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August 20, 2019 · 13 min read

Technical trends and trade-offs with a career CTO with Rich Brown

Three-time CTO, Rich Brown, put in his Fortune 500 time across the enterprise sector at Bank of America, SAP, and others. 

Ledge and Rich discuss the trade-offs of native and hybrid, cloud and local, and the true experience end users are looking for.

We talk about the evolution of Microsoft and the company’s re-evolution in the developer ethos with the acceptance of .Net Core.

Rich Brown

CTO of Digital Air Strike

With more than 20 years of technology and digital marketing experience, Rich Brown leads Digital Air Strike’s technology teams. Rich specializes in innovation, growth, transformation, team building and execution. Prior to joining Digital Air Strike, Rich was CTO at Rouse Services where he focused on modernizing the company’s infrastructure, platforms, applications and processes. Before Rouse, Rich spent 5 years as CTO at SourceLink designing and implementing marketing technology solutions for Fortune 500 clients including automotive clients BMW and MINI. Rich was also a Chief Data Architect building SEO and PPC keyword solutions for over 10 million daily affiliate marketing products with billions of rows of customer data. Rich has worked in various software engineering & management roles for some of the world’s largest companies such as SAP, Bank of America, American Express and Razorfish. Rich earned his Bachelor of Science from Penn State University and holds various technology and process certifications including a Design for Six Sigma Greenbelt. In his free time, Rich is an avid photographer and dog lover who enjoys traveling with his family.

Read transcript

Ledge: Rich, good to have you. Thanks for spending the time with us.

Rich: Hey, Ledge. Good to be here. Thanks for having me today.

Ledge: Cool. Can you tell the audience your story, a little background of you and your work?

Rich: Sure. It’s been a long history in technology. For me it all started back with the movie War Games a long time ago. Saw the movie, didn’t have a computer, got a book, started learning how to write programs using a book on Basic and started writing them on tablet. Eventually worked my way into getting a computer and decided to go to school for computer engineering. Along the way, have worked my way up through the software engineering and data side.

Most of my early career I dove into UNIX administration, working in companies like American Express and then on to joint development I worked for Bank of America and on to becoming a VP of Business Intelligence at Bank of America.

Most recently, I’ve been probably CTO for the last 10 years of three different companies, and I’m currently at Digital Air Strike. We’re a leading consumer engagement agency, and rolling out a lot of the new technology at Digital Air Strike. It’s kind of where I came. Built my way up from the tech side, and here I am today.

Ledge: You know I love talking about is people that you have roughly the same vintage that I have in this space. Not being new to technology, I always like to know, from your perspective, looking back on your career and the trajectory of the technology change, what’s changed? But more importantly, what’s stayed the same and come back around on the trends and the way things are done? I think the same patterns exist over time and we sometimes miss that.

what your perspectives are.

Rich: It’s true. One of the things that I see most lately that really amuses me is, back when we were doing development, I was post-mainframe era so we saw all the mainframe guys were the dinosaurs coming in and doing client server development. Everything moved from being able to do everything within the command line and writing programs in just an editor, to moving into visual tools and everything became GUI-based.

Then we had this whole programmers that came out who knew how to program in GUI but no one ever touched a command line. It just amuses me now that all my new front end developers that are sitting out here today – I was just sitting with one going through his code commits – everything is in command line. All the git tools that you’re using is all done in command line. It’s almost force where it’s come back around to command line.

Even in more of the modern technologies now, using Visual Studio Code and rolling out to Core with Docker containers, everything’s going to command line. You have to be able to write command line scripts. We’re almost going back to the days of where we were writing batch scripts, but now everything’s done through either Linux scripts or PowerShell scripts. It’s funny to me. The whole of the command line had gone away for a while and is now back in full force.

Ledge: Like DOS batch files and batch scripts and command line pipes. All those things that the front page generation didn’t get to play with as much.

You made a good point on the client server thinking too. One thing I’ve noticed, one of the trends, is we basically used to have massive servers in a room – computers that would do a bunch of stuff and a dumb client. Then you had really powerful client and didn’t worry about the server as much. Then you came back to, everything’s on the cloud and we’ve got the dumb client again, but now the client’s become really powerful so, are we going to start running payloads on our phone and not worried about the cloud as much?

It just goes back and forth to centralize – decentralize – centralize.

Rich: Maybe we see it with mobile technology in terms of the hybrid apps. I think we go through these cycles where we want to centralize everything because centralized technology becomes the cool thing, and it’s easier to do. Even from the mainframe world, client server was the decentralization. But nowadays, even though the clients are more powerful, at the end of the day there’s not really an appetite to support all the different clients and the challenges that they come along with, different clients.

That’s why I think for us today it makes it easier to be in the cloud. The more we standardize browser technology and the ability to run different applications within the browsers and the OS stacks, it is moving back towards desktop based applications, mobile based applications versus cloud based.

I think anyone who’s tried to run an HTML5 mobile app knows that the experience is just not the same as a native mobile app. It’s a perfect example.

Ledge: How do you come down on hybrid mobile frameworks and opportunities? Like the progressive web apps and things of that nature?

Rich: I think it’s an interesting play. I don’t know. I think their greatest… It depends on the functionality. If the functionality that you need is basic, I think they’re perfect. But the minute you start to need to do more things like camera access and custom functions, it becomes a little challenging.

I think they’re still in their infancy yet. I think they’re going to evolve, but I still think today there’s nothing better than native apps to get you the true experience. The hybrid apps, I’ve seen some lag in the apps in terms of the performance, and the last thing you want is end users being able to feel a lag. That’s the first turnoff that they’ll stop using your application.

Ledge: Absolutely. How are you feeling about Flutter? There’s still a lot of new discussion around that and seeing if that can hold up and produce that native performance.

Rich: It’s an interesting topic that I can’t even talk to, to be honest with you. It’s not something that’s even been in my purview right now.

Ledge: We have a lot of developers on the bleeding edge that are crowing about in the mobile space. But things come and go, and so it will be interesting to see if it gets any uptake.

Report back on that one later.

Rich: For sure. I’ll take a look at it.

Ledge: What’s the nature of the agency side work? What are you seeing from the client demand side? What are the key technologies and how are people deploying them?

Rich: For us, we went through this – and I’ve seen this with the last few companies that I’ve worked for as a CTO. My specialization has always been coming in and transforming teams, and transforming their legacy applications to something that’s more modern.

With Digital Air Strike, we’re a late-stage startup. Been around about seven years now. We’ve built up with these initial MVPs that turned into somewhat of a monolith application that was built on kind of a mix of .NET. It was cloud based but really just fork-lifted servers up to the cloud.

Now what we’re seeing is a more targeted approach to the development side. We’ve really deconstructed everything out into a microservices platform where everything we’re doing today is going into Docker containers versus the old way of doing monolith. We’ve got probably, at least today, around 200 different microservices that are doing very segregated tasks.

For us, it’s been the evolution of a .NET backend development with SQL Server into exploring more of the document data stores. Mixing in the technology for the backend. We have a mix now of Node. We’ve experimented a little bit with Go.

The nice thing about the microservices is, you don’t have to be consistent on a single technology. You can use what’s fast in terms of languages and in terms of frameworks. You can use whatever is best to handle that particular microservice.

That’s where we are. We’ve even migrated off from the .NET side. We’ve really migrated into using Visual Studio Code and rolling using Visual Studio Core. It’s a different world for us now. We’re rolling out .NET applications on Linux Docker containers, so it’s pretty cool.

Ledge: Being somebody in a shop that’s still embedded in and invested into the Microsoft ecosystem, how are you feeling about the evolution of that company? back in the news and they’re the most important thing. It feels very legacy, when you’ve been around. That it’s come around so long that now Microsoft is cool again.

How’s that sit in the developer ethos?

Rich: It’s true, and it’s really impressed me because the last 10 years or so I’ve really migrated away from Microsoft. I was a Microsoft fanatic early in my career. I was running a server at home and running SQL Server and a mail server, and playing with it myself outside of work. I loved Microsoft technology.

Then somewhere around the 2010 era or so, I started dabbling into some of the Apple products and became an Apple MacBook fanboy, and started to move towards that. But I think, under the new leadership, Microsoft has really done a phenomenal job at bringing themselves back and being relevant. They took down all the walls that Microsoft used to have in terms of their code source and everything they’re doing and they made their platforms more open. They’re actually doing some really cool development.

Yeah. I’m really impressed, honestly, with the way Microsoft has approached things over the last year or two. It doesn’t surprise me that Microsoft has now taking over as the most valuable company because they’re listening to the market, they’re listening to the developers, and they’re producing tools and products that actually help people out. I think it’s great. Their move to going into open source as well has really helped them. It’s allowing people to start exploring using the Microsoft products again without the significant cost that was always associated with Microsoft products.

Ledge: You guys doing anything with IntelliCode yet? I know that’s a little bit new, but really exciting announcement. I’m wondering how it works on the ground.

Rich: Yeah. We haven’t been here yet. It’s just something as well we haven’t dabbled in.

Ledge: I’m interested to see if actually crawling and using all the repos and GitHub as a training source makes for an interesting interactive experience that makes coding better. The promise of that sounds fantastical, so I really want to see somebody use it.

Rich: It’s super interesting, and I think that Microsoft acquisition of GitHub as well, that just blew everyone away. It’s going to be interesting because we see these companies… I know most of the companies I’ve worked with in the past have used Bitbucket a lot for the code store, mainly because Atlassian has established themselves as the powerhouse on the development side.

I think we’ll continue to see the evolution of this with Microsoft’s acquisition of GitHub. What does that lead for the future of their build servers and things like that? I think we’re going to see a lot more from Microsoft in the next couple of years as well.

Ledge: It’s interesting to see some of the press turn against Atlassian now, which was absolutely everybody loved Atlassian. Now if you own a little bit of the JIRA as an ‘antipattern’ and all these things.

Whether or not you believe it, it’s interesting to even see some of that ‘when the tide turns on Reddit’, so to speak.

Rich: Yeah, for sure.

Ledge: Last question. I love to ask everybody this. Obviously, we’re in the business of sourcing and vetting and making sure that people are just absolutely Tier A software engineers, so we have a very rigorous process with the interviews and the testing and the sort of things that we string together to make that happen. Yet we know that there are best practices everywhere.

I like to ask all the tech leaders that we have on, what are your heuristics for hiring developers, and then the process you use and the ways that you measure who you want to have on your team from a developer perspective.

Rich: A big thing for us with Digital Air Strike is culture. We really like to try and find the right fit in terms of culture. For us culture means… It means a lot of different things to a lot of people. We love people with diverse backgrounds and we think it brings to the table a unique skillset, but I think when it comes down to what we look for, is that we love to have people that are collaborative.

I think that times are changing in terms of developers. We always envision the old school developers as the guys who want to sit in the corner with the shades down in the dark and don’t want to talk to anyone. I think that’s changing. Over the last five years I’ve seen more and more developers come out and they’re really social folks. They like to interact with the business, they like to interact with each other and it’s changing the dynamics.

When we’re looking for people on the engineering side, we love people who can come in, they want to talk, they want to interact, they’re really personable. Then take it past that part, then dives into the tech side. We really like to look at, where does the experience come from?

One of the top things that we look for are, are people doing things on the side, outside of their main course of work, that is helping them learn on some of the newer technologies? There’s always going to be new tech coming out that we can’t keep up within the business world, and people need to know it. That’s a really big sign for us that someone’s going to be an overachiever is, do they have a side project going on or a side hustle? What’s their side hustle going on that they’re learning and doing other things. We find that is a big predictor of someone who’s going to come in, they’re going to put all their effort in, they’re going to try and do their best, just because they’re so eager to learn new tech and be involved in that. I think that’s a really big factor of us, aside from all the standard just tech questions and things like that.

Ledge: Normally I cut off there but because of that question I need to ask you, what is your side hustle?

Rich: That’s a good question. Photography, honestly. I’m a big photographer on the side, and so whenever I get a chance to get out and just… I love doing landscape and city photography. For me it’s a thing that gets me able to be able to focus on a moment in time. It gets my mind out of the work and out of everything else, and gives me some freedom to go out and enjoy things outside.

Ledge: I love that. Awesome.

Well, Rich, thanks for spending the time with us. Really appreciate the insights, and I’m sure the audience will as well.

Rich: Thanks, Ledge. I really appreciate it.

David is a Managing Partner at Add1Zero where his team provides lead-to-close sales execution for tech-enabled B2B services companies ready to leap from 6 to 7 digits of revenue. He is also a co-host of the Leaders of B2B podcast. When David isn’t working, he spends time with his five kids and frequently travels between Dallas and Nashville to keep his interstate marriage alive.