Software Sales Tips by Matt Wolach

Scale Your SaaS

Win More Deals by Knowing What Your Customer Needs – with Brady Jensen


Scaling a SaaS company is more than just a great product or a talented team. It’s a complex dance between understanding the market, aligning sales and marketing efforts, and continually evolving based on real-time insights. 

In this recent episode of Scale Your SaaS, host and B2B SaaS Sales Coach Matt Wolach sat down with Brady Jensen, the Founder and CEO of Aggregate Insights, shedding light on the nuanced strategies crucial for SaaS growth.


Podcast: Scale Your SaaS with Matt Wolach

Episode: Episode No. 295, “Win More Deals by Knowing What Your Customer Needs – with Brady Jensen”

Host: Matt Wolach, a B2B SaaS Sales Coach, Entrepreneur, and Investor

Guest: Brady Jensen, Founder and CEO at Aggregate Insights


Build a Robust Foundation From Start-Up to IPO

Brady emphasizes the necessity of starting market research from day one. This isn’t a phase; it’s a foundational element crucial for long-term success. 

As software companies grow, maintaining this diligence becomes challenging. Successors must ensure continuity in understanding market dynamics, as even a slight deviation annually can lead a company astray.

Unite Sales and Marketing: The Need for a Shared Truth

A key challenge many early-stage software companies face is the discord between sales and marketing. Establishing a validated single source of truth, transparently shared within the organization, becomes pivotal. This unity ensures a common understanding of market dynamics and prevents the blame game often seen when goals aren’t met.

Apply the Buyer-Centric Approach: A Game-Changer from the Start

As Brady highlights, the key to building and growing a SaaS business is intimately understanding your buyer. This isn’t just about crafting personas based on generic demographics; it’s about getting into the mindset of your ideal customer. Early-stage companies often overlook this, but the conversation points out how success hinges on this crucial understanding.


The Pitfalls of Blind Assumptions: Risks in Disregarding Market Insights

A stark reality brought to the fore is the danger of navigating blindfolded in the market. Often, SaaS companies formulate pitches, messages, and strategies based on assumptions rather than concrete buyer insights. This approach leads to costly experiments, unaligned efforts, and potential long-term damage to the business.

The Role of Win-Loss Analysis: A Pathway to Competitive Edge

A pivotal tool highlighted in the conversation is the value of win-loss analysis. Conversations with buyers who chose or didn’t choose your service unveil invaluable insights. These insights aren’t just about software sales cycles but permeate through marketing strategies and product offerings, fostering a culture of continuous improvement.


Brady Jensen

[5:11] “There’s really no better way to de-risk an early stage startup than understanding intimately who your buyer is.”

[14:43] “Toughen up. Talk to the buyer… You won’t do yourself any favors by hoping you got it right.”

Matt Wolach

[10:59] “One good quarter of win-loss can turn around and go to market.”

[21:22] “There’s improvement to be made. If we can’t have an honest conversation about what the improvements are, you’re destined for this, you’re on the tracks towards this big showdown.”


To learn more about Aggregate Insights, visit: 

You can also find Brady Jensen on LinkedIn:

For more about how host Matt Wolach helps software companies achieve maximum growth, visit


Check out the whole transcript of the episode here:

Matt Wolach 

Hello, and welcome to Scale Your SaaS really glad that you made it. Thank you very much. By the way, if this is your first time here, the goal of this show is to help you understand how to grow your company. So if you want to generate a bunch of leads, if you want to be able to close deals, if you want to scale your team and achieve an unbelievable valuation and exit, this is the show for you. Definitely make sure you subscribe. that subscribe button is going to get you all of the best leaders and experts within the industry, people who are going to share their experiences and what they know. So you can scale your SaaS and one of those experts is with us today. That’s Brady Jensen. Brady, how you doing?

Brady Jensen 

I’m doing great. Thanks, Matt. Absolutely.

Matt Wolach 

let me tell everybody who you are Brady. So Brady is the founder and CEO of Aggregate Insights. He is committed to fostering collaboration between sales and marketing teams to drive business success and improve alignment with external market realities. He founded aggregate insights in 2018, a pioneering venture dedicated to bridging the gap between sales and marketing. By enabling companies to validate assumptions through primary source research, the company helps their clients learn precisely what the buyers think, what makes or break a deal, and why customers needlessly churn and then what you can do about it, all of these things are super important to us as we grow. And I’m so glad he’s here to join us. So Brady, thanks for coming on the show. Thanks for having me. Absolutely. So tell me what have you been up to lately? And what’s coming up for you?

Brady Jensen 

Yeah, right now we’re heavy into sales kickoff season. So our clients are software companies, and every year sort of does do the same dance between marketing and sales, putting together what’s going to go out to the sales team as far as the pitch the message, how they want to go to market. And we play a big part in that, for those companies that want to get really clear about how they should be going to market in the context of what the buyer wants from them.

Matt Wolach 

Yeah, that makes sense. And it’s something that I think not a lot of early stage companies think about enough is, what do the buyers actually want? And what I have seen, in my experience, you tell me if you feel the same, the most successful leaders are the ones who’ve really done their homework and had those conversations with their customers with the market and truly understand that buyer and what they need. Would you agree?

Brady Jensen 

100%, there’s really no better way to de risk an early stage startup than understanding intimately who your buyer is, what they care about how they want to be sold to, how they buy the sorts of things that you’re trying to sell. Without it, you’re you’re just blindly walking around without a map that is available to you if you take the effort and and do the work to do that.

Matt Wolach 

I totally agree. So aggregate insights, you guys specialize in data analytics. How did the whole idea for this company originally what what came to you that said, we need this? Yeah,

Brady Jensen 

so I started the company in 2018. And this was after about a decade of time in software myself, I was first a seller, sold software pretty successfully looked at the product marketing folks and thought that looks like a lot of fun as well. And I wanted to try my hand at it. But what I had found is as a as a seller, there was always this lack of trust about what marketing was expecting us to do. Everybody who had been around for a while they’d they had sold, they had their own way of doing things. And the same sort of conversations I was talking about with the sales kickoff. Oftentimes were met with some skepticism sales would get in the meat in a room. Marketing would unveil the pitch and say, here’s how we’re going to have you sell this year. We’re going to even certify you on it which he’ll sales hates. But but puts up with and the salespeople will kind of look at each other half hung over and say, well, this just their opinion, right? Like, why should Why should I adopt a message the marketing folks want me to? And I remember as a seller thinking, well, if I am a seller and their marketing, they know what they’re doing. We probably don’t see what’s happening behind the scenes. They’re probably doing all their homework, they’re gonna bring their receipts, they just don’t show them to us, right. And then I joined the marketing team and was pretty dismayed to find out that every company I was a part of pre IPO startups that went public, early stage, you name it. They weren’t doing it. They literally were coming up with a pitch a position a message In a couple of hours in a conference room with some executives, without having any conversations with buyers without understanding whether or not it even landed with the buyers, and I got frustrated with it, I was part of some of these exercises where I just felt like we were doing a disservice to the sales folks. Bye, bye, getting up with such confidence to tell them how they were supposed to do things, knowing that they were going to be guinea pigs for a good three to six months, while us in marketing would tell them, well just just go out and pitch it and come back and give us your feedback. What did you hear from the market? Right? Well, that’s a very expensive. It’s a very expensive experiment, to have all these really high sale, high paid sales members who should be out there selling confidently helping you understand whether or not you and your opinions happen to be right this year or not.

Matt Wolach 

Yeah, I mean, it’s super expensive, not only their time spent, but the opportunity lost in the fact that your sales team won’t have any success because you didn’t do that research, you didn’t understand exactly what the buyer would need. And it’s just, I mean, falling three months behind in software is is crazy. Like that’s, that’s really hard. This industry goes very, very fast. And you just can’t do that.

Brady Jensen 

well, you can’t. And the even scarier part is, if it’s not working in q1, then marketing goes back to the, to the laboratory and comes up with another guess. Right. And, and you can waste a good year before you ever even find that you know what none of this is working. And then the executives get fired, after they point fingers at each other and decide who’s going to be on the chopping block, when ultimately there is a single source of truth the buyer, but nobody’s really talking to them in this context, sales, sales is there to sell marketing should be talking to them, I was talking to a fortune 500, cmo this week, practicing what we preach, I go out, and we do the same type of stuff, we talked to our buyer all the time to understand and what she told me where she said, marketers are scared to talk to the customer, which all the sudden dawned on me like, it’s why and that is the problem. Almost every marketer has never been a salesperson. Very, very seldom do you get one that was a salesperson and was a successful salesperson before they became a marketer. And it’s this refuge for people who actually don’t want to have those conversations. They’re scared. So you know, my message to the to anyone who will listen is toughen up. Talk to the buyer, you’re not going to do yourself any favors by hoping that you got it right. When you have a chance to get it right the first time.

Matt Wolach 

Yeah, it’s so true. Getting it right. The first time is critically important. And how does aggregate insights help with that?

Brady Jensen 

Yeah, so we do a variety of different primary research components. So you know, if you think about the consumer world, your your, your consumer brands are constantly talking to the buyer. They’re serving the buyer, they’re having in depth interviews with people, they’re doing focus groups on this side of the aisle, you know, b2b software that we spend our time in, folks, they don’t do any of this. So we start at the very beginning stage of saying, Okay, who is your buyer, and we build personas that are not focused on. Here’s, here’s Sally, and she is a soccer mom, and she drives a Mazda rod, who cares, right? What we care about is, can we build a persona that helps people understand for my ICP? Who is this person? How do I sell to them? How do I appeal to them, and it should be a document you can hand to sales and sales can run with and know exactly how they should appeal to this type of person not handed to marketing marketing can interpret it, they can figure out how to use it, it should be something that is enable sales right off the bat. So personas are built by having those direct conversations with the buyer and understand everything we possibly can about them across a bunch of different buyers so that we can start we can start connecting the dots. Right? What is what is the same about all these buyers? There’s no no way for you to appeal to every person in the room, but you can build a composite of the person and sell to that composite and you’re going to be a whole lot more successful than trying to read the tea leaves about exactly what each individual person in every sale sales cycle, wants, wants and needs. And as a companion of that, we also do a lot of work around helping companies understand what their differentiators are. In the marketing world that I come from, and all the clients who come to us differentiators are thought of as, what are we good at, which is a great start, it’s a good place to, to have to open up the conversation. But at the end of the day, I’m a great kite surfer. Nobody pays me to do it. And they never will, right. But I could, I could slap that on a resume, and it wouldn’t sell. You have to put in front of buyers, not what you’re good at. But the intersection of what is unique about what you’re doing doesn’t mean that you’re the only person doing it, but you should be doing it in a new in a unique way. What is durable, right? And in software? That’s always a big question, right? Can they code this thing and three months and take away? What I’m out there saying is what makes me unique? Or do I have a moat around me that allows some protection? Can I prove it right in a way that the buyer in my market will accept. And that’s different for all types of markets. There are very technical markets where that proof needs to be airtight, they’re somewhere, they may give you a little leeway. Those are all things that you can get in a room and have a conversation internally about. But ultimately, the final test is what does the what does the actual buyer value? Right? So we go out with having done that exercise with, with our clients to help take that and then say, Okay, Mr. Mrs. Buyer, what do you care about? What do you what do you place value in? And not only? How do the things that we think you should care about and place value in? That we do? But also, how does that compare to the market writ large, right? Like there are other players in the market. And it’s very simple to go find how people are trying to differentiate, go to any SAS website, and you’re going to see sort of three pillars, and they’re going to use that to anchor their value. And most of them are not taking this step. So you can go and actually find where can you steal, right? Where can you go and say, well, actually, that’s our differentiator, all we got to do is make a little noise about it and prove that it’s ours to have. So helping our customers get a stack rank of everything that a client that everything a buyer cares about. And where you can play the best comes into play. And it’s super important. The last two things are not necessarily on the front end. But it’s sort of in the mid funnel to the bottom of the funnel, is we do a lot of work around helping people understand market intelligence. So not just what does the buyer care about? Or what do they think? But what what’s happening in the market? What are other people thinking about? What are the points of view of the other players in your market, so that you can carve out a successful niche for yourself. And then we do a ton of win loss, which is very simply having in depth conversations with buyers who evaluated you, and chose to buy or chose not to buy. And they can give you a wealth of information about how you did not just in a sales cycle with your sales team. But what about the marketing appealed or didn’t appeal to them? What about the product worked or didn’t work for them? What would have made them change their decision for or against. And having that sort of historical look back to say, here’s what’s happening in our market, here’s how decisions are being made, allows us to then feed all of this stuff in and create this virtuous cycle where your personas are updated consistently. Your differentiations updated consistently, you understand your market in a holistic way. That’s just impossible to do if you’re not having these conversations.

Matt Wolach 

Yeah, and many aren’t. It’s unfortunate, because, man, just the amount of depth that you just went in and explain that is so important. And I can tell you, many, many are not doing it. I’m sure you know that for sure. I mean, these these insights are absolutely crucial. And my guess is I’m sure with the clients you’ve worked with. Once you have those, you have a serious competitive edge. Absolutely.

Brady Jensen 

We have clients who come to us and share that all of a sudden they’re winning 50% more of their contested deals because they’re doing this or they’ve raised their win rate by 10 full percentage points by doing this type of work. And it’s work that that can get put on the backburner if it’s not if you don’t think about how important it is right? If If, if you’re thinking about it, you’re saying, Oh, well, we should always do do more research, right? This is not research. This is not the sort of ivory tower exercise to put on a shelf and think of as like, m&a work or something like that this is boots on the ground. How am I going to tell the people who who are working here, how to behave, what to build, it all feeds into, you’re getting this massive competitive advantage, because you’re getting a holistic view, where other people are getting a very myopic view of whatever internal assumptions and hypotheses are floating around. And one of the big challenges, especially for executives is as the company grows, number one, you may have been the founder who started this work, right? But now you’re a people manager. Now you own a p&l, now you got all this other stuff to do, and it falls to the wayside. And no one picks it up. And you think, Oh, well, marketing’s probably got it, well go check and make sure, make sure that somebody’s got it, whether it’s a third party or it’s in house, it’s a lot of work. It is and it’s an it’s it’s tough to know how to make sure that it’s prioritized, especially when the other more near term sort of quarterly results, stuff creeps in, and you got to get that one pager out or you got to build a new pitch deck. But your if you’re doing it blindly like this, you can do more damage than good, by making adjustments to how you go to market.

Matt Wolach 

I’m sure that’s definitely not what needs to happen. And you talked earlier about sales and marketing and how a lot of times they’re at odds I come from the restaurant industry. And in restaurants, you always have the cooks and the servers kind of at odds, you’re really all the same team. But just because of the nature of each role, you start to question each other, for example, marketing thinks that the leads they’re giving sales are being wasted sales isn’t closing them, and sales says the leads aren’t good enough. And they’re not able to close those types of leads. So how can organizations bridge that gap between sales and marketing and make sure that everybody’s really working together?

Brady Jensen 

Yeah, from my perspective, it’s, it’s really about a clear and validated single source of truth. That’s actually, that’s actually sort of published internally for everyone to see. All right, like even this wind law stuff, which you may, you may think, Oh, we got to protect people. Because there could be some really, really damaging feedback towards one person or another. Like the best companies we work with are the ones that say, you know, what, we’re gonna hold court, we’re gonna do it in a very appropriate manner, no one’s gonna get picked on. But we’re gonna look at where the warts are, right? Like, the whole point of doing this is to say, we, we think our babies, the cutest thing ever. But there’s improvement to be made. And if we can’t have an honest conversation about what the improvements are, you’re, you’re destined for this, you’re on the tracks towards this big showdown. And I hear this all the time from from sea level marketers and revenue guys. They’re always saying, I got 18 months, and then one of the two of us is getting fired, right? Like, if we don’t make improvements to what’s going on, even if they’re doing relatively well, they’re not on plan, they’re not doing well enough, they’re like one of the two of us is gonna go. And nobody knows what needs to be fixed. And, and the, the intellectually curious ones are the ones that tend to hire us. It could be a marketer, it could be a revenue person, but ultimately, they all benefit from having having clear definitions and a clear and a clear sort of system of record, write about what the market is, and is not.

Matt Wolach 

Yeah, makes a ton of sense that I’ve seen those types of scenarios you just described for sure. So what advice would you have for software leaders who are kind of just starting out and need to make sure that they do things the right way?

Brady Jensen 

Well, to me, it’s doing this stuff from the start. Right? I think what I have seen a lot of is companies who are early stage, they get to the point where they’re like, We need to raise VC money, and they will and they will start to do this, but they don’t do it from the start start right. If you’re if you’re bootstrapped, or whether or not you’ve you know, coming out the gate with with VC funding, starting from the beginning, allows you to have historical context about what your market is and how it changes over time. And the biggest thing to me is as you get success Once you will, if you’ve if you follow this and you make the effort, you’re gonna see success. As soon as you get to the point where you’re no longer doing it as the executive, make sure it goes somewhere, make sure it continues on, because it’s gonna get lost in the shuffle. A lot of companies will hire a product marketer, maybe around the 250 person, Mark, maybe 200. And they become the first one that everyone thinks is continuing to do this. Well, there’s a big difference between 15 person startup and a 200 person startup and in that middle gap, nobody’s doing it. And then the product marketers, it’s not, it’s not their fault, the product marketer is oftentimes given 60 jobs. And the and the only way that they can do their job is to decide what they’re not going to do on the list. And this tends to get deprioritize because it feels like a long term effort. I’m telling you, it’s not right, one good quarter of win loss can turn around and go to market. So it’s not something where you have to say, well, this will change our business in five years, it can change your business in a quarter, if you let it, but somebody’s got to continually keep the keep the flame alive. From the start all the way through IPO or wherever the company ends up going. Otherwise, you’re gonna find that somebody drops it. And you end up one degree off every year for five, six years. And next thing you know, you’re in the wilderness and you have no idea what the market even looks like.

Matt Wolach 

That’s scary. Yeah, it’s, it’s something definitely everybody needs to take part of because it’s you definitely don’t want that to happen. Brady, this has been awesome, really appreciate you coming in and sharing all this insight and making sure everybody has a really strong understanding of this. How can our audience learn more about you and aggregate insights? Yep,

Brady Jensen 

so you can reach us at aggregate That’s a GGREGAT e Forward slash podcast. And, or you can reach me directly if anybody would like some more information. I am an open book when it comes to how to do this stuff. The truth of the matter is we get clients because we’re doing it day in and day out. We’re experts in it. But also because it’s really hard. So a lot of folks will look to us to help supplement rather than trying to accomplish this stuff internally, especially since having that arm’s length. Relationship sometimes will allow people to be even more frank with us than they could be with internal folks. But because of that, I’m an open book about how to do it. I’m more than happy to share and you can reach me at be Jensen@aggregateinsights as well.

Matt Wolach 

Okay, perfect. We’ll put all that into the show notes. So if you’re listening and need that, go ahead and grab it right there. Brady, this has been fantastic. Thanks so much for coming in and sharing all this with us. Thanks for having me. Absolutely. And everybody out there. Thanks for being here. Remember, make sure you’re subscribed to the show. So you do not miss any other amazing leaders and experts like Brady coming in and sharing all of their best expertise. You’re gonna love what we have coming up for you. So thank you very much for listening. Hope you got a lot out of it. And we’ll see you next time. Take care