Episode 109 Transcript

Brent Trimble: Welcome to the Professional Services Pursuit, a podcast featuring expert advice and insights on the professional services industry. Hello, everyone. I'm Brent, your host, and today I'm joined by Shawn Windle, Founder & Managing Principal of ERP Advisors Group. We're going to discuss a challenge that many firms face, especially as AI is accelerating change: how to choose technology that solves the problems that are immediate, while also building a foundation for long-term, scalable growth. We'll unpack practically what pushes a firm into an enterprise ERP platform, how to evaluate your next steps, and what separates a PSA from an ERP and everything in between.

Shawn, welcome to the show. I know this will be one that has a lot of relevance to many of the colleagues, prospects, and potential partners that we talk to. Before we dive in, give us a little bit of background about you, the firm, and then we'll dive into our Q&A.

Shawn Windle: Great. Brent and team, thank you so much for having me on your podcast. It's a pleasure to talk with you all. We certainly know about Kantata, and we have been a user for a while. Our firm that I started 15 years ago is very focused, niche, and boutique—which is all consulting speak for small. We're about 40 people. What we do is help organizations with independent, objective enterprise software advice. We help organizations figure out what they really need to do and whether they should switch or not. Hopefully, the answer is not, but if they have to, we go through a selection process, downward vetting selection process, and a 100% total certainty process that we've built. Most of us are from the Big Four, bringing methodologies together but focused on mid-sized organizations.

We help with client - side implementation services.We don't just write a beautiful recommendation and negotiate contracts; we actually stick around for the implementation, for a client to go live successfully. Our clients always go live. Our advice isn't just high- level theoretical; we're living this and have lived through hundreds of implementations with services firms. We work with other industries too, but today we're focusing on the services side.I'm grateful to be here. I'm going to share some practical tips of things that we've implemented ourselves, but we've worked with so many organizations—things that, if you're working in enterprise software, PSA, ERP, or AI, we're in the guts of it with over 50 organizations at any given time.We have a lot of best practices and things we'll share today, so I'm really looking forward to it.

Brent Trimble: That's outstanding and a lovely reference to the framework. We'd like to dive into that. Before we get started, our listenership, potential prospects, and potential partners, and those contemplating maturing both technology and process, tend to reach different thresholds of size and complexity. Professional services predominantly scale with headcount, practices, and sometimes acquisitions. What are the main criteria or thresholds, levers, or stepping stones as they ladder up that you typically find? It's tough to work in averages, but you spoke about midsize, so maybe it's there. What are the decision dimensions that bring a firm to you? They've reached a certain size, maybe a pain, maybe there's risk, whatever the criteria might be, that they contemplate that decision and push them to a more robust enterprise offering.

Shawn Windle: Our viewpoint is a little bit different than most technology advisory firms, to be totally honest with you. We don't really want clients to go through a change for enterprise software unless they have to. There are times where you have to change and times when you don't. Ultimately, growth is the biggest factor. We have firms that are scaling organically, like you mentioned, making acquisitions. In terms of the number of people that are part of the professional service organization, we may have had some bad practices or some things that weren't the most efficient way of handling time capture, invoicing, and resource allocation that we could get away with when we were a certain size. As organizations get bigger, they're spending all of this time reviewing timesheets and have multiple cycles going back and forth. Automation becomes necessary. There are many use cases that come with scaling people. That's definitely the first one.

But the second one, that's probably the most interesting thing that I would tell you, is that I think a lot of the organizations that come to us, maybe they've gotten through some of the establishment and they've got a great name in the market. I’m thinking of a firm that we worked with that was a group of lawyers—not a law firm; they were negotiators, labor contract negotiators. Their employees were driving them for more automation. I say that firm specific because, as you can imagine, these are people who've been negotiating major contracts over tens of thousands of people, hundreds of thousands in some instances.These folks had a lot of years under their belt, decades.Yet they're driving the organization to say, "You've got to automate this stuff because you're driving me crazy." If I want to spend more time doing more value-added work, be more utilized. That’s a second thing: a lot of companies that come to us, their employees are driving for innovation.

I would say the third thing is, like us, a lot of services firms are being asked to do more diverse services, more diverse billing models, and more of anything from our clients.We're figuring out how to do it. When you get that client and they love you and you love them after the first or second project, if you can get that third, fourth, or fifth client-for-life kind of idea, you start getting into more diverse services. It might lead you into more acquisitions with adjacent service providers that you bring in or even partnerships that you bill under your model.

The billing methods are just crazy these days, just the way that you have to invoice and time and not just things like paid when paid for your contractors, but invoice presentment, formats of invoicing, and integrations with these other systems that your customers are demanding.You're putting your invoicing and billing into their systems in new formats. These are all things that have been around for a long time.

I think that's the third thing I would say. Technically, customers are saying or when they come to us, our prospects are saying their customers are driving them for innovation, technically, that they don't know what to do about.There's more reliance, I think, on vendors like you guys and others to provide those solutions, but they're not sure about it.Those are the three key things that I see.

Brent Trimble: We have a hypothesis or, I'd say, a common thread with many potential clients and leaders in professional services firms. They have the “cobbler’s children” phenomenon; they’re delivering great innovation for their clients, providing solutions, strategy, and innovation, but their internal systems, tooling, and processes don’t always keep up. You mentioned the three criteria points. Many listeners can see themselves in that—maybe it is time to migrate from an early version of an SMB platform to something more rigorous that gives more capability. How do leaders balance delivering relief, strain, and compliance to their clients? In your case, employees can be a great catalyst for this. Maybe they came from a firm with better tooling and weren’t closing end of month with spreadsheets, but leaders also must avoid being frozen by indecision for fear of placing a bet for the future. The right partner, platform, and enterprise investment must pay off. How does that criteria, that decision, that lever weigh in?

Shawn Windle: It's such a great question, Brent. I honestly feel remorse for leaders that are in this position. It is a very hard position to be in. When is the time to not just invest in new software, but go through the organizational disruption of changing out, like the airplane engine in midair? Especially if your job is to do that for your clients with whatever kind of consulting you are providing—professional services, marketing services. There are so many things that professional services do, but they’re 100% focused on their clients’ needs, maybe 99% focused. Now we have this, "What do we do about our internal systems ?"

I will tell you this: my answer today is different than it would have been a couple months ago.If organizations aren't preparing for AI, they will get lost. I love being able to talk about this because I’m looking at these things myself as the owner of my business and working with large professional services firms—actually the largest in the world, with Accenture now in terms of management consultants, and even regional firms, and now my own. I know that in five years what we do will be totally different with AI. That is absolutely going to happen. I’ve had colleagues who have sold their businesses because they don’t know what to do and they’re afraid. I’m going to take a more aggressive stance on that and leverage this.

There’s a gradient approach to enterprise software that any organization has to take.I’m a management consultant.Of course there are gradient steps depicted with echelons.To get from unorganized processes that are more ambiguous in spreadsheets, more ad hoc, to at least getting common processes in place, to the next step of having professional service automation software—not just time tracking but PSA that has the lifecycle of a project and automates it—and now getting to integration with the financials, and even going into this next level of artificial intelligence and automation across that whole lifecycle.You will not get to that last step if you don’t have more defined processes and PSA in place.You have to have that core solution, end-to-end transaction processing, if you will.If you don’t have that type of solution, when you’re being asked by clients to do what you’re doing today but a lot less expensively, or your employees ask, "How are we going to leverage our systems here with AI today?" — first off, thank you for asking—my employees are more interested in our internal systems than ever because they’re also being asked by our customers what we’re doing.

In most of the services firms we work with, including my own, we have a lot of apps.We don’t just have one product.We’ve got Evernote, Box, Mavenlink, the Kantata OS, QuickBooks Online.I probably have 20 best - of - breed apps that my people use here and there—Smartsheet, Teams, Zoom.The list goes on.Now we have all this data.If you don’t have the core project lifecycle, resource management, resource allocation in a system, then when these tools really come to market and we figure out the security and the broad application of bringing in a Claude or OpenAI into your own automation and bringing this data together in a new way, you’re lost.

It is easy, especially for services firms that are cash - based.A lot of what we do with time and billing, there’s a lot of cash that flows through these organizations.If you’re not siphoning some of that off for internal investments in technology today, you are going to be in a world of hurt in a couple of years.I am never the opposite of Pollyanna—the sky is falling—I'm never that way in enterprise software discussions. I am now because I know, especially in all the industries we work in, the services firms specifically are the ones under the same pressures: it’s hard to find great people, it’s hard to retain great people. It takes 90 days minimum, if not six months, to get a great person up to speed. Once they’re there, you have to allocate them, resource them, find the projects to get them on. Our businesses are hard because we are so labor intensive. AI is going to help our current team to do more, and we will always hire and retain and try to build the best culture or best place to work. That’s the thing I’m most proud of in my business. I love that.

We have to prepare now.Now is not the time to wait.I can launch into a whole new thing if you want me to, Brent, about how to make the decision on who to bet your business on, because you are when you make these technology platform decisions.

Brent Trimble: Absolutely. That's a great segue into your referenced framework. Many of our potential partners are in the consulting space, whether they're advisory, strategy, IT, technology, management, managed service, or marketing. Many of them are verticalized and specialized—public sector, life sciences, or whatever the case may be. They have specialty and specificity. To your point, maybe they're scaling organically, or they have made an acquisition.

If you can articulate your framework without giving away anything proprietary, walk us through, in a theater of the mind, how you guide them through that process.What is your secret sauce in evaluating where they are, where they want to be, and then reaching a mature, enterprise - grade ERP or PSA—or both, or part of the equation ?

Shawn Windle: There are definitely some key things that I can share with you that I really hope help. I really hope that people hear this and can apply it. My model is simple, on purpose. Many times when an organization—and let's be more specific—there's this brave soul who decides, "We have to bite the bullet and change our software." It's usually one person, maybe two. I don't care how big the firm is. We were talking to a thousand-person professional services firm last week and there were two people. They were like, "We just know." They go to the board, or to the executive team, or they're on the executive team, and they get agreement to start the conversations. There's like one or two people. Maybe it's a team of five. Those people, we work very closely with them to understand what the real problems are that technology will solve and what it will not. Again, I feel like I'm preaching to the choir with the people that are listening to your podcast, but I love this audience.

When you're working with clients, the client has to understand what they need to determine if you're the appropriate solution for them.A lot of our sales qualification steps are just that simple step.When it comes to enterprise software, there is this general concept of, "Oh, I can just go buy an app and it's going to fix all my problems." Does that work in your business ? It doesn't. Why would you think it would work with enterprise software that way? People do. Maybe software is sold that way sometimes too; that's fine.

By really digging into where you are in that maturation process I described earlier, let's say that you are on a simple time tracking system and working with a simple accounting system. You're running into more people and your need and desire to dig into availability of your resources is bigger.Maybe you have a spreadsheet to do that.You start to see you've got all these one-off systems sitting out there.

The first thing I would say about our methodologies is we cast the net wide with an enterprise and really look at end - to - end processes, including sales, certainly the project lifecycle, employee lifecycle management, record to report, the FP & A reporting and analytics, and board reporting.A lot of our clients that are professional services have inventory they're dealing with now, especially our engineering clients. We see different billing models. You really want to take a look at all of your needs for real and what you need in terms of enterprise software automation. Then take a look at that around what you really think software can solve and what it cannot.

We have something super simple that all of us deal with: a utilization problem.My utilization rates are going down.I need to utilize my people more.I need a system to fix that.Maybe the system can fix a portion of that—visibility, tracking, analytics, reporting—but it takes a level of rigor that must be included that you might not have today.That might be the real problem why utilization is going down.

We often advise our clients that if you don't have a spreadsheet solution in place for whatever the problem is in your pro serve function, you might not be ready for that next level of PSA, to be honest. The transition happening in professional services today is incredible. I was just on a call before this one with a firm that's 300 people and they've got a ton of private equity. They're looking at rolling in more adjacent services.That might be the impetus.They're like, "We want to get to growth at the next two levels." Therefore, they're willing to go through all the effort of getting enterprise data together, accumulating it, and then going into a new app.

Discipline is part of every ERP and PSA implementation.If you don't have it now, don't think that a system is going to solve that particular problem.You have to do the undercut of getting the basics in, getting your project structure set, getting your time tracking processes and procedures in place to make the leap over to enterprise software.I was a process guy back in the day with Accenture.I love business process, but I would pull my hair out because we would design these incredible processes, but there wasn't a system that would automate those processes. If you understand what I'm saying and you get that the new enterprise solution, the new PSA, forces discipline—and it'll force the discipline across your team—and they're committed to that, maybe some people aren't, and maybe they're not in for the long ride with us because of that.The enterprise software decision makes a ton of sense because it does force in discipline.Again, Brent, I could keep going on and on and on.

Brent Trimble: Absolutely. That's a really good point. To your point, if there's not a system that is at least being done in measure because we only improve what we measure, you're at a very nascent stage. It's great to contemplate advanced tooling, but you have to be deliberate and judicious about that. Give us an example of a firm that scaled successfully because they went through this process, partnered with you, went through deep forensic understanding of themselves and what it would take to make the next leap in process, and ultimately selected an enterprise platform. It went well for them. Give us the inverse—one that did not and things didn't go well.

Shawn Windle: There's one organization in particular I'm thinking of that was a nonprofit, offering services around the energy industry, around the world. A very cool organization. They had purchased an application, an incumbent that one of the leaders of the organization had used at his prior firm. The prior firm had a business model that was different than the model of this new nonprofit. When we came in, it was obvious why they were in pain and why they needed to change. To your earlier question, they had the wrong tech platform for their model. Everybody knew it, and they were able to stretch, push, and grow to a certain point and then basically started to blow up as they had more people.

We did the analysis and dug under the covers, using the usual lenses of strategy, people, process, and technology.Strategy showed tons of growth and potential for more, people were very interested in changing, but also a little more mission driven, nonprofit, which was interesting.Business processes were pretty straightforward with what they were trying to do.Tech - wise, they had the money and the mandate from the board to become a more modern platform just in general.All the indicators were good for the change.

We got them into PSA solutions and a financials application, FP & A app, and human capital management.The approach we took was best of breed, meaning it wasn't just one app that did everything, it was individual apps that did different components. That helped them to scale, actually to double as a firm and expand geographic reach. They had people all over the world. That process was great because they knew they needed to change.

The biggest risk factor for them was the people, very bright.Every single individual in that organization was among the brightest people, the people you want to spend time with to learn about what they did, alternative energy things.They all had a lot of opinions.Sometimes that's not a good thing when it comes to enterprise software, to be totally honest. Leadership with a vision for what the system needs to do has to be firm to say, "This is the overall benefit of the organization." There were changes, for example in expense reporting, but the benefit to the organization was clear. We were able to manage those change management realities fairly well. That was a really good project.

Ultimately, they upgraded several years later to the next size solution, which was more of a tier one solution, because they grew to thousands and wanted a global integrated platform end to end within one system.It was a very interesting evolution watching those guys.

Now, we had a client recently.It was a heartbreaker, but we went through our three phases: the need, selection, and then client - side implementation services.In the selection process, we were down to two different vendors.One was smaller, the other was bigger, not just in terms of technology platform and footprint, but implementation and capability.We had to make a decision as a firm—who were we going to be into the future ? Were we going to have evolutionary growth and hit targets that were already set out, or were we looking at monumental, revolutionary growth into the future, 10x, 20x, 100x size organization, which would lead to a bigger app ?

We had a lot of really good dialog amongst all the key stakeholders, brought in the board for that too, and decided to go big.We went with the bigger platform and started the implementation.

I will tell you this: if you are going through or about to go through a PSA or ERP implementation, there is no project that has ever failed where somebody didn't know there was a problem first. That problem, if it had been dealt with, would have prevented major issues that kill projects. The accounting team on this project, very early on—and we advised the client on this—was not happy with the bigger software. They were used to using an incumbent solution or Microsoft product. We got them into this tier one type solution, and they hated it. They told us right from the beginning of the project during the demos. We saw them and thought, fine, I think we can do this. Once we got into it, it became clear that it was not going to work. We asked them to try harder, though it was a little more subtle than that. They did, and they still came back and said no.

We started having honest dialogs with the vendor about what to do.Ultimately, we were able to negotiate a deal where everything just stopped.Our client spent money, the vendor had a contract that they were recognizing revenue on, a multi - year contract that had to be halted.The software was not doing what we needed it to do.Ultimately, we stopped the project.

Was that a failure ? In a way, it was.I personally was on that project.It was pretty high level.When we were having the dialog with the client about their direction, there were several specific things that depended upon future growth, dealing with regulatory requirements and legislation that changed.

A lot of our services clients get one or two big clients that drive a ton of growth.That might not be the right reason to get into a bigger ERP, because what if that changes ? It is a big lesson: hitching your wagon to a technology provider when making these changes means making the best decision you can at any given time, but things will change.To be more realistic, we should have done the cheaper option and upgraded later. That's the bottom line, which is exactly what we did in that prior firm that I told you about as an example, where we could have stretched and gone for the bigger app, but instead went with best of breed in the short term to get a lot of business improvement and benefit versus stretching for the big one. If your business is driven by something that could literally change overnight, it is better to take the incremental approach, which is basically what happened with these guys, as well as the accounting team revolting against it.

Brent Trimble: That's a great practical story. We appreciate you being transparent there. It seems like the lesson really is not to overshoot and follow those gradiated steps. To some, that might sound painful to go through another reinvention in 7 to 10 years. Going back to your original proposition about services firms being very cash and talent intensive could be the right move in that case. I'm sure some of our listeners have found themselves in that exact scenario.

Shawn, this has been great.Thank you so much for giving us some of these practical insights.It's always great to hear about the projects that go well, but it's really helpful to hear projects that might not go so well and cautionary tales for our listeners out there.In your firm, as founder and principal of ERP Advisors Group, I understand you also have a podcast that folks can listen to around these topics and go pretty deep.For the listeners, please share where they can find you.

Shawn Windle: On all the podcast platforms, look for The ERP Advisor. Just like you said, Brent, we're focused on practical tips and tricks that we're learning from the field. We're covering trends and predictions for 2026 right now, as well as getting into coverage on AI. I am also hoping to have a podcast with you all on our platform to learn more about what is happening with Kantata around AI and some of these PSA solutions too. Please join us over there as well.

Brent Trimble: That would be great. Thank you so much for joining us today.

Shawn Windle: You're welcome. Thank you for having me.

Brent Trimble: As always, thank you for listening. We are going to wrap here with Shawn Windle, founder and managing principal of ERP Advisors Group. If you have any follow-up questions for myself or for Shawn around this topic of mature ERP enterprise or PSA selection, we would love to hear them. Send us an email at podcast@kantata.com. We would be happy to get back to you.

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