Most boutique founders believe AI leverage starts with a technical hire or an outside vendor. It doesn’t. The people best positioned to build AI that does the work are the ones who already understand the work, the founders and operators who know exactly what needs to get done.
In this session, Chris Prinos, Founder and CEO of Indigo Trigger, shows how his non-technical team built their own AI tools to create leverage and scale, including an AI “”chief of staff”” that runs project management across a half-dozen active engagements. The throughline isn’t any single tool. It’s a repeatable method any operator can use: define the role precisely, connect the tools you already have, and turn every correction into a permanent rule.
What you’ll get from this session:
- A repeatable method for building your own AI tools
- Why clear instructions beat technical skill
- What to hand off to AI and what to keep
Why it matters:
- The real bottleneck is role clarity, not coding
- Your existing tools can do more than you think
- Build leverage and scale without adding headcount
Greg Alexander: Hey everybody, welcome to the Pro Serv Podcast, brought to you by Collective 54. I’m your host, Greg Alexander. If you’re new to this show, this show is dedicated to founders of the boutique professional services firms, so what does that mean? If you are in the expertise business for a living, you market, sell, and deliver expertise, this is for you. On this show, we aim to do three things. We want to help you make more money, make scaling easier, and make an exit achievable.
But on today’s episode, I’m gonna try to blow up a myth. And that myth is, is that to build AI solutions for yourself or for your clients, you need to be a really technical founder, or you need to spend a lot of money building a technical team or hiring a technical vendor. And that simply just isn’t the case anymore.
And we have a member, Chris Prinos, who is in the process of doing this as we speak. His story is very interesting, because it’s not complete yet. He’s in the process of building this, and he’s had some quick wins and learned a few things, and he’s willing to share that with us. And Chris is the CEO and founder of Indigo Trigger. And, Chris, welcome to the show. For those that haven’t met you just yet in the community, would you please give us a formal introduction?
Chris Prinos: Sure, thanks for having me, Greg. Chris Prinos, founder and CEO of Indigo Trigger. We are a services and consulting firm, that serves the media and publishing industry, with a focus on revenue operations, technology, and process, so everything in the lead-to-cash space. Supporting media and publishing companies. Very niche. We work with platforms like HubSpot, Salesforce, a lot of tools that are vertical-specific, but helping these companies with technology and getting the most out of their tech stacks.
Greg Alexander: Okay, very good. And Chris, as I understand it, you are not a data scientist, machine learning engineer, you’re not an AI guru, is that correct?
Chris Prinos: That’s correct. And my journey or sort of entry into AI probably started about 8 months ago, when I sort of got into the gateway drug of Lovable. Which I think is a great way to think about those platforms, and I quickly learned about the art of the possible, you know, with some of these tools, and it’s been an amazing 8 months, really.
Greg Alexander: Yeah, 8 months in this world seems like a long time, and things are evolving so much. I think Lovable was my gateway drug, too. That’s a good way to say it. It was my marijuana. Hopefully, I’m not going to graduate to the hard stuff, but right. All right, let’s jump into it.
One thing that I liked about your approach, and we’re doing something similar, so maybe I’m biased, is that it’s your understanding of the role itself. Clarity around a function, job function. And then you’re building the technical solution around that role clarity. And that’s unique, because sometimes I see people start with the tech, and then come to the role, which I think is a mistake. You’re doing the inverse of that, so just start with that for me, please.
Chris Prinos: Yeah, so, you know, not unlike probably most of your members, you know, when you do big tech services engagements, you’re in the middle of a lot of different kind of standard processes. Statement of work development, requirements gathering, managing projects and project boards. Readouts to customers — and historically, and still, these all take a lot of time, they involve a lot of tools, and it’s just not something that’s very scalable.
So what I challenged my team to do after the reunion last year was, first of all, get immersed in AI platforms. We got everybody Claude access, and access to tools like Lovable and Chat and all that, and I just asked them all to make it part of their day, and basically, the art of the possible — have these tools help you with whatever you need help with, and see how far you get. And that’s kind of where we are right now. We’ve got a few folks internally that have done an amazing job developing stuff I would have never imagined we’d have, like, 6 months ago. And some of these tools, not only are they helping our internal team, they’re also starting to be deployed to our clients, and we’re starting to think about how to take them beyond just our clients and to others, and make them generally available.
Greg Alexander: You know, and I understand that one of the early solutions that you built, and that it’s in its early deployment right now, is what you’re referring to as the AI Chief of Staff, which is running project management across a number of your projects simultaneously, and I find sometimes when we talk about these things, a real example can be illustrative in a lot of different ways, so tell us a little bit about what that is.
Chris Prinos: So, one of the tools that’s been developed internally is called Sable. It was built by one of my senior project managers, and what it does is basically puts a layer on top of some of our core tools. So, we use, obviously, email is one of them, email’s connected, Slack. We use Asana for project management, Toggle for time tracking and workforce or resource management, and then Fathom. So, the Fathom Notetaker we have, which joins pretty much every meeting our team members are in, whether it’s customer support or project planning.
So it really brings those tools together in a way where it can then use agents to do daily updates, statement of work building for me based on these Fathoms that are automated, pulse check on projects, scope creep. There’s about a dozen or so agents that are running, and you can just ask it, it gives you a morning brief. That’s really what it’s doing. So if you do those kinds of things — document management readouts, managing a project board, trying to keep customers on task, and automating assignments — that’s really what it was designed to do.
Greg Alexander: Yeah, interesting. And you mentioned that you had internal team members build this for you, versus hiring an external third party to build it for you. I’m sure you considered both. Why did you decide to go internal for this?
Chris Prinos: Well, that’s what I had available, so first of all, I wanted my team to figure out, because I had had a lot of luck with my gateway drug in Lovable, and I assumed my team members, because I thought it was very easy — I don’t have a development background. But I can clearly articulate a problem and what I’m looking to solve. I think anyone that can do that can leverage these tools and get pretty far.
Greg Alexander: Yeah. And if you found the tools at this stage — and maybe use this Chief of Staff example — is it a productivity-increasing tool, meaning it’s making existing employees that much more productive? Is it a tool that’s bringing a whole new capability that you didn’t have previously? And then there’s the associated benefit. Is it a system, so to speak, where it’s doing work that might prevent you from having to hire a new employee, so thus increasing the profitability? Tell me a little bit about the benefit of the tool.
Chris Prinos: Yeah, absolutely. So, immediate productivity gains — I mean, developing statements of work, drafting, that stuff takes a lot of time. And these tools are excellent at that, especially when you have a note-taker running that has transcripts and decisions, and knows who’s talking and when these decisions were made. I think you’ve said on previous calls, these tools do better than any person almost. They make sure you don’t forget stuff.
As far as productivity — that’s a big one. I’m looking to roll this out right now. It’s piloted within 3 users in my company. The challenge right now is how do I get it out to all the users? There’s some setup that has to be done and a little bit of training, so that’s kind of where we are now. But my goal is to allow each project manager, who typically manages two to three projects, to go up 4X.
Greg Alexander: 4X, wow. That would be quite a productivity enhancer. So, could I imply from that that you no longer have to hire 4X project managers?
Chris Prinos: That’s right.
Greg Alexander: Yeah, so, I mean, the cost savings of that is enormous. And those project managers that are going to increase their output 4X — I mean, they’re going to be that much more valuable to you. They’ll have better jobs. You know, if the firm is that much more profitable, there’ll be enough money to go around for everybody. I mean, the business impact on that is enormous.
Chris Prinos: I can also give people who aren’t project managers a project manager, and I don’t need to have a dedicated project manager for them, you know what I mean? So we have a lot of those kinds of engagements where I have really sharp solution architects and subject matter experts, but having a ride-along PM for them is expensive, so now I can give them that PM ride-along agent, and everything’s sort of tracked for them. That’s been a huge, huge help.
Greg Alexander: You know, I’ve started talking to members about the three things that you get when you go down this path. So the first is the methodology itself. So in this use case, it’s the method to manage a project, which I’m sure you guys have a very well-thought-out method there. The second is the technology — the AI does two things. It enforces the method, you know, sometimes people don’t follow the rules. And then it scales the method, because it can be done on every single project now, every single task, so to speak. And then the third one, which is what you just mentioned, is capacity. I now can give you a project manager where previously I couldn’t, and that extra capacity is doing the work, which is bringing a lot of value.
You know, if we take the task of writing an SOW — and I’m a recovering management consultant myself, and I know what a pain in the ass that can be, and how many back and forths that can involve, especially depending on the cooperation from the client — when you’re writing an SOW, how do you determine what the AI does versus what the human does?
Chris Prinos: So it’s a good question. We’ve been using sort of the About Me files. There’s a way to set these tools up to sort of define your guardrails on tone, and what not to do, what to do a lot of, so you kind of have to structure things — when you’re using Claude, Cowork and some of those platforms, it’s important to set the foundation right, so it can be repeatable in how it does what it does.
My concern was losing that personal touch. I always thought, well, no one’s gonna be able to write an SOW that’s as compelling as me with the right tone, and that’s just wrong. The real challenge is me losing time writing a perfect SOW when I could have 6 or 8 of them out there in an automated way that are pretty damn close.
Greg Alexander: Yeah. Earlier, you talked about how you were connecting to your existing tools, and you rattled a bunch of them off — Asana, etc. And this is something, for some reason, I haven’t seen members take full advantage of. And to me, this is the low-hanging fruit, because once you’re connected to all these systems, the tool starts to compound its value, just because of the source data. When did you start doing that? Was it easy? Was it hard? Any advice for listeners on that front?
Chris Prinos: Depending on what platform you’re using, these platforms now, most of them are quite open. Anything with an API key or anything like that — HubSpot, Asana, Fathom — I mean, you can connect them to a Lovable environment or Claude Code in under 5 minutes if you have the credentials.
I think when you’re structuring something like this, planning for the connectors is important. What tools do I want to bring together? Once you get the connections and the plumbing done, then you can kind of unlock all kinds of capability. I can have leads coming into HubSpot that are creating Asana projects that are talking back to HubSpot, and pulling email and looking at Fathom Notes, so the connective tissue — those connectors and the plumbing — are really important. I would not be afraid, if you’re a non-technical user, to just get in and start connecting some of your key business systems. I would caution, again, there are some guardrails around how to get stuff connected to your email, and how to do that.
Because you want to be careful about what you’re putting out there, but that is one thing I think we need to do more of — security, structure, governance, and sort of the charter for how we’re gonna operate with these tools. And again, that’s something we hadn’t necessarily planned on, but now that we have all these agents running and different team members using different tools, that’s a new problem I’ve got to deal with.
Greg Alexander: Yep. Have you gotten to the point where you’ve had clients say to you, hey Chris, I want a discount, because I know you’re using AI, and therefore your labor cost isn’t as high?
Chris Prinos: No, not yet. My clients, I think probably like everyone else’s, they want a job well done, on time, on budget. And I think the last thing they’re thinking about is how I’m getting it done. The problem is when it’s late, or when it doesn’t work, so I haven’t hit that roadblock yet.
Greg Alexander: Yeah, which is good. I hope you don’t. Sometimes I hear members say that they’re getting that from their clients, and I’m like, are their clients crazy? They’re getting a higher quality product faster. Like, isn’t that the dream?
All right, well listen, this was a good conversation. I appreciate you sharing with us your journey, where you are in the journey. Congrats on the progress that you’ve made so far. What’s next? Where do you think you’re taking this?
Chris Prinos: So, we’ve started to get our customers involved in a bunch of the platforms that we’ve been building. There are three phases that I see. Getting the internal team agents and tools and foundation set. Packaging those up into a solution that I can bring to our customers in a well-packaged way. And then, how do I then figure out or monetize that so that anybody could use what we’re doing? We have this idea for this outcome agent that we’re building, and we’ve already got customers in some of our tools, so the next step is really hardening some of that stuff, and then figuring out how we can take it to market.
Greg Alexander: Yeah. That last step is really exciting for you, because if you get into outcomes, you’re now divorcing revenue from expense, meaning you’re delivering value to the client without labor. The scalability of that, and the margin of that is really high, so keep me posted on how that’s going.
Chris Prinos: Sounds good, thanks for having me.
Greg Alexander: All right, thanks again, Chris. Just a couple calls to action for listeners. So, if you’re a member, and you want to hear more of Chris’s story, attend the member private Q&A session, which we’ll have on an upcoming Friday, and you’ll get to ask your questions directly.
If you’re not a member, and you think you might like to learn more, I’m going to direct you to my new Substack channel. You can find that at Greg Alexander, C54 — C as in Charlie, the number 54. And on Substack, I talk about what’s happening in the large professional services space as it relates to professional services, and I translate that to what boutique owners may learn from that.
But, thanks again, Chris, and thanks for everybody listening. I wish you the best of luck as you try to grow, scale, and someday exit your firm.