Ledge: Sherri, thank you for joining us. It is really cool to have you on.
Sherri: Hi, Ledge, it’s great to be here. Thank you.
Ledge: For those who don’t know you, would you mind giving a two- or three-minute background story of yourself and your work?
Sherri: I have been a software engineer in the software engineering business for over 25-plus years. Prior to that, in my twenties, I was actually a musician so I know a lot of software engineer who are really super creative. I was a musician in my twenties and I realized that I was poor and probably needed to do something else.
So I became a software engineer and moved up the scale. I’ve been in all kinds of organizations from a company called “Abacus” which was purchased by DoubleClick and eventually sold to Google.
I was the CTO for the State of Colorado so I was in government for a little while. I was at a company called “Beeline” which does a lot of contingent labor which is probably near and dear to your heart.
We sold that in August. Recently, I just joined The Nature Conservancy as their new CTO. They’ve never actually had a CTO before.
So you name it, I’ve probably done it in my career.
Ledge: That’s a fantastic story. Talk a little bit about that. Never had a CTO ─ now, what? What did Day One, Year One look like in that scenario?
Sherri: It’s really interesting. They’re are a great science organization and they do really transformational science. But, a lot of times, that lock, if you will, and the white paper over somewhere . And so, where I’m coming at it ─ they said, “Hey, there’s a lot of technology out there. We probably need to be leveraging it in a different way than we are. Can you come help us?”
I’m really starting to just come up with strategies around everything every way that technology might actually be able to make the world a better place.
For instance, we’re leveraging drones in certain areas. They can go and view areas that we couldn’t necessarily get to and understand the impact of climate change or whatever.
Then, there’s also a big data play at The Nature Conservancy because there’s this great science that had you actually make that from theoretical to applied. And so, we’re leveraging big data like Data Wide and those kinds of things.
I’m about three months in so there’s still a lot around my strategy that has to be borne out but it’s coming together and it’s a super exciting time and it’s also, of course, very needed in the world.
So we’ll see what happens.
Ledge: That’s so interesting. In an organization that big with that big of a footprint, probably doing all kinds of science collecting all kinds of data for years, is this like all over the place? If there’s no unified strategy or person thinking about that, is this going to be a big project to bring it all together and bring coherence to that huge data capability?
Sherri: That’s exactly what it is. They’re a global company so they’re in every country and all fifty states have chapters. So there is a wide range of, I would say, both data and even products that have been built.
So to try to wrangle that into a place that’s consumable for all and our global level is where it’s going to be a challenge.
I’m building a small team. I literally had no one to start. So we’re putting together a small team that will start to kind of figure out where the most impact that we can make and how quickly we can make it.
So, for instance, one of the areas that I’m very closely involved with is called “Measuring our Impact” and we’ve never been able to actually measure the impact of TNC as land preservation across the world. And so, that’s a big data play. We’re looking at remote sensing. We’re looking at all kinds of data and how we can start to really understand where we’re being impactful and, perhaps, where we need to spend more resources.
It’s a huge challenge, for sure, and it is a lot of data wrangling. But it’s also super exciting because the scientists are very excited about it and everybody kind of want to play in that large space.
So lots to come and, hopefully, you’ll hear a lot more about it in the coming months.
Ledge: You’ve, obviously, been involved in all kinds of team building and organizations that you’ve acquired and organizations you’ve been hired into. Maybe compare and contrast a little bit. It’s like, “I’ve been handed a team” or “I’ve acquired a team” versus “I’m building a team from zero.”
What are the lessons there?
Sherri: I’ve had it all. In my last job at Beeline, I was handed a team. They had a team at that time of about probably fifty or sixty developers and DevOps, etc. When we merged, I was at a company called “IQNavigator” and we merged with Beeline about eighteen months ago.
Then, it doubled in size. How do you bring two disparate not only technologies but disparate cultures together?
And you know the challenge and I think anybody who was there would say it was a really big challenge. But we did it and we sold it and did well on that.
But there’s a lot of what I call “shaking hands and kissing babies” kind of thing. You’ve got to go around and really try to make sure that people believe in the goals that you’re setting and if they are on board or not kind of thing.
I’ve been in this role where there’s nobody and I’ve got to figure out how to stand up the organization.
Similar in the government, I was the first CTO they had in Colorado and wound up standing up an organization of enterprise architects, then then eventually took over all of the applications in the state and then wound up having five or six hundred people. But that was really interesting.
And then, I was at a company, a startup, called “Pay Simple” and they had outsourced most of their technology to a company in another country. And they hadn’t really had any rigor around it at all; they just kind of outsourced it and turned their backs on it.
So I had to come in and actually wound up bringing all of that in house and hiring all new development organization. Meanwhile, we actually sealed the deal with American Express so I was in this transition phase with technology and wounded up signing on one of the largest financial companies in the world. So we had to meet these grand SLAs with a small startup team.
And we did it. It was actually very fun but it was a lot of late nights and a lot of “How can we do this together?”
I think probably what I would say is that anywhere that you are, you do have to build a team that believes in what you’re doing and where you’re going. If you can do that, then you can do great things. And I’ve seen it time and time again.
Ledge: You’ve worked in these different scenarios and I’m wondering as to the path as you moved from engineer up to CTO. I’m sure lots of our engineer brothers and sisters out there are thinking that maybe there’s a path for them; and, at the same time, there are a lot of people who don’t want to do that and want to stay an engineer and bits and bytes and that whole thing.
How do you know where you are on a leadership track versus the hedge of “I want to stay here and actually deliver my craft”? What was that evolution like?
Sherri: I’ll give it in two ways. One, as the leader in the organization, I think you do need to understand that there are people who don’t want necessarily be CTO. And that’s fine. I mean, there are career paths for everybody.
And I think that getting people in the right seat for what they want to do and where they feel passion is the right way to go. You don’t want to promote someone who doesn’t really want to. If they don’t want to get up every day, why bother? So I do think that there’s a place for everyone there.
For my personal journey, actually, it was kind of an interesting one. I started working at this company called “Abacus” and it was a very small company. And I was maybe the fifth or sixth developer. It wound up that I became friends with the guy who had written all of the code. We would drink beer together.
I said, “Hey, teach me everything you know” and he wound up doing that. Actually, it was a very hard time for me because it was literally 24 by 7 by 365 with just me and him, basically, because nobody else wanted to do it.
When we IPOd, he wound up making some money and left kind of in the middle of the night and I wound up having to take on that role. I didn’t want it. I didn’t want to actually manage people. I didn’t have any desire to do any of that, going back to your question.
And I struggled with it for a couple of years but wound up really embracing it and loving the CTO kind of world.
I don’t know if I was strategic in wanting to learn all the systems and taking that on. People say I either was lucky or strategic ─ I don’t know which one. But, at the end of it, it wound up being the best thing for me. I was the go-to girl at the time. And so, when he left, I was kind of the last man standing, if you will.
There’s always opportunity for people if that’s your trajectory. I think you just have to look to see where you can make an impact and people will always remember that.
That’s probably the most critical point for people who want to become CTO or wherever you want to be in your career.
Ledge: Going back to the question before that, you talked about in-housing a team that had been offshored or outsourced and, obviously, you’ve been in a bunch of different organizational frameworks.
I’m working remotely. We espouse and have a lot to do with the remote work culture and thinking. I just wonder how that fits into the big organizations.
It’s almost a mandate now that you have to be able to support it but there are great things about having people in person as well. How do you fall on remote and distributed engineering teams?
Sherri: I think you just have to do it today. I know that there have been times when large organizations have tried to bring in everything in-house and I don’t know if that works. I think especially with the software engineers, in general, it can be one of those things where you’d want to work by yourself for a while.
“Hey, don’t talk to me for a couple of days. I’ve got to finish this coding job” or whatever.
But I do think there’s also a really good thing to be said about coming together and seeing someone eye to eye. And so, what I try to do with all of my dispersed teams is that as much as you can, try to get together on some level at some point anywhere maybe in the world that you can. It really does help create teamwork.
One thing that I’m doing right now with The Nature Conservancy ─ it’s a very dispersed organization. I’m a remote CTO. I’m live in Sedona, Arizona and there’s no one else here with me.
But I go to Denver a lot just because I want to meet people. But we also are creating what we’re calling the “innovation lab.” It’s a design sprint basically for a week; and so, we’re going to bring teams in to do things, whatever it is that we want to do that week.
It’s getting a lot of traction because I think people want that kind of human touch when they’re trying to design something or they’re trying to brain storm or whatever.
I anticipate that it’ll be pretty popular.
So I think as much as you can, see someone face to face; it really does make sense. I think Zoom and those kinds of video conferencing is really important.
As much as I don’t really want to wash my hair, I do whenever I need to get on a video call.
It’s good to see people face to face. But I do think video conferencing is one of the ways to do things if you can’t get together.
Ledge: Fantastic! Last question: We try to be a useful resource to engineers all over the world of different types and people who are exploring different career paths.
Just maybe some light career wisdom that’s gotten you through those days when things weren’t going your way or when engineering was hard or being in an organization was hard. What are some lessons learned or some places that you can impart some wisdom?
Sherri: I think that’s a great question. I think the best thing that I’ve learned is that when bad things ─ and they’re going to happen especially in software engineering; things are going to crash and bad things will happen ─ you have to remember kind of where you are in the world.
I’ll give you an example of a gentleman who actually accidentally brought down our email server at one of my jobs a long time ago. And he was completely freaked out because it was the way we got a lot of business; a lot of sales came in through email and stuff.
I watched him for a little while and he couldn’t figure out how to bring the system back up. I brought him into my office and I said, “Look, I’m not going to fire you for this. Bad things happen. Let’s just figure out how to fix it and it’ll all be good and we can go and make nice with the rest of the organization.”
And he literally was able to fix the problem in ten minutes after that. And so, I learned that you’ve got to take it into context. A lot of times, when bad things happen, people go to “I’m going to lose my job. I’m going to lose my house because I don’t have work.” It goes to this gigantic thing when it’s just a freaking email server.
As a manager and a leader, trying to keep people kind of with that context ─ but also the person just trying to make sure that you keep that context of “Hey, the system is going to come up eventually; we’re going to figure it all out” really helps keep that cool head and you’ll solve problems a lot faster. And I’ve seen it over and over again.
Ledge: I love that. Great insights! It’s like nothing is that important that you have to lose your soul over it. We are still pushing servers and software and it will come back up.
I can’t do better than that. I’m going to leave it right there.
Sherri, thank you so much for joining us.
Sherri: Thank you, David.