Deltek utilizes win-loss insights for CI—and then shares them broadly to create a competitive edge

August Jackson

Vice President of Market Intelligence & Competitive Strategy

August talks about how capturing and sharing win-loss insights is a competitive game-changer for his company. Deltek uses win-loss analysis to learn more about their competitors, identify broader industry trends, and conduct internal War Games scenarios with their sales team.

Jeff Foots interviews August Jackson, VP of Market Intelligence and Competitive Strategy at Deltek, about his experience with Clozd and win-loss programs. August explains that his role involves tracking over 300 competitors in various markets, focusing on leveraging competitive intelligence and win-loss data to enhance Deltek’s strategy. August shares his early experiences with win-loss interviews, highlighting their ROI and how they guided investments to improve business outcomes. He discusses specific instances where win-loss insights informed strategic shifts, particularly around improving sales processes and addressing buyer concerns. He emphasizes the importance of integrating win-loss findings across the organization, using a dedicated team member to communicate insights to product, sales, and marketing teams. August notes that Clozd has helped Deltek navigate market shifts due to macroeconomic changes, enabling them to adapt more effectively. The conversation also covers the use of war games to simulate sales scenarios and identify improvement opportunities, demonstrating the practical application of insights gathered from win-loss interviews. August advises that securing buy-in from senior leadership is crucial for a successful win-loss program, framing it as a tool for sales improvement rather than evaluation. Lastly, he discusses the evolving role of AI in competitive intelligence, suggesting that while it will streamline information processing, the challenge will shift to effectively applying those insights in decision-making processes. August concludes by expressing his passion for competitive intelligence, noting its impact on strategic business decisions.

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Q&A

Jeff: Hi, I am Jeff Foots, a program manager here at Clozd. We're here today to speak with August Jackson of Deltek regarding his involvement with Clozd and win-loss. Well, just to get us started, I guess give us an introduction for yourself and your role there at Deltek.

August J: Absolutely. So at Deltek, I am the Vice President of Market Intelligence and Competitive Strategy. I've been at Deltek for five years. Most of my career has been in competitive intelligence in professional services and consulting and telecommunications and the like. At Deltek, the competitive intelligence program covers over 300 named competitors in various industries, geographies and segments. Deltek sells software and solutions to project-focused organizations, and we sell software all over the world. And the competitive dynamic in each one of those markets can be completely different, and that's why we have so many competitors that we're tracking. Part of the competitive intelligence program is of course, with the win-Loss program also.

Yeah, yeah. Tell us more about that. What interests you in win-loss, given your background in competitive intelligence?

Well, my first exposure to win-loss was in the early 2000s. I was at a telecommunications company and we started doing win-loss interviews with sellers there, and very quickly saw the return on the investment from the time that we were spending in those conversations. And it was very rudimentary relative to what we're doing today. But still very quickly in a very capital-constrained environment, we had very clear guidance on certain investments that the business can make in order to really make a difference in our ability to win business. So we're able to provide those sorts of ROI figures based on opportunities that were lost or at risk based on missing functionality that if we close those gaps, we could turn around and turn those into revenue opportunities. It was a tremendous success. We got great competitive intelligence from the exercise as well, and so I've been a big fan ever since.

Great. Yeah. Tell us, really, when looking at competitive intelligence, how has win-loss really helped you there? Is there an example where it's helped change your focus or your strategy based on what you've heard back from buyers and sellers?

Oh, absolutely. One of the things that we're working on right now is with our internal compete data from our CRM system, we were seeing some interesting trends in terms of opportunities that were not turning into wins for us. And we were looking for insights to help us understand what could we do in order to drive more of those opportunities to a successful close.

And we were able to focus some of your time, as our consultant, on conversations with those prospects. They looked at us, they looked at some of our competitors, they kicked the tires, and they decided, well, we're really not ready to make the move right now. And based on the conversations you were able to have with them and some work we were able to do internally with some war gaming and some other exercises, we saw some very immediate opportunities for us to move the needle on getting some of those prospects that just weren't ready to make the move, how we could make them feel comfortable that this was a good time and a great opportunity for them to choose Deltek.

Great. Yeah. I definitely want to talk about the war games here a little bit more in a second. But based on some of the things that you've heard from the feedback that you've gathered with win-loss, how have you helped share that information with the greater organization? How have you continuously integrated the win-loss program into Deltek?

Yeah, it takes a good amount of internal work as well. So I've got one of my members of the team who is just an absolutely voracious consumer of the insights from these interviews and looks at the insights and sort of pre-digests them for various stakeholders in the business. And with insights from individual interviews or trends that he observes from multiple interviews, we'll go on a little bit of a communications roadshow with product and sales and product marketing, sales enablement and say, Hey, look at what we're seeing from the voice of the prospect, and here are some of the opportunities. He does a very good job of connecting the dots with other initiatives that are underway in the business as well to say, here are some opportunities for us to validate what we're doing, maybe change tack on a couple of different things, but really great insights that are immediately applied in the business.

Awesome. Yeah, integrating with the business can be really, really important obviously. Looking into that, I guess, have you seen any kind of areas where the market has shifted based on the feedback that you've gathered from Clozd?

That's a really interesting question. The market is shifting so much right now because of some very significant changes in the macro environment, interest rates, inflation, those sorts of things as well. So one of the things that win-loss and Clozd have helped us do, I think, is navigate some of those changes and transformations, understand how those are affecting our prospects and what we can do in order to mitigate some of implications of those macro changes for them and be a little bit more successful in the market than we would otherwise if we didn't have those insights.

Okay. Yeah. Getting back to that topic of war games, I definitely want to hear some more about this. Tell us how have you guys utilized the feedback from Clozd to really, I guess, implement these kind of internal war games?

Yeah, so this exercise I was talking about, the insight began with our compete data, as I mentioned before, lots of opportunities that did not go to Clozd one in certain scenarios and situations, and we wanted to understand what was going on there. So we worked with you to target those scenarios for win-loss. Some great insights came back and we thought, okay, they're telling us some things about the sales process. And what are those opportunities for us to intervene in the sales process to improve our chance to win? So we looked at... I'm struggling to not give away too much. I don't want to give away the farm and all the secret sauce that we have here, but looked at those specific opportunities to intervene and to change how we do certain things. But we wanted to test ourselves. I go, okay, well, we think we're pretty good at this, but are we pretty good at that?

So we ran some simulations in a war game exercise, and we had different sales teams basically face off against one another in these pursuits. And we had people also playing the prospect. I got to play a prospect once, and it was a lot of fun, the shoe being on the other foot a little bit there. And realized, Hey, here's some opportunity. Here's some things where we show up really well. Here's some opportunities we have to close some gaps, and here are some new things that we now need to go back and work with Clozd to revalidate and update as well. So that kind of informs the next cycle of win-loss interviews also.

So a number of efforts across our go-to-market teams are underway right now around sales enablement, product marketing, the whole organization just really coalesced around these findings.

Great. Yeah, I mean, that sounds like a pretty big project or task to undertake with the war games. How did you get some buy-in or engagement with some other leaders to really pull off a project that big?

Well, the compete data and the insights from Clozd really helped a lot because there was some reluctance at first. Some people thought, well, I'm not sure that's the priority. We've got other concerns. We've got other challenges. And we were able to use the data and the win-loss insights to illustrate the fact that this was actually a high return on investment exercise, that with some relatively modest changes, we would be able to win more. And these are some prospects that are very early in their maturity, their process of maturing their business. So the lifetime customer value of winning the customer at that point was really quite high. And so the data that you helped us bring to the floor helped us convince people that this is a priority worth focusing on.

I know one of the areas that we wanted to focus on with your guys' win-loss program was really to understand the user experience and user interface that Deltek offers. Tell me a bit more about that. How has the feedback from Clozd help kind of shape and strategize your guys' product roadmap?

Well, if you're a software company, getting feedback on user interface is one of the most difficult things to get. Because it's a little bit like if you've seen the movie Fargo and people are describing Steve Buscemi's character to Francis McDormand, and they say, oh, he was just kind of funny looking, funnier looking than most people even. And it's like, can you tell me a little bit why he was funny looking? No, he was just kind of funny looking. And that was really the quality of the feedback we were getting on our user interface.

And we sell enterprise resource planning software, and it's not the most fun software in the world to use. So the feedback that, Hey, I might not be the biggest fan of your UI, isn't really that valuable because you go on G-II, you hear what people are saying about our competitors, and they're saying the same thing about their UI. So it's kind of like, okay, what about it is the issue and how does that translate for the prospect of the customer to issues in their business, in time to value into adoption of the software, into accuracy of people submitting their time sheets, those sorts of things. And the interviews that Clozd was conducting were able to get us that much more specific level of detail that just no other methodology was giving us.

Great. Obviously it was helping with your strategy and product. Were there other areas you feel like Clozd has really been helpful in helping shape the strategy at Deltek? And if so, how has it helped you guys change priorities?

Sure. So one of the things from a competitive intelligence perspective that's been really valuable is getting insights from the voice of the prospect and the voice of the customer on competitor roadmaps. Because the competitors are saying things in their demos and in their briefings to prospects that they're not necessarily publishing on their websites or talking about in their events and those sorts of things. So we get a much better view of what they're prioritizing in those conversations. And then also we get that view of what they're saying about us, whether it's accurate or not, but recognizing here are some of the things that we need to make sure we're either closing a functional gap if it does exist, or closing a perceptual gap in the market if say a competitor is saying something that's not accurate and we're not aware of it, so we're not able to sort of head that off at the past. That's been very valuable too.

Great. We've been running your win-loss program for a little while now. Tell us, if you were to give advice to someone that was starting up a new win-loss program, what's some of the things that you would try to tell them to look at or start with?

So one of the things I've been really fortunate to have at Deltek is buy-in from the very senior leadership in our sales organization. And I've endeavored to run win-loss programs at places where I did not have that buy-in. And just to say that it is much, much easier if you get that particular buy-in.

So when I landed at Deltek, the chief sales officer at the time immediately understood the value of what I was talking about when I mentioned win-loss. And the incoming chief sales officer that followed him, she also understood it right away as well. And some other senior leaders within the sales organization came in and saw the insights that we were delivering and the value of those insights so quickly. So my initial critical advice for somebody starting a win-loss program is to work to get that buy-in from senior sales leadership.

Got it. We talk about that a lot, actually kind of at Clozd in regards to getting buy-in with sales. Tell us a bit more about that though, in regards to what does that mean? I think the fear is always when you say you get buy-in from, it means that they have to go and do a lot of work potentially, right? How do you get that buy-in from those leaders?

Yeah. The biggest concern that I've seen from sales leaders in various settings and sometimes from individual sellers as well, is the sense of this win-loss program is evaluating me and is here to test and inspect me and my performance. And one of the key things is to really convey how win-loss illustrates what's going on in the system. We might find, for example, in an opportunity that a rep might not have shown up as well as he or she might've preferred, and that is related to the systems of enablement around them. Did they have the right collateral? Were they enabled appropriately on how to speak to that? Did they have the right tools to do appropriate discovery and share that discovery with the solutions engineer and that sort of thing. So there's this exercise and root cause analysis that follows from everything that happens in win-loss.

And then another angle of this too is to work with sellers to help them understand how win-loss is an opportunity for them to turn sort of anecdote into data. Hey, you're saying that there's an issue here and to everybody else in the business while you're doing that, that sounds like an excuse. But with win-loss, particularly when you have an objective third party that's conducting the interviews and everybody can see this is directly from the voice of the prospect, and they're seeing that across multiple opportunities. All of a sudden that goes from being an excuse for why you didn't win to something that the business needs to fix. And so it is a tool for sellers to help close the gaps that are keeping them from succeeding.

Absolutely. We've seen a lot of change in the marketplace, like you talked about, we're seeing probably one of the biggest changes in regards to technology with the introduction of AI recently. How do you see the evolvement of win-loss and competitive intelligence evolving over the next few years?

How much time do we have? I could talk about that for a long time because artificial intelligence is going to be a really significant transformation agent for both win-loss and competitive intelligence. I lived through, at the very early part of my competitive intelligence career, the introduction of the search engine. And prior to, let's say the introduction of Google in particular, if you could find your competitor's annual report, you were a competitive intelligence rock star. Then Google comes along and all of a sudden, well, that's really easy to find. And there was a sense of some stakeholders in the business that, well, maybe we don't need competitive intelligence anymore. And the transformation that occurred in terms of delivering value is all of a sudden there's a pivot from information scarcity to now the problem is there's too much information and a lot of it's unreliable, and how do we make sense of it?

And then all of a sudden, what I call the horizon of value in competitive intelligence moves to making sense of a large volume of information as opposed to finding the needle in the haystack, that sort of thing. We also got to be a little bit more discerning in terms of things like triangulation, getting pieces of information from multiple independent sources to have greater validation of the data that we're getting as well. So I see that transformation kind of being analogous in AI as well. Because you think here's a large language model that you can point at a huge amount of information, whether that's the World Wide Web, whether that's all of your win-loss interview transcripts, something like that, and you can ask it really interesting questions. And that's going to streamline a lot of the work that today is sort of the bread and butter of win-loss or competitive intelligence.

But then that horizon is going to move because the human need for insight and information is sort of never ending. And I think I'm seeing some of it already because the challenge now seems like it's becoming the application of insight. Like, okay, we've got all these great insights. I've got to varying degrees or another, generative AI tools that can help me make sense of the volume of information better than I could before on my own as a stakeholder, but now what do I do with it? So I think from just what I'm seeing in very, very early days, that's where the potential horizon I think will land.

Great. Well, August, I want to thank you for your time today. It's been great chatting with you about your experience with competitive intelligence and win-loss. I guess just one last question for you here. Is there anything else you'd like to share with somebody that would be new into the competitive intelligence space to help get them excited about competitive intelligence?

I would say that this is the most fun job in the world. You get to take on these really interesting challenges with these great questions and issues that you're trying to inform. When all the cylinders are firing in a competitive intelligence function, you can really see the way you are helping executives and leaders make decisions, whether that's positioning a particular product within a pursuit or whether that's making a particular acquisition or building a product roadmap. And it's just really great to see that and have that influence and impact on a business.

Great. Well, once again, thank you for your time today, August.

Thank you, Jeffrey.