Win/Loss Analysis: How to Turn Customer Insights Into Revenue

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All right, I'm here with Drew. Drew is founder of Buried Winds. What's going on, Drew?

Doing great, Matt. How are you?

Good. Yeah. You came to our event in Austin. I think that's where I first, first met you. Were you a drive last year or was it just Austin?

No, I wasn't. I. A lot of people followed Dave for a long time, but I wasn't really even aware of Exit 5 until I saw some advertisements for Austin and I was like, I should check this out. And So I joined Exit 5. I don't know, a few weeks before, like the community a few weeks before you visited Austin. And I was like, I've been missing out. And so I started engaging in the community and going to the live event was like an awesome way to have it come to life. For me and kind of jumpstart how I could take advantage of Exit 5 just as a learning tool, as the networking tool and just as a community for me.

Nice. Cool, cool, cool. Awesome. Love to see that flywheel in effect.

Yeah.

So yeah, tell me a bit about what you're working on right now. Tell me a bit about Buried Wins.

Sure. Well, I am a product marketer by trade. I am a competitive intelligence and win loss agency owner by profession. It's called Buried Winds. And then I, I guess by passion I'm a, you know, mediocre golfer, avid home cook, lover of music and stuff. And then I live in Austin, Texas with my, my wife and my two kids. I have a six year old daughter and a three year old son. But Buried Wins is an agent started after a long time focused on product marketing to help B2B companies win by better understanding their customer. And it's something that I found startups do actually pretty well and the focus on getting feedback, customer, customer understanding. But there's just like kind of gap that emerges as they become bigger B2B growth companies usually like the 20 million, 25 million range and they've got now 10 sellers and a product marketer and they're just focused on executing and so there's just a strong need there. And I bought it before I had done the work before internally and I was just excited by where it could go and how people could use it to help their business.

Yeah, cool. One thing I love about win loss interviews just over like a standard customer interview is like there's a reason for the chat. You know, sometimes you do customer research and it's like, yeah, let's just jump on a chat or a call and I'll ask you some questions for 30 minutes and you'll learn stuff for sure. But after a while those get a little bit stale. Like you're kind of hearing the same stuff. But with winloss it's like, you know, there's a specific reason as to why you won the deal which you know, may get similar over time and lost the deal. But there's something that's very actionable and like it's a fresh cut for a lot of people. So it's really impactful.

Totally. And I do think it's misunderstood too though. And one of the things I mentioned this before we started recording but I really thought about there are three changes I think that product marketers can make. That's really, I think what this episode should be good for marketing leaders for sure. But the three things, changes they can make that. My dream is that I arrive at Burlington, I get to drive next year, and like five product marketers come up to me and say, hey, I got promoted because I changed these three things and it changed this episode, kind of changed how I thought about win loss and it gave us the tools to improve how we go to market with sales, marketing a product. So I'm excited. I'm hoping that that can be what kind of my contribution to the episode. But certainly the community is.

That's amazing. Well, hey, I love that.

Before we get too deep into any of that, though, you were at Pizza Time. You were at a company called Pizza Time, and on your LinkedIn it talks about you did something like 40 plus interviews and it impacted how you went to market and the campaigns you ran. I'd love to hear what was that like for you?

Yeah, yeah, for sure. So Pizza Time, funny name for a company, but we were a virtual catering service. And at the time we were really small company that kind of blew up during COVID Right? Everyone was doing these virtual meetings things and wanted food delivered to them. So we did, we fulfilled that. And there was no product team really. Like, the founder was the builder of the tool and he just kind of built the software and started selling it. But when I came in, I didn't really know much about who the customer was. Like, nobody knew in the company. We just knew people bought the thing. So, you know, I was like, hey, like, I need to sell to these people. There's no onboarding, there's no training, so I need to go learn who they are. So it was literally just a matter of, you know, reaching out to some initial, like power users and getting interviews with them. But then after that it was like, you know, how can I set a couple of these meetings up maybe every month? Like, I didn't try and overdo it, but it was like, maybe every month or every week, can I do like one of these just to keep myself sharp? And the process was pretty simple. Like after I did the interview, I would just send over some notes like in the Slack channel, and just say, hey, like I spoke to this person. They're head of HR at this company size and they love our tool, but wish it did this or they, you know, whatever the, the conversation was. And pretty quickly we started seeing patterns. In this case, it was like people wanted some healthier food options catered because at the time we just catered pizza. But not everyone wants to eat pizza all the time for lunch. And so anyways, that's how that. That got started, and we ended up launching a product that was, you know, a healthier food option. So it was really that simple.

Awesome. Yeah. It makes a big difference.

Absolutely. But cool. You said there's three changes that you want people to make or three mindset shifts, however you phrased it. So why don't we start breaking those down?

Sure. Yeah. So the first one is that executive teams, marketing leaders, even product marketers, people obsess over losses. Almost everybody I talk to in my business, they're like, you have to tell us, go interview people who we lost, find out why we lost. And sure, that's an ingredient to the recipe, but, like, it should not be the meal. And I think people like, we know this, right? We just. It just hurts more to lose than it does to win. So we. We obsess over that. But if I asked you, do you want a hundred more of the your best customer, like, do you want to go win a lot more of them, or do you want to go spend all that time, like, trying to win back people who didn't choose you because they maybe weren't a good fit? I think 99 out of 100 people in the Exit 5 community would say, oh, let's just get more of the people who, like, love us. But for some reason, when it comes to in laws, we get real obsessed with those deals that we lost. Why? And so what I coach people on is, yes, do close lost interviews, but there's a whole world of other things you should consider. So when buried wins does research. We, yes, yes, close lost. Close one. Just wildly underrated. I think people think, oh, we won them. We can go talk to them at any time. But they're so useful in, like, identifying who is a good fit. This is like, is your icp. Why do they pick you? Why do they almost not Right. They probably talk to competitors too. So there's a wealth of information there. What was their criteria of buying? Like, what triggered them to start even evaluating people that landed them, like, with you. And questions like, hey, what concerns do you still have? You picked this vendor, but are you nervous about anything? Did the perceptions change at all? How's the sales experience? Like, there's so much in close one that you can should dig into. So that's the basics. Close one and close loss. But you can apply that same stuff to, like, churn problems and renewal. You should be running win loss on deals that churned a year later or renewed or if they downsold. Right. So it maybe wasn't a logo churn. It was a dollar churn. Go figure out why because that's, that's a massive problem too and it might be even just leading to future logo churn. So that's a big one. And then my favorite because it's, it's maybe just the juiciest is competitive research. And I don't do secret shopping. I think it's a fine thing to do. I didn't feel good like running a research agency and being like misrepresenting who I was in order to get the information. And so I just had to get creative because people were asking for it. What we do, and I recommend people do themselves is we'll go talk to former sellers or former product managers from the competitor. So I'll reach out on LinkedIn, I'll offer compensation for it and I'll sit with them for 30 minutes or an hour. And I'm very direct and upfront like who I'm calling on behalf of and why I'm here. And hey, follow your whatever agreement you made. But man, this stuff we'll get from people who sold for your competitor, it's so good. It's like how do they position against you, how they positioned against other folks? Why did they win? Why did they not? How can we beat them? Like, they'll tell you everything. And salespeople are corn operated so they'll often talk like you pay them cash, they'll sit down and tell you a whole bunch of shit. Oftentimes they'll tell you they'll too like and also like, hey, if that company's hiring, let me know. I think I can make an impact there. But that output tends to be some of the most prized by executives and marketing leaders. And so I think if you combine competitive research, churn win loss, existing win loss and don't just focus on pipeline deals that you lost, the depth of information, what you can help product marketing sales with is just, is just so much bigger. And so that's number one. Don't get stuck there.

Yeah, let's break that one down a bit. There's so much good stuff in there. So obsessing over the losses and the win loss part of it, is there maybe a ratio of like I want to speak to these many deals that we've lost and these many deals that we've won in a set period of time. Like hash. How do you look at that?

Well, I think you should be realistic about who's going to talk to you and like at what conversion rate. The hardest part about my business is recruitment, like getting people to even just talk with us. Yeah. And so we're often getting, you know, 20% conversion rate on outbounds to people we're talking to. Sometimes it's lower. Depends on the industry and seniority. But I think that a good program just looks back, either back a period of time or forward and collects all the deals. Right. And you should expect, let's just aim for, aim for 15% of conversion rate. Right. And, and if you're too picky about like, oh, let's go grab five losses and five wins. Yeah. You might get one conversation. You feel like it's not working, but that's not like really what it's about.

Yep.

So yeah, it's, it's. You do want a good mix of both, but I don't think it's about targeting like one number, a certain number that you need.

Gotcha. Yeah, gotcha. That makes sense. Cool. On the competitive research front, you talked a bit about doing competitive research and combining that with other things, but just like at a high level or broad stroke, like when you say competitive research, what kind of stuff are you looking at usually?

Yeah, well, win loss is inherently competitive research also. Right. You're hearing why people bought from you versus someone else. And so in that lens you're getting the customer perspective. So layering on the former seller perspective is like how they sold against you. It's a lot about how do you go to market, what are the perceptions of people. And sometimes it's not even the reality. Right. There is a company, large company, that I was working for through varied wins and they were losing a lot to this competitor that was much smaller. And we found out that the competitor was positioning them as, hey, we're so small, we're so scrappy, we're going to be so dedicated to you. Our customer service will far outshine this, like behemoth. They're not going to care about you. The reality is my client had a bigger customer success team than the entire startup of the company. Who was positioning that against them? Right. And so once they knew that they could be proactive about that messaging and how they could support them. And so competitive research, when I think about it, is how do you engage with the client and put yourself in the best position to win a deal when it is competitive, whether it's the features that matter, the things like customer success. Example I just gave pricing and packaging, like know how they're positioning against you so that your team is in the best position to win.

Got it. And do you see this? I mean, let's Say, you know, you're in a position where you're not as fortunate to have a company like Buried Winds come in and do that stuff for you. Like, is this something that you think just, you know, your average marketer could do? They could hit up a, you know, some sales reps or former product managers from another company, offer them some, some compensation, maybe it's out of the marketing budget and just run these type of interviews.

Yeah, 100%.

Yeah.

Everything I say today can be done internally. I think it ends up just being a, a size and scale thing. Right? Like when you've got enough actually as you get bigger, you, that's when you start hiring it. Not because you have more people, there's just end up being more product launches and more pricing and messaging work to be done. And for some reason win loss everywhere I've been falls kind of to the bottom of the priority list. Like we always know we should be doing it and for some reason it sinks low. Startups are born out of this. Like, oh, we talked to the customer, we are the customer, we've got to be there. But as you add all these functions, it becomes about execution, right? Oh, we got, we figured out we have some product market fit, let's go execute against it. And in marketing that's like, okay, we've got to run digital campaigns, we got to improve our branding, we've got to get the website right, what our conversion rates. Well, enough time goes by and it could be a year and all of a sudden you haven't talked to the customer a while and the expectations are potentially different. Your competitors that you're facing are potentially different. And so yeah, your question was, can you do this at home? Like, yes, you should be doing this at home. If you do nothing at all, go interview close one deals. It's going to be easiest for you to do. They're the most receptive. And go, go talk to a former seller from your competitor. It's going to, that is the, maybe the number one thing that will go get you promoted. When you present that report to your executive team on how people are trying to beat you and give you the tools to make that stop and actually jump ahead of them. It's awesome.

Cool. I love that. I think at some point in this, this chat it'd be great to just kind of go over how you would run one of these interviews. I don't know if you have that coming up in your plan.

Sure, it's not, but I'm happy to go through it.

Yeah, I think that's Great. I think again, so many people know they should do it. I don't think a lot of people know how to do it. You're a pro. So why don't you walk us through how you run those interviews?

Sure. Should we get through the three things real quick and then jump to it?

Let's do it now. On topic.

Yeah, yeah, yeah. Okay. So when I think about a generalized win loss interview, I think about the buying journey and I try to walk them through kind of all the steps of the buying journey in a pretty casual way. We'll interview internal stakeholders and I like highly recommend you do that from the start. Right. So the first step in like going around this interview is developing your question set. And in order to develop that question set, you could do it internally with what you think is right. But you should really go interview the head of product, the head of sales, the head of marketing, and figure out what are their goals, what are their assumptions. And that will give you a research output that is like much more tied to what they want to accomplish, the revenue goals for the company. So the output becomes better because the questions are better. The other piece of that is just buy in. Like if you present a head of product or sales advice at the end, they're going to be like, hell no. They're like defensive and you're like, who are you to be doing this? If you come to them and say, I want to help support your goals, I'm going to do this research with customers. How can I help you go so much better. So first step, like figure out the questions you're going to ask. When I go through it, generally the timeline is like, what even triggered an evaluation? Is the first question, why did you even talk to my client? Okay, great. When you started evaluating different vendors, what were the criteria you used? And so they'll talk through the criteria. Sometimes they'll talk about, you know, a spreadsheet they built in comparison and you can ask them like, oh, can you show that to me? And the greatest interview is when they'll just screen share and they'll show you like the matrix they built. That's great. So what triggered it? What, what was the criteria they used to buy then strengths and weaknesses of of your pitch. As you go through these questions, really remember that they are a guide. I probably use the questions for 60 to 70% of the time. But like, what you're really looking for are red flags, growth opportunities in that conversation. So you like deep dive when you can sense that they want to say something. There was A problem here or something they loved. Don't get stuck in your questions. So you're going through why they bought, what they were looking for, how you, how they compared them to the competitor, and then certainly don't forget to ask about the sales process itself. Right. Because they'll tell you maybe a lot about the companies, the differences. But it's really good to know, hey, what is some of the other the competitive vendor do well. And I've heard, hey, they brought the head of product to the sales conversation as well as the sales consultant and the seller and made it feel like a great enterprise deal. You brought a kind of one junior seller and it really made you feel kind of inferior in that sales process even though the products seem equivalent.

Right.

And then there's a couple questions that are my like go to ending questions. So you'll interview your team, you'll go through the buying journey, but here's some like nuggets to go steal. One of my favorites is, hey, if you were head of product or the CEO of my company, what would you do to better serve people like yourself? Like, how do you build a company that serves Matt at exit 5? And they will all of a sudden it kind of unlocks a new perspective on how they were thinking. That's the journey of it. And it should feel like a casual discussion where you're really looking at threads to pull. You're not trying to fill boxes to the questions you have. You're looking for those kind of gems to bring back that could change your business.

Yeah, totally. Yeah. That's honestly like some of the biggest mistakes I've made earlier in my career when doing any type of customer interview is I have my set of questions five through 10 and I'm trying to just barrel through them. And you know, maybe I'm building a little bit, but I'm more junior and I don't have the confidence to hold these type of conversations. But the best thing you can do is like you ask something once they answer, pause, write some notes on a piece of paper and as they're talking write some follow up questions on there. Because that's usually where the gold is. I mean, even if only question one and two take you the whole 30 minutes or hour.

Sure.

If that's where the nuggets of gold are, then hey, I don't see a point as to why you should just try and get to the questions for the sake of it. Right?

Yeah. And I record all the conversations so that I can get them transcribing. We like totally Listening, like the whole job is listening for interesting things. You can go pull up.

Yeah, totally. Love it, love it. Cool. Well, I think we have a good idea of like, you know, some things you would ask during these interviews. But why don't we cut back to, you know, some of the changes that you want to see some product marketers make with this stuff.

Yeah, well, it's funny, like I accidentally gave answer too, which was it is far too often people design these like projects or programs by themselves and the way to really win is to bring the other leaders into the mix. Right. Both to design better question sets and to get their buy in. So yeah, I accidentally slid back into number two because it would be so relevant. You said how do you do it? I will say one thing I didn't mention in the how do you do it? Is the. I get asked all the time, like, why do people participate? Why do people. Come on. It's hard for us to get conversations. And there's four reasons why people participate in interviews. One is incentives. People's time is worth money. And I think there's far true assumption that customers or prospects will just jump on the phone and talk to you. And maybe they will, but it's the right thing to do. I genuinely believe it's not a bribe. It's like, hey, I need your time. It's valuable to me. Let me compensate you in some way. So one is incentives.

What does that compensation or incentive look like?

Yeah, for like a SaaS product marketing leader, sales leader, we tend to give $85 for 30 minutes of time.

Cool. Is that like an Amazon gift card, that type thing?

We use a tool called Tremendous and it lets us just like send them an email where they get to pick. They can pick from gift cards they can pick from. They can take the cash directly into the bank account or make a donation. So all those like options are nice and I don't have to worry about it because I used to do amex gift card.

Got it, got it. Okay, cool.

So one was incentive. Two is goodwill. So if they bought from you, they want to see you get better. Right. And so that makes sense. The third is guilt. And so a lot of times when you're trying to sell software, you've met with someone four times, five times, there's the initial meeting, maybe there's a demo involved, proposal calls, and even if they didn't go with you, didn't mean that, you kind of build some sort of rapport. So a lot of times companies, even though they didn't choose you are willing to meet because the seller built some sort of relationship. So you got incentives, you've got goodwill, you've got guilt. And then the final one is just passion, right? Like they love you or they really hate you and they want to share, I would say like one in, I don't know, eight conversations, you say hello, introduce what you're doing and get your permissions. And then all of a sudden you're like, it's so obvious they want to tell you something, like, hey, I have some questions. But like, so what's on your mind? And they will go hard in one direction, positive or negative. So those are the four reasons why people do it. And I think if you keep that in mind and incentivize them, you'll get a higher rate. And then don't forget, it's like any sales motion we get, over 50% of our acceptances come after the first email, right? In a cadence, the second, third or fourth note. And so, so often it's like this side project from a product marketer. They'll ask somebody for an interview, they won't offer any incentive and they don't do any follow up. And it's like if you, if you ever try to guide a SDR to get a business meeting that way, you'd be like, you're not, you're barely touching the job. So. But I understand the resource constraints, but I think that's why a lot of programs just never get off the ground.

Oh yeah, that, that's a great one.

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Go check them out from a timeline perspective. How long after the closed one or closed lost are you sending out that sequence of emails and what does the sequence timing look like?

Sure. Well, the sooner you send it the better.

Yeah.

You know, for win loss interviews you are trying to learn about their buying experience. People conflate win loss with like product research and that's okay. But if you do win loss at like renewal time, that's when you learn a whole lot about their usage. But the sooner you send it after the buying experience, the better. We tried so many different ways to be successful in recruitment and actually the number one way we have it be successful with acceptance rates is we actually have it sent on behalf of the account executive. So usually rev ops will do it. You know, you don't want to give the sales teams time is like a golden treasure that we are not allowed to touch. But if you can send it from the account rep, they've got the relationship, it gets into their inbox, they make the introduction. It's just more Likely to be successful. You asked about cadence. We'll send, you know, the first email gets sent by the account exec. And then, you know, you do it internally or we will follow up maybe three or four business days later. Just say, hey, we sent this first note. We'd still really love to talk to you. And then the other two cadences actually have a kind of a change in tone. One of is an increase in incentive. Right. It's like, hey, we offered you $85. We really care and we really want to know. Here's $105 if you could just spend 30 minutes with us. And then the magic email that we worked really hard on is an email that says, hey, Matt, we reached out. Should we mark you as not interested in the interview? We don't want to bug you anymore. Yep. And that actually gets a bunch of people to pop up who are like, generally interested, but they didn't want to jump in at the time, but don't want to be taken off the list. They were like compelled enough to do it. They kept reading the email. So there's that like, hey, should we, should we mark you as an interested email? So we generally do like four emails. And then, you know, if we need more interviews, when you hit quota, we use LinkedIn, like direct messages.

Cool.

And then we'll make phone calls if we need to. And that. That is the lowest rate, but you'll get interviews that way too.

Cool. Love it. Love it. And yeah, I'm assuming especially with the email stuff, like it would be pretty easy to. For marketers to automate most of this. Right. It's like set up a trigger. Could be in Zapier or whatever it is and want a deal set to close. 1 you an email goes off and they just get put into an email sequence in HubSpot or whatever tool you use, so. Sounds super easy.

Yeah. It's not different than prospecting a new deal. Right. Or trying to get an mql. The difference is just getting them to show up to the meeting is the win. You know, you don't have to then sell them. Like that's the goal is having that conversation.

Cool. And you said about 30 minutes of time is what you ask for, Right?

That's the standard. We'll do these things called VIP interviews, where if there's like really important customer they wish they had a hundred more of, we'll go do an hour with them. But generally the value comes from doing 10, 15 of these interviews that are 30 minutes and connecting the dots. Right. Like what themes are popping up because it's too easy to be anecdotal about a story and it feel like a really important thing. But then you're no better than like a salesperson in a forecast meeting demanding a product because their client said it would have like closed the deal. And like any product team is not looking for that. They want to say this percentage of customers have said it. It represents this dollar opportunity. And so you gotta have enough conversations to be credible in that, in that meeting.

Cool. Cool. Yeah. And I wanna double click on something you said earlier about this is an opportunity to learn more about the buying experience. I think that's a really great point because so much of the time, a lot of the time when you think of, I'm gonna talk to customers and interview customers, it's so that I can influence the product so that we can create the right things and win more deals that way. But the truth is that your product might be already really good, but the issue is how you're talking about and selling it. So I love that piece. But when you do these interviews and your experience, are you seeing both things? True. Like, are they getting a lot about the buying experience and the product roadmap or the product features, like what usually comes out of it? In that sense?

Sure. Yeah. On the product we do get things from the product side and a lot of times it's, hey, in our buying criteria, they had to have this integration for it to even make sense. Like if they're not connected to this accounting system, we just can't do it. Yeah, they had to have these security requirements. So it's more about that critical things that you need to buy. But what we're getting a lot of is what inspired them to choose you versus a competitor. Right. We might find out that, hey, the competitor, although smaller, talked about their expertise in this one industry. And so they, they showed us all these clients that were just like us. The reality is like, maybe my client, they've got, they serve a bunch of industries, but even within that industry they have far more clients. But they didn't talk about it in that way. And so that, that made the deal not go through. I mentioned, like, who are you bringing to the meeting? Sometimes it's about how are you demoing or even just like the, the engagement of the sales team, how responsive is the sales team? And this is really not about, like, is blaming sales for anything. It is about being a great partner to equip sales. I wrote this down because it was like last week Dave said on LinkedIn, Great marketing makes sales easier.

Yep.

Right. And so much of this work is to, like, help arrive that meeting with the buyer in a better place to buy. But also this is marketing work that, like, can help them be more effective. So you can learn about how sales can be more effective, what they should be pitching, kind of what marketing positioning can do. You mentioned that for pizza time, that helped kind of how you thought about the. The positioning and the copywriting, the messaging.

Yeah. So one question I have is, you know, part of this is getting feedback on the buying experience. And I've worked with a fair amount of sales people in my day, and I know that they can get quite defensive sometimes. Not all of them, but we all do it right. When somebody tries to pick apart at work. So how do you, first of all, getting the buy in to get that feedback on the things that they're doing, and then how do you deliver the feedback in a way to the sales team that is not offensive to them or stepping on anyone's toes?

Yeah. Well, it starts with involving them from the beginning. Right. Talking to their sales leadership and saying, like, I'm doing this for you and on your behalf.

Yeah.

And then the key is you are a conduit of the voice of customer. It is not Drew coming and saying that, like, sales is messing up. It's a client or prospect saying some part of their buying experience wasn't great.

Yeah.

And that is objective. Right. That's not like me versus you. You need to fix something. That's like, we're on the same team. We have to hit a four forecast number. Here's evidence that I found. Like, how can we together go use that evidence to help you win more? I think that's. That's the shift. It's not like me saying there's something wrong. It's me surfacing something that came up and asking, how can we make this better together?

Nice. Nice. I like that. Yeah. So it's about the framing up front and. Yeah, pretty much it's all about framing. It's about how you're talking about why you're doing this and what it is that you're doing. And it's just like, I'm trying to help you, and I'm just going to literally take what they said and give it back to you on a silver platter. So I like that.

Yeah. I mean, all. I have a deep belief that product marketing. I'm a career product marketer. It is essentially, in some ways, it is useless because we don't do anything. Like, we don't Build, we don't sell, we don't actually put campaigns out into market. But if we can, like learn to influence through empathy and really care about other people's goals and make sure that the work we do enables them, we can be such impactful strategic partners. We can make a massive difference in an organization, but not if you're not there to help them. Like, we don't do anything, but we can be so impactful. We do a lot. Like, we have so many jobs, there's so many things you can do. But it's really important to keep that in mind.

Yeah.

And one thing in that kind of strategic product marketing lens that comes up is one of the most frequent learnings that companies have over and over and over again as I do this work for them is they will ask me, hey, is pricing too much or do we need this integration? And the answer is not yes or no. The answer is we talked to a bunch of your customers and 60% of them said no. They're actually thrilled with what you're providing today and 40% are complaining. The better question is, should you be going after that full customer set? Is that 100% the right customer set or is your ICP that 60%? And if you focus sales efforts and marketing efforts on that group instead, it's not about fixing a product problem. It's not about fixing a go to market or messaging problem. It's out narrowing the customer segment. And people hate to do that because it's, you know, they're like, oh, well, our TAMs, now it's 1 billion instead of 1.5 or 2 billion. It's like, yeah, but let's go win a huge portion of that instead. And that comes up over and over again.

Yeah, that's such a great point. I love that one so much. And I see it even here at exit 5. Like, you know, certain customers will give feedback about our community or about something and take all feedback seriously, obviously. But for sometimes it's like this is not the person we're building this product or community for. So as much as we want you to be happy and obviously we'd love for you to pay us, but if it's not the right product for you, then you probably shouldn't use it. And we're just going to continue building for that one or whatever that Persona group is. So I think that's such a good one. And I've been at companies before where the CEOs like, we got to do win loss interviews. I want to know why we're losing deals. And a lot of the time if you look at the people that we're losing, it's people that we were never going to win from the start. Like they just weren't the right people in our funnel. We're just so desperate for sales that we were talking to them. Yeah, but the focus was just wrong up front. So I think that's an awesome point.

Well, and I'll give like a really tactical like here's how to go start in a little bit. But one of the keys here and whether I'll tell you for, for starting quickly or however you're doing it is far too many people started win loss program and just apply it to their whole business like all the customers. And the more focused you get, even within your own customer set, the more powerful the results. Because you can connect more dots. Right. We talked about the amount. When I say 10 to 15 interviews, start connecting dots. That's like within your fintech mid market segment. It is not SMB mid market enterprise in your health and beauty and fintech. Right. And if you have a smattering of different company size and different industries, what can you really pull from that? A bunch of anecdotes. And those can be useful but not in the same huge powerful way. So the more you narrow your focus, the more impactful the lessons will be because you'll really get to notice trends.

Cool. Love that part. And you said you're going to get into more of the tactical how tos. Why don't we do that?

Yeah, I'm going to end with how win loss should look and then how to go do it. So the third point that's really critical is when you get you have this conversation now you've got a transcript. It seems obvious, but far too many internal teams or vendors will do one of two things. Give you like pass on a transcript with a highlight or give you kind of a dashboard where you've got a bunch of like themes. And I think you need to treat it like if you're going to go to a board or an executive meeting, what would you do for any other product marketing presentation? Well, you think about key takeaways, an executive slide and then you'd pull up red flags and opportunities. You'd include customer proof in every step of the way because remember we're a conduit, we are not. It's not our opinion. And so that's what makes like a great report and that's what makes it convincing. And that allows that presentation you tie to all those questions you got from the sales leaders and from the product leaders. And if you put it in that format, format matters so much. Presentation is everything. So if your job is a product marketer and you want to incentivize and influence the company to make changes based on your learnings, put in a format that they'll understand, build it into customer stories that the sales team can use to go win deals like understand how product operates. In their case, it's not only format, the other piece is timing. So you're going to have so much more success if you're planning win loss. Around your quarterly business reviews, around your sales kickoffs, around your board meetings. So we try really hard when we meet with a client to say, hey, I know you want to start this program monthly, or I know you want to do this 12 week project, but what internally is coming up. If you've got something in nine weeks, maybe we should focus all the scope around getting you to that because decisions are made there. Anything that happens after is going to be like useless. And my biggest nightmare as a product marketer and certainly in buried winds is just the work gets put on the shelf. You get stuck in Confluence or Google Drive and it's like, well, that was a bunch of time wasted. You got to put this stuff to use. And format and timing is the biggest way to do it.

Love it. The point about the conduit, so at what point are you adding some opinion in there? Right? Because you want to, you obviously want to translate information back to the company and not make it seem like this is just my opinion. It's what people said. But they probably, or maybe not, but I'm assuming they probably would want the product marketer to have some ideas as to like, here's where I think we're going wrong. Here's some potential fixes. I want to open up the floor for discussion, but here's where I'm thinking, so how, how does a product marketer balance that? Should they or should they just simply relate both?

You should not do interpretations before you bring the draft around to that same core group. So before you present to the executive team and the board, bring it to the sales leader, share what you heard, use her context to then start to form recommendations, meet with product and do the same thing.

Right.

Barry wins, works with the company externally. We'll do the same team with same thing with our core team. We'll present, hey, here are the 10 things we learned and they'll tell us, hey, 1, 2, 5 and 8. Those are critical. They're really important because of this and like, let's form a recommendation together. Items 5 and 9, like actually not great. They're like hot topics. We tried that already. Like remove those and you're doing the same thing as an internal vendor of Win Loss. You're meeting with different people, you're starting to form your hypothesis. And that way when you go to that meeting and you make those recommendations, you're both conduit of customer voice. But the recommendation are coming with some backing. It's not something to get defensive about, it's something that they're inspired to go change. And so it's just about starting with the core meeting, testing some hypotheses and then making recommendations once you have better context.

Cool and small thing, but I assume this, this comes down to how the company works itself in the culture. But are you doing all these meetings like virtually or are you doing it Async? Because I could see a world where it's great that you're setting up this program, but now you've added like so many more calls into everyone's calendar, especially if it's this cross collaborative process. So how do you run it? Do you have an opinion as to how that goes?

Yeah, I mean, I think it's gotta be done live, but I don't think it has to be that many meetings. Like, can you get 20 minutes with the head of product and sales? If you're going to invest a whole bunch of time and resources to go do this, just make sure you're asking questions that's going to lead to impact. And then, you know, get on the calendar of the standing meeting to present the information. And when it comes to, I don't know if you're asking this, but when it comes to interviews of your customers, just like you're doing interviewing internally, so much is the follow up question, like so important. And so much value comes from what happens when you hear something intriguing and you pull on that thread and you lose that asynchronously. So true. Help them understand why it's important. Try to limit the time you're going to take from them. But Live lets you dig deeper and understand things you would absolutely just not get Async.

Cool. Love that point.

Okay, do you want to hear what I think people should go do? Like tomorrow?

Yeah, let's do it.

Okay, so 2025, you got your marketing, your sales kickoff, like how do we support this? Or what comes out of it. Most people think of Win Loss as a program like something you have to start and do month to month and it becomes like A whole big thing. You should not do that. What you should start doing is you should look at the second half of 20, 24. You go backwards because you've got all these deals that you haven't touched yet, wins, losses, renewals. So that's the first thing. You got a bigger pie. And then you run a like six week sprint and you invite a bunch of those to conversations and it is just such a better bang for your buck and time and resources to go backwards first. And you learn a ton. You can shine a spotlight on what's working and not working. You can shine a spotlight on maybe things that are being changed or not. You can validate things. It also kind of lets you get buy in for the program going forward. If this is something you do want for your organization, doing a six week pilot with a limited scope and timeline, you're gonna get that approved a lot easily, More easily. And so yeah, start by going backwards. It kind of just proves out the value of the program. And so I really recommend stay focused. If there's a customer you're trying to go with next year, move into a new market or there's a big product thesis and investment, pick one thing that you want to go solve for. Really learn a customer segment that is going to make a huge impact on the business. Go back two quarters, pull deals that look like that. Set up a bunch of interviews over two weeks, 30 minute sessions and then come out with a report that has a. Not just focus on losses. Right. Close one, close loss. Competitive stuff. And it involves your, your company in a broad way and that is in a format and timing that's like effective because it's the beginning of the year and I think you're going to see just awesome results.

Cool. I love that. I think it's important to stay focused. Like you said, it's something I mentioned in the beginning. But you could always jump on calls with customers and just ask them stuff and you will get insights. Like you'll get a lot of good insights. But what I find is, you know, those insights first of all start to become a little stale over time. But they just kind of sit in a shelf somewhere and there's not really much to do with them because they're not attached to the higher goal. Right. So in your example, let's say you know, your company's building a new product for a certain segment of your audience. Well, not only is it going to be easier to get buy in because now whoever's leading that charge is going to want that feedback, but it's just going to be more impactful. Right. It's like the stuff you're learning, you're going to go implement right away, and then you don't have to worry so much about in three months down the road going back to it and being like, oh, what do my customers care about again? Because you implemented the thing right away and applied it to a thing. That problem you're trying to solve right now.

Yeah, totally.

Love it. Cool. So where are we at, Drew? Do we have anything else, or you think we can wrap it up?

I think we can wrap it up. I mean, I would say that I. I'm on exit 5 if you have questions, like, I'm here to help anybody. I think that if you are at a company that's doing, like, $50 million or less, like, do this internally. Go run at it internally. If you can at a bigger company, do it. Otherwise, like, evaluate kind of different options and vendors.

Yep.

But, yeah, hit me up. I would love to help the community with any questions specific to your company or on LinkedIn. Love to connect with anybody from E5 there.

Cool.

Yeah, good luck with it. I, like, really hope to be in Burlington. I hope to see you drive, and I hope that you tell me that you got promoted because you learned something in this process, talking to a competitor, talking to a buyer that, like, changed the way you sold and it made a huge impact.

Love it.

And I guess finally, if anybody's interested, I. We went back and forth. I have this new director of operations. He's incredible. We're running these, like, a single win loss reports, and only for Eve. We'll kind of finish that in December. But I decided for the interview with you, like, only E5 members within, like, a couple weeks of the interview going live. I'll do, like, one win loss report for you if you're, like, in a bigger B2B company. But this is a pleasure. I was so excited about this and talking to you, and I really hope. Yeah. That it was helpful.

No, this was awesome. Drew. Win losses, like you said, it's one of those things that we all know we need to do, but we don't. I always view product marketing as the most important function of marketing. Yeah, you're not running the campaigns or doing that stuff, but you're setting the foundation for everything else that happens. So this kind of stuff is essential to doing that for the team. And you laid out some gold here and some awesome stuff. Hit Up Drew on LinkedIn or Exit 5 if you have any questions. Drew, this has been awesome. And thank you so much for your time.

Yeah, great to see you.

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