Mastering Serial Acquisitions

Mastering Serial Acquisitions

[00:02:50] Kison: Well, let's jump into it. Let’s kick off with a little bit about your background.

[00:02:55] Gwen: I'll just say that at this point in my career path, M&A generalist seems to be the best way to describe myself—short and sweet. But to provide a little bit more color than that, I will say that I started out in a career path that was really highly technical.

[00:03:10] Gwen: If you go back enough years or decades, you’d see me with my sleeves rolled up, doing software engineering, enterprise application integration, focused on middleware architecture and service-oriented architectures.

[00:03:20] Gwen: Back before everything was so cloud-focused, I was really working with a lot of web-native and hybrid environments, at the forefront of that move to cloud. I then ended up working with companies like Oracle and Apple, focused on solution architecture, and veered into M&A work somewhere along the line.

[00:03:40] Gwen: I’ve built and led a number of M&A functions—tech, product, platform, go-to-market—sort of around the table at companies like Microsoft, Google, eBay, and Maersk. I’ve created greenfield models within brownfields, if you will, and taken away learnings of what seems to work and what doesn’t.

[00:04:00] Gwen: I’ve created a lot of frameworks over the years and taken learnings from that. That brings us to today, and I’ll pass it over to Tracy.

[00:04:10] Tracie: Gwen, you have definitely taught me a few things along the way! My career path didn’t start off in tech—anything tech, actually. I was a litigation paralegal for a number of years, about 14 years, and then went to work for Oracle in their contracting group.

[00:04:25] Tracie: Then, somehow, I became a negotiator, negotiating contracts. And then Oracle started acquiring at a rapid rate back in 2009. I sort of landed in the deep end of M&A by accident and then couldn’t swim my way out of it. So here I am—and I love it!

[00:04:40] Tracie: A lot of people question sanity when you say you love M&A, I think. But I love the fact that you get to solve something on a regular basis and really get into the day-to-day operations of new companies. It’s exciting. Your day is never the same, and yet, you’re trying to create repeatable processes.

[00:05:00] Tracie: So how do you do that in such a crazy world? But I would say I’m definitely a generalist at this point. I don’t think I have any one particular space that I’m better at—you just pick up pieces as you go and move along. So, that’s me.

[00:05:15] Kison: Both of you have very interesting backgrounds—the fact that you didn’t take a traditional finance or banking route and ended up here, coming from operations and law backgrounds. I’m really excited to have this conversation.

[00:05:30] Kison: You’ve both worked with large strategic acquirers. What do you see as the most common challenges for large acquirers, like Microsoft, Cisco, and Google, particularly in the integration process?

[00:05:40] Gwen: I'll start off with maybe a super obvious point, but there are some nuances around the implications of this point. Inherently, a serial acquirer is, of course, transacting an ongoing flow of deals—whether it's an acquisition, a divestiture, or something in between.

[00:06:00] Gwen: You have this accumulation of deal projects that you've just transacted, all at various stages of planning or integration. You also have this anticipation of future deals, and all of that represents one of the strategic levers that you're pulling to execute on your corporate roadmap.

[00:06:20] Gwen: That’s the basic assumption. The implication of that, of course, is that you have a number of plates to spin, and they're all spinning at various phases of what they're going to do.

[00:06:30] Gwen: The key challenge that serial acquirers face—and that I honestly haven’t seen supported well, either in planning or execution—is making sure you have an awareness and a fundamental understanding of what part a particular deal plays in the bigger picture.

[00:06:50] Gwen: From a change impact perspective, what would happen to the deal thesis or the indicated integration strategy if one of the other pieces changed—or vice versa?

[00:07:05] Gwen: So really, the interconnectedness of the transactions is a key piece that serial acquirers face, which buyers who wouldn't be categorized as such wouldn’t necessarily deal with.

[00:07:20] Gwen: Another thing, of course, is that you need to consider the ongoing resource needs, prioritization, and definition of roles so you actually have an operating model—whether it's super lean, with only a few dedicated resources and a bunch of what a lot of us will lovingly refer to as the "volunteer fire department" model, or whether it's a more structured M&A function.

[00:07:50] Gwen: It’s about making sure that you have the strategy piece—an awareness of the bigger roadmap—the resource model, at least a minimum viable one, and a readiness to repeatedly execute.

[00:08:00] Gwen: Then, ideally, of course, you need the framework. You need to have a way to repeatedly operate and a strategy and philosophy around how you do deals. But really, those are the basic building blocks.

[00:08:15] Gwen: Tracy, did I forget anything?

[00:08:20] Tracie: No, I don’t think so. But it really is the building blocks that you need to picture. If you need an image, think of it as building a path to integration. That’s what serial acquirers need to keep in mind and have an approach for as they move forward.

[00:08:30] Kison: What I picked up was that the complexity really comes from having these deals at different stages of the deal lifecycle. Also, understanding how each deal correlates to the big picture and the interconnectedness of these deals—because they're all going into the same company and will have their own different impact.

[00:08:50] Kison: And then there’s the resource model—how you’re prioritizing resources and how this is going to evolve as changes happen in the overall operating model. So how do you do it? The typical private equity playbook says you build a hundred-day plan and go execute on it. But now we’re talking about a lot more complexity because of the nature of doing deals in a series.

[00:09:20] Kison: Now we need to figure out how to manage the short-term needs while also aligning with long-term objectives. What’s the secret sauce?

[00:09:30] Gwen: It's probably helpful for your audience—and even for us as we walk through this conversation—to start simple and build from there. The secret sauce really lies in having the awareness and ambition to understand that, as a serial acquirer, you need a repeatable model.

[00:09:50] Gwen: That’s step one: recognizing the need for a model that merits prioritization of resources and focus in order to establish a minimum viable model—and then iterating from there.

[00:10:05] Gwen: Another crucial aspect is not losing sight of that priority at an executive leadership level. And I’ll note that, in a number of roles I’ve been in, and a number of companies I’ve worked for, there were vastly varying degrees of understanding and commitment at the executive leadership level.

[00:10:25] Gwen: That commitment—or lack thereof—either maintains the foundation for having a repeatable model that's actually viable, or it keeps you in a very reactive mode, where you’re just executing on a per-deal basis.

[00:10:40] Gwen: Being reactive means you’re not very cost-efficient, you’re not mitigating against external factors that might prompt the need to pivot, and you're just not ready for change if you’re constantly reacting.

[00:10:55] Gwen: So really, it’s about having that awareness and the commitment to establish the model. Then, of course, you follow through with things like defining a cross-functional RACI so that you understand who is doing what.

[00:11:10] Gwen: You also need to define how you execute the deals, who is responsible for creating and iterating on the functional playbooks, and, most importantly, work with the executive leadership team (ELT) on an ongoing basis for education.

[00:11:30] Gwen: They need to know what to expect from M&A practitioners and functional leaders, and they need to understand what’s required from them—things like setting clear direction, articulating corporate priorities, and explaining how the strategic roadmap should guide deals.

[00:11:50] Tracie: If we’re talking about the secret sauce, we also have to recognize that executive leadership is sometimes looking at an entirely different part of the universe. We need to bring them out of that black hole, so to speak.

[00:12:05] Tracie: Gwen, you hit on the education piece—that really is the secret sauce when it comes to acquiring companies. If executive leadership truly understands what it takes to integrate a company into their go-to-market plan, that’s a huge win. They think they know, and it's no slight on executive leadership—they just have different priorities. But they also have to bring their thought process down to the operational side to really understand what it takes to get to integration.

[00:12:40] Tracie: That’s the only thing I would add—education is a huge piece, and it’s ongoing throughout the process. It’s not just a one-and-done thing, because as you reach different phases, there are different levels of information that need to be discussed and decided upon.

[00:13:00] Gwen: That reminds me of something. In one of the companies we worked at together, Tracy, I saw just how crucial humility is for M&A leaders when working with the executive team.

[00:13:15] Gwen: There’s always some tension—stakeholders will say, "If only we could get this executive to understand or appreciate what we do!" But as M&A practitioners, we also need to bring humility to the table and seek to understand what matters to the executive team.

[00:13:30] Gwen: It’s about translating what our objectives and needs are into their language. That’s a relatively straightforward exercise, but it’s often challenging.

[00:13:45] Gwen: For example, instead of talking about M&A deliverables and methodology—which the executive leadership team (ELT) may not fully grasp or care about—we need to frame things in terms of what matters to them.

[00:14:00] Gwen: The ELT may not care that you’re working towards a day-100 milestone or that you have specific deliverables for a pre-sign deal review. But they will care if something is going to delay or prevent joint sales teams from going to market with cross-selling and bundling acquired products with existing products.

[00:14:30] Gwen: They’ll care if the deal impacts their ability to enter a new customer base or a new region. That’s what we need to communicate—so it's an exercise in translating our objectives into their priorities and commitments.

[00:14:50] Kison: Step one is admitting you have a problem. I like what you said—awareness and ambition. Having the awareness and ambition to build a repeatable model is key.

[00:15:10] Kison: From there, it’s just about getting started. Having a minimum viable product (MVP) and iterating on that model. Leadership commitment is going to be important.

[00:15:20] Kison: You also mentioned RACI—which for those who don’t know, you can Google it—but it stands for Responsible, Accountable, Consulted, and Informed. It helps define who is doing what.

[00:15:40] Kison: Then you also need to define how you execute deals. And then we get into working with the ELT for education—making sure they’re clear on direction.

[00:16:00] Kison: And you mentioned that education is about helping them understand the thought process behind operations. But also, it's about us seeking to understand what the ELT actually cares about.

[00:16:15] Gwen: Yes, absolutely. Because at the end of the day, M&A is just one of the strategic levers at the ELT’s disposal.

[00:16:30] Gwen: We all know there are specifics and nuances in M&A work that you don’t see in organic initiatives. But fundamentally, it’s just one of many strategic options.

[00:16:50] Gwen: So we need to keep an eye on the broader corporate objectives—the strategic roadmap—because M&A is just one way to execute on those objectives.

[00:17:10] Kison: I keep hearing that post-merger integration (PMI) is where most deals fail. Tell me—is it the long tail of integration that makes it so difficult?

[00:17:30] Kison: I get that people experience fatigue. Maybe that’s why people came up with 90-day or 100-day plans—because after that, people just check out.

[00:17:45] Kison: I want to hear from you. You’ve done this—what makes integration so challenging?

[00:18:00] Gwen: The day one to day 100 segment of deal projects really deserves a closer look. And I’ll pass it back to Tracy in a moment because there are some helpful examples we can dig into.

[00:18:15] Gwen: But beyond that, the long tail of integration is definitely about fatigue. Many of the same resources who are executing the deal post-close have also been involved since due diligence.

[00:18:30] Gwen: So for them, it’s a long process.

[00:18:40] Gwen: Another reason is that a lot of integration charters and M&A playbooks tend to stop at day 100. Because beyond that, you’re getting into greater complexity.

[00:18:55] Gwen: The bigger challenge—and I would argue the bigger test of maturity—is setting a clear direction for getting to the end state.

[00:19:10] Gwen: And that requires understanding where the acquired business fits into the bigger roadmap—both in terms of product portfolios and corporate strategy.

[00:19:30] Gwen: But another thing that happens post-close is executive turnover.

[00:19:40] Gwen: You often see key deal sponsors shift roles or even leave the company entirely. So now, you’ve got a new person in that role who doesn’t have the same context.

[00:19:55] Gwen: And that can cause issues in execution. It can disrupt the through-line of decision-making and integration strategy.

[00:20:10] Gwen: Another factor? External market forces.

[00:20:15] Gwen: Maybe the economy shifts. Maybe there’s a financial crisis, or a pandemic happens.

[00:20:30] Gwen: Now, all of a sudden, your budget and resource availability change, and you have to execute your integration plan with fewer resources.

[00:20:50] Gwen: All of these things—fatigue, turnover, external disruptions—they make long-term integration really hard.

[00:21:10] Gwen: But another key reason why integration struggles?

[00:21:20] Gwen: A lot of companies simply don’t understand what a full-fledged, cross-functional integration plan should look like.

[00:21:40] Gwen: I’ve seen this across companies I’ve worked with—there’s just a lack of understanding about what integration really requires.

[00:21:55] Tracie: A good example of this is contracting. You’ve got pricing. You’ve got underlying agreements that were negotiated pre-acquisition. And all of that impacts your customers and partners post-close.

[00:22:30] Tracie: When you acquire a company, their customers expect everything to stay the same. But it won’t. So what does that interim period look like for them? How do you transition contracts, terms, pricing, and support?

[00:23:00] Tracie: Do you leave their existing terms in place and gradually shift them over? Or do you rip and replace their contracts with your standard terms? That’s a massive decision, and it has ripple effects.

[00:23:30] Tracie: Because if you rip and replace, you risk alienating key customers. And if you don’t, you could be stuck with non-standard pricing and terms for years. That’s why contracting is a big rock issue in post-close integration. And by the time you get to it, everyone is exhausted.

[00:24:10] Gwen: Contracting is a great example—not just of complexity, but of how integration touches multiple cross-functional areas.

[00:24:30] Gwen: People often don’t realize how much contracting decisions impact things like billing, taxation, sales enablement, and customer experience. For example, how you bill customers impacts how you're taxed. The terms you commit to in different regions impact what sales teams can offer. Pricing affects commission structures and incentives for your sales teams.

[00:25:15] Gwen: So when people argue, “We must do this,” and someone else says, “No, we can’t do this,” those debates often come from very different perspectives. That’s why you need a guiding framework—something that aligns everyone across functions.

[00:25:55] Gwen: That’s where the North Star comes in. Ideally, you define the North Star pre-sign—internally. And then you iterate on it throughout the deal and integration phases.

[00:26:30] Gwen: The North Star should be the foundation for all integration planning. Any decision—big or small—should align with it.

[00:26:50] Gwen: That way, when you hit complex issues like contracting, you’re not debating in a vacuum. You have clear principles guiding trade-offs and decision-making.

[00:27:10] Kison: So the North Star is really about setting direction. That makes sense. But what about structure? I’ve seen a lot of inconsistency in how companies approach integration.

[00:27:40] Kison: Some companies just hand integration off to the business unit and say, “Here, it’s your problem now.” Others have a central integration team—but they bring them in late after the deal team has already made decisions.

[00:28:10] Kison: And then I’ve seen companies where integration folks are embedded with Corp Dev from day one—some even leading parts of the deal process. What have you seen work best? What are the pros and cons of these different models?

[00:28:45] Gwen: It’s a great question. And the truth is—there’s no single “best” model. I’ve seen centralized teams, decentralized teams, hybrid models—you name it. And they all can work. But they all have trade-offs. The biggest non-negotiable factor is accountability at the executive level.

[00:29:35] Gwen: No matter which model you choose, if you don’t have ELT support and buy-in, it won’t work. I’ve worked at companies where nobody at the ELT level was accountable for integration.

[00:30:05] Gwen: And what happens? Once Corp Dev and the IMO (Integration Management Office) wrap up their work, the deal gets tossed over the wall—and nobody owns it. No executive is tracking whether integration is succeeding. There’s no escalation path for issues. And there’s no decision-maker when trade-offs need to be resolved.

[00:30:50] Gwen: That’s when things start falling apart.

[00:31:05] Kison: So decision-making accountability is key, no matter what model you choose?

[00:31:15] Gwen: Yes. That’s the foundation.

[00:31:30] Tracie: And you can’t leave out the steady-state teams. A lot of companies treat integration like it’s just a temporary project—but it’s not.

[00:31:55] Tracie: At some point, the acquired business transitions into steady-state operations. And that team needs to be involved early. Otherwise, you end up with another disruption at the end of integration when everything gets handed off. Bringing in steady-state teams sooner rather than later is one of the best strategic moves you can make.

[00:32:50] Kison: That makes a lot of sense. Let’s talk about decision-making. You’re bringing two different companies together. They each have different ways of making decisions.

[00:33:15] Kison: And integration is all about making a lot of decisions—fast. How do you do that? How do you make integration decision-making work?

[00:33:45] Gwen: This is one of my favorite topics. First, you need to have that North Star. The North Star starts as a set of assumptions—tied to the deal thesis and initial model.

[00:34:25] Gwen: But as the deal progresses, you need to iterate on it and align it with real integration plans. Second, you need a decision log. Document who makes which decisions, what decisions have been made, and what still needs to be resolved.

[00:35:10] Gwen: And third, you need clear information flow. Who needs to know about decisions? When do they need to know? How do we communicate them? I like to call it the nervous system of integration. If information doesn’t flow properly, people make their own assumptions—and that’s when things get messy.

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[00:36:10] Kison: So assumptions are a big piece of this.

[00:36:20] Kison: Two big pillars I’m getting—planning decisions ahead of time and then logging decisions as you go.

[00:36:35] Kison: You start with broad assumptions. Those help you plan when decisions should be made. Then, as decisions get made, you log them.

[00:36:50] Kison: And then, when you do make those decisions, you have to map out who needs to know and how to communicate that information.

[00:37:10] Kison: I feel like decisions turn into a tree structure—you make one decision, and then all of a sudden, a bunch of smaller decisions pop up. Does it actually look like that?

[00:37:35] Gwen: It often does. Let’s take contracting as an example. There are always downstream impacts when you decide how to handle contracts.

[00:38:15] Gwen: If you change contract terms, that impacts pricing. Pricing impacts billing and revenue recognition. That, in turn, impacts sales compensation and tax structure. So yes, decisions absolutely cascade into more decisions. That’s why you need a structured way to analyze trade-offs.

[00:39:15] Gwen: I always start by asking: “Do we have a reason to do this now?”

[00:39:30] Gwen: Because sometimes, there’s no immediate urgency, and you can defer a decision until you have more information. But other times, there’s a regulatory deadline or a business-critical need—and you have to decide now.

[00:40:00] Gwen: That’s where your North Star comes in.

[00:40:10] Gwen: You map the decision against:

• Value creation—Does this align with our deal thesis?
• Compliance—Are we legally required to do this?
• Cost savings—Does this drive efficiencies?
• Customer and employee experience—What’s the impact?

[00:40:40] Gwen: That framework helps prioritize which decisions to make when.

[00:40:55] Kison: That makes sense. But what about the stuff that pops up unexpectedly? The little challenges nobody mapped out? How do I keep people from running to me every time something unexpected happens?

[00:41:25] Gwen: That’s where accountability comes in. You need to empower functional leaders to handle their own decisions.

[00:41:50] Gwen: That means defining:

• Who owns which decisions?
• Who needs to escalate decisions?
• Who just needs to be informed?

[00:42:10] Gwen: And if something does require escalation, that escalation should come with:

1. A summary of the issue.
2. The trade-offs of different options.
3. A recommended course of action.

[00:42:40] Gwen: The worst thing you can do is just surface a problem without any proposed solutions.

[00:42:55] Tracie: And you also need a structured way for people to ask questions.

[00:43:10] Tracie: I’ve seen companies implement integration help desks—where employees can submit questions or issues and get routed to the right functional leader. That keeps people from escalating everything to executives.

[00:43:45] Kison: So we’re creating accountability structures and help desk mechanisms to filter issues before they hit leadership.

[00:44:00] Kison: That makes sense. What about decision tracking? Humans forget things the next day. How do you actually make a decision log that works?

[00:44:40] Gwen: First, you need a single source of truth. It could be a shared folder, SharePoint site, or a deal-specific workspace. But people need to know where to find key decisions.

[00:45:20] Gwen: Second, every decision log should track:

• The decision made
• The rationale behind it
• Who made it
• When it was made
• Who needs to know

[00:45:50] Gwen: And third, you need consistent communication about key decisions. Some companies do a monthly newsletter recapping recent decisions. Others have standing meetings where teams review and align on key decisions. Whatever you do, the goal is to keep everyone on the same page—so people don’t make decisions in a vacuum.

[00:46:50] Kison: That’s really helpful. I like the idea of tying decisions back to the North Star—so people always know why a decision was made.

[00:47:10] Kison: I think this would be especially valuable for roll-ups, where you’re doing the same types of deals repeatedly.

[00:47:30] Gwen: Absolutely. This approach is critical for roll-ups.

[00:47:45] Kison: We’re going to be talking a lot about roll-ups in 2025—maybe we can collaborate on an M& A Science Fair session around this.

[00:48:00] Gwen: That would be fun.

[00:48:10] Kison: Last question. What’s the craziest thing you’ve seen in M& A?

[00:48:30] Tracie: Oh, I have one. We acquired a company in the UK and planned a major system cutover.

[00:48:55] Tracie: We did months of testing. Everything looked great. Then, the day we flipped the switch—everything died. All customer data, all system access—completely gone. I thought we were going to have salespeople jumping out the window.

[00:49:55] Kison: Wow. Was this a day one cutover?

[00:50:05] Tracie: No, it was day 100+—a full system migration. And even with months of prep, it still failed.

[00:50:35] Kison: That’s crazy. Gwen, what about you?

[00:50:45] Gwen: There was a particular deal that had been struggling for several years.Technically, Corp Dev and IMO had already bowed out. But the executive leadership team (ELT) said, “We never captured the value of this deal. Can you unblock it?”

[00:51:25] Gwen: So, IMO leaned back in to drive integration forward. After months of work, we finally got to a critical SteerCo meeting. We presented three or four key decisions, with clear trade-offs. And the main deal sponsor showed up and said:

“I don’t know what all this noise is about. I didn’t read the proposals. I don’t know what you’re asking for. But integration is already done.”

[00:52:35] Gwen: That was one of the craziest things I’ve ever heard. It was a fundamental misunderstanding of what integration actually means.

[00:53:05] Kison: What did they mean by “integration is done”?

[00:53:20] Gwen: That was my next question. Their definition of integration was:

“The contract is signed. The company is legally ours. So, we’re integrated.”

[00:53:50] Tracie: That’s a huge issue in M&A—“integration” means different things to different people. We had a big aha moment around this in one of our previous roles.

[00:54:20] Tracie: For many people, integration just means ‘we can sell the product’.But that’s not integration. That just means you got lucky enough to continue selling without disruption.

[00:55:00] Gwen: Exactly.

[00:55:10] Gwen: It’s a good reminder that education and communication matter. You need to define integration clearly—so everyone understands what it actually means.

[00:55:40] Kison: Thank you both, Gwen and Tracy. This has been a great conversation—I learned a ton about decision-making. You’ve helped me become a better M&A scientist today.

[00:56:20] Gwen: Thank you. We’ve learned a ton from your conversations with other practitioners. Always a pleasure.

[00:56:45] Kison: The pleasure is all mine.