Engineering Leadership Series - Tim Steele
Today we have another outstanding guest in the Engineering Leadership Interview Series. Tim Steele, the Chief Technology Officer at Aries Solutions, joins us to discuss growing up in Chicago at the Dawn of the Internet, the distinction between networking and building real relationships, and how he approaches leadership to make a positive impact and empower his team to be the best versions of themselves.
Tim has over 17 years of industry experience and has a wealth of knowledge on multiple topics.
Aries Solutions is a global partner specializing in composable commerce, assisting businesses in implementing headless technology for successful launches. They offer services such as commerce replatforming, cloud migration, cloud-native application development, microservices/API enablement, cloud DevSecOps, site reliability engineering, quality assurance/testing, and headless CMS implementation.
Enjoy the interview and give Tim a follow.
More Information
https://www.linkedin.com/in/timothysteele/
https://www.ariessolutions.io/
The Interview
DoneStreet
Looking over your previous jobs. You've had a lot of pretty interesting ones. One that stood out was that you worked at the Federal Reserve right before 2008. Out of curiosity, were there signs of the coming crash? How was that role?
Tim
That was actually one of my first opportunities coming out of school. I actually graduated in graphic design. I have an art degree. But I've been working in tech for a while. They were looking for web designers or web developers to help with some site redesign stuff. And I said, well, I’m looking for my first job out of school and if somebody can get you in, you say “yeah, absolutely”. I didn't have that much insight into it. I was pretty low, you know, first entry level job web developer. It was just exciting to be there. So in terms of signs, I wouldn't have seen or known anything at that time.
DoneStreet
You touched a bit on your Art background. Maybe you could tell us a little bit about your past and how you got to where you are today.
Tim
Absolutely. I got into web development early during the dawn of the web. My dad had an ad agency in Chicago and got a free sample of GoLive CyberStudio 1.0—before Adobe bought it. This was the Earthlink dial-up era. I started experimenting with it, and while my dad’s agency was focused on print, I got curious about websites and began exploring and playing with it.
From there, I moved into more formal web development, working on early e-commerce projects where you’d embed prices in hidden form fields—think Internet Explorer 5 on Mac. After graduating during the MySpace and early Facebook era, when websites started being taken more seriously, I landed my first post-school job at the Federal Reserve Bank.
Since then, I’ve combined development with design and UX, working across finance, insurance, and retail. I like retail and e-commerce. It’s fast-paced and aggressive. I worked at companies like Sears and Express, which were pivotal experiences, and now I consult in the e-commerce space.
DoneStreet
It sounds like you were a little bit ahead of the curve. Combining the UX perspective with the software engineering side. Nowadays everything is user experience focused and asks how do you really do user centric design. Did you have that foresight or did it just kind of come together the way it did?
Tim
It’s like web development felt like a new medium for art. I know Apple made Skeuomorphic and back in those days when you made a website it was kind of like you could do some cool artistic type stuff. I remember working on a website for a travel agent where the background was sand, and the content sat on a wooden plank. It was all about creating immersive, artistic experiences. This was before mobile or iPhones became part of the web (pre-2007). Back then, people used desktops, and 960 pixels was the optimal width for web design.
Over time, UX evolved into its own art form. Initially, engineers focused on the backend—the ones and zeros—while the interface was secondary. Combining engineering with design was a shift, and it was exciting to be part of a movement that treated user experience and design as equally important. Early events like An Event Apart in Chicago really influenced me. An Event Apart was a lot of creative and art in web development.
DoneStreet
Do you have artistic passions outside of the technical side of things? Do you paint or do any other creative outlets?
Tim
Oh, yeah. I mean, I don't do as much anymore. I've been busy. But I have a daughter and I do a lot with her in terms of teaching her how to do like figure drawing and comic book drawing. She's into the anime style, so trying to go through and teaching her how to draw shapes and all that is kind of fun because it brings me back to my roots of doing it as well. But I still love to draw and sketch. Pencil, paper and charcoal has always been my favorite medium outside of digital.
DoneStreet
You've been with Aries Solutions for roughly 2.5 years now. How did you get hired there?
Tim
I actually worked with Jake, who's the CEO, when I was at Express. We handled the first headless implementation of commercetools, which is a big enterprise commerce platform in North America. Jake was the project manager there. I was director of E-Commerce at Express at the time and we really worked closely together to launch that over there. Then we kind of went our separate ways for a little bit. I went into a bigger GSI, that's Valtech. Then I kind of took a break from that and while I was trying to figure out what I was doing next, Jake reached out and was like, “Hey, we could really use somebody like you over here. Do you want to come join Aries?” And I said, sure. And so we ended up getting back together.
It's been fun. I like working with Jake, clearly because I chose to do it twice. I worked with him the first time and chose to do it the second time. And it's been good, it's been exciting. Aries, and being a part of it, especially as it's been continuing to grow as a consulting agency. I’ve experienced a lot of new challenges I hadn't hit before that aren't even technology related and that's been fun. That’s been exciting. So that's kind of how I got hooked in there.
DoneStreet
You mentioned that there's some challenges that you face that are non technical. What types of challenges are those?
Tim
In consulting, you often need resources globally. For example, I had to figure out how to set up a hiring office in Buenos Aires, which was outside my E-commerce technology focus. Then all of a sudden you’re thinking, we have to do a lot in terms of implementing HR software which is less technical and more closely tied to running a traditional IT organization. So you get exposed to a little bit more of a full blown IT organization that maybe you wouldn’t have gotten if you just stayed in a bigger company.
DoneStreet
Speaking about Aries Solutions, it looks like there are two different components. There are some open source projects, and then also the consulting side. Is that correct? Can you expand on that a little bit?
Tim
There are multiple facets to it. Aries Labs serves as our open-source wing, focusing on composable offerings. There are two ways to go about it. You can sell it as a vendor, as a platform and as a product. We decided to not necessarily do it as somebody selling it as a product, but more open source IT to say hey, this is our expertise and these are things that we’ve built that we find useful. Instead of selling these as products, we open-source them to showcase our expertise and share tools we’ve found useful across projects. Companies can use and modify these tools under open licensing—though not for resale—making it a DIY resource for teams with strong engineering departments tackling in-house transformations. And we can offer expertise and components and code to help. Think of Aries Labs as the Magnolia Network for composable commerce, offering components, code, and expertise to support those building their own solutions.
DoneStreet
On the consulting side, it sounds like you offer some sort of initial planning consulting and also full builds as well.
Tim
Yeah, we do everything from strategic to implementation. So if you're going through headless transformation, we will talk to you. And we will do everything from helping you get your project set up and kicked off, keeping it on track, and handle the whole management of it. We can also help doing the actual implementation and we can do full projects.
DoneStreet
I know there are a lot of headless e-commerce solutions, a lot of different languages as well. What specific tools do you typically use? Any frameworks?
Tim
I think the biggest platform that we use is commercetools. That's a lot of what we do in the headless composable space, especially commerce. We’ve got a lot of experience doing it. That whole MACH ecosystem of headless platforms, we’ve touched most of them. It’s helpful when you get into content management or search or even the ancillary ones like payments. Or service for email service providers and everything in between. We work at a lot of different companies, big companies, and so you kind of see all the different patterns and players.
DoneStreet
In recent years we've seen kind of a huge boom in the e-commerce space, but also an evolution of going to mobile and everything else. What sort of the trajectory from here on out do you see? Maybe AI becoming more commonly integrated or are there any other interesting trajectories here?
Tim
I think AI is playing a bigger role from a consumption perspective. So I mean we see it, Google now for instance. I always laugh, somebody did a picture that shows Google 10 years ago and it was like the first box is the thing you searched. And now it's Google today and it's an AI result, local results and ads. And then, it's finally like, here's the thing you search. Joking aside, the AI one is up front. Google's always been, you search for something, how do we get the result to you as fast as possible? Right? That's kind of their thing. And so from that, from an AI perspective, if they can take a look at all of this data that they've amassed and give it to you, especially in terms of products and commerce and E-comm, I think that's where we start to see AI.
Microsoft as well. Chat GPT is becoming more common. I think you're going to get more of AI in terms of the customer perspective. I think you go on Amazon and if you're looking for something just as simple as, I need a pencil holder, it gives you something like 14,000 results. How am I going to find the one that I actually want to buy, right? And I think what AI has been good at is how do I take a bunch of data and summarize it.
I think we've seen that be sort of successful in that regard there. And I can see that from a shopping perspective. As department stores got shelf-less and went e-com, the merchandising offerings got bigger. Finding ways to help customers get to that product that they want and are searching for and check out became more important. I think AI can definitely start to drive some of that.
DoneStreet
So you see AI almost complimenting the shopper more than necessarily the site. Or do you see the site having an AI helper who then facilitates on behalf of the customer as well?
Tim
No, I mean, I see a lot. I see it helping a lot more for the shopper. I know that there's a lot of talk in using it for products. And we've heard and talked to customers who want it for product descriptions and other uses. The way I look at it is like, give me a day when Disney's gonna feel comfortable sticking a computer generated description in front, next to Mickey Mouse. And that's the day that AI is gonna be okay with generating content without having any human interaction. These big brands, the ones that have like the most valuable brands, are never gonna trust a computer without some sort of human intervention.
But I think maybe we'll someday get there, who knows? I do think a more immediate use is that we start to see a customer trying to find something on the Internet where you have all of this data feeding into behemoths such as Google search results, Amazon, Ebay. For example, I'm on Home Depot and they've got a huge selection of tools from every manufacturer and I’m trying to narrow it down. How can you take massive catalogs and try to figure out my intent and give me a better selection or curation of products.
So, if we take it and translate it into the physical store, you're going to walk into a store and instead of trying to go to your grocery store and figure out what bread you want from an entire aisle, you walk to the bread aisle and somebody says, “Hey, based on what you told me and other shopping information that we have, we think these are the three that you're actually looking for.” And you can say, “No, I do need whole wheat and that's the brand that I tend to like”. And “Yep, thank you.”
DoneStreet
I'm unsure if this is a significant use case, however, I would imagine maybe AI can help in situations where the customer doesn't necessarily know what they want. They just know they want to improve their living room or they just have some sort of general goal and they're just kind of exploring.
Tim
Yeah, it’s like an AI-generated Pinterest board. Imagine trying to redesign a space like a kitchen or living room. Pinterest started as a place for ideas, and now, companies like Ikea show you different styles and setups. But scaling that to generate specific samples, like a modern living room based on current trends, could be powerful. The challenge is tying these ideas to real products. If you show a clothing item that's out of stock and suggest a similar one, conversion rates drop. Customers want exactly what they saw, so missing those retail basics can hurt customer engagement.
DoneStreet
How do you approach the leadership? What do you think makes someone a good engineering leader? Are there certain things you try to do more of and certain things you try to avoid?
Tim
Yeah, I think there's a handful of things. I think from my perspective as an engineer, jumping from actual hands on engineering into management. I had a pretty good mentor. As a manager, I was still doing a lot of involvement in P1s and helping solve issues. And I felt good because I was in there with my team. I would be like “Let me take this one.” You know, kind of like the general leading the charge in battle. He pulled me aside and was just like “How did you get so good at P1s?” And I was like, oh, I did a lot of them. He's like, cool. And if you keep doing them, how is your team going to get good at P1s. And it was like, oh....
And so it's sort of that weird thing of like, I want to be there to help you and support you, but I also need to get out of your way. That way you can build the knowledge and experience that you also need. When I talk to engineering leaders underneath myself, one of the questions I sometimes ask them, and I'll ask them even on other things is “Well, is this person doing it wrong or are they doing it the way you wouldn't do it?” Because those are two different answers. If it's wrong, great, we need to correct it. But if it's not the way you did it or you would have done it, that doesn't mean it's wrong. It just means it's different. And it could lead to better outcomes or different things.
It’s important to give people space to grow. It can be hard because it’s tempting to just say, "do X" when you see something. One tip I give is during pull request reviews, instead of providing direct feedback, ask a question. For example, instead of saying, "I don’t think you should do X," try, "This is interesting. Why did you approach it this way? Have you considered this?" This encourages them to share insights and provides that space to grow and to innovate and to learn.
DoneStreet
Yeah, I think that's great insight, and I think that's something that a lot of leaders struggle with. The idea of letting go. That's why you end up with people who micromanage or they kind of let their ego get in the way. It's a good perspective to share and it’s an important tactic to really enable your team to succeed versus holding their hand and overlooking them.
Tim
Yeah, hire the right people and get out of the way and let them do a good job.
DoneStreet
How do you go about building a strong team? How do you find talented engineers and how do you find people who would be a good cultural fit?
Tim
Yeah, I think cultural fit is the bigger key. While technical skills are important, long-term growth in engineering comes from learning to work effectively with others, including non-technical business users. Software is built by people and for people, so understanding user needs, even from non-technical perspectives, is crucial. For example, if you talk to your parents and they can’t figure out how to turn something on, it’s a good indicator that it was built by engineers who had never talked to anybody like an end user.
At our company, we assess technical skills during screenings but place significant emphasis on soft skills. Traits like raising concerns about deadlines, voicing alternative approaches constructively, and fostering team communication are vital. If you create an environment where it’s okay for people to raise their hand and raise concerns it’s a better setup. Bad news doesn’t get better with age. Building that foundation of communication, building a team culture where everyone wants to work together so that everybody feels like they're working towards the same goal. To me that goes beyond just having a solid technical foundation.
DoneStreet
Yeah, That’s also a great insight and I think there's a few key takeaways there. One is you want to hire the right people and maybe not everyone has like the same skill sets that make them talented, however, you can identify what are good skills in different people. And then as long as they have the building blocks of communication and empathy they can succeed. It sounds like those are the type of people you try to surround yourself with and build a team based off of.
Tim
Yeah, if I'm teaching somebody how to learn a new language or a new framework, or if I'm teaching somebody how to work with other people, the former is much easier to teach somebody on the job rather than the latter. So how do you find people that are kind of coming with some of those basic good building blocks of “I work well, I can communicate well, and I understand how to work together to reach that common goal.
DoneStreet
Are there any potential hires that really stand out in your mind from your past, where you found them in a unique way? A situation where you were surprised or really blown away by the person, the individual?
Tim
I still keep in contact with some people I've worked with like 15 years ago and I'll grab coffee with them when I come through town. I'll tell you one of the things I miss about working in Chicago. I love Columbus, don't get me wrong, I just love Chicago. But one of the things that was most interesting about Chicago as an early tech career was that everybody worked in the Loop in Chicago back in the day. So you took the train into the city, or you took the L into the city, into the downtown area and then you got off. And if you change jobs, your commute didn't really change, you just might take a left off the train instead of a right off the train. Because of that, you got to meet so many new people because somebody would change a job and they would work two blocks that way and then you get lunch with them and they bring co workers and you met people and then they might change. And all of a sudden you had this big friends network of people that were constantly asking “What are you working on? What are you doing? How are you solving this problem? Oh, you're using that tech, we're using this tech. What do you like about it?” From that I have some people that I've worked with at multiple companies that I followed or they followed me. And I think from that perspective, building those longer term relationships are great.
And like I said, whenever I go through certain cities, I'll always be like, “Hey, you want to grab a cup of coffee and just tell me what you're working on?” Not like, what are you doing from can we sell you something? But more like, what are you working on? That's cool. I might talk to somebody and they say we're trying to solve this problem. And I'm like, hey, I know a guy that hit the same thing. Here's what they're doing. I don't know if this helps you.
DoneStreet
What the secrets are to being successful? Do you think there are magic bullets or what do you think the key building blocks to being successful are? And what advice would you want to give your young yourself?
Tim
It’s not just Networking. Networking is important, but it’s really about building meaningful relationships. As your career progresses, you naturally form deeper connections with people, often working with them across multiple jobs and crossing paths many times. When challenges arise, it’s valuable to know someone who can solve the problem, even if they don’t know every technical detail. Early in my career, I focused on knowing all the code answers, which is crucial, but technical expertise only goes so far so don’t only focus on the technical side.
The real key is developing people skills and forming relationships where you and others want to work together again. When you need help or someone else does, your name—or theirs—comes to mind. Nurturing those relationships is vital: grab coffee, schedule a quick Zoom, and check in about life, family, and hobbies. These connections make all the difference.
DoneStreet
I like the distinction you made there where there's networking, which can be very surface level, but relationships go a lot deeper and are a lot longer lasting and more meaningful.
When you're 80, looking back at your life, what do you want to have accomplished?
Tim
Yeah, I’ve been pondering that. I don’t know if there’s a clear career answer. I know we talked a lot about people and relationships and that kind of stuff. I had an intern who worked with me for a summer. It was good and I enjoyed having them as an intern. Then they went on and they did a whole bunch of other things. Years later, I was passing through and I asked them if they wanted to grab a coffee or a bite to eat and to catch up.
They came up to me and they were like, “That three months with you, you were one of the best bosses I ever had. You taught me xyz. When I started working, I'm like, I know this because Tim taught me. And I knew this because Tim taught me this.” And I was floored. It was such a sincere, genuine, compliment.
I was just trying to grab a cup of coffee to see how they're doing. And for them to come out and say that, it touches you. That compliment, that stuck with me. And it was one of the nicest things somebody has said. When you talk about, what do you want in 80 years? When I'm 80 years old, it would be nice if people thought “He was a great person to work with. He was a great person to grab a coffee with. He was a great person. You know, I have a kid. Like, he's a great dad. He was there, you know, being married, wanted to be a good husband.”
It’s like, what’s the type of mark you want to leave on the world? Technology lasts for a couple of years, it's always going obsolete. It gets back to the relationships though. I guess it’s something along the lines of “That's the type of person I'd want to work with again if I had the opportunity to build the dream team. I would call Tim to be a part of it.” And I think that to me is where I would want to be at 80.
DoneStreet
That's an awesome answer. Yeah, really positively impacting people's lives and leaving a really strong legacy.
What types of topics are you excited about or trying to learn about now and do you have strategies or systems to learn about them? Is it reading books, is it podcasts, anything specific?
Tim
Yeah, I think one of the big things I’ve been digging into this past year is business-to-business (B2B). Since I work in retail, my focus is on how B2B is evolving. Personally, though, I’ve also been fascinated with Mesoamerica and early civilizations—just reading books and soaking it in.
On the work side, I call this the “Domino’s Pizza Tracker generation.” People who grew up tracking their pizza online now expect the same transparency in B2B. But so much of B2B still relies on outdated methods like faxing or constant calls. Now, these new buyers don’t want to call someone to check on an order—they want to look it up themselves. The industry is starting to evolve, borrowing ideas from B2C, but also addressing unique needs.
For me, I like reading—it's quick and fits into daily moments, like while eating a bowl of cereal. Listening or watching videos doesn’t hold my focus the same way. Reading helps me grasp concepts, but the real insights come from talking to people. I’ll read all I can, then ask someone directly: “Does this make sense to you with your experience?” They can confirm yes this is what we’re experiencing or that's not my experience at all. And you're like, okay, well then tell me what your experience is. So, yeah, I think from that part, I'm really interested in doing a bunch of research on that.
DoneStreet
In terms of Mesoamerica and history, have you recalled any interesting stories or anecdotes or anything that really stood out?
Tim
I read 1491 and then I read 1493, which has to deal with the story of Columbus who sailed the Ocean Blue in 1492. So it was like pre Columbus and post. I guess growing up in school, you spent so much time talking about early civilization and Rome and Greek culture. Rome and going through European history in the Middle Ages and the Dark Ages and all these different things. And the Renaissance and especially art. I just felt like there was so much more there, especially living in the Americas.
There was just so much there around what civilization was like, and some of the weird factors that go into why. For example, how much mosquitoes played a role. It's incredible how much mosquitoes played a role in the development of civilization and the Americas. Yellow fever and all that stuff just drove so many different social and economic forces. And you're like, wow, the mosquito. You would have never thought it. You're not in a high school learning about mosquitoes in your history courses, right? You're learning about history in America and World War II, and all that stuff.
DoneStreet
Where can we send people to follow your work and updates professionally? Personally, are you active on Twitter? LinkedIn?
Tim
LinkedIn is where I'll post those type of updates. I know the Aries Social is also good at what we're doing at Aries. We're pretty good at posting about conferences and other things we're going to. Anybody who is watching this, don’t be afraid to reach out. Reach out, say hey, I read your interview and want to grab coffee with you. Like I said, I'm a big coffee drinker, so I'm always up to try to meet new people and see what's going on.
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