Jason Wilcox: Overcoming Hiring Hurdles in the Era of AI and Emerging Technologies

Disclaimer:This transcription of the podcast is AI-generated and may contain errors or inaccuracies.

Matt

My name is Matt, and I will be talking with Jason Wilcox about product leadership roles and best practices for managing remote teams. I wanted to ask you the first question, and this is based on my research. So what I really noticed when I when I'm talking with the engineering leaders or tech leaders, in in Europe versus US, right, on the LinkedIn profile. I see, like, a clear message on LinkedIn and your too, that you write a lot of numbers for instance, like, cost reduction, budget owned, improvement, and everything is in numbers. So I really appreciate it, but it always, like, caught my interest, like, how do you do it and what do you do? So, like, like, a long introduction, but the first question that I wanted to ask you because I saw pretty impressive results regarding cutting the costs, over time, like, in a different organizations on the engineering side. And this year, it's a lot about optimization, focus.

Last year was a lot about cutting the costs. But maybe you could give some advices to other leaders, engineering leaders, where to look for the cut, cost cost cutting and how to optimize the structure.

Jason Wilcox

Yeah. So, you know, my approach, it it's probably a little bit different than a lot of engineering or technology leaders. I think as most people come up through technology, they think about costs around, personnel. They think about cost of, hosting and integrations with vendors and some of these items. And it's true. Right? These are all costs.

They're all items that really have to be accounted for. I think where I find some of my success, though, is it comes a little bit from my background in managed services and dealing a lot with contracts. That's an area that I find a lot of technical leaders gloss over is the fine print and contracts, negotiating out costs, understanding that even after you've engaged with the vendor, the vendor wants to work with you. And so, you know, if you're in a a downturn, right, you know, in in your industry or you're growing and you're seeing your economies of scale get out of whack because you you didn't think about that growth, you know, I I think in those situations, someone who is comfortable working with contracts, really digging into them, and working with the vendors, can find a lot of success, especially because it's just not a skill that you find traditionally around small and medium business, c suite, and technical leaders. You really have to go up that you know, up the board, right, some of these much larger conversations. And then those technical leaders are very good at it. But in that small business and medium business space, you can find a lot of headroom if you're really good at managing those contracts and really constraining and putting guardrails around.

Matt

K. Thank and thanks for that, Jason. And another thing I wanted to ask you, because you work on a different positions as a director of engineering, head of engineering, CEO, and various organization, couple hundred people. So that's, that's already some kind of, like, a good scale. And I'm just wondering what is your approach to having, like, the team structure around you? So be who is usually your partner in crime? How do you structurize it?

Jason Wilcox

Yeah. On the engineering side, typically, my partners in crime are the product owners, product managers. They you know, a really good product owner or product manager can make or break a CTO or a head of engineering. I think, I'm seeing an evolution of this position. It's the CTPO, so I assume it's a combination of a technical leader and product owner.

That would be really hard. Right? I think when you're 5 or 10 people, right, and you're you're a CTO because you've got a business card that says CTO, you know, it's your first time doing it, and you're maybe building a SaaS application or something like that, it's very easy to work within that product. But as things scale, the demands of time on the CTO and where you're where you're living and working really mean that you need strong partners, right, as as you've indicated. And for me, the product owners, the product managers, that's that's really that that sweet spot for me. Because if I have a good product owner, if I have a good product manager, it takes a huge amount of stress off of the product management side, and I've got someone who can really track down information about the product, who can work with customers, who can provide really good information that then I and the engineering team can take and build. And if you don't have that, you end up going through iteration after iteration.

And, honestly, with as companies scale, you know, there's in the startup world, there's that idea of, what is it, build fast, write, and break things. And that you can only do that for so long. But if you have someone good in product, you can really much earlier get into a better iteration of the product without breaking a bunch of things or doing work that ends up getting thrown away.

Matt

And you've mentioned interesting cost about the CTPO. Yesterday, I re I was recording, one one episode with a leader from from sweet Sweden, from one of the fintechs there. And you were talking about it that, you know, usually in a company, you have a sales team and marketing team. And to get them on the same page without, like, a lot of hassle and fights, it's really difficult. Yeah. We are discussing that the product and engineering is a bit of kind of, similar constellation. Right? So you need a really good leaders leader or leaders, on the CPO or CPO or CPPO to kind of, like, connect those 2, 2 bodies.

Like, have you have you experienced that?

Jason Wilcox

Yeah. I I well, I've not experienced the the joint role. You know, for for me, I I do think it is there are really good CTOs and technical leaders out there. There are really good product leaders out there. I've I've only come across a few people who I would consider, even if their title didn't say so, were really good technology and product leaders. And it's what I find and, again, I'm you know, my experiences with private equity, VC, small medium business, and in those worlds, I've not come across a CTO who is visionary the way like a CEO or CPO is. You know, typically, in a smaller company, the CEO is serving as that CPO role, and it's there's good synergy there.

And on the cross section, I've really never come across someone who's in a CPO or CEO role unless they're a CEO, but they're an engineering background or something like that where they can translate the the technical well. There's just so much to do across those two pieces that I think, you know, 1, it's bandwidth and time, and 2, I it's a very rare skill set to be able to handle both of those well. I think most of what you're gonna find is someone who does one side really well and does the other side average.

Matt

Makes sense. And how about the the team setup? Right? Remote, hybrid, on-site. I'm just wondering what is your approach, and do you see, do you see some kind of trends like this year? Because you are really close to Silicon Valley, so maybe you see some kind of concept that are evolving there and what is acceptable or prefer? How Yeah.

How how will you see it?

Jason Wilcox

You know, I've I've run teams in all capacities. I've run, you know, in in house teams that are on-site.

They're in the office. I've run onshore hybrid teams. I've run completely offshore remote teams on onshore remote teams, all that good stuff. I I do like the the in office aspect. I think that there is a collaborative nature that can get lost a little bit when you're not working that. But the fact of the matter is the trend and the just the adoption is people wanna travel. They wanna do different things.

And and, honestly, if you have hired and trained up the right talent, then it's not really a problem. You know, if if you're if you're bad at hiring, well, you're gonna find the remote working aspect very difficult. Right? Because remote management, remote leadership is more difficult than in house leadership. So if you're struggling with leadership or management already, you're not hiring the right people, it's a recipe for disaster. But if you're if you're good at hiring, if you're hiring the right people, then the letting them be remote within reason, can work out pretty well. You know, I think where people falter is if they're remote and then they're trying to allow people to work whatever the local hours are.

There has to be a little bit of give and take. You know, right now, the team that I run is I have people in the US, Canada, Europe, Thailand, India, Pakistan, but we have a core set of hours where everybody knows that they're on, and that that allows people to collaborate. Right? So you have a certain people that they're on for a bunch of hours, and then they overlap with other people who start their day. But it works really well. And like I said, I think when you bring on the right people, you'll you can have very good success there. And that's the trend. Right? Remote's not going away.

You know, I've I've got a developer, like you said, in in Thailand. He he loves living there. He moves there. He goes out on the weekends. He goes out during the day, and people wanna do these things. And so if you have the right processes in place, you know, it's it's a good situation. I do I do miss the in office a little bit sometimes, but, you know, the remote is a good situation.

It is what

Matt

it is. And for how long

Jason Wilcox

are you remote? I've been now remote since, essentially, the the COVID 2020.

When COVID hit it's funny. I I was actually, on vacation. I was on a photography trip in California, and so I didn't really realize what all was going on. And I got back into cell service, and my IT manager at the time gave me a call. He said, hey. The company's going remote.

I said, okay. Well, we've we've been working on this. We had a proof of concept.

What's the time frame? 1 week. Oh, okay. 1 week. Alright. Well, that's a little different. And so we most of that team, we sent remote.

That was a company of about 300 people. And then since then, I've had the opportunity to be in the office a little bit, but for the most part, I I've been remote day in, day out. And like you said, there's pros and cons.

Matt

And I'm looking always for some concerning approaches, or the practices. And when we last talked, you you had, like, a few good examples that I think you could share today. You know, I'm I'm looking for something that works for you from the, I don't know, engineering or leadership perspective or team building, but it's

Jason Wilcox

not maybe so common, you know, on the market or not many people are, talking about YIP. So, yeah, I I remember, that that was a fun chat. We went through a few different things. I I think the biggest one for me that I think about is the it goes back to that idea of build fast and break things. I I think, Mark Zuckerberg at Facebook coined the term, and, you know, startups especially have really glommed on to that. And I think larger companies, smaller departments within those companies have glommed on to that. And it's not that there's not a place for that ideology, but I think it's I think it's right at the beginning. Right? If you if you're a couple founders and you're trying to vet out an idea, I I think that ideology makes sense.

But I've worked with companies that, you know, they were they consider themselves a start up, but they were a start up, you know, 5, 10, 15 years ago. They're not a start up anymore. You know, they have hundreds of people, and they still have that mentality. When I work with those companies, you know, either directly or in consulting roles, what I find is is that the break fast or the the the go fast and break things philosophy ends up in a lot of work that gets thrown away and a lot of repetitive work because you you just get to a point where there has to be communication collaboration amongst the teams. You especially if you have different teams working on different parts of the same product. And I I mean, I've watched I I've watched insane stuff where, you know, department a builds a feature that department b had already built, and they spent months building it because no one asked if it existed. And and I, I've been blown Jason, and it I just sit there and I watch.

I'm like, man, a single 30 minute conversation would have saved 8 developers 3 months worth of work. And and I see that a lot. And so, you know, I'm I'm a big proponent of slow is smooth and smooth is fast. And when I measure velocity, which I think a lot of engineering departments don't do maybe they say that they do, but it doesn't happen as much as they do as as they think. But when you actually measure velocity, you can get to a really, really good velocity with the idea of, hey. We're gonna have good spec documents. We're gonna have good sprint planning.

We're gonna make sure that people feel really comfortable with the work that we're gonna do. We've vetted out the thing that we're building for whoever the end user is. And then from there, you're not going back and you're not iterating a ton on the feature. You're not building features that you've already built. You're not building features that then get sunsetted a month later. But if you if you've gotten to a little bit of size, especially if you're more than one team that's working on a product that go fast and break things, it just I I think people think it works well, but the metrics that I've seen just don't hold up.

So sorry, everybody.

Matt

And talking about, some lessons learned, I feel like each year I have this moment. Right? Like, I figured out something, and it changed my mind completely. And this could be, like, a small thing, and I'm just wondering what was your latest moment, you know?

Jason Wilcox

Oh, my my latest moment. Yeah. That's a good question. I, you know, I will say that I started out, you know, purely in technical tactical. I I'm an engineer by trade. I never really thought that I'd be in a leadership capacity. I never thought that that would be the pathway that I would take.

So I know coming into this, my biggest moment was, you know, working in a in my first leadership role and just realizing, man, there's an entire skill set of things that I don't know how to do. That's probably where most of my moments come from are skills that I never thought I'd have to develop or enhance, that, you know, I have to. And a lot of the time, it's soft skill sets. I I think my biggest it's not it's kind of an moment, I guess. But for me, now that I have multiple people, you know, multiple leaders under me. Right? So a manager of people and a manager of managers.

It's remembering when I had the moment for my managers who are having the moment. Right? So it's it's situations where, you know, you're you're talking to someone and they're saying something around, like, oh, yeah. I'm I'm working with this person and trying to build up this skill set. Or, hey. I'm gonna I'm gonna switch this person over to this because they don't handle this situation very well. And I I remember, you know, I asked a question like, oh, okay.

Well, when you talk to them about that, like, what did they feel like their struggle was? And, you know, it's the conversation, well, I never talked to them about it. Oh, well well, you need to. Right? Like, you need to have that conversation, that communication. So my biggest moments are are really helping people work through the moments that I've had, and it's not to say that I don't have my own, you know, for certain. There's a world of information that I'm gonna need to learn and and pick up.

But for me, that that's probably the the latest moment is just, yep, I've been in that spot, and you you have to make a change, you know, a a deliberate change if you're gonna if you're gonna solve those problems effectively.

Matt

And and for me, it's kind of not a surprise that we mentioned the soft skills. I mean, like, the bucket of the soft skills because I have a feeling that as a leader, despite all of those books and maybe some trainings, it's all the time training on a job. Like, I

Jason Wilcox

don't know. With the soft skills, you need to kind of, learn learn with the people. So, like, even if you read something, even if somebody will tell you something over the training, it's still, like, the the lessons you get from the your daily job. Right? It well, it it is. And I think at a certain point, good leaders will make a conscious choice to seek out people who are really good at a skill that they're deficient in. Look. Again, I I was an engineer.

When I came out of college and when I went to college, one of my favorite things about my program is I had to take 3 humanities classes. That's it. Right? I don't in in my mind, I don't need that crap. I don't need communications. I don't need any of that stuff. I wanna be an engineer in coming out, doing it.

And then just realizing, especially coming to that first role, like, oh, the way that I communicate, my communication style is awful. Right? My my management style is awful, and it should be. Right? I've never been a manager. So, you know, it's something that has to be developed. But, like, for me, I I'm I am very lucky in that I married up.

I am punching way above my belt, right, with my wife, and her, you know, her development, her skill set was people management and communications and working with people. And so, you know, I was lucky in that moving into that direction, I could start to ask her questions and develop that skill set because, you know, I I'm very comfortable saying, like, my communication skill set, a lot of my soft skills were very underdeveloped as a tactical engineer. And so moving and and being successful with leading people, I had to develop those skills or I was gonna fail.

Matt

That's interesting. So I have a similar story with my wife. So I think I learned from her negotiations and the a lot of soft skills and the empathy, to people to kind of understand.

Jason Wilcox

Yeah. The the the these are big piece.

Matt

Okay. So, but, on another hand, right, we have 2,024, and all of us, we have our pain points and challenges. And I'm just wondering, in your case, what do you type in the Charge GBT or Google? What kind of pain points and challenges are on your plate?

Jason Wilcox

You know, I'm probably boring in this respect, because you probably hear this every day as you're talking to people, but, right, Gen AI is easily the biggest challenge. You know, it's it's crazy. Right? We have a we have a technology that's growing faster than any technology we've ever dealt with. And at the same time, companies are looking at what they can do with Gen AI and just trying to figure things out. And a lot of it is, hey. We think it'll do this.

We think it'll do that. Everybody and their mother now has a chatbot that does something. Right? But it can do so much more. But there's so many areas around it. Information security, actually developing metrics and ROI to show that it is an effective tool. You know, when I came on at Source, we there was a AIML proof of concept that was just kinda kicking off, and, you know, asking very basic questions around the project, things of okay.

What are we trying to solve? We're trying to reduce man hours. Great. Okay. Well, what does that look like now? We don't measure that. Oh, okay.

Well, if you don't measure it, how are you gonna know if you improved it? We don't know. Alright. So but a lot of companies that I talk with are going through these same pain points of we have this amazing tool. Everybody tells us it's amazing, and we know we have to do something with it, but they they don't know what. Right? And it's, you know, it it's very different than, you know, you think about, like, I'm old enough to remember when, you know, Microsoft were in Excel became really big or, you know, things like Outlook became really big or Gmail came on the scene or Google search.

These had very clear use Jason, and they've they've developed and evolved, but someone could pick it up and you could explain it. Man, trying to explain things like ChatGPT to a lot of people, you know, out in just the general industries and and the business environment. Again, they know it's important, but a lot of people are struggling to figure out, okay. How do I actually make it have a positive ROI on my business? And it's tough. It's tough. It's a very nascent technology that, you know, it changes radically and super fast.

Matt

Yeah. It's a lot of r and d, right, and proof of concept.

Jason Wilcox

Yes. It's a lot of proof of concepts. But but, again, it goes back to I think people are used to proof of concept projects where especially in small, medium business, you know, your some of that is gut decision. You know, it's like, yeah. I think this is gonna improve it. You put it in there. You maybe do some back of the napkin math, and you say, yes.

We we got some efficiency gain, and this was the right way to go. This one, it's it's it's tough because it's a lot more expensive to do the proof of concepts. You need people who are very new, and they have a an interest in things, but they're not necessarily gonna have a lot of experience. I I I was chatting with someone, and they were asking my, opinion on if they were gonna hire someone for, like, an AI ML role. You know, they sent me over their their job rec spreadsheet, and it was stuff like 5 years experience in chat GPT and this and that. It's like, that still hasn't been around that long. You're never gonna find that.

And if you do, stay away from that person because, you know, they're they're blowing smoke up your booty. That's really interesting because it reminds me, you know, when

Matt

I was starting with my, my my my my company in in in Poland that we we said, like, we want to focus on JavaScript. Right? And back then, the React was, as a prominent in that, framework. It was really fresh and new. Right? And we were starting playing a a lot of it implementing on a different kind of, for the different businesses. But the thing was, it was always funny for me because it's the same thing that you're saying.

The people are asking, hey. We want somebody with React, but somebody with 5 or 8 years experience. I'm saying, like, hey, man. This is, like, 2 years on the market. So, like, how come? How how can we do it? You know?

Jason Wilcox

It's funny you bring up React. I remember the same thing with React. Like, when they came on the scene, people were super excited about what you could do about it. And, you know, I'd go through job postings. People would ask me to review a posting for their company if I was consulting with them. And all the time, it'd be that HR, like, yeah. We're looking for someone senior, so we want you to have 5 plus years of experience over at since hey, guys.

This has been out for 2 years. You're not gonna find this. Right? So you you need to temper your expectations and understand what you're getting into with the new technology. And AI, machine learning, not so much, but I think AI has become this general term for, like, automated data science, generative AI. It's it's this amorphous blob now that people think about. But the things that they think about when they think AI, yeah, they they just haven't been around that long. You know?

I I I don't know what to tell people.

Matt

Let let me another interesting topic, because I know you you have a lot of interest in the AI area. So I'm just wondering what is your view here. So, like, my bet my bet for the future is I think we'll do more software and faster so we can start, faster to to do to deliver. We can optimize the processes. You still need the experienced people to do it. Right? And I compare it to, to the music industry or creating the music because I I I like to create music and produce.

So yesterday, I saw some, AI kind of, algorithms and, like, applications, so you can generate whatever music you want in whatever style, and it sounds like perfectly crafted. Right? But I think it's a good point to start, and you can, you know, play with the stuff really fast and create some kind of sketches based on which you'll create the music because this is how the motor songwriting is being done. So they have, like, a part of the Michael Jackson thriller. Right? And they want to create something simple, similar, and they are doing this for years. So they put the part, and based on that, they build kind of the music.

So the same, I can, like, see in a music industry today and in the software development. But I don't know. Like, what is your your view here? Maybe you see it, differently.

Jason Wilcox

You know, I I think when it comes to using AI and software development, I think I think you're gonna see a a bell curve. There are, I think, a lot of junior developers or people who are not developers, but they see, like, oh, this tool can help me write some basic stuff. The problem is is the output that you get now is still pretty basic, and you're not solving any novel problem with that basic stuff. So I think you're gonna see people on that side of the bell curve using it a lot and putting out frankly a lot of garbage. Right? Like because they're gonna put something out and then they have to tweak it, but they don't have the skill set to actually tweak it. And so you're just gonna end up in that repetitive nature.

When you hit the top of the bell curve, I think you're gonna end up with those mid level developers who they're good developers. Okay. Now they're starting to use, some of these tools to act as almost like an automated paired program, doing bug remediation. Some of these items, like giving them ideas, so it's gonna make them faster there. And then I think at a certain point, I don't know that we're seeing this yet, but you're gonna see really senior developers to your point who they understand the specificity and some of the some of the gotchas in software development that, you know, the the very small underlying pieces that take a piece of code from good to great. And they're gonna be able to start to use things like JAD, GPT, GitHub's Copilot, those those items to ramp up the speed of how they develop. Right? Like, hey.

Give me a stub of this, and then they're gonna be able to quickly add to it. And so I don't know that we're seeing that as much yet, but I think I think we are as this technology develops a little bit, and senior developers are gonna start to buy into this. Or mid level developers are gonna move into that senior senior developer position where they can do some of that. You know, things like architecture. I've I've played around with chat GPT, and I've said, okay. I wanna I wanna test, like, what can it do?

What can an architect? I I mean, it's not there. Right? It's it's it's not it's not creating things. It's really if I tell it something, it's spitting out generalities, or it's telling me what I told it in a different way. Right? But but as it improves, and I think as these mid level developers move to senior and senior kinda take this on, you're gonna see quick ramping of good software because they compare it with, hey.

Give me 80%, and I'm gonna fill in 20%.

Matt

It reminds me, like, a picture. I don't know if you have seen it from Amazon warehouse where you have this humanoid kind of like a suit, so we can weigh you can, like, carry, like, heavy objects. Right? So it's like being a developer on steroids, something that

Jason Wilcox

says. Right? Exactly. Yeah. I I think, you know, the good developers I know sometimes technical people, engineers, IT can be a little persnickety sometimes on things that they feel like might be taking their job. But when you learn to work in unison with it, I mean, you could you can get some great economies of scale. I don't like you said, I think we're a lot further out on the on the smaller end where you add people who are developers or they're just new to it, and they're trying to use this to, like, oh, I can just tell it kinda what I want, and it's gonna build what like, it it's gonna you're gonna ask it for a box.

It's gonna build you a very basic box. I think a lot of those people are gonna get frustrated because they actually want some customization. They want some specificity, and they're not gonna be able to marry that with their skill set where it is right now.

And, Jason, I

Matt

have the last question that I wanted to ask you. It's about any, like, books, resources, conferences, I don't know, podcasts that have been particularly influential on you, to your mindset maybe in something and, you know, that you could recommend?

Jason Wilcox

Sure. Well, I'd say conference wise and it was the first year that it happened, so we'll see how it goes. But I did attend the Microsoft Fabric conference. We were looking at, utilizing Fabric. We already are very heavily in the Microsoft stack, and we want to level up our data analytics, our business intelligence, and and the way that we do that. And I was blown away with some of the stuff that Microsoft is doing.

You know, it's yeah. We we all we all hate subscriptions. We hate monthly fees and all that, but what they've put together and the resources that they've put behind Microsoft Fabric and now on their kinda data governance side with Purview in those areas, it's it's cool. Yeah. It's it is really starting to level up, the analysts, the data people that I work with, and it is going to I've always been a little hesitant around the idea of a a data citizen. I I feel like there's a lot of challenges around that concept. A lot of guardrails have to be put in place.

This is going to help a lot of companies put those guardrails in place and make people effective at data, which I think is exciting. So conference wise, Yeah.

I was I was blown away. I really I really enjoyed it. I got a lot out of it. So I I would highly recommend that one. And it's still small enough where you could have really good conversations with product owners, product developers, VPs at Microsoft, things of that nature. Book wise, you know, if you're looking to go into leadership, I don't know if I've come across a book that is specific where I would say, this is a great book specifically for a technical leader and not necessarily other leaders. I think if you're gonna be a leader, you have to apply your domain knowledge to whatever the the the leadership pathway is that you are.

But I know, like, your next five mute moves by, Patrick Bet David, and principles by Ray Dalio. Those are ones that I reread. I'm I'm I'm really passionate about talent development and team development, and you have got to be transparent. You've you've gotta have a process where you feel comfortable having good and difficult conversations with your team, you know, the the people that hold that back and and don't have those conversations, I think they really lose out on developing where the people that kinda come up to them or report up to them can develop into, and and they lose out on on raising all those boats. So, yeah, those are those are the things I'd recommend.

Matt

Awesome. And, Jason, thank you so much for all the insights, for all the Google recommendation and conference. You I think you are the first one who recommended the conference. I always mention in the conference, but, nobody could, like, you know, recommend me any. So thanks for that.

Oh, sure, man. Appreciate it.

Jason Wilcox

No. The this was great, Matt. Yeah. Appreciate the conversation.

Glad you reached out. I'm always happy to chat this stuff and, you know, share the share the wealth, share the knowledge.

Matt

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