Clozd: My name is Brady Tengberg. I'm the head of client success here at Clozd, and I'm here today with Scott Varner, who was one of our directors of program delivery. Scott, great to have you today.

Scott Varner: Great to be here.

So today we're going to talk a little bit about stale insights and how to keep a program fresh over time. Scott, you've been at Clozd for a long time. Tell us a little bit about your background here at Clozd.

Yeah, I've been doing win-loss for four years. I've been able to work with, at this point, dozens, approaching hundreds of different clients, many of which we've been working with the entire time I've been here. Companies doing win-loss for four years, continuously evolving, staying fresh.

Yeah, that's very true. And Scott, one of the things that I think is really interesting about your role here at Clozd is you obviously started as a program manager, someone who was working directly with clients. You ended up working with a lot of our most enterprise, our largest clients over time. As you mentioned, a lot of those have been around for quite a long time, and now in your current role, where you've actually shifted into more of a direct role, where you're overseeing a lot of different types of programs, you have a lot of context on how different programs operate.

Yeah.

So Scott, one thing I wanted to talk to you about today, in the last year and a half that I've had here at Clozd, one comment that I've heard often from people is that whenever they're starting their win-loss journey, everything is really fresh, right? You start to talk to your customers and you get really excited. You start to learn new things and then, slowly over time, people start to come to us because they start to say things like, "We're starting to hear the same thing over and over again, and things aren't quite as fresh as they were before." Talk to me a little about that. Why is it important to have fresh insights in a win-loss program?

I mean, why do companies do earnings calls every single quarter? Why do they always give updates? I think there's a lot of stakeholders that are looking at businesses and they want answers. What's driving your performance? And also do you have awareness of the factors around you? Because if you're not continuously having a hunger to learn about your competitors, about your customers, about your market, you're probably dying a slow death or you're not aware that other people are innovating around you, yeah.

It's very true. Yeah, especially for customers who are in very saturated, very mature markets, it is very important to make sure that you're always up-to-date on what's happening around you as well. So Scott, whenever you're talking with a customer who's coming to you and is starting to have these thoughts around their program, starting to hear the same things over and over again, what are the typical warning signs that they're talking about? What are the things that they're noticing in their program that are leading them to come to that conclusion?

Yeah, I mean, I think a first warning sign is are they getting engagement with people around them? If I'm running a win-loss program or any sort of program where I'm touching customers, it probably means that I'm seen as a source of information, as a source of answers. So biggest warning sign you can have is different teams aren't coming to you to ask questions, whether that's the sales leaders, the product org, it might mean that they don't have questions, or it might mean they're not talking with each, or they also aren't in tune with you as a source of information.

Yeah, that's really interesting. I think it's a very salient point. I can imagine if you're the one leading the program and you're constantly sending out your newsletters to the organization or sharing the insights, you probably can feel like you're almost doing your part, but then if people stop engaging with you, it probably is a very good sign that maybe what you're delivering to your stakeholders isn't actually that relevant anymore.

Yeah. I think warning sign number two is there's a comment that people will say, which is just, "Oh, I think the headlines are the same." We measure, win-loss a lot by decision drivers, the things that are customers are basing their decisions on. People say, "Things aren't changing." Or, "The headlines are the same." That's typically a warning sign that we're not paying close enough attention to the why or if there's a shift in the underlying themes behind that.

Scott, for a lot of the programs that you run, I imagine you're running a very long program for a long time with one of your customers. How, as a program manager, do you view your role in helping to make sure the insights stay fresh for your points of contact?

Yeah, I mean, I think largely as a facilitator, as an advisor. I think, in step one, if I think of an example of a big org that had been doing win-loss for several years, and they actually directly raised this question like, "Our insight's stale, our CPO doesn't know that we've been learning anything new." So I saw myself as first facilitating some questions to say, "Okay, what are the biggest questions that stakeholders are asking right now and try to organize what's the objective? What are some key priorities the business has? Is our win-loss program currently mapped to those?"

And then step two was to facilitate a discussion around, "Okay, let's look at the way we're measuring customer decisions right now, and let's really look and see, when we establish our win-loss program initially and establish, here's our drivers, here's our system of measurement. Have we evolved as a business since then? Have we introduced new products? Have we introduced new capabilities? Do we need to be kind of keeping track of different things?" Sometimes we just shift the measuring thing.

And I think the third way I see myself as a big facilitator is, well, someone's got to go talk to customers and someone has to go drive our interview guide, someone has to ask these questions, and let me make sure the questions that you've honed are going to get you open-ended answers. Because sometimes you're asking the right question, but you're not giving enough room to the customer or to the buyer to give the why behind their answer because that is the part that likely should be shifting the most over time, yeah.

That's really interesting. And I know a lot of people, when they first start out doing these customer interviews, they often can feel a lot of pressure to have an interview guide and to almost treat it like a phone survey, right? Where it's a very rigid set of questions and prompts. And I think your point there around really leaving your customer a lot of wiggle room to dictate where things should go and make sure that, through your questions, that you're not trying to force fit them into the box you've already created, which would end up being a lot of confirmation bias.

Yeah. I think there's another thing that comes with that too, is the questions are one thing, making sure we have room for the people giving answers to breathe is one thing, but also paying attention to like, "Well, who are we talking to?" Is another. When I do a win-loss program, when I do a report, you get to a certain number of data points, certain number of interviews, and there's a lot of qualitative research out there, we'll say. If you have a certain number of data points, this is going to give you enough to represent a high percentage of your customer base. So if you're doing win-loss for years, you should be getting enough data points that you can now slice and dice the data in a ton of different ways that become really exciting.

That when I have enough interviews that are going deep and rich, I can now segment that by persona. How do things shift based on the title of who I'm speaking with? If I'm talking to in a big enterprise cybersecurity deal, am I talking to an analyst that's going to be interacting day to day with the software? Because they're going to see things entirely different. They're going to want different things than their CISO who's several layers are moved and they're looking for different things, so if I can cut the data in that way, I'll get to some really cool insights.

But then, for one big customer, they have a few core products that serve a lot of people globally, can we look at the answers based on industry? Can we look at it based on geography? Can we find different headlines that are slightly different? And then the next thing too is like, "Well, when we go share those headlines with the business, different people are going to ask different questions about the data, and they'll push me, as a facilitator, as a person, that oversees all those conversations to think differently about the conversations that I had." And they might share some inside baseball with me about, "Well, here's something that we did to specifically serve this customer, this segment, this industry." They'll give me that detail, and then I can think back and realize, "Oh, I can see how this actually reflects in that segment. I can see how this impacted that customer in a meaningful way."

Scott, one phrase that I've heard a lot in my career is that there's always a law of averages, right? You have all these different things that happen on the periphery of your business, but then when you group everybody into one large customer base, things do start to get a little bit muddled. It's like, "Well, if I'm looking at an enterprise customer versus an SMB customer, they actually might have very different preferences, and they might have very different feedback for your business. But if you're just considering your customers in one large aggregate, the answers might not be that different."

Scott, one question I have for you in particular, if you were somebody just starting up a win-loss program right now, how would you start designing the program to make sure that the insights don't become stale over time?

Yeah, step one is making sure I am plugged into the needs of the business. I would say wherever you can start with visibility and buy-in from different leaders or if you can't get that visibility from leaders, get buy-in from people that know what leaders in different pockets of the business want to hear. Because when we go tap directly into the customer, we're tapping into the most powerful source of information that business can have. If we're having a third-party, unbiased conversation, we can likely pick up things that they wouldn't be able to pick up if they were asking those questions themselves. So when we come back and we have an initial win-loss report to share, in addition to answering the most important question, why are we winning and losing our business? If I can have insight into what are the priorities of those different leaders, if I can give them little nuggets, usually I can really grab their attention.

They're going to ask those follow-up questions that I talked about being super important to help me see new layers from the conversations that I had. But then they're also going to do, I think the most key thing, which is they're going to say, "This is a great insight. We need to act, we need to take action on." They're going to take that insight and put it into the hands of somebody in the org that reports to them or somebody that can drive meaningful change and that means that the Win-Loss program served a purpose. The win-loss program gave them something that they could act on and do something with. So then the next time we come back, we can say, "Did that effort have an impact? Did that ever work?" And if you have a motion of doing that from the very, very beginning, your program's never going to go stale, your program is always going to be serving the strategic priority of the business.

I love that comment in particular, Scott, because I think a lot of times things that we'll hear from customers is that in the past, they felt like they're not learning anything new from their customer, and one of the first questions that I always go to is, "Well, have you changed anything in your business that would make you expect to hear something different from your customers?"

As an example, we worked with one customer who had been hearing a lot of frustration from their customers about their pricing model, and they heard a lot that, "Hey, the product is great. The user interface is great. The UX is great. All of that is really good. The licensing model, it's just not working for us. It's too high, it doesn't work for our business." And they heard that for six months, for nine months, for a year, and they started to tell us, "Well, we're just hearing the same thing over and over again."

And very directly, I said, "Well, have you actually shared this with anybody in the business who could do something about it? Because from our side, it is starting to seem like maybe your customers are saying that because you haven't changed anything." So I think a really good litmus test or a bar to hold yourself to as a win-loss practitioner is to make sure that if you are hearing things, do something about it. Actually go and drive the change in your business so that then, in the next round of interviews, you can then go and test, how did this action or change actually land with the customer base itself?

Also, make sure you're doing it continuously that I can get an insight that, "Oh, my workout regimen has gone stale. I need to introduce some more cardio." I can't stop after doing that just one time. I need to continuously do it in order to take action.

But I think there's another example I had just from a win-loss interview yesterday, where I was talking to a VP of global sales and we asked this question about how do they think about perceived value or ROI for this specific type of solution? How were they approaching measuring ROI? And what she said to me, I thought was an interesting, she goes, "I'm very careful with ROI. I can't over-index on that because every vendor comes when we're buying something and they say, 'We can save you $2 million or we can accomplish this for you.' And a business is complicated that a lot of these can be soft measurement that, 'Do I think that this is going to impact our business in some way?' Yes, but we're doing a lot of things, so we can't attribute everything to just one data point."

Which I think is just the example of when you're doing win-loss, if I have really good insight on pricing and packaging, one, two, three interviews might not be confirmatory that the strategy is working when there's a whole litany of things that might be impacting things, so you have to have this continual muscle and a desire to get a lot of information so that you can really make sure with confidence that our strategies and our efforts are working now and will continue to work in the future.

Scott, one thing that we haven't talked about yet today, but I have seen work in other programs before, is actually changing the scope of who you're interviewing, especially along the customer journey. So a lot of times customers will come to us and they'll start by saying, "Hey, we really want to figure out our win rate problem." So they will only focus on new business wins and losses in their enterprise segment.

Or they'll say things to us like, "Hey, I really want to figure out why I'm churning so many customers in my mid-market space." So we will only look at churned customers in mid-market. Now, when a scope of a program is very narrow like that, you probably could start to have some repetitive information over time, so many customers then start to pivot across different parts of their business and do interviews and projects. What are some of the pros and cons of that approach?

Yeah, I think one pro is it's actually a really easy way to make sure you're getting different insights, that if you change the scope, you're going to be asking different questions, so inherently you're going to get different answers. I think the con is you sometimes lose a little bit of a pulse into the real-time factors of a business. I think about NPS became a really popular question that every org wanted to tap into, and I think there was this mistake that some people make that... I'm going to go right back, which is benchmarking. Like, "I want to answer a question on win-loss right now, and then I want to come back to this in three months or in six months with the intention of, 'Let's see what's different now, let's benchmark.'"

Which can be effective where you give yourself time to say, "Okay, we're going to make some goals, we're going to make some actions, we're going to seek this change." But what you lose, when you're only focused on the benchmarking that rigidly, is you're losing the real-time pulse factor into what's happening in all of these different areas that I would say, where you can, evolve your win-loss program by having a bigger scope, but if you take the foot off the gas, you might be missing some important trends that are happening in the moment.

And you also might lose, like going to the gym, you might lose a little bit of the effectiveness that all these different stakeholders in the business, a product leader needs continual insight into how new customers are thinking about the product, how the customer's using the product, thinking about it, and the ones that stop using it are thinking about it. That, if I'm making important product decisions, I can't just base my quarter on one of those subsets, I need to make my decisions in a way that serves all of those in the right way at the right time.

Well, Scott, you've had some really interesting insights here. It is very obvious that you have a ton of experience in this space, and I'm grateful you were able to talk to some of our customers today. To summarize, Scott, if people are having a win-loss partner that is starting to feel a little bit stale, I think one, leveraging a third-party vendor could help a lot because there's a lot of expertise in having a third-party involved where we could ask things in different ways and we have less confirmation bias, things that we already think that we know.

I think two, one thing that you said that I really liked was being able to iterate your program over time, to make sure that you are going deeper on certain questions, that you are continually digging further and further into the customer and leaving them opportunity to speak up.

I think three, we also talked a little bit about actually changing the scope over time a little bit, and if you are narrowly focused on one area, you don't need to hop around to different areas, but you can expand the scope and make sure that you're asking questions to CISOs and also into the analysts and also into RevOps versus sales leaders, kind of changing the scope of who you're talking to, but making it more additive over time rather than hopping, so that you can retain the benchmarks as well.

Scott, anything else for our customers and viewers today that you think would be relevant for them to know about how to keep program fresh over time?

Yeah. Never forget, your competitors and other alternatives are out there trying to learn the same things about you. Your competitors are continuously going to be trying to expose your vulnerabilities, so don't be Blockbuster and don't think, "We're leading this market." And forgetting that you have other competitors trying to offer deals, but you also have new alternatives like Netflix, people that are getting hot in AI that are also trying to come and erode your market share.

That's true. Yeah. You never have truly fully learned everything you can about your market because your market changes every single day.

Yeah.

Okay. Thank you, Scott. It's been a great session today.

Keep winning.

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