CTO Wisdom with Joel Schlundt | Beyond the Program

Tim Winkler: 00:00:00

Hey, listeners, Tim Winkler here, your host of The Pair Program. We've got exciting news introducing our latest partner series Beyond the Program. In these special episodes, we're passing the mic to some of our savvy former guests who are returning as guest hosts, get ready for unfiltered conversations, exclusive insights, and unexpected twist as our alumni pair up with their chosen guest. Each guest host is a trailblazing expert in a unique technical field. Think data, product management, and engineering, all with a keen focus on startups and career growth. Look out for these bonus episodes dropping every other week, bridging the gaps between our traditional pair program episodes. So buckle up and get ready to venture Beyond the Program. Enjoy.

Eric Brooke: 00:00:53

Welcome to CTO Wisdom. My name is Eric Brooke. This series will talk to leaders of technology at organizations. We'll understand their career, what was successful and what was not, and what they learned along the way. We'll also look at what the tech market is doing today. We'll understand where they gather their intelligence so they can grow and scale with their organizations. Welcome to Joel, who we'll be chatting with today. Hey, Joe, would you like to introduce yourself, please?

Joel Schlundt: 00:01:32

Thanks Eric. I'm Joel Schlundt. I'm the CTO at TextUs. Um, we're a There's this SMS platform that specializes in conversational as well as campaign based messaging. Awesome.

Eric Brooke: 00:01:46

Joel, could you tell me a little about your journey to becoming an executive in technology? Sure.

Joel Schlundt: 00:01:53

Um, I've always had technology around in my life. Um, I've had a father who was an early adopter, so, you know, we always had the newest technology, whether that was, uh, Or a personal computer in the house at a very early age. I was always encouraged to explore and I think that just really founded a natural curiosity around technology and. Um, a lot of things in that space and from there, um, you know, I was given the opportunity to participate in. In programming camps and in other software related, uh. Activities that, um, really kind of fostered this, this love of technology starting even as early as elementary school. And from there, um, just really went on to, uh, a more traditional computer science education, and then, uh, started my development career. Um, and through that, uh, experience. Um, I've had the opportunity to do a lot of different types of things. Um. And whenever opportunities arise, I always volunteered, um, again, just I have a real natural curiosity around. Uh, technology and in different types of platforms or or systems. And so that gave me a really interesting, interesting perspective and experiences that I might not have normally been able to have otherwise. So now I have I done software development, but I've worked on more system implementations system integrations. Through these different experiences, I've been able to, um, really learn what I'm more, more passionate about in, in what I, what I excel at and also the areas that, um, aren't as, as interesting or, or, uh, fulfilling for me, which has really helped me kind of guide my career as well.

Eric Brooke: 00:04:07

I'm interested, you talked about that you had a computer in the early days. Um, can you remember what

Joel Schlundt: 00:04:12

it was? Yes, so, um, our first computer at the house was a Commodore VIC 20. Oh. Uh, and then from there, we, uh, moved to an Apple II, um, and then had a Commodore Amiga, and then, uh, eventually an IBM PC clone.

Eric Brooke: 00:04:35

Okay. And you mentioned in that you like to jump into things that you didn't necessarily know or understand, like, how did that help you progress in terms of your career? Sure.

Joel Schlundt: 00:04:47

Sure. So, I think You know, very early on in my career, even at my 1st job, we had a systems administrator for our work group. And, um, what was really interesting is that a lot of the development. Team didn't interface or interact with them very often. That didn't make a lot of sense to me. I mean, we had to work closely in concert with with 1 another, but there was like this natural or or almost a barrier. Uh, in between the groups, and I just was curious about what they did and how they did it. And, um, what work. Uh, looked like for them, and that gave me a much better understanding of of what they were trying to accomplish, how they're supporting our team. What it looked like to support kind of a work group of our size and some of the challenges that. That they would run into on a regular basis, I think that just gave me a great, a greater sense of empathy. For for the work that they do in open up, you know, more information in in, um, different technologies that I had never seen or been exposed to. Yeah,

Eric Brooke: 00:06:03

knowing the stack and being having no fear of the stack. I definitely say is a good mark of a good engineer when you kind of like. Um, when was the 1st time you started doing management?

Joel Schlundt: 00:06:17

So I started to, um, take on more software architecture responsibilities. Um, you know, at a point in my career, and that really kind of led me down this path to to management. I had to start coordinating and collaborating across. A large number of different technology teams had to have a much better understanding of of business requirements in in what we were trying to deliver for the business. And that that sort of work was really energizing for me and really, um, kind of put me on that path. And from there, I started to take on engineering team responsibilities and started to run in and lead engineering teams and then started to get responsibility for other groups, um, like QA and databases and, uh, DBAs, um, and then systems, um, And since was administrators and so on,

Eric Brooke: 00:07:21

how was that transition for you from say, an individual contributor as a software engineer to management? Was it easy? Was it hard?

Joel Schlundt: 00:07:33

It wasn't something that I ever expected to do. Um, it wasn't something that I, I planned or set out. What I found was interesting is, um, I really enjoyed the people side of, of the, of that work. And I take a lot of satisfaction in helping others succeed and grow professionally. And that was something that I, I really didn't understand kind of before getting into this. As much, um, you know, there, there's always a drawback to, you know, hands on keyboard kind of work. Um, there's ways that that. That desire to be more directly involved or or. Closer to the technology, but I found that I, I've been able to balance that with, you know, a lot of the other things that that come with this job. The people side, the scaling challenges, be able to have a greater purview over the business. I think, um, make up for some of those, um, times where I'm not as close to the tech as, as I used to be.

Eric Brooke: 00:08:45

And so then you went from management management and eventually you were managing managers. How

Joel Schlundt: 00:08:49

was that? Um, that scaling was challenging. Um, and I think like as you progress and get higher, I think those, those types of challenges where you're learning how to delegate in And distribute work more appropriately are hard to do, um, and, you know, take time and in more energy than I think a lot of people realize and. You know, when done well, it, it feels really, really, really good. And when it's challenging, you know, it's sometimes hard to diagnose, especially when, when groups are getting really, really large. Yeah. Um,

Eric Brooke: 00:09:34

are there any bits of wisdom that you can talk about? Cause obviously you said it was a little harder. So were there things when you, uh, kind of more in that managing managers that you didn't know at the beginning and then you felt, and then you started to find your way with it. Sure,

Joel Schlundt: 00:09:51

I think the, the big learning for me was you have to give people room in, in space to take risks, um, and, and make their own decisions. Um, you can help guide them, but the more that they can decide and work independently, the, the better off you both will be. And that was hard for me. You know, I'm sure there are a number of cases, a number of occasions when I was more of a manager than I would have ever wanted to be. And in those situations, you know, the, the team doesn't move as fast or as successfully as they could. And, um, you know, the, the other thing about being able to take risks is, is again, making sure that they understand that you, you are supporting them all the way through. And if mistakes are made, we'll deal with those in a reasonable and logical way. And, um, when something bad does happen that you will have their back and get them through that situation. And typically people will learn a lot more going through those, those types of mistakes, um, and end up in a much better place long term anyway. Um, and it's hard because you need a real sense of trust, you know, with your managers, um, and you have to be willing to let go and and see mistakes happen along the way. And that's hard, and it's not always pleasant and there are going to be some. Awkward situations or difficult situations that you're faced with. Um, and and that's, you know, really, um, what I found to be the most successful for me is, is again that that strong support system and be able to give them independence in in some decent

Eric Brooke: 00:11:57

guidance. Yeah, Joe, I would agree. It is hard that part of the journey is probably 1 of their real shifts away, but there's definitely a shift from. Um, individual contributors and engineer to managing people. But that next one to like managing managers is hard, but it gives you many more opportunities, as you say, getting business value, being able to influence the team. Um, and then watching people grow is a beautiful thing as well. Like they've got this, this is awesome. Cool. Okay. So the next step, um, from like your managing managers and now you're an executive, how was that journey for you?

Joel Schlundt: 00:12:41

It was an interesting one. Um, again, it was one of those situations where. It seemed like a very natural progression, but it wasn't necessarily something that, that I was planning for. Um, and the, the thing that I've, I've liked most about, about that is again, being able to have a wider purview, um, and to be able to learn more about, you know, how a business is structured, how it runs. You know, what are, are more effective ways to do things. And then just, I really liked the sense of partnership, you know, with other business teams. Um, I, I, I really feel like technology is an enabler. Um, I, I am a big believer in, in not doing technology for technology sake. And it's like, how can we provide, you know, value and be a force multiplier for. All the other business teams that we're interacting with and, um, you know, that that moved to more of an executive level, you know, really gave me that that kind of experience and was able to to really teach me a lot about, um, those business areas and really develop those, those type of relationships and partnerships with the other business teams.

Eric Brooke: 00:14:09

That's awesome. Were there kind of skills that you had to learn at that stage of the job beyond like the business domain and obviously what the other teams are doing and other departments, were there other skills that going back in time, this would have been really good to have all kind of like build up, as I would say, like a director of

Joel Schlundt: 00:14:30

sure. Um, I wish I would have known more about, um, budgeting and In budget cycles, um, that has come up in in is something that I, I deal with on on such a regular basis. I would have wish I would have had more knowledge around how that works and typically works in in different kind of business scenarios. I've seen it done a bunch of different ways and in there are reasons for those different ways, but I wish I would have known and understood that better. Um, you know, public company reporting versus private venture backed versus private equity. You know, those, there are all kinds of different scenarios that you run into. Um, but understanding kind of how all that works and it ties together really leads to a lot of other things from a business perspective. Yeah, absolutely.

Eric Brooke: 00:15:29

I think finance is really helpful to know.

Joel Schlundt: 00:15:32

It drives a lot of decision making, and the more you know about it, the better you are. Um, the other thing is just really understanding communication styles and, um, understanding how to communicate at that level and more strategically versus tactically. Um, that was another kind of big shift that I saw in, in moving from. You know, very minute details, which like engineering is all about to more strategic views and be able to talk more directionally was something else that I, I wish I would have understood more and better in getting into this because that's super important, especially when you're trying to justify some decisions or help push push the team in a new direction. Yeah,

Eric Brooke: 00:16:32

absolutely. I think I learned a lot myself from like sales teams, um, about how to sell, to be honest, and learned a lot from marketing teams about how to show the return on investment along with product. Um, I agree. So what does success look like for you and what has helped you be successful?

Joel Schlundt: 00:16:55

Um, success for me, like I said, is, is really having technology be a partner to the rest of the business. Um, and, and that partnership is really important. The, the things that that really facilitate that is having a high level of empathy for, for those other groups. Like, you mentioned sales, being able to actually go through a sales demo and see where the platform shines where it doesn't. Understanding the struggles they go through in, in, um, kind of. Addressing those sales objections, um, and, you know, I think that's important for for technology groups to really understand. And I think it again just makes them better. Um, same goes for, like, customer experience. Understanding, like, what your customers are going through, how they're using the product. Um, what their what their day to day use looks like. Is is so absolutely important in and again. You want to build and deliver the best quality price you can without having that understanding. I don't see that how that's possible. And what I found, too, is engineers want to do a good job. In general, and they want to make sure that they're delivering value. And the more insight you can give them into how your customers are using it, or how the team has to support it, or how sales has to sell it goes a long way. And typically they have. A lot of great ideas to help make all of that better. Um, it's just enabling them to, to have that voice and to gain that empathy. Um, and when those teams have that empathy, I think I, I've seen the most success. The other thing, too, is balancing. The needs of the business versus the needs of the, the team and to make sure that we're pairing up opportunities for individual and professional growth as we're, we're building product or, or delivering features. And, you know, there's often a lot more flexibility. That you have in being able to craft experiences for for your team to to experience that growth. Um, then you realize, and I've, I've been. Um, very fortunate that we've, you know, through the course of my career have been able to. Um, a lot of folks in ways that were. Very specific to them and allow them to either get into new areas of technology or or new focuses or. Um, you know, complete career switches and and do that in a way that was positive for everybody. Like, there was a positive outcome. And I think that's that's super important to me to, um, success is not just delivering the future on time. It's also delivering it in a way that. That the team can grow in, in, in develop as well,

Eric Brooke: 00:20:12

um, in terms of like success, like, obviously, at the exact level, we also get pressure around, like, how is the team performing? Um, we often hear particularly recently in the last year, a lot about productivity, um. What is you? How do you balance? Because you've talked a lot about empathy, and you've also rightly said there's a balance between the team and the business needs. How do you find balancing the pressure that comes from, whether it be from the board, the CEO, sales, marketing, with what your team is capable of delivering?

Joel Schlundt: 00:20:50

That I think is one of the biggest challenges. Um, and, and, and problems to solve, you know, in this, in this type of position. Um, and, and I think it really is around balance. Um, you can't just focus on product delivery, um, without worrying about the platform or the people. Um, because eventually you will fail, and I think most people understand that deep down, but super willing to admit it. Um, and I think, you know, what has helped me, you know, in these types of areas is just to be able to have frank conversations and really explain. You know, why we have to balance and why we have to spend time in other areas. And make sure that that is understood sometimes it takes a number of conversations to make that happen. Sometimes we have to approach it in different ways. You know, being able to find and strike that balance of work, I think is really the key. Um, what has also helped is understanding. And to be able to understand again, like. The finances of the business, the pressures that sales are under. Understanding kind of what the sales goals look like, um, how we're supporting this, how we're marketing it so that you can fit into those natural cycles that those other groups have and understanding that, um, helps really tie the technology work more closely to the rest of the business. And again, you know, really helps with that, that overall partnership as well. Yeah, I love what you

Eric Brooke: 00:22:48

said about the cycles because each part of the department has different cycles they have to worry about, even whether it's the people team and the end of the year or the finance at the end of the month, like, yeah, absolutely. You need to have a good understanding of your partners in the exec. Okay. So what is something that you're trying to figure out at this moment?

Joel Schlundt: 00:23:12

Just like you said, uh, the, um, problem around striking that balance, you know, we're, we're a very ambitious team. We have lots, lots that we'd like to get accomplished. We do have limited resources. How do we maximize the return on our investment in terms of, of, of money and people, and, um, that's tough. You know, we, we, we want to maximize developer productivity that requires investment. Which is going to delay features, which potentially could could help fund, you know, additional resourcing. So, you know, we're working through kind of finding the right balance for the team in, in making sure that. Our engineering team is as productive as it can be. And we're delivering what we need to and still keeping the platform. I'm stable and operational for our customers and that's. That's tough. Um. The other kind of thing that, um, has been top of mind is, is working on, you know, building and scaling the team and dealing with some of the diversity issues in tech that, that we, you know, commonly see. Um, and, you know, this has been something that, that I've thought about and worked on for a long time. Um, there's a lot of kind of systemic issues just in technology with. With the type of people it attracts and is able to to keep inside of tech, um, versus being able to bring more, um, more diversity. And I've also learned that it's, it's really more a more holistic picture of of how businesses run and how they can attract non traditional candidates to these types of roles. You know, whether that's like, flexibility in terms of of working hours and in location or better benefits for family and medical leave. Um, maternity and paternity leaves all of those things play a huge part in that. In order to, to really make a difference in terms of diversity in engineering, um, hiring, you really have to think about the bigger picture and in all of those things together. Yeah, um,

Eric Brooke: 00:25:41

I think engineering obviously is interesting at the moment because we're going through big changes in terms of like, we're in 2023 with chat ttbt for, um, and people are interested in see how much this, um. Predicting of the next word, um, will actually really help and obviously it does great at summarization. So I feel like we're in for a big shift, um, over the next few years, which I think will be interesting, may open up opportunities for diversity in a way that it didn't exist before. But I also agree with you, it should be a goal for all of us. Okay. Um, what is your interaction with the exec? What does that look like? Could you give us like an example of what it's like an exec to work with other exec?

Joel Schlundt: 00:26:39

Sure. So the, I keep using the word partnership. I really like that. Um, I like to have partners across the table, um, that I'm working with. Um, and not for, um, I don't think you can be successful if, if you're in an order taking or a role, um, it really has to be an equal and equal conversation. And I've been super fortunate that I've, I've been able to work with a lot of great. Um, peers and, you know, the, the thing that I, I, I find really interesting, you know, folks that, that are willing to share and, and let you into more of their space. And give you more information about what they're doing, what they're struggling with. I think it's been, um, super enlightening to me and really helpful in understanding ways I can help or, or just even be more empathetic or, or, um, helping in, in more strategic ways in, in terms of like longer term roadmap planning or, or technology initiatives. And, and the other thing too, is, um, You know, at this level, we have to be pretty, um, candid with one another. Um, there are usually lots of really difficult decisions that have to be made in, in, um, in those situations, you really want to be able to, to have a high level of trust and to be able to, to put everything out on the table. And that was not something that that I completely expected or really understood coming up, but the better executive teams and better groups really have a candor that that is special in in can really make a huge difference. Um, and, you know, when you don't have that, it can be a more toxic environment. And much more difficult to get things done. Yeah,

Eric Brooke: 00:28:46

I agree with you, like, the candidness is very important, and the ability to give each other feedback and not take it personally. Because often you're giving feedback, not just about the person, but sometimes the department and people in the department. Um, but partnership, absolutely. I love it when you hear them talking about either the thing that they've discovered or the thing they're trying to solve. And like, as engineers, our core kind of like skill sets, problem solving in the end. And I don't think that ever goes away, regardless of what level you need, um, and being very open minded to understanding of a trade that you don't know as well as your partner. Um, but yes. Okay. So what about the interaction with the board? How does that feel different? And what kind of experiences do you have

Joel Schlundt: 00:29:33

around that? In dealing with a board, I've, I've seen and heard horror stories around very adversarial relationships or, or, um, very misguided relationships. I've had really good experiences in, you know. Being held accountable and in really, um, questions around how and why we're doing things, but also in a very constructive way. I think that the best boards really will push, push you to think harder and different about the problems that you're faced with. Um, and also provide just such a level of experience that, that, you know, if, if you're seeing a problem, they most likely have had an experience with it or, or something similar. Um, or no people that have and can help direct you to those, those folks to, and it's really being able to use them as a resource. And, and, you know, there's just a lot of learning that typically goes on, um, in the board interactions that I've had. Um, which has been great, um, and super, super helpful for. For not only me, and my function, but but the business in general. Awesome.

Eric Brooke: 00:31:07

Yeah, I feel bored. They ask questions a lot about finance and how the return investment relates, and it's an amazing growth opportunity. Um, both the technical and non technical. Um, I've certainly also seen them being very helpful in recruitment. Um, so they are, um, a different environment, but something worthy learning about and supporting. Okay. What are you seeing in the wider tech market these days?

Joel Schlundt: 00:31:36

Um, like we've talked about, um, I think A. I. N. G. B. T. And and kind of advancements that have been made over such a short period of time. I think it's really, really interesting what software engineering looks like, you know, even next year could be dramatically different than what we're seeing today. And I think that's exciting and a little bit worrisome. Um, just because it's not clear how all of this will play out. I do think it does have this interesting effect in terms of being able to to make like software development and and even technology more accessible to many more people, which I'm all for and, you know, I think the other thing, you know, just from a, from a. Tech market perspective, you know, we have a lot of very cyclical, um, things in technology. Um, we, we tend to repeat, um, on a pretty frequent basis. And, and, you know, I think we're, we're kind of at the next cycle in terms of understanding where front end development is going to go. Um, is that going to kind of continue on its current course or make kind of a radical shift? You know, we're starting to see just the starts of folks moving away from cloud based hosting to more self hosting again, which again, I think is an interesting scenario and may have some merits, you know, in very particular situations. But I think we're going through again another one of these change cycles where we're going to see a lot of different, uh, different ways to think about how we deploy applications again and how we think about front end development and web development in general. I mean, I think that's going to be interesting over the next, you know, 24 to, uh. 36 months. Thank you.

Eric Brooke: 00:33:44

What helped you grow or helps you grow and scale now? Like, what are the things that help you, whether it be books, podcast mentors? What are the things that are helping you scale

Joel Schlundt: 00:33:54

and grow? Sure. I, I try to listen and consume as much content as I can. Um, so I, I don't have a particular podcast in mind, but I, I listened to a lot of them and I try to try to look for again. Opinions or views from, from folks that, that are in different spaces than my own. Um, so either really, really large organizations or, or startups in different markets, those types of situations. Um, I've also had a number of mentors that have been super helpful, like to me, you know, over the course of my career and just understanding management in general and, and, and how to deal with team structure and organization change management. Um, and. They have been instrumental in helping kind of set that set that groundwork up and being able to talk with kind of ongoing and I try to listen to everybody that I can, um, you know, whenever there's an opportunity, like, again, I, I really like to see what people are thinking and how people how different people are going through these same sorts of challenges. And I just really try to keep my ears open as much as I can. Awesome.

Eric Brooke: 00:35:24

Thanks, Joe.

Joel Schlundt: 00:35:25

What do you do for fun? Sure. So, um, I have 3 daughters and, um, they're, they are, um. With my wife, what we spend a lot of our free time doing spending time with them participating in their activities. We've gone through marching band and lacrosse and now we're into debate. So, a lot of different types of things like that outside of outside of family, we, we are a Disney family. We like to go to Disney world and Disneyland and enjoy that that side of things as well as traveling. And then, um. You know, I, I, uh, have always been around, um, technology, but always have had, um, kind of interactions with video games and end up doing a fair bit of, uh, gaming. When I get a chance, so, um, classic consoles and and older arcade games is my preference, but still have the next generation. Consoles as well.

Eric Brooke: 00:36:36

Cool. Is there a favorite ride at Disney that you like, or a favorite place to go?

Joel Schlundt: 00:36:41

Um, I love the Haunted Mansion. That is probably my favorite go to. And then, um, you know, we just have family traditions around certain things. Uh, and, um, you know, we always make sure we have at least one Mickey ice cream bar. While we're at the parks. Awesome.

Eric Brooke: 00:37:05

Joel, thank you very much for your time today and your transparency. Really appreciate your time. Thank you. Thanks Eric.

Tim Winkler: 00:37:33

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