Founders looking to scale beyond $5–10 million often hit a wall: their existing model works in the lower middle market but breaks down when selling to larger companies. In this episode, Justin Wasserman and Jimmy Leppert of Empactful Advisors share how boutique firms can move up-market and win business from the Fortune 500. They cover how to position services for enterprise buyers, navigate complex sales with multiple stakeholders, overcome pricing objections, and deliver at scale. For founders ready to trade volume for value, this is a blueprint for landing larger deals with more sophisticated clients.
TRANSCRIPT
Greg Alexander: Hey everybody, this is Greg Alexander. You’re listening to the Pro Serv Podcast, brought to you by Collective 54. This show is dedicated to founders of boutique professional services firms, so if you’re in the expertise business. If you market, sell, and deliver expertise for a living, this is for you. On this show, we hope to help you make more money, make scaling easier, and make an exit achievable. And on this episode, we’re gonna talk about a subject that’s near and dear to a lot of small services firms. And that is how to move upmarket. And what I mean by that is move from doing small deals with small clients to doing big deals with big clients. And many of our members don’t have any experience in the Fortune 500 space. But some of our members do, and two of those members are with us today. They have… Probably combined, maybe, I don’t know, close to 50 years experience doing big deals with big clients. And they were kind enough to come on today’s show and share their wisdom with us. So with that, let me bring in Justin and Jimmy, and have them introduce themselves to you, and then we’ll dive into the questions. Why don’t I start with, Jimmy? Why don’t you introduce yourself, and then we’ll move over to Justin.
Jimmy Leppert: Great, thanks, Greg. Excited to be here today. I’m co-founder and managing partner of Empactful Advisors. I’ve been in this space for 20-plus years. what got me into it was, early on being a medic in the military and trying out for Special Forces, injuring my back, and quickly personally experienced both the, the good and the bad of the U.S. government, the U.S. military, and the U.S. healthcare system coming together, and it’s like, how can one person navigate that and actually drive change through it? And that led me to… a number of different careers, but ended up here in professional services and strategy, and specifically. And it’s been a great ride, and excited to be here today. Thanks, Greg.
Greg Alexander: Excellent, and Justin?
Justin Wasserman: All right, thanks, Greg. Also excited to be here. Jimmy’s other co-founder on Empactful Advisors, have similarly been doing this work for, I guess, 25, 26 years. And what I’d say, what got me into this work, I’m a organizational psychologist by training. But I quickly became a corporate turnaround specialist. And although we were saving companies, in some cases, billions with a B, I just felt like something was missing from that work. There wasn’t enough humanity and humility in that work, and I thought there was a much bigger opportunity to do the hard stuff, the financial improvement, with the soft stuff of leadership and culture. Which is where Jimmy and I bumped into one another about a dozen years ago, and we started the firm three and a half years ago. So, lovely to be here.
Greg Alexander: All right, excellent. Alright, you guys are always so well prepared, and I understand that you have a top 10 list with a bonus number of 11. on this topic, so I’m gonna throw it over to you guys and have you go through your top 10 list.
Justin Wasserman: Sure, sure. It was fun, fun creating it, Greg. I’ll kick us off with number one here. As folks think about how you’re going to be moving upmarket, one of the things that might be a little bit different is you’re not just selling a solution, you’re navigating a system. And what we find is in smaller companies, decisions can be made quickly by a founder or department lead. But in Fortune 500s, you’re often selling into a matrix of stakeholders, so we find that, you know, different members of the SLT, as well as procurement and legal. You know, you might have one person who can say yes, and you might have 20 people who can say no. So really thinking about the full system, what’s in it for them, what are the risks involved, is really important, I think, in moving upstream. So that’s number one.
Jimmy Leppert: And number two, again, from the lens of, if you’re moving upstream, and so you’ve had some success with smaller, maybe medium-sized companies, it’s like, how do you begin to make that leap? And there’s some mindset shifts that come along with that. And one of those is the sales cycle is naturally longer. And as Justin was saying, as you’re navigating a system, and even if you get a yes from the economic buyer and his or her executive team, you’re good to go. It’s… you then need to be navigating a, interminable labyrinth of legal and procurement. And you really need to prepare for this, and this is why I think you’d come… You would have beaten Justin and I in terms of a competitive advantage if you have some diversity of revenue across smaller and medium-sized companies that can help carry you through this journey of it could be 4, 5, 6 months, even before you get your MSA fully executed through the legal department. In our experience. some people would probably tell you not to do this, is there are consulting firms that say, no, we’re not going to start work until we sign the full MSA. for us, that we see that as a competitive opportunity for us to go in and say, no, we will start the work even if we don’t have the MSA signed. So I don’t know, Greg may feel differently around this, but as you’re getting started with Fortune 20 companies. You gotta get your foot in the door, and sometimes that’s saying an initial yes to something, taking a calculated risk. And making the leap with that.
Greg Alexander: So the advantage of small firms is you can go fast, right? So, I can see why that is an advantage for you. All right, what’s number 3?
Justin Wasserman: Number 3, touching a little bit on what Jimmy just mentioned, procurement is a gatekeeper, not a bystander. And you’ll likely need to get through a formal procurement process that includes vendor onboarding, compliance checks, security assessments, standardized contracts. And we would just say be ready with the documentation and the ability to quickly understand their unique process. And every Fortune 500 company’s gonna have their own process, and I think showing up with a degree of flexibility is really important. Are you a firm that’s easy to work with? We’ve worked with some boutique firms in the past that would redline a Fortune 100’s 100-page MSA document, and they’re not interested in one of those red lines. That is their MSA document. Take it or leave it. And so, I think it just… Jimmy talked about mindset shifts, one of which is really being open.
Justin Wasserman: I think being comfortable with the ambiguity that comes with contracting with some of these new organizations, and demonstrate to them that you can move faster than they can.
Jimmy Leppert: So, number 4 is trust Trump’s tactics. And a key element of this is what we found is what worked for small and medium-sized businesses that we’ve been selling to, it has not worked for us when we start moving, you know, upstream to Fortune 100 companies. And a key part of this, not saying this doesn’t happen with those other companies, is these Fortune 100 executives are able to, … you know, when they hire a consulting firm, particularly in our space, the strategy space, a big part of it is, like, they’re putting their… their career on the line, that they’re like, you know, I have to be hitting, you know, exponential results on a yearly basis. And the easy thing for them to go do is very well-established large firms, like McKinsey, as an example. You know, the phrase, you can’t be fired if you hire McKinsey. And so what we found to be able to get our foot in the door with that is really doing this as it’s such a unique opportunity for you to come in and help support them in a career-defining moment. And as you do that, you’re going to get repeat business over and over again. So the degree of credibility you bring, the references, the track record. is more important than clever sales tactics as you go in there. And so one specific area of this is, how are you creating case studies that are Acknowledging very similar challenges and opportunities as your clients at the enterprise level that you’re talking with there. And through that all, it has to have measurable, measurable impact across the board.
Greg Alexander: So, number 5.
Justin Wasserman: Yeah, building on that, I wish this was true across the board, but in many cases, enterprise buyers are buying outcomes, not outputs. The reason I don’t say it’s not shared across the board is there are big, large firms, think Accenture, Deloitte, others, and we find ourselves often up against MBB, McKinsey, BCG, and Bain. But what we’re finding as a real competitive differentiator for us is our clients don’t care about how many hours you work. It’s really about the results that we can drive. It’s about shifting from time-based to value-based billing, and clearly, to Jimmy’s point, defining that ROI clearly. you know, our average return on consulting spend is a 26X. You give me a million bucks, I’ll give you 26 in return. Having that kind of quantitative analytics to support the work, and then having the references and the case studies to support that, I think is really, really important.
Jimmy Leppert: Number 6, relationships are essential. But they’re not institutional. And a key part of this is you can’t rely on one champion. Multi-threading, particularly multiple relationships across departments and functions, becomes more and more critical as you’re working in a Fortune 100 company. And we can’t underscore this enough, that if your work goes very well, oftentimes someone will be shifted, promoted to another part of the enterprise. You have to be ready, both in terms of, you know, whoever’s coming in, that you already have a well-established relationship with them, and if you don’t, that you already have relationships elsewhere, that you can be making up that revenue. So again, it’s not just this single relationship, it’s multi-threading relationships across.
Justin Wasserman: Number seven, enterprise clients want partners, not vendors. Honestly, being called a vendor is worse than the four-letter word for us. I, you know, I think we’re at a point in our careers where we only want to work with people who we’d be… who we’d consider, you know, inviting to our wedding. So, act less like a contractor, and really strive to become a true strategic advisor. Can you help them meet their KPIs? What’s in their PMP? How can you help them be personally successful? How deeply do you understand their industry? What we find is the Fortune 500 buyers are really looking for long-term relationships. And I would say in the last, maybe, 12 to 24 months, we’re actually also seeing a fair amount of vendor consolidation. Where companies are really looking to, kind of solidify their preferred partner list. And being a part… being one of those partners on that list is a really important antecedent, I think, to just getting future at-bats.
Jimmy Leppert: Number 8, internal politics can kill a great deal. So, what we found over and over again is that oftentimes, even if you’re driving measurable value, it’s… there’s these internal politics. Think Game of Thrones at the top level here, you know, with these Fortune 100 companies, it is cutthroat. And I think a mistake that a lot of professional services make as they’re moving upstream here is They assume, well, well, this executive already knows how to navigate and negotiate these politics, and you can’t make that assumption. You need to be helping them. You need to be creating the collateral. You need to be helping create the talking points. you need to be coaching them through, like, well, the CFO, what is he or she? What’s in it for them? Like, what is the key thing that you… and it may be something outside of the project you’re working on, but it’s like, hey, we gotta hit this additional metric with it. If we want the CFO to be on board. So don’t… don’t make that mistake of assuming that these folks are… are actually highly competent in navigating and negotiating the politics.
Justin Wasserman: Yeah, beautiful. I, you know, to Jimmy’s point, we’ve been in some situations where we were delivering great work and great results, and lo and behold, we later found out that we made someone or someone’s department look really bad. So, I think one of our greatest competitors is the internal strategy officer and his or her team, and there’s been instances where suddenly we arrive on the scene, we help them drive results at a speed that they thought were unprecedented, and the first thing the CEO does is look to the chief strategy officer, wondering why he and his or her team hasn’t done the same. And so, here we are, we did great work. And then, for a variety of reasons, we find out we’re on the street. So really thinking about that broader system, is really important. Number 9, you’re the guide, not the hero. Make your client the center of the story. We find in the enterprise world, the egos, the politics, and visibility, I think, really matter. Executives want their initiatives to succeed, their team to shine, their name on the wind. And so, I think we see our role as to clarify, to help clarify their vision, to reduce their risk, and to really empower their success. So. We find, you know, you are not Luke Skywalker, you’re Yoda. And that’s about bringing your plan, the tools, the support, but it’s about your clients taking credit. I think that’s how we win, kind of, the long-term loyalty game. And so, I think just in a very pragmatic sense, when you’re thinking about, you know, your case study, your pitch, your presentation, you know, framing it around their challenge, not your brilliance, framing it around their breakthrough, not your process, framing it around their victory with your help. Is a really important part… a part of, I think, how we show up and really differentiate ourselves from… from very large firms in this space.
Jimmy Leppert: So, number 10, this is gonna be a controversial one. … So this is, you know, how can you put the client in the foreground and your brand in the background? And this may seem antithetical of, like, well, this is our time to shine around… our slide decks and having our brand up there, etc. What we’ve found is, once you’re getting in with these Fortune 500 companies, what becomes a competitive advantage… so every other major… just assume every other major consulting firm is in there with you. And their brand, they’re spending tens of millions of dollars on that. What none of them are doing, but what we do. is we put the client’s brand in the foreground and our brand in the background. So all of a sudden, they actually see us as an active team member. Actually more than active, a proactive team member. And they’re like, wait a second, like, how do you already know all these different, you know, our slide deck format? you know, our language. They’re like, you know, how long have you actually been working with us? And so what that does is it immediately… we have arguments with our marketing department on this, so know that that is going to happen, and it’s about finding a good balance with this. Every client is different, but it’s being open to, like, how can you be seen, really, as a trusted strategic business advisor to these executives. Like, that’s what is most important. And if you’re putting… constantly putting their business In the foreground, they are going… you are going to stand out remarkably from every other consulting firm.
Greg Alexander: And I guess you have a number 11?
Justin Wasserman: Number 11, impeccability is the minimum standard. You’re now competing with the big dogs. So, to Jimmy’s point, just assume that every large firm is in that same client system as you are. And that means that you’re no longer just competing on insight, you’re being measured on presentation, on precision, on professionalism. Your new competitors are the global consulting powerhouses, and they’ve got brilliant decks, they’ve got polished storytelling, and they truly have military-grade attention to detail.
Justin Wasserman: So what does that mean for your decks? It means they’re clean, they’re intentional, they’re typo-free. It means that every data point should be sourced and defensible. It means every recommendation must be business case ready. Every meeting should have a purpose, an agenda, a crisp follow-through. I think just showing up with that sense of impeccab is really important, because we find you know, I used to have an old manager who… his name was Ed, and we called him Edit. He would even edit his own edits, and he could see a typo from 10,000 miles away. If you brought a brilliant deck into a meeting with Ed, he couldn’t think if there was a typo on it. And so that level of precision and intentionality around how you show up and everything you do is table stakes. The… the… the true value you bring is… has got to be the other stuff.
Greg Alexander: Guys, this was a fantastic… top 10 plus 1. I was feverishly taking notes and keeping my mouth shut, because I wanted to catch all of your wisdom. I do have one question that I’m gonna ask on behalf of our members, because I think they’re gonna be asking themselves this question. All of these things make a ton of sense once you’re in the shop. And it’s how you stay there. So they’re great, pieces of advice. I’m thinking about my own career and how these things played out, so I can endorse what Jimmy and Justin are sharing based on my own experience. But what about the founder, who’s got this great little boutique, who can do all these things, but they just can’t get in the door? How do you get your first Fortune 100 company.
Justin Wasserman: Hmm. Jamie, you want to go first, or let me jump in?
Jimmy Leppert: Sure, I’m happy to jump in. So, it’s particularly, it’s having an unreasonable sense of confidence in doing it. Like, if you’re even considering it, like, it’s, so many of the firms that are… that are the incumbent firms that are in these large Fortune 100 companies. They’re there just because they’ve been there. And that’s the way they’ve… and so it’s going in with a different mindset around, like. Like, I can drive this value. I have a track record, and it’s knowing that those skill sets and results are highly transferable from the context that you’ve been working in into that. So one’s around that kind of that mindset with that. And then it’s… it’s how to meet those, you know, Greg in the boutique talking about the ideal client profile. It is really getting crystal clear on who that one individual is, what he or she is thinking, feeling, what their concerns are. And then as the boutique goes into it, it’s like finding where they’re searching out for answers of that. So that’s different conferences, you know, it’s how to be having a presence around that on LinkedIn, it’s writing articles with that. But it’s being proactive. You know, it is going to these conferences where, you know, if you have a list of these 20 different executives from 20 different Fortune 100 companies that you say, we can help solve, like, this specific problem for them, it’s… I guarantee you, they will be speaking at a conference, each of them, over the next 12 months. It’s like, plan that out. Get that on your calendar. You can even sometimes, beforehand, working with the event specialist, of saying, hey, I’d like to meet with this person for an interview, either before or after. It’s… And that’s why I say it’s kind of this unreasonable sense of confidence, that it’s like, you’ve done the work, you’ve gotten the results, now you just… you gotta figure out a way to get in front of the person with this.
Justin Wasserman: Love that. I love that. What I would add to that is, I think what Jimmy and I have been surprised by is although we’re working in the C-suite of these Fortune 500 companies, the budgets that some folks have at a… you know, L… like, L1, if that’s your SLT, L1, minus 2, minus 3, minus 4, we’re seeing 7- and 8-figure budgets, that many levels down below, so keep in mind that you know, we may be thinking about, how do I get into the C-suite of a Fortune 500 company, but know that there are several hundred buyers with really significant budgets, so you don’t have to aim for the top right away. The other thing I would say is, how can you reduce that buyer’s risk? So, one of the ways that Jimmy and I reduce buyer risk is we are willing to put a percentage of our fees at risk. Now, for every dollar I put at risk, I want to earn at least a dollar of upside, so I’m able to say to a prospective client, you’re going to pay me more, but I’m reducing his or her kind of out-of-cash, you know, out-of-pocket cash up front, because you’re up against a lot of incumbents, to Jimmy’s point, and so what are the ways in which with that, that outsized sense of confidence, really differentiate yourself at the door. And I would think anything that you could think about doing that helps minimize that sense of risk for that buyer and makes it easier to getting to yes, I think once you get the foot in the door, good things can happen, but it’s true, Greg. It’s … it’s hard to get that first foot in the door.
Greg Alexander: So I’d like to add to what Justin just shared, and I’m going to speak directly to our younger members. So when I founded my firm, I was 36 years old. And I got into the Fortune 500 following Justin’s advice. I wasn’t in the C-suite, I was buried down in the org chart. However, I very, very deliberately pursued young executives that were my peers. Peers in, career, peers in age, peers in experience, etc. And I decided to invest in those relationships because I knew that those were the future leaders. And my career and their career paralleled each other. So if I helped those young executives when they were younger, and I earned their trust and followed these 11 items, as they progressed through the organization, they brought me with them. And 10 years later, I was in the C-suite. Because I was the person that they trusted, I contributed, even in a small way, to their career success. They knew they could trust me, they knew I was playing the long game. So if you’re a young founder out there in the Collective 54 community. That might be, an effective way to get started. Just remember, you’re playing the long game, and don’t think transactional, think relationships, and, you know, again, be the guide on the side, so to speak, to use, Jimmy and Justin’s advice. So guys, this was a great session. I think I actually rounded that up to 13 items, so that’s a lot of advice in a very, very short amount of time. We’re gonna end the podcast here and save, you know, the follow-up questions for the private member Q&A session, but you guys are always willing to contribute. Thank you so much on behalf of the membership for coming here today and sharing your wisdom on a topic that’s of very high interest right now, so thank you.
Justin Wasserman: Thank you, Greg. Really appreciate it.
Jimmy Leppert: Thanks, Greg. Our pleasure.
Greg Alexander: Alright, couple calls to action as a wrap-up here. So, if you’re a member of Collective 54 and you want to move upmarket and get into the C-suite of the Fortune 500, look for the invitation for the private member Q&A session, and we’ll double-click on these and you can ask questions. If you’re not a member of Collective 54, and after listening to this, you’re interested in becoming one. Go to Collective54.com and fill out an application, and we’ll get in contact with you. But until next time, I thank you all for making time for me and listening to us today, and I wish you the best of luck as you try to grow, scale, and someday exit your firm.
Note: This transcript was generated by Zoom.