David Ackert has spent more than a decade refining an executive roundtable model that quietly transformed how his firm grows. What began as a way to deepen relationships with a small group of peers became a repeatable system that generates recurring revenue while feeding a high-quality services pipeline. In this episode, Greg breaks down David’s model and why it works for boutique professional services firms that want leverage without volume-based selling.
What you’ll get from this session:
• How David Ackert designed executive roundtables as infrastructure, not events
• The signals that tell you whether your firm is ready to apply this model
• The structural choices that turn community into a long-term growth asset
Why it matters:
• One-to-one relationship building does not scale on its own
• Most community efforts fail because the model is misunderstood
• David Ackert’s approach shows how trust, revenue, and growth can compound together
TRANSCRIPT
Greg Alexander: Hey everybody, this is Greg Alexander. You’re listening to the Pro Serv Podcast, brought to you by Collective 54. If you’re new to this show, this show is dedicated to founders of boutique professional services firms who are trying to grow, scale, and someday exit their firm. So if you’re in the expertise business, this is for you. On today’s episode, we’re going to talk about an interesting approach. To generating recurring revenue, And generating a marketing channel simultaneously. In the professional services space, and for today’s call, we’re going to call it the Executive Roundtable. Some people call it other things, like communities, or memberships, or mastermind communities. Our guest today, David Ackert. Refers to it as executive roundtables, as I understand it. And he’s been doing this for quite a while, and he’s got a lot to share with us. And I think members of our community might want to consider this. So when I was talking to David, I asked him if he would be kind enough to come on the call and walk us through his journey with it. And of course, he said yes, he’s always contributing to our community. So, David, there might be a few people who have yet to meet you. Would you, please give yourself a formal introduction, and then we’ll dive into it?
David Ackert: Sure, I’m David Ackert, I’m the CEO of Pipeline Plus, and the author of The Short List. Our firm specializes in growth optimization for professional services, particularly law firms.
Greg Alexander: Yep. Alright, well, let’s start at the beginning. So, give us a definition of an executive roundtable, so everybody knows what it is, and then tell me a little bit about, like, how you got involved with them in the first place.
David Ackert: Sure. So we call this our Roundtables Initiative, and It, is essentially a gathering of… like-minded, similarly positioned people in our industry who are either existing clients or prospective clients, and they… we facilitate gatherings on a fairly routine basis. You know, Greg, one of the things you might even liken it to is Collective 54. We have an annual in-person get-together like the reunion. We have virtual events throughout the year, like you do. And the members participate because they want access to each other, they’re interested in peer learning, but they’re also interested in the thought leadership that we bring to these forums.
Greg Alexander: Yep. Give us an idea of the size. Do you have one? Do you have multiple? And how big are they, and how do you curate the group in particular?
David Ackert: Sure. Well, maybe I can answer this question by touching on the other one that you, that you… that you referred to, which is, how did this all begin? So, everything at Pipeline Plus starts with the shortlist method. So, for folks who aren’t familiar with the shortlist, it’s a book that I wrote, it came out last year, and it is a business development methodology. And a few of the things that we learned in our research while putting that book together was that for any individual who is in a rainmaking or business developer role. Those who outperform the rest of the herd tend to have between 9 and 35 targets, so they get very focused and purposeful on who they’re going to prioritize, and they need to have 14 interactions, on average, between first contact and first contract. So there’s this whole trust-building exercise where you’re having helpful interactions, helpful, meaningful interactions, before someone is going to do business with you. And the other thing that we learned was that you need to have at least one in-person interaction every year. This can’t all be virtual. It simply doesn’t work well that way. Now, this is very effective for those of us who are whale hunting, but the challenge here is scale. So once the company had grown to the point where I wasn’t the only person making rain, and I had a team of people, and we had sort of a portfolio of clients now that extended beyond these numbers that I shared with you, we needed to build something that would enable us to, have these interactions across different communities. So we started off with one roundtable of about 15 members. We’ve since grown that one to about 25 members, and for me, I capped these out at 30. We now have 7 roundtables, and they are situated around market segment, so we have A couple of roundtables that focus on smaller law firms, we have a couple that focus on what you might call the middle market, and then we have roundtables that focus on the top 100. And we also focus them on roles. So, we’ve got a CMO roundtable, a COO roundtable, a managing partner roundtable, because these people want to feel like they’re, you know, hanging out with other people who think like they do, but also have the same kinds of problems and solutions that they have. So, you don’t want it to feel too much like a grab bag across roles and across market segment.
Greg Alexander: Yep, okay, very good. Now, what I have seen, and I’d like to get your perspective on this, is there tends to be 3 flavors of these things. There’s one where everybody pays due, so it’s a revenue-generating, group. For example, that’s what Collective 54 is.
David Ackert: Yeah.
Greg Alexander: There’s another one where it’s free, and people show up because it’s more of a, a marketing channel. You know, people show up, you get to know them, and then you have something else to offer them. And then there’s a third where it’s a combination of the two. So, which do you deploy, and do you have a preference, or is it a it-depends type situation?
David Ackert: No, I think, you know, the more opportunistic one can be while always putting the member experience first, the better. So we do charge a membership fee for these roundtables. And, frankly, that does two things. One, it ensures that those who pay the membership fee are likely to take the whole experience a lot more seriously. They’re going to show up to our events, and they’re going to also expect it to be of a certain caliber, which we want. That’s on-brand for us. But, so I’ll give you some numbers. About a quarter of our gross revenue is comprised of these membership fees, so it is a significant part of our ARR, our business model. But over 50% of our pipeline is represented by Roundtable members. So, not only do we have revenue coming in from their membership dues, but about half of these Roundtable members are either already engaging us in services, or they’re in discussion with us on engaging for additional services.
Greg Alexander: Yeah, okay. We’ve had some members try this, and it not go so well. You and I have spoken about this, because I think… I’m not sure everybody understands how to do it, right? and how much work it actually is. So, in our conversation that we had, you… Emphasize for me how important it is to have a great facilitator. So why don’t we start with that, and then let’s expand beyond that to say, like, what it truly means to deliver a great member experience.
David Ackert: Sure. Well, this is a little awkward to talk about, because I think I’m a great facilitator, and I think that has been part of the key to our success. But I will say that we’ve coached clients on this strategy who are not particularly good facilitators, and many of them have been successful as well. So what I would say here is. Recognize the extent to which facilitation is truly a superpower of yours, and if it isn’t one, either consider having someone else on your team facilitate these, or if you really want to be at the hub, which, you know, would make sense, then you’ll want to shift your strategy on how you Get content into the room. So, Greg, for instance, you’re an excellent facilitator, but, you know, if this was just the Greg Alexander show, we’d all get kind of bored, right? It’s like, you’re bringing in members all the time. This podcast is an example. You’re bringing in all of the good minds in Collective 54 to contribute to this body of insights. Now, what we’re doing that’s a little bit different from that is Sure, occasionally the members will share a case study on what they’re doing at their firm, and the other firms find that useful, but… They are more interested in Thought leadership from outside speakers, who are industry experts. Which then prompts discussion among the members. So what it does, it sort of sets the stage for them to exchange ideas with one another, right? So whenever we bring in an external speaker, we say, look, you have about 30 minutes, okay, maybe 40, and then you need to stop talking. Let the members then react to what you’ve brought forward, and for the next 40 minutes, they’re gonna exchange ideas. They’re gonna say, well, does that work at your firm? And, oh, that did work? How did that work? Oh, you amended it? Really, how did you tweak it? Right? That’s where the real juice is, because theory, at the end of the day, only gets you so far.
Greg Alexander: Yeah. I’m in a group called YPO, you’re probably familiar group. And my chapter in particular, I mean, it’s almost all external speakers. And it’s facilitated in that same way, so you make a really good point. So, let’s say you’re somebody listening to this, and you might want to do this, but maybe you’re not a great facilitator. Bringing in experts that not only are experts in their domain, but also experts in how they communicate their domain, meaning they’re a great facilitator, is a really good idea. I would encourage many of our members to consider that, and I’m saying that just because most of our members, not all of them, but most of them, are domain experts first, and facilitators second, and I think they would be… it would be beneficial to them to have a professional facilitator present. Let’s talk about the other items. For example, so you’ve scaled this quite a bit. I mean, that’s a lot of groups that you have, and that’s a decent size of number of members per group. How did you acquire the members?
David Ackert: Well… And I want to touch on one thing you just said before I jump into this. You talked about domain expertise. Now, when I started these roundtables, my domain expertise was pretty exclusively business development for professional services. As I’ve run these over the last 12 years, I’ve developed other areas of domain expertise, which helps keep this from being a business development roundtable, which, frankly, I don’t think my members would be all that interested in. So, the theme has to be broad enough that it starts to touch on things like strategy, and it starts to touch on things like talent acquisition, and it starts to touch on things like… just like without YPO, right? That covers a broad range of things. But if your facilitator was only good at marketing, let’s say, you would get pretty bored with that, right? So again, you want to make sure that you are not being overly ego-driven in the way that you are driving this agenda. Whenever we go… whenever we start crafting our content for every year will typically go to the members first and say, what do you want to hear about? And oftentimes, they’re not putting business development on the list. They’re putting things that, you know, I would be better bringing in an external speaker on and maybe providing a little bit of context or color. So, you have to think of this less as a lead gen engine. And more as something that is enriching the professional lives of its members. If you do that, within a year or two, business will come, right? This is how good business development works. You give, you give, you give, and then you get. But you’ve got to be willing to play the long game. So, now let me talk a little bit about recruiting members, the last question you asked me. Initially, and if any of you have a copy of the shortlist, in chapter 17, I really kind of flesh this out and provide a sequencing and kind of an example of the messaging that you might use, but at a high level, you’ll want to start with your own shortlist. So, who are your own clients, right? Who are your own influencers, market influencers, who you would consider to be connectors that you’re already focused on? Pull them together into a group where there’s a common theme, and you’ll have your first roundtable, more than likely. And even if that only comprises, let’s say, 6 people. Well, then you ask each of them to invite someone from their network, and now they’re recruiting on your behalf. Now it’s 12. And by the way, half of that room is prospects, so congratulations, you just used this mechanism to get to make some new connections. And then, over time, you’ll find that as you’re bringing in speakers, these are referral sources and other experts in your network. Collective 54 would probably be a great pool of people to bring in, assuming that they’re interested in talking to your roundtable. But this is a great way to help people who have referred you work, or relationships that you’re just looking to develop along those lines. Once you get to 4 roundtables, and again, I’m only speaking from personal experience, others may have different capacity, but I found that it was very difficult for me to facilitate and run four-plus roundtables. So at that point, we have a full-time employee who’s a director level, she’s very sophisticated, very competent, really knows what she’s doing, and frankly, she’s elevated this whole initiative way beyond anything that I had done. But that’s when this really started to scale, was when it stopped being the David Ackert Show and started being something that was being built to scale.
Greg Alexander: Yep. Okay, so that makes a lot of sense in terms of recruiting the first group of members, and then having them help you recruit beyond that. And I can see how that would scale very quickly. That’s what happened with us as well. That then comes to the second challenge, which I think sometimes people underestimate, and that is retention. When you have a community, groups, and people don’t show up, or they quit, you know, it’s a bad experience for the other members that are there. You know, they start saying, well, you know, all these people are turning over, why am I still here? Blah blah blah. So, having a really well-thought-out retention strategy is important. Did you… do you agree with that, and what is your retention strategy?
David Ackert: Sure. I do agree with it. I think that the larger you get, the harder this is. Yes. So, we still, you know, we have 7 roundtables, over 100 members across all the roundtables. It’s still a fairly manageable group. If it were twice or three times that. I think what we would find is that while, yes, that core group of superfans grows, the next ring out and the ring out after that also grows. So the people who are, you know, kind of borderline committed becomes very large, and those are the people that you’re throwing a lot of energy at to get them to stay engaged. And then those people in the middle who are, you know, almost superfans, but sometimes they go dark for months on end, and you… again, you have to keep pulling them in, right? So again, this is why it’s not really scalable to be my job. You’ve got to have a team that is doing this sort of thing. Now, in terms of the retention strategy itself. I will say that we’re doing something that, you know, you’re also doing in Collective 54, which makes a lot of sense. We have virtual programming on a fairly regular basis. It’s not quite as aggressive as the C54 cadence, but ours is once every 6 weeks, there’s a webinar, and we’re usually bringing in the client perspective, so these are all professionals… these are buyers of professional services who are talking about what has them buy or not buy, what has them put out an RFP versus just give the work to the preferred firm. What has them price and push back on pricing? And, you know, these are the kinds of things that our members are very interested in hearing about, so they do tend to show up to these virtual events. But for the in-person annual retreat, we don’t get 100% attendance, and that’s when we have to do things like send them their member gift, or send them a summary of what they missed, or like Collective 54 does, we have a library now that we’re building of recorded content that they lose access to if they stop being members. And so, you know, some of it is providing value, and obviously just doing your utmost to be a genuine contributor to their learning curve. Some of it is also leveraging a little bit of FOMO, because they lose access to the community, and they lose access to this library of content. And we all know how human nature is. I mean, Greg, I haven’t logged in to the Collective 54 website all that often, although I keep telling myself, oh, I can miss that session, because I’ll always go back and watch the recording, right? And it’s one of the things that keeps me engaged as a member. I can’t imagine a day when I wouldn’t be able to tell myself, well, I could log in and watch the 5,000 hours of content that I’ve been meaning to get around to, right? But all of this is part of making sure that… it’s like… you know, people talk about gym memberships, like, do gym memberships have value if you never go to the gym? And I say yes, because the difference between being able to tell yourself that at least I have a gym membership, at least I’m that committed, all I have to do now is get into the habit of going to the gym. And not even having a gym membership? Boy, that is someone who is really lazy.
Greg Alexander: That’s a good way to think about it, for sure. And you know, I actually have a friend of mine in the gym business, and when I was starting Collective 54, he started walking me through the economics. Now, it didn’t translate to me, but the gym economics are, sign up 10,000 members and 1,000 are going to use the gym. Right. So the capacity plan there is rather interesting, but that’s physical equipment and all that, but it is an interesting thing to think about. Yeah. I also noticed, if I understand correctly, you have membership tiers. Is that correct?
David Ackert: You know, I was playing with that idea, last year, and we… what we ended up doing was coming up with a tier where if you want to put your CMO in one roundtable, and the managing partner in another roundtable, and the COO in another roundtable, and you basically have a firm-wide membership, there is a discount applied. So that’s about as far as we got with that, because we played with a couple of different members. I think what you’re doing with the Era 1, Era 2, Era 3 is very smart, but it doesn’t really translate across the board when the… when you don’t have a tip of a spear like AI, like, it’s sort of a no-brainer. You can’t avoid this. Sooner or later, you’re gonna have to get on this train, right? And we haven’t been able to figure out exactly what that would be for our member base.
Greg Alexander: So, some learnings for the audience on this. So, when I launched Collective 54 in January of 2020, we launched with tiers. We had a grow tier, scale tier, exit tier. It absolutely bombed. We faceplanted. The reason why it bombed is because it made recruiting members very hard. They were like, well, I don’t know, in my grow scale exit, you know, what’s in the growth tier? What’s in the scale tier? It created all this confusion. Which made it difficult for people to opt in. So then we did away with it. For the reasons that you just said, like, there wasn’t really some burning platform, some pressing issue, and we just went to one size fits all, and that worked great. And then recently, last year, we introduced tiers again, and we were very nervous about it. Now, this is called Era 1, Era 2, Era 3, as you mentioned, and it has to do with the way and the aggressiveness you’re going to apply AI to your business. And it’s very clear what’s in one tier and what’s the other tier, so that’s going very, very well. So my… the lesson I would share with the audience is you don’t have to do tiers, only go to tiers when it’s necessary. It’s better to not have tiers, but when you get to the point where your community business has matured and you want to increase the value you bring to members, and therefore increase the price they pay proportionally to that value received, tiering is a good idea. Because that then allows you to keep the membership small, but also still grow the revenue stream. For example, I mentioned YPO. YPO has 50,000 members. Think of the retention obstacle that that presents. I mean, I would never want to try to do that. I mean, it’s just… to me, that wouldn’t be an enjoyable business to run. I mean, it’s a personal choice, but still. A 90% retention rate on 50,000 people, I mean, you’re gonna lose 5,000 members a year. I mean, gosh, that would be so hard. So if you’re not gonna scale to thousands and thousands of members, then you have to figure out a way to add more value to a smaller number of members, so that the dues can increase proportional to that value. So, that was a learning that we had, dumb tax that we paid early on that I wanted everybody to avoid paying.
David Ackert: I have one thought here, that… this is something that we’re planning to roll out. This, I think, will work, because it is something that members have asked for. So again, we didn’t sort of impose this tier system. We asked them, well, you know, what is something you’d be interested in? And it’s kind of an emerging leader tier. So right now, you know, it’s COOs and CMOs and managing partners, you know, people who are at the pinnacle of their either division or at the firm who are participating. But all of them are grooming a successor, or all of them have a second in command. And while, currently, if they can’t attend, they can send a proxy, that’s not the same as having a dedicated group for that number two. That’s, I think, the next stage of evolution for us in terms of tiering. So it’s like, oh, you know, if you sign up for a particular tier, we’ll include a group for your, you know, number two. Or, would you like to also put your number two in this director-level roundtable for an additional fee, right? So you can start to play with ideas like that.
Greg Alexander: Yep. I think that’s a great idea, and I want to make a point around it. I used to be in Vistage many, many years ago, another one of these groups, great group. And they had a program like that, but they mixed me, the owner, and with number twos, and I would go to the meetings, and I didn’t feel like I was in a room full of my peers. So it’s very important that those are distinct cohorts, because, you know, if you’re building a peer group, executive roundtable, whatever you want to call it, it’s gotta be peers, or you show up, and you look around the room, and you’re like, I’m in the wrong room. Yeah. So just be, just be careful with that. All right, well, just one more question for you, and then we’ll save the rest for the member Q&A session. So, if you were somebody in our community who does not have this today, but likes the idea of it, for all the reasons that we stated, and they wanted to get going on it, you know, is the advice just go to, you know, 5 or 10, you know, fantastic clients who will opt in because you ask them to, and then build from there? Or is there other ways to get started, in your opinion?
David Ackert: Yeah, I would start small. I mean, I’m a big fan of baby steps before you, you know, try to run a marathon. So, I would say get 6 to 8 people together for a one-off, and just say, hey, there’s this hot topic in our industry, and I’ve got some opinions on it. I have a friend who’s a really good speaker on this topic. I’m just reaching out to an exclusive group of people in our client base, in our inner circle, to get everybody together to talk about this. We’re just going to have a 90-minute virtual think tank, if you will, around this topic. And what you’ll find is that, A, that’s a lot easier to stand up quickly, B, you’ll start to get a flavor for the appetite for these folks to, you know, exchange ideas, but then C, afterwards you can reach out to everyone and say, boy, that went really well, and I got great feedback, and now we’re thinking of serializing this. Can you think of others who you’d want to… and they’re going to be excited about it, too, because you’re still in this honeymoon phase, right? And so, all you’re committing to is that one webinar, conference call, whatever you want to call it, but that’s kind of how you pilot something like this.
Greg Alexander: Yep. Great advice. Okay, so members that are listening to this, a few calls to action for you. So first, I would pick up David’s book called The Shortlist. I have read it myself, I wrote a review for it, I think it’s fantastic. Secondly, after reading that book, if you want to get better at business development, there’s many things in that book you can implement. This is yet another idea that David might be able to help you with. I would encourage you to get in contact with David. Also, if you’re a member, we’re gonna double-click on this. These podcasts are meant to just be an introduction to the concept. If you’re interested in this topic even more so, David is going to host a private member Q&A with us later on. You’ll be able to ask direct questions of him. Look for the meeting invitation. And if you’re not a member, after listening to this, you think you might want to be, because you can learn things from people like David, go to Collective54.com, fill out an app, and we’ll get in contact with you. But David, you are a great member, you’re always contributing to our collective body of knowledge, so on behalf of the membership, thanks for contributing today. I appreciate it very much.
David Ackert: Thank you, Greg, for the impact that you’ve had on our business and in my life.
Greg Alexander: Great, awesome. Okay, so, thank you all for listening and for walking me into your busy schedule. I treat that as a privilege. Until next time, I wish you the best of luck as you try to grow, scale, and someday exit your firm.