• Why buying AI tools produces micro-assistance scattered across an unchanged process, and how to recognize it in your own firm before mistaking it for transformation
• What leaders miss when they review finished output instead of watching how the work actually gets done — and why that gap is where real inefficiency hides
• How OTM built the case for a dedicated non-billable seat focused entirely on process redesign, and the margin math that justified it after the fact
• Why erasing the whiteboard — starting from how the work should run, not how it runs today — is the only way to move from tool adoption to genuine change
• Every firm now has access to the same toolbox; the competitive advantage lives in process redesign, not in what was purchased
• This is the rare transformation a founder cannot hand off — middle management will optimize around the existing process, not redesign it

Jeff Klaumann: Hey everybody, welcome to the Pro Serv Podcast, brought to you by Collective 54. I’m Jeff Klaumann, I’m the president of Collective 54, and I’m your host. If you’re new to the show, here’s what we’re all about — helping you do three things: make more money, make scaling easier, and make an exit achievable. Everything we record here is built exclusively for boutique professional services firms. So if you’re in the expertise business, if you market, sell, and deliver expertise, this show is for you.

Almost every firm in our community has bought AI tools by now. We often assume that buying the tool is what creates adoption. It doesn’t. Most teams politely ignore what the firm bought. Today we have a firm that did something about it — they funded a full-time role whose job is to fix that. And the person in that role doesn’t start with the tools. She watches people work, one at a time, and builds from what she sees. What she is really doing is changing behavior, and that’s the show today.

To help us get through it, I have two guests from OTM. Miles Kailburn, the CEO and co-founder of OTM — he’s a long-time Collective 54 member and has been on the show before. Jordan Jackson took on the role we’re going to be talking about today and built it herself, including the method we’re going to walk through. She is the Director of RevOps and Service Design. I’ve known them for a while, and their approach to solving this challenge is what makes them great role models today. Miles and Jordan, welcome to the show, great to have you on. I gave everyone the headline, so in a minute or so, why don’t you tell them about OTM and the problem you solve for your clients?

Miles Kailburn: Thanks, Jeff, and thanks for having us on. My name is Miles, co-founder here at OTM. We’re based just north of Denver, Colorado, and we work primarily in the B2B professional services and SaaS space — typically consulting, advisory, firms that sell expertise. Not dissimilar, very aligned with C54 — that’s why we joined. From our perspective and how we work with clients, we’re a sales-led, marketing-supported consultancy, which means we start from sales outcomes and build marketing around to support them. That’s been our focus, that’s how we’ve built our team, and those are the tools that we play in.

Jeff Klaumann: Fantastic. How about you, Jordan?

Jordan Jackson: Hey! I’m happy to be here. I’m Jordan, and I bring a product development design mindset to this role. Like you said, it’s really fun — based in user behavior. I love OTM, and I’m really happy to be working with Miles. They’re cool people.

Jeff Klaumann: Fantastic. All right, Miles — most founders stop at buying the tool. You went further and funded a full-time seat to drive the real change. Walk us through that decision, what made the seat worth it, and what did you weigh its cost against?

Miles Kailburn: Jordan joined us many years ago, so her engagement here with us predates a lot of this — she joined on the accounts team. Her passion and background was also in product design, and I got to watch her really light up on those types of projects. Simultaneously, probably three, three and a half years ago, we started to look at and identify that we really need to think about how we design our services. This was pre-AI workflows, pre-agents. We started to play in this space — how do we actually be intentional about the services we design? Our clients’ experience with our services, how we deliver them. That really stemmed from our marketing work and customer journey work, and we started to take that methodology and look internally.

Being the visionary here in our company, I took it to our two other partners and said, I actually think we have a person and an opportunity to build a service design role. A couple of those people are certified in service design as well, and they looked at me like, what are you talking about? And I said, well, I’m pretty sure that if we spend time committed to how we design and deliver and build our services, good things will happen. Jeff, there was no framework, no mathematical Excel sheet computation. What it was is an opportunity — both in a person and externally in the market, and internally with our team — that really pointed to, this is an area we should invest in. And that started us down that path.

That timing also lined up really well with how we deliver work and the tools we then use to deliver that work. Jordan’s role has rapidly evolved into managing revenue operations as well as service design — and service design for us is heavily technology-based, heavily people-based, and the marriage of the two. Just like most things, there wasn’t a formula. As much as I wish I could share a mathematical formula for it, it’s a hope, a belief — a belief in a person and a vision.

Jeff Klaumann: Yeah, that’s exactly it. It’s a vision, and it’s entrepreneurship. That’s the driver — take the risk.

Jordan Jackson: There’s a book — I forget which one — but it talks about red threads, people finding what they’re really passionate about, and they’ll do really great work. I saw that we were using Notion in a way I thought was bad, and I asked if I could redesign it, and I was told no. So I did it on the weekend anyway and sent it to Miles and Val — hey, you didn’t pay me to do this, but it can be better. Seeing that red thread and leaning in was key. And the timing was very, very good, because it was before the AI wave. So I had my sea legs before technology started getting crazy.

Jeff Klaumann: Fantastic. So Jordan, Miles convinced Val and the other partners to make the decision, and somebody had to actually figure out what the job was. What did the role look like in those early days, and what has it turned into?

Jordan Jackson: Yeah, it’s funny — I didn’t actually realize this until you started with the opener, but my first meeting with Miles, I asked, what do you want me to do in my first 90 days? I was anxious being a full overhead person, and I needed to make sure I provided value. And he said, I just want you to observe. I said, but then what? And he said, for the first 90 days, I just want you to observe.

I didn’t realize, like I said, that that’s still what I’m doing. In the early days, it was just being really curious — I was in a lot of cross-departmental meetings, watching how we deliver, shadowing people and finding opportunities. Some of our early services we mapped out on a whiteboard, old-school style, from beginning to end of how we do it. In the beginning it was a really rigid approach — oh, this is a friction point, this is an opportunity point. Very structured. But it’s evolved to something much more fluid.

I still observe — that’s probably one of the key things I do. I shadow the team. Pretty easy to do on Zoom; they can just kind of work and I sit there and ask questions. If I notice that their actions are getting a little clunky, I think maybe they might be trying to pretend they use tools they don’t use, or maybe they feel a little awkward. I just lean into that curiosity and ask: alright, if this tool were broken and you didn’t have it, how would you approach this? I’m getting to the core of what they’re trying to accomplish and how they do it. Because if while I’m shadowing, the tool isn’t working for them, then it needs to be redone or we need to rethink it. So it’s really leaning a lot into observation, and in addition to big initiatives, making those quick wins so the team trusts that I’m there to make their job easier and better.

Jeff Klaumann: Wonderful. Love the observe mindset. Being watched, though, is not necessarily comfortable for some people. What happened on that first call, and how did you get somebody past that uncomfortableness?

Jordan Jackson: Yeah, so there’s a lot of trust in the team. There are people who are super honest with me — they’ll say, hey, I’m doing this in a bad way and you’re gonna be mad at me, and this is how I do it. They know and trust that by showing me the ugly middle, I’ll make it better. Then there are moments where team members might be insecure, and that’s where I try to ask those curious questions: okay, forget this tool — how would you do it if you only had a calligraphy pen? How would you approach this? I’m getting to the core of how they think and how they work. Sometimes separating it from the specific tool — how do you use this Claude skill, for example — really helps, because then it gets them back into their passion and their specialty, and they can talk about their strategic mindset instead.

Jeff Klaumann: So you also run AI roundtables, and you have people handwrite their prompts, then read them out loud to each other. Why by hand, and what happens in the room when they read them?

Jordan Jackson: The AI roundtables are a little bigger than just AI roundtables — they’re also change management touchpoints. Twice a month, the goal is to increase team adoption in tools, systems, processes, and rapidly changing technology. One of the first sessions I did was about prompt engineering, because everyone can lazy prompt. Our clients can lazy prompt, you can lazy prompt, Miles can lazy prompt — just write a social calendar. The true core of being really good in this day and age is being strong at prompting.

The way I set up those AI roundtables is: the first 10 to 20 minutes I talk about the concept and give a demo, and then the second half or more is always a really targeted exercise that relates to the team and to the role. For the delivery team, we might have 5 different roles on there, and I’ll think of an idea for each of them. When I got to the first one where I wanted them to write by hand, it was because I wanted them to really think about the STO framework — the Situation, setting the LLM context, what the situation is you’re working on; the Task at hand; and then the Objective, or the outcome. And that outcome is the one I keep going back to.

So I made them write it by hand, and then I made them trade, and they graded each other on how well they did S, T, and O. That trade also helps, because then it’s not me grading their work — it’s their peers grading their work, and everyone talks about how to get better.

Jeff Klaumann: Super helpful. Love the STO approach — big game changer when you tie it back to an objective or an outcome. So, say a founder is listening. They’ve bought every tool, they probably have a stack of them at this point, and they think the tools are being used, but absolutely nothing’s really changing. Miles, what would you tell that founder? And Jordan, what would you tell whoever is on the receiving end of that tool?

Miles Kailburn: Yeah, what we see most commonly is you buy the tool to assist, and then you end up creating a series of micro-assistance points in how you’re currently doing the work. You’ll see minor improvements in efficiency, minor improvements in quality — but you never actually unlock and break away from that fixed process. So from a tooling perspective, take it back to a blank whiteboard. We’ve got huge whiteboard walls in our office, and we use digital ones with our remote team. Take it back all the way to that level, and stop looking at the tool as the solution. Figure out how you want this to run. But you really have to let go of sacred cows. When I say blank slate, I mean literally take an alcohol wipe and erase the whiteboard.

It’s hard. My team has gotten very comfortable with the fact that to me, every whiteboard is blank. It’s probably a bit of a hurdle, but on the visionary side, you absolutely have to let go and start from that blank slate, because how you do it will have no correlation to how you’re doing it now.

Jeff Klaumann: 100%. And how about you, Jordan? What would you tell the person who’s been handed the licensing for the latest and greatest tool?

Jordan Jackson: Well, first of all, everyone has access to the same toolbox these days. So it is now standard that you should get really good at using these tools, because your clients have them, your colleagues have them, your bosses have them. The playing field is more leveled with building and with technology. So in my opinion, the best career move for anyone in any position is to get really good at using new technology, at prompting, at letting go of the sacred cows — which is very hard. We should get a cow sticker for our whiteboards or something.

To the managers trying to make it happen — you do have to have that product mindset centered on the user and how it affects their work. In the early days, before some of these skills existed, I was building clunkier n8n workflows to try to help people. There were fewer places in the system where a human could manipulate and interact, and it felt like you were just handing something to a robot and getting robot stuff back. Now I’m really intentional about where the human sits in that process and can control it, so that it actually feels good and easier to them. So really make sure you pay attention to when the human adds the value, versus just letting the system run it.

Jeff Klaumann: Jordan, let’s make this real with one person — no names. Take us through one of those shadow sessions start to finish. What did you see them do, what went on the list afterwards, and what did you build for them?

Jordan Jackson: Yeah, I’ll talk about my favorite — the most recent one, because the most recent one is always my favorite. I shadowed our ad specialist. In ads, there’s really intentional work you do for specific campaigns, but once a week you just need to spot-check ad performance. We had a standing task for her — standing procedures to go in and look at everything and see how it’s going. But when I shadowed her, I didn’t realize that when she opens her task list, every task is named the same thing. She just has this list where it’s all labeled something like “weekly ops.” So she’s having to create her own systems outside of our system to manage her work.

Now there is a program that goes in and fully customizes every single task she has with the most up-to-date rolling data. She doesn’t have to look at a task list and think, which client is most important? She can immediately scan it and know, oh, I need to address that one first. There’s quick prioritization built in. And I would have never known that if I hadn’t sat in her shoes, because when I look at all of our work in the system, I see all of them — I don’t see it from her login screen. Yeah, that one’s pretty fun.

Jeff Klaumann: That’s great. This really is the power of observation — a great proof point back to what we were saying at the very beginning. So, one final question and then we’ll wrap this up. Most members, most founders, are not going to start off and make the big bet on a full-time role dedicated to this next week. Miles, why don’t we start with you — if you were talking to a founder, what’s the one thing to do to start getting the team moved in that direction? And then Jordan, I’d love your point of view as well.

Miles Kailburn: Yeah, I think — depending a little on size, but generally in the C54 membership and ProServ space — the founders and leaders really need to be actively involved in this space. It’s not something that can be delegated. It changes how you work, what you deliver, how you deliver. The requirement is that as a founder and leader, you roll up your sleeves and start to work on this. We’ve seen this time and time again in conversations — it’s scary, it’s daunting, it’s different if you’re not a technical founder, but the tools will help train you if you just ask them to. Roll up your sleeves, and you really have to develop a base-level understanding of what’s going on to even understand how it applies to your vision. I’m a firm believer that cannot be outsourced.

Jeff Klaumann: Yeah, couldn’t agree more. You just can’t delegate it to the middle — there’s a conflict of interest, essentially, as the visionary and the person who is in the position to disrupt things. Jordan, how about you? What’s your one recommendation?

Jordan Jackson: You actually need to see what the team is doing. Focusing on outcomes is really important — at a leadership level, you might just see the final output. But understanding how they got there, what their method was, will take you farther. And I’ll also say: I have watched our margin points improve over and over again, consistently, through this work. Before we even had the power of AI, there were services we were paying to deliver — and I don’t think everyone knew we were paying to deliver them, because the team was delivering them in seven different ways. I have watched literal margin improvement consistently through this effort. So as scary as it is to fund a non-billable overhead role, the ROI is there.

Jeff Klaumann: You went there, Jordan — thank you, that’s fantastic. Miles, Jordan, on behalf of the community, thank you so much. This is fantastic. I really appreciate your contributions to the Collective. Thanks for being here today.

Jordan Jackson: Yeah, absolutely.

Miles Kailburn: Thank you, Jeff.

Jeff Klaumann: Members, Miles and Jordan will be joining us for a private member Q&A, where you can ask them your questions directly. And then two calls to action before we wrap up. First, if you’re not a member and you want to keep the conversation going, head over to Collective54.com and start a conversation with our AI agent. Second, our founder Greg Alexander has a new book coming out soon — it’s called The AI Native Boutique Firm: How Founders Build More Valuable Firms When Services Become Software. It’s available for pre-order on Amazon now, so check it out. Thanks for listening. Until next time, I wish you the best of luck as you grow, scale, and someday exit your firm.

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