Leading Customer-Focused Legacy System Transformation with Jeff Miller

In this episode of Innovation and the Digital Enterprise, Patrick and Shelli talk to Jeff Miller, Vice President of Engineering at LinenMaster.
Jeff discusses his journey in the tech industry and his role at LinenMaster, a leading laundry management solutions provider. He delves into his previous roles at various prominent Chicago technology companies, focusing on his work to modernize platforms and streamline operations. We talk about his earlier interest in tech; he built a computer when he was a kid! Then Jeff shares insights into this hands-on approach, the challenges of transforming legacy systems, and the importance of iterative development. He discusses his leadership philosophy of roadmapping transformation with the customer in mind and building trust through execution.

• (00:00) Introducing Jeff Miller, VP of Engineering at LinenMaster
• (01:14) Jeff Miller's Career Journey
• (04:38) Roadmapping Strategy at LinenMaster
• (06:24) Technological Transitions and Innovations
• (09:36) Leadership and Decision-Making
• (09:37) Jeff's Early Interest in Technology
• (12:58) Rebuilding Trust and Modernizing Software
• (25:02) Advice for Tech Professionals and Founders
• (28:47) Conclusion and Farewell

About Our Guest

Subscribe to Your Favorite Podcast

If you'd like to receive new episodes as they're published, please subscribe to Innovation and the Digital Enterprise in Apple Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.

Podcast episode production by Dante32.

Full Show Transcript 

Patrick Emmons: Hello, fellow innovators. This is Patrick Emmons.

Shelli Nelson: And this is Shelli Nelson

Patrick Emmons: Welcome to the Innovation and the Digital Enterprise Podcast, where we interview successful visionaries and leaders and give you insight into how they drive and support innovation within their organizations.

Shelli Nelson: Today, we're thrilled to have Jeff Miller, the Vice President of Engineering at LinenMaster. LinenMaster is the leading laundry management solution and has been pioneering innovative software solutions for the healthcare, hospitality, food and beverage, uniform, and dust control industries since 1995. Jeff brings a wealth of experience to his role at LinenMaster, having previously served as the hcief technology officer at Yello.co. His strong academic background includes a Bachelor of Science in Computer Science and Mathematics from UW-Madison, where he also served as the President of the Skydiving Club. Jeff's leadership and expertise in engineering have been instrumental in streamlining operations and driving technological advancements at LinenMaster. We're thrilled to have him on the show.

Patrick Emmons: Welcome to the show, Jeff.

Jeff Miller: Thanks for having me.

Patrick Emmons: If you don't mind, kick this conversation off with a little bit more about your role at LinenMaster and then love to dig into your background and some of the places you've been before.

Jeff Miller: Yeah. I'm coming up on my one-year anniversary at LinenMaster. Prior to LinenMaster, I had been at a number of Chicago tech companies. Starting with eshots, which is a Fortune 500 B2C marketing firm, then moving over to Enova and working in the fintech space, working on a number of the largest brands for Enova, but then also working to found the platform team there to standardize practices across the different brands that Enova serves.

From there, I moved on to NCSA, which is a bit like a marketplace between high school student athletes and college coaches, trying to make both parties make the best decisions for their future. Then there was a brief stint at Fooda cut short by the pandemic, but I really love that team and we did some great things trying to recover from the pandemic, but then ultimately moved on to Yello, where we helped the Fortune 100 companies and the federal government do a lot of early talent recruiting in a highly compliant environment, very security focused based on our clients that we served.

And then that rolled into LinenMaster. Like I said, I've been there for about a year. I thought it was a good fit primarily because they had a lot of needs to modernize the platform to attract different customer segments, and I really just kind of fell in love with the management team. The tech is one thing, the industry is certainly very niche. That is what our private equity firm, Mainsail, really focuses on, which is these software industries in very niche categories where we can go in and bring modern practices, modern technology to a segment that maybe just has been ignored for some period of time.

That's where I really saw myself being able to make an impact is coming from a hands-on engineering background, just being able to really get in the weeds, make some assessments, help drive the platform forward. Definitely got into a lot more than I thought I was going to be getting into but here we are.

Patrick Emmons: Well, that's why you're on the show. If it was like everything went great and it was well-defined when I got there, then it'd be a pretty boring show and we probably wouldn't have you on, to be quite frank. I have somebody approach me recently and they were looking for a new role as a president CEO and they wanted an organization that had a certain net margin and they had a great culture and they had a great product. I'm like, "That job doesn't exist. Nobody's leaving that job. "You got to find the one where it's like there's good bones and maybe it's not loved enough or they're going through some transformation. But you're not going to walk in and nobody gets to just be the head coach of the Kansas City Chiefs. You go in as an assistant coach and then work your way into taking Andy Reid's job, but...

Jeff Miller: Yeah. I've phrased it to friends and/or family that any of these roles you step into at a vice president or CTO or even at a director level, there is a reason they're hiring you. It's either a growth challenge that they're having, it's a potentially recovery from somebody that wasn't a great fit in the role, technological problems. There's always going to be something that you're stepping into. For me, that was really kind of a roadmap challenge, legacy technology challenge. As you mentioned in the intro, we've been around for 30 years. The technology has grown over time, but I will say it's the first time I've been doing desktop application development in quite some time. That gives you an idea of where some of our products are at.

Patrick Emmons: So much there. I mean, so much already. Yes, 30 years old. When did LinenMaster start making this move to the big investment on the tech side of it, because I got to imagine 30 years ago, it was not... Maybe it was that original desktop app that you guys were working on or they were working on, but when did that shift happen? Was there somebody who preceded you in this or is this a continuation of Mainsail's focus on growing this organization?

Jeff Miller: The previous owners had started the technological transition. We were one of the first in our space to move to the cloud, which seems like a big deal for them, but we all know that a lot of businesses did that decades ago.

Patrick Emmons: There's a lot that haven't and they're called banks.

Jeff Miller: Yes, that's true. Yeah, that's true, that's true, that's true. They went with a thick back end, thin client approach. They took a lot of the backend logic and technology, moved that to the cloud as well as the databases, and then retained this thin front-end desktop component. Now, we're kind of just finishing that transition, which is rebuilding some of the backend components to be a little bit more modern software, modern frameworks primarily for developer efficiency and security and all that type of stuff, and then slowly transitioning that thin client to the web. It's kind of a dual track approach, where we're rebuilding components or reusing components where we can.

Generally, I would say we're taking a service-oriented approach to the integration of multiple products that the business had, taking a lot of the same learnings that I had from Enova, using Enova's language, which for those that don't know, it's a B2C or B2B lending. There are components of lending that apply to anything regardless of what market segment you're going after. You apply for a loan, there's a credit decision made, there's a funding of a loan, there's payments.

What we did at Enova is standardized a lot of that so that we could leverage those services across the business. We're taking a very similar approach here at LinenMaster, which is there's payments, for instance. Clients make payments to a laundry. We'll isolate that out as a service, integrate it everywhere, and then delete the old code that powered it, and then just continuing to iterate through the different functionality that the platform has.

Patrick Emmons: Very cool. I guess a number of the places you've been at previously, I think there's some of the more recognized tech shops in Chicago. The Yellos, the Enovas, NCSA, Fooda. Anybody who's in tech, they know these names. What do you think is the biggest challenge you've faced as you're stepping into LinenMaster and setting that kind of culture? Because I would imagine it's great that the executive team is something that attracted you. I think that's fantastic. I'm sure you've got plenty of stories of why that's a big part of your success, but when you get involved, you really got to put down some planks of just even foundational stuff. What are some of the lessons you learned? First of all, am I right? Second, is there anything to be learned from some of the challenges that you faced taking on this opportunity?

Jeff Miller: Yeah, I would say I changed my onboarding philosophy pretty substantially coming into this role at LinenMaster. As you mentioned, a lot of these companies that I've been at previously have very strong cultures, very strong presence in the Chicago tech community, and I didn't view it as my role to come in and completely disrupt things. We'd make changes along the way, but I want to take some time, maybe two, three months to learn and observe, two, three months to suggest changes and nudge people in a different direction, and then maybe make some more declarative changes after that that get us to the goals we want to get to.

There's a lot more of assimilation into the culture while putting my influence on it. LinenMaster, for better or for worse, had relied on a lot of contract talent when I joined. There were a number of big projects going on that I felt like I needed to take a little bit more aggressive onboarding plan to because I just wasn't convinced they were going in the right direction for our long-term strategy. There's, quite frankly, just a lot of investment going in. There were some projects that we stopped, there were some projects that we changed course, and this all happened a month or two into my employment there. There really was no learning and assimilation phase. I mean, I was learning as quickly as I could about the business, about the direction, about the industry, but given some of the high-level investment, we just had to make some changes faster than I probably would have in previous roles.

Patrick Emmons: Pretty cool.

Shelli Nelson: Jeff, I know in a previous conversation we all had, you mentioned that you built your own computer at one point. Can you tell us more about that?

Jeff Miller: Oh, sure. I mean, I guess that's the origin story of getting into technology. When I was growing up, we had computers in the classroom, and then I think I was about fifth or sixth grade when my dad got the first computer in our home. After a year or two of getting used to working on our computer at our house, I did the standard thing I think of at the time of complaining to my dad, "Well, this doesn't have enough speed or not enough memory." I probably was playing a video game or something like that and it wasn't operating at the level I was hoping for. He just kind of threw out there, "Well, then you buy it yourself." Well, of course I couldn't afford that at that time, but it was a lot more economical to buy the pieces and put it together.

That's kind of the path I went down and just steadily learned and bought pieces, failed a couple of times, and eventually got a working machine. I think that started the technology desire in my career. That's where it started. Web development kind of came pretty quickly after that like a lot of people. Started with PHP because it was just there and available and then carried that into college. That's kind of the origin story of where I started with technology.

Shelli Nelson: That's awesome.

Patrick Emmons: How old were you?

Jeff Miller: I think it was sixth or seventh grade when we actually started putting that together. Yeah.

Patrick Emmons: Wow, that's impressive. That's why you got into programming, that's why you like writing software. That's the origin story, huh?

Jeff Miller: Yeah. I think unlike some technologists, which there's no value judgment here, for me, using technology to obtain some sort of outcome was always the thing that really drove me. Whether it was making my life easier in some way or whether it was nowadays like impacting a business or impacting an industry, I do like to make sure I understand what is on the cutting edge of technology with AI and Agentic AI now and all these different things. But unless it solves a business challenge or solves a personal problem of mine, I'm less interested in it until I can apply it. It's the same thing that correlates with my learning style as well. I can read or listen to seminars all day long. I will get some information, but I will not lock in that information until I practice it. That's just my learning style. It's like my personality, just diving in and trying to make an impact.

Patrick Emmons: Interesting. One of the things that you brought up with your new stint at LinenMaster was there was a big effort going to build something that... This happens all the time where it starts out and you're going down a path, and then things change, realities change, understanding change, calendars change, and suddenly you've got to make a hard decision. I'd love to hear you tell your story around that because I think leadership is not found when things go well, right?

Jeff Miller: Yes.

Patrick Emmons: How do you handle that situation? How did you handle that situation and make sure that all stakeholders, clients, employees, executive, and then do what's right for the business?

Jeff Miller: Yeah. Mainsail came into the business in 2023 and started building an executive team, started running their playbook essentially of how to usher these relatively small upon acquisition SaaS businesses into larger forces in the industry. There was a person in the role that was always meant to be somewhat temporary until they found a long-term owner for the technology of LinenMaster. In conjunction with an outsourcing partner, they had come up with a plan to re-platform all of our products. That was clearly my number one objective is to get my arms around this initiative, to basically build confidence and trust into the plan, and then ultimately execute it.

It's really at that step two where I got hung up, which was building confidence and trust in the plan. The more questions I asked and the fewer things that I could verify in the process just made me feel uneasy about all this. With the confidence of our CEO, we decided to just put a pause on all spending on all projects until we could get a better belief in the plan. This is a quite nerve wracking decision for me. As you mentioned, it was maybe two, three months into my time there. I was still learning, I was still trying to understand, and we all know that time is precious. It's the thing we can't get back. I felt like if we stopped this and had to stop for a while, it could be pretty detrimental to the business or to obligations that we'd put out there.

We rallied the troops in terms of the executive team, got everybody aligned, got the stakeholders aligned, and came out with a slightly modified plan. Then we kind of attacked it in quite a different way from a tactical perspective. I truly believe in iterative development and trying to release MVPs. We got to make sure that they're viable. That was one challenge of the original plan is that some of the MVPs were just too minimal and such that it just didn't help customers enough that they would adopt it. We reevaluated the plan, we reorganized around the new plan, which was essentially the strangler approach to our current application. The reasons that we liked this better than the original plan was I am just not a big fan of these big bang releases that happened. You work for 12 or 14 months and show progress all along the way, and then on one magical day, everything goes out and it always goes perfectly.

Patrick Emmons: Always. Always.

Jeff Miller: Of course I've actually never seen it work perfectly and so I try to avoid those.

Patrick Emmons: It makes me think of Noah's Ark. Not to be biblical in any way, shape, or form, but there was a big bang there day for them of does the boat work, right?

Jeff Miller: Yeah.

Patrick Emmons: I don't believe it did. I bet that thing was leaky. I get the feeling like they're putting the animals on and the ramp didn't work or the door was too small. You know what I mean?

Jeff Miller: Exactly. Exactly.

Patrick Emmons: There's no way. Grand plan, I'm a hundred... I hate to interrupt you, Jeff, but I'm with you 100%. Before we wrap, I do want you to explain the strangler pattern because I think that's a critical element that a lot of people when they're like, "Oh, we got to rebuild..." The amount of time you have to rebuild is very, very small.

Jeff Miller: Exactly. We took an analysis of... Well, the other part of the big bang approach that I was really not comfortable with is that our current customers were going to be some of the last to see the benefit of our work. If we were building this all along the way, we might be able to get smaller or new customers onto the new system, but our current customers would have been left sitting there with the old software that they're used to. With the Strangler approach... I think it's technically called the Fig Strangler approach, but I was exposed to it at Enova through Griffin Caprio and I think it comes originally from a Martin Fowler post.

But the goal here is to take business logic, encapsulate it, and then move it into an environment you're more comfortable with. The reason I'm using somewhat fuzzy language is because its strategy might be different for different sections of the application. For us, one section of the application can literally almost be cut and copy and pasted, encapsulated, put an API around it, and just interact with it a little differently. And then we can also use that in different places. It just has a number of benefits testing and all of those type of elements, whereas some of it we need to rebuild because of some of the data models are a little wonky, as you can imagine, over 30 years. Things just kind of grow in ways that you don't anticipate.

And simplification, too. There was a business rule added here and a business rule added there. They're kind of going against one another. Can we coalesce these into a more logical pattern? For those, we're rebuilding and we chose to take on one of the hardest parts of the application first just so we could set the baseline for the rest of the development so we could do better projections and all of those type of things that a board wants to see. So roadmaps and projections and metrics that demonstrate that we're going to hit the roadmaps.

We took one of the hardest areas, we rebuilt it, we simplified it. It's set to launch here in about two to three weeks and we're doing an internal launch first for our customer service team. They'll get to see the latest and greatest, and then we will work to roll that out to a beta group. But the strangler pattern, as we're executing it, customers can either use the new software and have a very simple view. Or if they have a more complex use case, they can always fall back to the older software, because we're writing to the same database, we're modifying the same data sets. There's a natural growth strategy or fallback plan if things don't go well. That's how we're executing it. And for us, I'm just much more confident in our ability to not only project to the work, but also get something out to customers as quickly as we can.

Patrick Emmons: I'm going to assume that getting functionality out to customers, part of that, from my experience, is... I mean our job in engineering is to get value to customers quickly, securely with quality. But that idea of 12 to 18, I think you're being generous of 12, 18. The right course is 24, right?

Jeff Miller: Yeah. Yeah.

Patrick Emmons: I mean it generally ends up to be 24 months of no new features, and then you waited two years to get back to the functionality you already had. Boy, as a customer, am I jacked?

Jeff Miller: Yeah, exactly.

Patrick Emmons: I actually don't know if you remember way back when Azure was a prototyping tool. I'm sure you're aware. I'm just saying for our audience. They made a decision in 2010 where they're like, "Hey, we built the wrong thing." They told all their customers, "You don't have to pay for the next year of licenses, but we need to rebuild." It took a year to rebuild their whole application and I just had a massive amount of respect for that move.

Shelli Nelson: Wow.

Jeff Miller: Yeah. Wow.

Patrick Emmons: That's some bravery, right?

Jeff Miller: Yeah.

Patrick Emmons: But isn't that a big part of it, though, is like it's about building trust with the customer as well like, "Hey..." Because you mentioned the customers who got you here are going to be the ones who last benefit. It doesn't seem like a good business decision.

Jeff Miller: Yeah, it's not all of the decisions that led up to it. I don't want to put any blame on anyone because there were some other challenges that they had to deal with before me coming in. I had the kind of benefit of hindsight on some of those things, but definitely we had trust to rebuild with both our internal customer service team and external customers. We wanted to show a string of releases that were positive for everyone. We launched a new product at the beginning of the year. We relaunched a product that I was alluding to that was a little... It was too minimal of a product, and so we augmented that and relaunched it. We have the project that we recalibrated when I started. That project is launching here in two weeks. And then we have the fourth project, which is the first step of the strangler rebuild launching in three weeks.

My whole goal with coming into 2025 was to rebuild trust through demonstration of activities. We can all talk all we want and these customers have heard a lot of talk from the whole industry, honestly. Now we've just got to execute and we have to then start communicating our plan and building customer requests into that plan. There's a lot of work to go for sure, but for me it was we just have to demonstrate that we can get you great software on time with security and all of those types of things. That's the stage we're in right now.

Patrick Emmons: What is your greatest takeaway from that? What is the thing where... I can tell from when we've talked before and today, you carry forward so much of you mentioned the things that you learned at Enova, like how they're different, and applying those types of metaphors or approaches. What is the thing that, in your time at LinenMaster, that you think had the most impact?

Jeff Miller: In terms of most impact, I have to think about that for a bit, but what I will say is that the collaboration with the executive team has really been invaluable. We have some that have been in the industry or with the company for quite a long time and then we have some "new blood" like myself that is coming into both the industry and the platform and all that type of stuff. I think the collaboration that we've been able to do together, bringing different perspectives has been really valuable, and it honestly raises the confidence of the whole group.

There's no way I could have stopped that development without the confidence of the CEO and our chief customer officer. Obviously, it's implied that the board is onboard as well, but I think my CEO did a great job of working with them to make sure they understood that we had to pivot a bit but we're going to ultimately get more out of it.

I'd say the learnings... Maybe it's obvious, but being able to change your mind without being erratic. I had one idea of how this software would eventually be modernized. As I learned more, as I discovered more about the industry and about potential competitors or partners, we are changing our approach to being a lot more like a service-oriented architecture platform as opposed to the kind of monolithic approach that I was going down. I guess just not being set in my ways, trying to be adaptable when you learn new information, I would say that just continues to be something that helped get us here.

Shelli Nelson: I really appreciate what you said, Jeff, because I was curious, with all your past both success and failures, was it hard to come into this role and not have some biases around what's going to be successful without taking a step back and, like you said, really collaborating with the leadership team?

Jeff Miller: Yeah. I mean, in these roles, CTO, VP of Engineering, people expect you to have an opinion. When they turn to you and say, "How are you going to do this?" Of course you can say, "I'll get back to you," but you have to get back relatively soon here. They don't want you to take a four-month study about how to do this. I think that was quite a balance to balance the efficiency or knowledge that you have coming in with discovery of new information and how we should go forward, because a lot of the things, not only in our industry but just in every business, are uncertain. A pandemic can pop up and you might have to pivot or other exogenous effects like that. For us, they're mostly self-imposed. Different partnerships popping up, different opportunities coming on our plate. And trying to adapt the plan to be adaptable to all of those different outcomes was, I guess, the thing that I would say I grew the most from is just things changing quite frequently. How can we coalesce this into a cohesive plan that we can actually stand behind?

Patrick Emmons: Well, since we're busting out big words like exogenous, I'm just really putting it on here. Nice work. It's not often I get a new word. That's a new word, but it's great advice and great perspective to have of, yes, the best laid plans of mice and men, right?

Jeff Miller: Exactly. Exactly.

Patrick Emmons: Awesome. Well, I guess wrapping up this conversation, you've been doing this a while. You've seen a lot. You've been through different types of industries. You've touched a lot of bases. What advice would you give to other tech professionals or founders or people looking to get into, I would say, more of these firefighter roles where it's like, "Hey, you're coming in. They're going through transformation, there's expectations, there's a rough calendar"? What would be some of your advice or key takeaways? If you could talk to yourself five years ago, what would you say?

Jeff Miller: Yeah. I think the book Extreme Ownership, some people don't like it because of the military analogies that are in the book, but I think it's just a phenomenal book to set your mindset about how you should be thinking about your role and your impact on a company. But there's nothing that's not my job. This is my problem, this is my job, so to speak, and you have to own those things. Yes, you can delegate them out, yes, you can adapt, but you really have to own the results and the outcomes that's happening in your organization. I'd say that.

If you're on the up and coming end of the spectrum, I would look for areas that you can own that may not be desirable. Those are the easiest ones to grab because no one else wants them. If you get really good at that thing, you just become invaluable to the company. I think for me, the example of that was Enova had a mentorship program when I was there and I was assigned to our chief compliance officer. We were just talking about general growth strategies, but it became clear that a lot of times when they were on calls with regulators or governing bodies of any sort, that they could really use a technology hand there.

I was still very close to the code while still managing a team. Being able to contribute to those conversations, whether it was an internal conversation to prep them for a call or eventually jumping on calls with the CFPB or other, like I said, regulating bodies, that was a role that no one really owned in engineering. It was kind of a, "Oh, let's grab this person over here or that person over there for one-off events." But that cohesiveness of having a singular voice, I think, for our compliance partners was really helpful. Not many people get out of bed to say, "I'm the compliance guy," but I definitely adopted that role so that I could just add more value to the business, add more perspective to the development teams when they wanted to maybe cut a corner that was part of the compliance programs. I had a personal stake in this now, so I could easily explain to them why we have to document X, Y, and Z as opposed to just YOLO and let's ship it.

Shelli Nelson: I'm sure that built a ton of trust, not only with your team but across the organization.

Jeff Miller: Yeah. And it's served me in roles since then. Like we were just talking about right before the call, we're gearing up for our ISO audit here at LinenMaster, and then SOC 1 and SOC 2 will be coming right after that. Just having done this in a couple of different organizations, you can distill best practices, you can say like, "Oh, this process is a little clunky. I know we have to have a process here, but I know it can be streamlined." You can bring that perspective and compliance and security is going to be something that we're always interested in regardless of the industry, I think.

Patrick Emmons: Absolutely. It's everywhere. I don't care. I think it's great wisdom to go embrace those things, because the more you make them your enemy, it's not going to make it easier, right?

Jeff Miller: Yeah, for sure.

Patrick Emmons: I also suggest people get to know the CFO, because if you want your projects paid for, it never hurts to have a solid relationship with the CFO.

Jeff Miller: Very true. Very true. I think since the whole executive team.

Patrick Emmons: Totally. Well, Jeff, I really appreciate you taking the time today to speak with us and share your stories and your experience. Congratulations on all the success and we wish you nothing but the best in the future.

Shelli Nelson: Yeah. Thank you, Jeff.

Jeff Miller: Sounds good. Thanks for inviting me.

Patrick Emmons: We also want to thank you, our listeners. We appreciate everyone joining us.

Shelli Nelson: And if you'd like to receive new episodes as they're published, you can subscribe by visiting our website at dragonspears.com/podcast or find us on iTunes, Spotify, or wherever you get your podcasts.

Patrick Emmons: This episode was sponsored by DragonSpears and produced by Dante32.