create that.

I think project management is so fundamental because it’s a fascinating look at how a group of people, more often than not with very different skills, come together to create something. And I think it’s a fundamental skill because at the end of the day, isn’t what we’re all trying to do in companies: work together with peers and collaborate deeply with other teams to create something that is of value to the company we work for, be it a small company or a large company. And I love that project management grounds you on the fact that all of these people have to come together, and they have to make it work somehow. And so I do think it’s a great skill to have in any situation.

The flip side of that is product management, which is owning the life cycle of a single product. Product management is a microcosm of project management in that you’re trying to pull together a cross-functional set of individuals with the focus on a single product outcome. You’re bringing together designers, developers, engineers, and teams of people. And realistically, as a product manager, you’re responsible for the entire lifecycle of that product. And while not directly responsible for the teams, you’re responsible for unifying those teams with that common vision.

And so while it is similar to project management, it obviously has a very different tone and different focus and a very different outcome. Product management is practiced somewhat differently depending on the company you’re in oftentimes. But I do think at the end of the day, the heart of it is that I am owning the lifecycle of this product as a product manager, which means I’m not just here to think about new products, new ideas, but I’m here to see the creation, the management, and the fostering of this product as well as, if you’re there long enough, you see the end of life of that product. Particularly if you sunset a product that isn’t doing so well or isn’t getting the traction you think it deserves from a customer and a user base.

Cathy: So they’re both different views into how you get people to coordinate their activity for a purposeful end, but one is more focused on the timelines and the tasks, and the other is more focused on the product itself and where it is in its lifecycle and what value it’s bringing to the organization.

So what did you take away from your time as a product manager?

Abby: I took away a couple of things that I still come back to on a regular basis, both in the work I do today advising as well as my last role as a CTO, which is, the hardest job of any product manager is trade offs. Not just what are we going to work on today or tomorrow, but the harder question is, what are we not going to do?

And it sounds simplistic, but I will say it is one of the hardest things that PMs have to struggle with, because you have to figure out what those trade offs are. And sometimes the trade offs are big: it’s end of life in a product, it’s deciding not to do something that people think is really interesting. And sometimes it’s small: hey, we’re not going do this feature this time, or, you know what, we’re going deprecate this feature so that we can invest more in this other feature. But small and large trade-offs are a core part of a PM’s job, which is justifying to yourself and to your team what choices we make and why. 

And those trade offs often are very dependent on the market, your user base, your customer base, or the advance of the business: maybe your company is shifting gears, maybe your company is shifting and pivoting into a new direction.

There are so many different inputs to this decision making, it’s a hard lesson to learn, but I think it’s a very powerful one. It’s something that I bring in the work I do and have done as a PM, and I think it’s also something I bring as an executive and a leader. Because our job is not just to say what are we going to work on and spend our time on, but what are the things we’re just actually not going to do, and why?

Cathy: It sounds like a strategic role in that sense that you would continually be facing these strategic trade-offs between what you want do, what you can do, what customers want, and what’s going make money. And so that sounds like it’s actually a really good warmup to some of the things that people would face in leadership positions. 

Abby: It’s an amazing warmup because your hardest job as an executive, beyond just hiring and fostering a fantastic team of people, your hardest job is figuring out what do we spend our time on.

Time is your most precious element in a company and in a team. And as a leader, it is your job to help your team manage that. And oftentimes, it isn’t just saying what we’re going do, it’s what are we going to stop doing? And why is that important? It’s something that I think a lot of leaders struggle with when we see companies that are spread too thin or people are overworked or you see their portfolio capabilities that are really broad and you have to say, okay, is that the best use of their time?

And if not, could we focus on fewer things and do those amazingly well? Do we go a mile wide and an inch deep, or do we go a mile deep and an inch wide? And I think those are always the trade-offs you make as a PM, and as executive and leader, and even as a company, like where do we want to spend our time and what do we want to do differentiate ourselves?

Cathy: You have also been a CTO, which people think of as really high level, perhaps the highest-level kind of technology role a person can have. What excited you about doing that role?

Abby: This particular role, I got excited because of the team of people and the product they worked on. So I was CTO at Puppet up until recently. And for those of you who aren’t familiar with Puppet, it’s an industry leader in DevOps, an infrastructure automation software company.

But more than that, it was a fantastic team of people that were working on a problem that I still think is super important, which is, how do we automate aspects of infrastructure. And that may seem very rudimentary and very in the weeds, but it’s super important. Because as we look at where we’re going technologically speaking, everything that we deploy our applications on is being rewritten as we speak and have been for the last five, six years. And the only way we’re going be able to do this at greater and greater scale, which is the trend we’re on, more and more applications are being developed, more software is being created, businesses are, really software centric. Now, the only way we’re going to achieve the ability to do this at greater and greater scale is through automation.

And so it still remains an important problem that a lot of companies and products are trying to tackle. I was passionate about the product and the team and the opportunity to go and really unify engineering, product, design, and security together and work on a hard problem. It was just too much fun to pass up.

Cathy: It sounds like that’s a theme for you, that you like these roles that end up synthesizing things together, and the synthesis of those challenges it sounds like was the real nugget of what you were interested in that CTO role. How rare was it to be a woman CTO?

Abby: There aren’t many of us. I would hesitate to guess at the number; I’ve only met one or two others, only a couple of other women CTOs. It’s especially rare in infrastructure because there aren’t a lot of women or historically haven’t been a lot of women, particularly in enterprise infrastructure.

So it is rare. Sometimes as a novel person in an organization, how do you use that novelty aspect of who you are to bring something interesting to the table? And so you talked about synthesizing and collaboration. Obviously as a CTO, your job is first and foremost to set strategy from a product and a technology standpoint for a company.

But more importantly, it’s how do we bring a team of people together and align behind that strategy so that the company can move forward, be it product-centric or a tech company to a larger company. CTOs are responsible for driving forward that technology strategy and that vision. The only way to do that is to unify a group of people behind that vision and get them excited about the role technology plays, and so there’s a lot of fun in that.

It’s a lot of work, I’m not going to lie. At the end of the day, when you’re able to really execute on that, it’s a nice experience.

Cathy: So that makes me wonder. You mentioned that enterprise infrastructure is a common thread for you in your career. How do you define that?

Abby: It’s a good question, and I should probably elaborate. I think about enterprise infrastructure, I think largely about the software that runs the hardware. For me, I also acknowledge the hardware that sits underneath it, and so when I talk about hardware and software of infrastructure, what I mean is the servers that sit in the data center and the software that sits on those servers that allow us to write applications and services that we think of today.

Everything from the applications that sit on your laptop to your iPhone, all of that software sits on top of underlying infrastructure. When we talk about the cloud, it’s not some ubiquitous place, it actually is somebody’s data center that your software is sitting on.

And so for me, I get excited about the hardware and the software that sits in data centers and allows us to write these amazing applications and services, and it powers all of the work that we do. It’s a weird thing, I guess, to be passionate about, but I think it’s pretty interesting.

Cathy: I think you’re making a pretty good case. It’s the underlying support to everything that everybody does in an organization. With so much of our work being digital, there’s very little that we could do without having a really skilled person keeping an eye on both of those underlying layers of our work.

Abby: None of it works without it, so it’s a pretty important piece that sits behind the scenes. But I do think there’s a lot of power in the innovation that happens there as well.

Cathy: Yeah, absolutely. And I think a lot of that innovation might be invisible to others. But to be at the face of having to confront the spaces where that innovation is necessary, I think you’re making a good case for that being pretty important and interesting. 

You also were the CEO of an open-source software foundation. Can you tell us what that means, and what that means you were doing?

Abby: Yeah, as CEO or oftentimes executive director of an open source software foundation, specifically Cloud Foundry Foundation, I had the pleasure and the joy of running that for nearly five years. It’s an interesting business because an open-source software foundation is technically a not-for-profit company.

From a US tax standpoint, you can’t donate to it. It’s not a philanthropy. But what it does allow you to do is, think of it as escrow for software. Once software is contributed to an open-source software foundation, it can never be transferred to a for-profit company. And why that is important is because one of the most important pieces as you develop and co-create open-source software – which is oftentimes multiple companies, oftentimes competitive companies contributing to a single source of software – is you want a neutral place where everyone can be on equal footing. You also want to make sure that no one can just decide that, you know what, I don’t want to do this anymore. I’m going take it and go home. And so this operates as an escrow, like I said, of software. But what most importantly it does is it allows a central governing body, so a neutral third party, to own the IP and the assets that are contributed to the open source.

And so our job when we run a foundation is to have oversight of that trademark and that IP. It’s our job to manage that, foster it, and encourage a large community of participants to contribute to that. So you want to continue to foster engagement and participation. And that can be through community engagement and contribution to the use of it in downstream. In open source we refer to things as upstream and downstream. Upstream is the open source bits that sit in a neutral location. Downstream is oftentimes where someone takes those open-source bits and transfers them into a commercial product. 

Cathy: Could you give an example?

Abby: So today open source is in nearly everything that we use, in about 96% of the world’s software. So it’s everywhere. Now you’re going to say, wait a minute, there’s some of this software that I pay for, and you are correct. Small, tiny libraries are pulled into larger proprietary code; at the other end of it, an open-source project has got some type of integrated services or UI or wrapper around it. But somebody has decided to commercialize and monetize, and so it can take a lot of different forms. There’s a big gamut between those things, from a library to a fully formed product. But open source is where we are leveraging that shared IP today, shared knowledge, shared library, shared capabilities, and we’re also using it to drive a greater and greater investment in innovation.

Enterprise infrastructure as a technology is evolving quickly. A lot of that innovation is happening in the open source. When we talk about cloud native architectures, most of those architectures are open source. Everything from Kubernetes to Envoy, Togo, these are all open-source projects that are acting as aspects of the infrastructure layer that we’re creating to run and manage these applications.

Open source is everywhere, and it’s used in very different ways, and foundations are really a great way to structure those larger projects where you want to drive and encourage that shared collaboration and contribution from a lot of different providers.

Cathy: That is so interesting, and I think non-techy people may not really appreciate the extent to which all of the for-profit tech that we purchase and use is based on this layer of shared open-source code that people can then build proprietary stuff on top of. 

So why does this matter for users, for the tech landscape? Like why was this something that you really felt like you wanted to get involved in?

Abby: I found it really interesting to be part of the evolution and innovation of technology with so many different contributions from so many different people and different companies. But also the downstream impacts are so vast. You’re really impacting a larger market versus one company and one product.

So that was obviously very exciting. I got a chance to work with some amazing people To those that worked for Cloud Foundry Foundation, shout out to all of the amazing groups of people we had there. But also all of the companies that used our product and contributed our product. Our community was fantastic, and it was just really a fantastic all around experience.

The opportunity when you work in open source is you get to really collaborate, not just with your coworkers; you’re collaborating with hundreds, sometimes thousands of people at other companies across the world, in other areas of expertise, and there’s a lot of beauty in that opportunity to bring together not just a cross-functional team, but a cross-company team. Individuals that are working on building a single project, and there’s a lot of excitement and interest in that. And I think that’s not going away. We’re seeing it really go up and up. 

But I do think why it’s important for everyone to understand the impact open-source software has. We’ve gotten used to readily available code and open source, but what we haven’t thought through is, where’s this code coming from? How is it maintained? How is it supported? And those are questions that I think people are going to start asking a lot more in the next couple of years as we start to look at, and start having conversations around software supply chain and security and compliance. And where did this come from and not only has it maintained, but what are the licensing requirements around it? What’s the impact? And so I just think it merits further conversation and intentionality, but I don’t think that the role of open source software is going away anytime.

Cathy: It sounds like it’s the scale and the complexity and the potential for impact and the difficulty of the near-term and the long-term questions that really excite you and that make it important to manage open source software intentionally and well.

So speaking about the scale of impact and the complexity and what excites you, in this chapter of your career, you now have turned to investing, serving on boards, and being an advisor to early stage startups. Why did you make the move into this kind of work?

Abby: Well, I would view it all as supplemental. I will one day again go back to operating full-time as well. But in the meantime, I’ve been advising early-stage startups, particularly those in the enterprise infrastructure space, for many years.

And several years ago I finally bit the bullet and started tacking on to my advisory work, you know, putting some money in it as well. And for me it was a vote of confidence in the product and the team and the opportunity. I love to both contribute time and money to startups that I think are solving really interesting problems.

And for me it’s of a lot of fun to mentor and advise. But it’s also a great way as a technology executive to keep close tabs on what innovation is happening across the ecosystem. What are people working on and what are the challenges they’re seeing? So I view it as a multi-sided input for me. The board work is similar in that I love to spend time with other CEOs, helping them be successful in the work they’re doing and trying to bring some of my insights and hard-won lessons to the table as well.

One of the things that I always say as an executive, and I’ve heard this from someone else, so I forget who I’m cribbing this from, but I do a lot of my best strategy thinking in other people’s boardrooms. Because it’s one of those things where you give advice to people and you’re like, you should do that, and why did you not think about this? And what about that? And then later, when you’re reflecting back on the conversation and the discussion, you’re like, wow, that’s good advice. I should totally take that advice too, cause I’m not doing those things. 

And so it’s just a great way to get out of your head and out of the day-to-day business while giving back and meeting other great board directors and CEOs, but also it’s just a great lens on the work you’re trying to do as well.

Cathy: Yeah, I relate to that because as somebody who tries to help people learn and develop at work, I have noticed that it is very difficult to apply a new set of skills or a new lens to your own role and your own work first. That’s probably the hardest thing to do. It’s much easier to apply it in a neutral space where it’s somebody else’s problem. It just is so clarifying. Then you can take the lessons from having done that mental leap to apply an insight to somebody else’s domain, and you can bring that back to your own domain. I think you put that really well. 

All right, so you’re an investor. How do you choose what companies to invest your time and money in?

Abby: I’d like to say that I have this very elaborate, well-defined thesis. And I broadly do, but I tend to invest and advise those companies that are in my area of expertise, which is enterprise infrastructure, be it dev tools and automation to all attributes of the work we do in security. So I tend to invest largely in those areas where I feel like I can bring something to the table.

I’m an early-stage investor, and if you’re not familiar with investing, there are stages. Everything from Angel to pre-seed to seed to A, B, C, D, and so on. I tend to invest pre-seed and seed rounds, which means I’m looking at products early, products that don’t have product-market fit yet. Teams that are early. And so at that stage of company, you’re buying into their vision for the product, but they don’t have traction yet.  And that’s why a team is so important as you think about early stage investing, because you’re really making a bet on that team and what they can build and can they iterate and innovate fast enough.

If you are thinking about getting started in investing, and you want to invest early, then that’s just something you’re going to have to think about and look for.

But as far as choosing which companies to spend my time and money on, it comes down to the team and the product and the vision for me. I get excited about fantastic founders that have compelling visions and those products. I get excited about the product and the opportunity. And when you get off a call with a founder and you leave it excited about what they’re building and oh, here’s where this could go and here’s the opportunity this could bring to the market.

For me, that’s really what powers my choice; it just makes it fun because then you’re just as excited as the founder is about what they’re building, and you just hope to be able to support them.

Cathy: I love that answer because a business idea is a business idea, but are the people the right people, do you believe in them? It sounds like that’s very much part of how you think about things. 

So your investment lens is really around companies that make tools, platforms for developers, that sort of thing. What kind of trends are you seeing?

Abby: As for the trends I’m seeing, obviously, my lens is enterprise infrastructure. So there’s a lot of other things happening, even just in tech, that I don’t spend a lot of time thinking about. So I don’t think about consumer, I don’t think about biotech. 

But as I think about enterprise infrastructure, there’s a lot of innovation that’s happening on the automation and the layers that sit above the hardware, and we’re going continue to see a lot more innovation there.

Obviously, the buzz of the day is generative AI. Everyone’s talking about ChatGPT, and you know how amazing it is. I do think we’re going to see generative AI pulled in more and more commonly in tooling, but we’ve been trending that direction for years anyways, which is automating as much as we can, simplifying as much as we can, democratizing access to technology to a broader set of people that may or may not have the depth of skills necessary to run these environments at scale. And so we’re seeing that innovation happening on the tooling side, alongside greater visibility into what you’ve got and where you have it and automating those insights in meaningful ways so the teams can run their environments in a much more efficient and effective way. 

Cathy: Abby, you have worked in technology roles, and now you’re also an investor and you work a lot with the leadership of startups. All of the startup stuff has got this sort of inherent risk to it, right? Because nobody really knows if this early-stage company is going get off the ground or not. What have you learned about how people manage that kind of risk?

Abby: I would say that working in and for startups is inherently risky. There’s no such thing as a sure thing with startups. We’d all like to think that we have very calculated risk management, and we’ve picked a good one. But at the end of the day, not every startup succeeds and the number of startups that succeed, what we call is unicorns and beyond, there’s not as many of them that make it that far. And so there are a lot of startups that don’t make it anywhere or that have small exits or just go out of business. And so that’s my way of saying that if startups are inherently risky, the idea is that you’re rewarded for that risk-taking through equity.

So we talk a lot these days about equity, stock-based compensation; you’re rewarded for that risk by equity in the company and the potential that several years from now, maybe that equity will be worth something. But it is, at the end of the day, still a risky bet for both the company, the work you do, et cetera.

And so to work in and around startups, one of the things that’s really important is to get more comfortable with risk. And I feel like that’s something, particularly those of us that are, let’s say, women of a certain point in our career, that hasn’t always been encouraged in the work we do. We were taught to follow this ladder or follow this plan or check all these boxes and things will be fine. And I think that is okay to a certain point. 

But if you’re working with and around startups or even I think even in a large company these days, your ability to take and handle risk is becoming more and more critical. Particularly the higher up you go in an organization as an executive in a large company, you’re still going to be expected to balance risk. You’re going to need to be able to say, okay, what are the bets we can make? What are the things we can do? And when you’re making those bets, be it a small bet or a big bet, there’s always the likelihood that it will not pan out. Now, the flip side of that is if it does, it’s amazing. And wow, you are a hero. But there’s always the risk that it doesn’t, and it doesn’t work.

I think more and more, people, particularly women, should be told that it’s okay to take risk and it’s okay to fail, and you’re going to learn a lot from that and you’re going to take that on. Because I don’t know about you, but for me personally, I’ve learned more from my failures than I have from my successes.

There are a lot of things that I’ll never do again, but I did that once and you know, I won’t do it again. But an important thing as a tech executive or working in or with startups, is really getting comfortable with that level of risk. And if you’re going to advise and invest in the company, you also have to be comfortable with that risk.

For me, I just got comfortable with it years ago, and so now I am way comfortable being out on the ledge and saying, I don’t know, this may work and it may not. I guess we’ll find out, but that’s okay. We’re going to learn a lot along the way. You know what, if this doesn’t work, here’s how we’re going to do the next thing, and here’s how we’re going to iterate on that and try it again and try it again.

That’s such an important lesson that I learned both on the software and product side. There’s no product that’s ever been successful first take out the door, no such thing. Products are iterated on over and over again. Feedback, iteration, collaboration, it’s always a very involved effort to get a product out the door that works and that we all love.

And the same is true for the work we all do collectively as leaders. You’re never going to get it right all the time. So how do you iterate? How do you learn and just keep moving it forward? Maybe it’s just my personality is I have a strong bias to action, so I want to always be moving. We’ll learn, and we’ll shift gears, and we’ll try again. But for me, I have that strong bias for motion, which is something that I look for in both companies that I work with and companies that I work for.

Cathy: Yeah, so it sounds like a kernel of advice that I could pull out of that: anybody who is in an early stage of their career, who has an interest in the kind of reward that you get from being a founder or from being an early-stage investor, should start early on thinking about their attitude toward risk and the ways in which they can learn from failure. That if people examine these things early on and start doing some purposeful, intentional work there to try to see risk as an inherent part of upside reward, and also as a thing that can be learned from when things don’t go as planned, that would be a really important piece of advice that you would give.

Then layered on top of that is, you know, anybody from a group that may not historically felt safe taking risk, or may not have been encouraged to take risk, you know, in particularly thinking about girls and women, that would be a particular area where you would say women in tech could take a good look there and do something to support themselves so that they can be more comfortable and successful with the inherent risks that are wrapped up in being really innovative and at the cutting edge.

Abby: Yeah, I would say that getting comfortable with risk is something I think that all people should start to work on, and not everyone is comfortable with that risk. And I think if you’re not comfortable with high degrees of risk, obviously you should moderate what you do around that. Like I say, if you’re not comfortable with high degrees of risk, don’t become an early-stage startup investor, don’t work for an early-stage startup. Just those are, there’s things you can’t do. But I just think there’s isn’t anything that we do, particularly in the bigger bubble of tech, there’s no sure thing ever. 

Now, I will balance that with, for underrepresented minorities, women, people of color, there is obviously our ability to collectively take risk, have, more on balance than say, cisgendered white males, and that’s, unfortunately there’s systemic challenges there, and I’m not going to say that doesn’t exist. There is inherent, systemic privileges that don’t necessarily work for underrepresented minorities, particularly in tech.

However, on the whole, getting comfortable with taking risk is important part of the role, and figuring out how to balance that is important. And if you’re on an executive, you’re going to have to figure that out. You’re going to have to figure out how to take risk, for you personally, how you do that as a leader, you’re also going to have to figure out how to balance that risk with your team.

Because there isn’t anything that anyone is working on that’s truly innovative, that is not inherently risky. There’s no sure thing. There’s no guaranteed outcome. And in fact, I feel like as a whole, uncertainty is actually probably more of a common theme today than ever before.

We just saw the last three years hit by a pandemic that nobody was expecting and really planning for. And I think we’re going to continue to see more of that uncertainty. We’re in the midst of a massive shift. The digital transformation conversation we’ve been having for the last 5, 6, 7 years is actually really starting to come to fruition.

We’re seeing automation happening more and more. We’re seeing jobs being replaced and moved, and the work we do as a worker in these companies is changing. And so there is a ton of risk in the system today. And so figuring out how you’re going to navigate that as a leader is critical to your success as a leader, but it’s also super critical for the success of your teams and the people that work for you. And figuring out how you can balance that in a way that’s positive and focused, it’s a hard job, but I think it’s one of the most meaningful ones.

Cathy: Abby, it was such a pleasure to talk to you today, and I know you’ve expanded my thinking quite a bit on the tech that surrounds me and the people that make that tech and the people that thrive in that environment and how we can all, regardless of our roles, work to be more aware of the risk around us and find ways to collaborate with our teams to manage it in a way that feels positive and results in learning. So thank you for inspiring me, and I hope everyone.

Abby: It was my pleasure. Thank you for having me. It was a lot of fun.