After leaving a long sales career, David Rubinstein spent a year meeting more than 300 founders across 41 countries and turned what he heard into a framework for how companies sell now. In this episode of Founded & Funded, David sits down with Madrona’s Anna Baird and Eric Wong to dig into why AI left buyers with more information and less clarity, why deals stall out of fear rather than disinterest, and how founders can cut through.
The conversation covers selling against build-it-yourself AI objections, the return of in-person selling, and why the founder’s own brand is more important to drive pipeline.
This was originally an AMA with Madrona portfolio companies, but we wanted to share David’s full sales playbook with founders, GTM leaders, and operators for a grounded look at how buying behavior shifted and where to focus when the old tactics stop paying off.
Listen on Spotify, Apple, and Amazon | Watch on YouTube.
This transcript was automatically generated and edited for clarity.
Anna: David had this amazing career in sales and as a sales leader. And then Dave, all of a sudden you’re interviewing founders, like over 250 of them in the last 12 months. Talk to me, what happened?
David: I’ve been on this crazy journey over the last 12 months. Having been in sales for a long time, I was starting to feel a little bit burnt out last year. And I’m like, “I’m going to take the summer off. I’m going to play a bunch of golf. I’m going to live my best life, and I’ll figure out what I want to be when I grow up in the fall.” And that was my plan. And what I realized really quickly is that I’m not good at doing nothing. And this FOMO with everything that was happening in the world, not being in the game was really hard, but I didn’t want a boss. And so I had to create a project for myself. So I went on LinkedIn on June 9th, and I said, “I’m going to meet 30 founders in the next 30 days.” I wanted to meet people and learn and see what was out there and add some value.
And what I learned really quickly was the majority of founders that I was talking to, so probably 80%, had never sold before, and they were thrilled to have an opportunity to talk to a go – to-market leader. They’d tell me about their business, I’d provide some perspective, and at the end they’d say, “Hey, this is great. Can we meet again?” And then they’d say, “Hey, I’ve got colleagues who’ve also started businesses. Can I introduce you?” And then the aha moment for me came when someone said, “Are you documenting your journey anywhere?” And I thought, “I’m not, but I record every call, so I will.”
Why the Old Go-to-Market Math Stopped Working
Fast-forward to today, about a year later, I’ve met with over 300 founders across 41 different countries, and it’s helped to codify what I believe is a different way of selling. There are three things that I see driving change in go-to-market that make the world radically different. The first is that the math doesn’t math anymore. I think many of us grew up in a world where go-to-market was a math exercise. You hire this many reps, they make this many calls, it generates this many meetings, it generates this pipeline, you hit the number. But over time, the same tactics got weaker. Tools made them even weaker. Scale imploded the math. And so now inputs go up and outputs actually are going down.
“The math doesn’t math anymore,” — David Rubinstein
The second thing is competition. You come up with a product, and you’re competing with an incumbent, and you used to know where that incumbent had gaps, and you’d build a solution to fill those gaps. The challenge is that the incumbent is evolving so fast, you actually don’t know where the true gaps are. And the second piece on that is that there are new entrants coming to the market every day that you’ve never heard of, and you’ll never be able to keep track of all the people that you’re competing with. That was never a problem.
And the third thing is that the buyer is now talking to more people than they’ve ever talked to before. Before, where you had a really unique idea, there are 10 other people that do something kind of sort of similar, but not exactly. That’s tough. And the buyer has less job security than they’ve ever had. So they are really, really nervous right now. They’ve got more choices, they’re more nervous. And most people will tell you that the change right now is that buyers are more informed due to AI. I don’t think that’s quite right. Buyers have more information, sure. But more information without a way to tell vendors apart isn’t more informed. It’s actually more confused. And that’s what’s going on right now. That’s the shift.
So the people that you’re talking to are not slow because they’re not interested. They’re actually slow because they’re scared. This isn’t about running the old playbook harder, this is about finding what’s the real constraint. And that’s what my SPRINT Framework is designed to diagnose — what’s really holding you back.
The SPRINT Framework for Diagnosing a Stalled Deal
So with that, we’ll start off, and you’ve got to have an acronym if you want people to remember; it’s a minus SPRINT. S = speed. Speed creates attention. When it’s missing, you get great first calls that go nowhere. So the first call ends, we’re all high-fiving each other. We crushed it. It was great. It was an awesome first call, and it goes nowhere. The fix is making sure that you’re showing the prospect a mirror. They have to feel seen. That’s what’s going to turn an education call into a business call. So when you think about speed, do you want to have calls that make buyers think that was interesting or do you want to have calls that make buyers think? And that’s a fundamental thing about speed is how quickly can they feel seen in the call? Because when they feel seen, they lean in. When they don’t feel seen, you look like everybody else. So that’s speed.
P = Problem, the problem creates urgency. When it’s missing, the buyer agrees with you and still does nothing. So think about, are you a painkiller or are you a vitamin? Most founders I talk to can understand what problem that they solve. Very few can answer the question, what’s changed to make solving that problem now actually matter? The majority of problems that exist have existed for weeks, months, years. There has to be a catalyst to make someone act now, so understanding what’s changed is really critical.
The third part of the framework is Results. Results create belief. So when they’re missing, your case studies sound like marketing. The fix is getting the how before the number. When you lead with the number, you’re marketing. If you show your work, you’re providing proof. So I’ll give you an example. We helped a customer reduce churn by 30%. That’s a marketing line. Our agents surfaced the most at-risk accounts 90 days before renewal and designed a customer program for bottom quartile accounts. Our CSM activated the plans; that’s what drove 30% churn reduction. When you have the how before the number, results are believable. When you have the number first, it’s marketing. Everyone you talk to is looking for real results that are believable.
The fourth thing is Implementation. And this is the one that no one really focuses on, but it kills so many deals. Implementation creates confidence. And when it’s missing, deals are going to go dark with no stated objection. Every founder has had a deal that went dark for reasons that probably aren’t put in the CRM. So you had a great demo, you had an engaged buyer, you talked pricing, you scheduled the next call, and then silence. So you go, “Okay, I’ll call that close loss, no decision. Close lost, budget froze.” But those deals died for a reason the buyer never said out loud. And you’re losing more of them every quarter because the buyer’s job security is worse and the noise out there is louder. The number of people that they’re talking to is significantly greater than it’s ever been.
The Question Every Executive Buyer Asks Late in a Deal
So the one question every executive buyer is asking themselves late in a deal is what happens if this doesn’t work and my name is on it? They’re all thinking that. It’s not about your product; it’s about their career. And until you answer it, which means surfacing it first, they don’t move. So the right move, and this is really powerful, has two parts.
The first is you’ve got to surface what they’re thinking before they say it. So it goes something like this, “I want to address something most buyers are thinking, but don’t say out loud: what if this doesn’t work?’ That’s when you’re controlling the call. That’s what you’re doing to make someone feel seen. When you do that, you are different than every other vendor.
Then the second thing you do is you say, “Look, there’s risk in trying this. There’s also risk in not trying it. The difference is one you can see and one you can’t.” The idea is being upfront about the things that they’re thinking about. If you say that you’re great at everything, you have zero credibility, but if you can be honest about how they’re feeling and the risk that they’re experiencing, you look radically different than everyone else that they’re talking to.
There are three, what I would refer to as hidden fears that exist within implementation. The first is headcount: I don’t have anyone to run this. They’re feeling bad about sunk cost. And so that’s where you’ve got to be able to say, “Hey, the tool that you picked was actually the right tool at the time that you picked it, but what got you there won’t get you here. And a lot of the data that we can get from that other tool, we can import it, and it will actually allow this to start a lot faster.” But you’ve got to get them confident that they didn’t make a dumb move and that making this choice doesn’t make them look bad.
And the third thing is speed to value. Everyone is looking for quick wins, whether they articulate it or not. They need to be able to show their leaders, their board that they are leveraging technology to run their business more efficiently. So whatever your product does, I would strongly advise that you have a win that you can provide in weeks, and you can define what that win looks like. But along the journey, the person who put their credibility on the line needs to be able to say, “No, no, no, I’m going to show you that this is going to work and I made the right choice and we’re going to see it in a matter of weeks.” Most founders treat implementation as a checkbox at the end of a deal. I think we’ve got to move it further up the conversations and sooner.
In 2026, implementation is a bigger part of the deal than it’s ever been. You have to remember the buyer’s default is not moving. Every minute that, as a founder, you’re spending talking about the features that your product offers without addressing the risk of moving, the default of do nothing is going to win.
The Trigger Most Founders Leave Out of Their Customer Profile
The next one is niche, and niche creates fit. So when it’s missing, your pipeline is full of maybe accounts. The test is, do you know industry, segment, role, and trigger? Most of the founders I talk to know one or two, maybe three. Industry and segment, I think, are pretty obvious; role would be: what’s the title of the person that you’re calling on? Trigger is one that most don’t have. And trigger is what is the situation that your prospect is experiencing that is perfect for your business? When this happens, you should be licking your lips like this is the best prospect we could be into because that’s what you have to understand. And most people can’t necessarily articulate what the ideal customer profile is. If you can’t articulate those things, really what you’re doing is you’re hedging. And there are a lot of businesses out there that are hedging. “We’re not really sure who we sell to yet, so we’re going to have this huge ICP that we go after, and we’re hoping we figure it out.”
The last thing that I want to highlight is trust. And trust is an interesting one because founders can walk into a room with a level of credibility. You can talk about the rooms that you’ve been in and the people you’ve engaged with and the things that you’ve seen over the course of your career, and that builds trust, and that’s a tremendous amount of credibility. The challenge that happens is trust doesn’t transfer. So when you hire a salesperson, and they watch you sell, and they try to repeat everything you do, and they can’t sell, it’s because the trust didn’t transfer. Providing them with the tools in order to be able to do that is really important.
Anna: I love the addressing the fear because… And we just had a CFO conference and the CFOs were saying a couple of things, and they’re looking at all the products they’re buying. And they’re like, “We’re trying multiple things because we’re not sure what’s going to work and which one’s going to have the fastest result.” And the other thing you’re saying is I need to see from the business cases exactly what ROI we’re going to get here or what is that time to value? So just know that, we just heard from, we had almost a hundred CFOs at a conference and this was part of the conversation, they’re the ones who are approving obviously the deals that we’re talking about here. So I love the highlights on what does this mean and the fear that people have of losing their jobs is absolutely real.
Guest Question: One of the things I wonder about is relationship selling. I’ve met a number of people who probably could use what we’re doing, but I also don’t want to be the person in the room who’s like, “Hey, I just met you. Buy my stuff and let’s get married.” How do you approach that?
Why the First Seven Minutes of a Sales Call Are Wasted
David: And a lot of what I’ve learned about my own style and what I’ve seen out there is people are worried too much about the relationship. My view, you don’t hear a lot of salespeople say it, but I believe, a typical meeting, you have 30 minutes with someone. Is the extra few minutes you spend in the beginning talking about the weather or something like that — does that actually matter? Or when someone gets off the phone with you after 30 minutes, do you want them to think, “I really like her, she’s really interesting.” Or do you want them to think, “Wow, she made me think differently about my business. She could really help me. I’d like to talk to her again.” I’ve seen hundreds of conversations. People are wasting so much time on those first seven minutes of nothing, of literally nothing.
So when I do a call, I do a first call with someone, I get right to it, and I say, “Hey, I want to be respectful of your time. I know it was hard to get this scheduled. Is it okay if we jump right in?” It was a little shocking when I first started doing it, but people were really receptive because they are busy and they did come to learn. And what I found was that if people find that they get value out of the conversation with you, you get more second conversations by providing value and making people think than you do by making people like you. And so that’s one of the biggest mistakes I see people make is over-indexing on being someone’s friend and not really on focusing on diving into their business and making them feel seen.
How to Sell Against “I’ll Just Build It With Claude Code”
Guest Question: One of the things that’s changed, I think for us in the last year is this irrational belief that everyone can build things themselves with Claude Code. The default is no longer doing nothing. It’s, “Hey, I can actually build this internally. I don’t even need to get engineering time. I’ll throw this sharp junior I have on this,” we’re fighting a build versus buy, but in a totally different dynamic. I’m curious, how do we manage that belief that someone has without disqualifying ourself in the process?
David: Yeah, it’s very hard and very real. I look at the analogy with build versus buy. If you think about Salesforce, there’s nothing that Salesforce actually built that anyone else couldn’t have built, but they continued and they continued and they continued and they had something that it’s harder today to follow that model. And that’s kind of the point of your question. I think the speed piece is going to be the first part that’s most important. So before you talk about how what you build is better, you have to make sure that they feel seen. And so what most founders do that I see is someone says, “Hey, well, I could build it.” And your response is, and I say you, but anyone’s response is, “Well, no, you couldn’t. It’s harder than you think. Let me show you why it’s so hard.” That’s the normal response, which with all due respect is wrong.
And so the way I take a situation like that is, “Really? Okay, tell me more about what you’re building.” And “Wow, that’s really smart. Let me understand how you’re approaching that. Sounds like you’ve got it all figured out. Out of curiosity, what made you decide to even take a call with me?” And sometimes when you compliment someone or where you share what they’re doing really well and that they don’t have any challenges, they’ll go, “Whoa, whoa, whoa. See, actually, I wouldn’t say it’s perfect.” “Really? Tell me more.”
And so rather than go head-to-head, because there’s a lot of scenarios where the founder’s natural instinct is, “I’ve been thinking about this problem all day, every day for this amount of time. I’m smarter at it. I can do it better.” Let them talk about what they’re doing. And then the more they talk and the more you ask some questions, you’re actually going to see some chinks start to pop up and you say, “Well, really? Okay, how are you handling that? ” “Well, that’s actually something that we’re stuck on. Can I share with you something that we’re doing in our business?” So it’s a lot of asking for permission. So you ask them, you talk to them, you find an opening. Can I share with you?
Anna: Yeah, Dave, the one thing I’d just chime in on that too, one of the things that I’m also starting to see is there is a keeping up. So everybody started like, “Oh, I can build my own. I’ve got a Claude Code. I’m going to show my bosses how great I’m at. I can Claude Code this, and we don’t need to buy any other tool.” And it’s amazing, except then the next model comes out and then there’s something else that is even faster. And that also is the other component to this to be able to say part of what we’re going to do for you is be the expert sitting on the edge of technology to make sure you’re getting the best every single time something changes because it is going to change so fast. So just one other angle that has been a little bit helpful is to be the partner that’s going to be the expert for them so they don’t have to keep staying on top of this all the time.
David: But that’s a really important point, Anna, because a lot of the companies that I talk to and see, they’re betting on the jockey, not on the horse. They’re making a decision on selecting you not because of what you do today, but because of their belief about where you’re going and are you the right person to take them there? And so that’s really important. If I decide to buy from your company today and six months from now you have the same offering, I made the wrong choice. And so making sure people believe where you’re going is important and that you’re the right person to take them there is so important than making a decision.
Eric: Dave, you want to take one off of chat? The question says that, is it better to attach to a category of technology or an old-school competitor? Because the world’s used to trying to figure out, hey, if I’m going to buy you, what am I replacing? Or if it’s truly horizontal, you take a, hey, the world is changing approach in position a little more broadly. So what’s your thoughts on positioning specific or more broadly?
David: I feel very strongly that the more specific you are, the better. Every category is getting more and more crowded, and it’s getting really hard to compete. There are lots of call recorders that exist, and everyone is a little different. I worked with a company that had a call recorder designed for regulated industries. And so it did all the same things that all the other call recorders did, but they only targeted regulated industries, working with financial services, pharma, and others. And that allowed them to build out the business specifically for those use cases. And when you start to think like that, it’s very easy today to copy features and do that. It’s very difficult to pivot your company to go after a completely new vertical.
And so that was a really good example of someone who started narrow. The companies that I talk to that I’m seeing have the most success, they are really clear about who they sell to. They’re, in many cases, building a wedge, which is the narrowest group that you can go after. And they are so intentional when they have those conversations. When we think about speed and niche, they’re often kind of linked together, as if you have a really tight niche, it’s much easier for the person that you talk to feel seen and to feel like you understand their space. And those companies are the ones that I’m seeing that are growing the fastest.
Why AI Sales Prep Gives You the Average, Not the Edge
Eric: With the top-of-funnel math not mapping anymore, what are you seeing to be the most effective ways to break through early and earn the first conversation where there is so much noise and buyers feel overwhelmed by similar messages? There’s another question that’s similar to this, with all the AI tools out there, how do sellers differentiate? Everyone comes prepared and highly customized. So I think those have similar connotations. I think it’d also be interesting beyond the full sales cycle in that first call, how do you differentiate and cut through the noise?
David: As far as differentiating, so everyone walks in, they have the same prep tools, they’re using the same AI to do the research, and they’re walking into the meeting the same. I think that’s when everyone’s experiencing. And oh, by the way, sometimes the solutions that you’re selling may be similar too. So it’s just very difficult to stand out.
What most people may or may not be aware of is when you’re going in with most of these AI tools that I’ve seen that are doing the research and preparing, the AI is typically an average of all the information that they’re seeing. So the AI that it’s providing is, this is the safe way to engage with this potential buyer. This is the safe way. It is not, in my experience, the sharpest way. And the way that you stand out is not taking the research, which oh, by the way, is better than anything we’ve ever had. How do you leverage maybe some of that research to come up with sharper insights and use that as a starting point but not the endpoint?
And this is something where it’s going to take a whole set of training and coaching for your sellers. I’m spending a lot of time with founders doing that, which is kind of saying, “Hey, how do you become sharper? How do you walk into a meeting and help someone see that mirror, see themselves?” And my goal when I have a conversation is I actually want you to feel a little bit uncomfortable. I want you to wiggle in your seat a little bit and feel a little bit of tension and feel like, “Oh, he’s onto me. He knows that I actually don’t know this answer or that I don’t have the data to make this decision.” That’s the part I think. It goes toward, am I your friend or am I somebody who’s going to show you a mirror and be honest with you and let you know what I’m seeing about your business, but also be the person that can help you solve it?
So in the situations where the product’s the same, the research walking into the meeting is the same, the way you show up for that meeting and the difference between the person that spends seven minutes talking about the weather and the person who, a minute and a half in, says, “Hey, thanks so much for making the time. Is it okay if we jump right in? What I’m hoping to accomplish today is X, and this is how we’re going to do it. Is that fair?” And asking for permission, that feels radically different. And at the end of the day, the person that they’re going to put in front of their boss is the person who’s going to make them look good, not the person that they like. So-
Eric: If you move beyond the deal, the first call, a similar concept, but a different part of the stack, if you think about all the channels out there, indirect, direct, prospecting, all the ways we build a funnel to generate deals, what’s changed the most and what types of adjustments do we need to make in those channels that have changed and what do we need to do to see the meaningful improvements?
Why the Founder Brand Now Drives Pipeline
David: One of the things that’s interesting that I’ve seen over the last year plus is that the founder brand has never been more important. What I see is the founders that have a brand, that have a perspective, that put themselves out there, that are engaging publicly, those companies, I’m seeing a significant degree of success because that’s creating pull. There are a lot of places where if the founder doesn’t have that pull, that all falls on the salesperson.
So where I’m seeing success, the first place is founders building their own brand, founders having a strong perspective about where they’re seeing success, founders being willing to talk about things outside of their own product. If you’re a founder and you’re having product conversations, again, I’m not intending to offend anyone, but you’re lessening your gravitas. You don’t have the same feel, the same impact when you’re talking about the features of your product in your public posts.
When you’re talking about bigger things, bigger industry challenges, like regulations, other things that have macro implications, or just bigger topics that your prospects are wrestling with that have nothing to do with your product, you’re in those conversations, you’re in those rooms, that’s powerful. And so what I look for is I look for founders that embrace who they are, that embrace the problems that their company is solving, but are willing to be part of bigger conversations, of tangential conversations, not in the everything has to map exactly to my product.
It doesn’t work for every category, but for a lot of the categories I’m closest to, I’m still seeing LinkedIn while there’s more and more noise there every day. I’m still seeing wild success for the people that do it well. I think that in person has never been more important than it is today. The concept of selling in your pajamas has been… The 2020s are the pajama decade for sales. And I think as we get further into the 2020s, I think we are moving away from pajamas and back into selling in person. So those are some of the things that I’m seeing.
Anna: Those are great highlights, David. I will pile on: I see founders who are a big presence who are talking about these macro issues in their industry and seeing a ton of inbound coming from that. So I’m going to double down on that because I think it is a great highlight. It’s thought leadership. They want that partner who’s going to be with them six months from now who keeps thinking about what’s next, not just the pain you solve today. You show them the pain you solve today, and then you tell them you’re thinking more broadly about this, and I know the next pain and the pain after that that we’re going after as a company.
Eric: Let’s shift gears a little bit and do another one that I always like. Dave, what are you hearing, what are your thoughts on free pilots versus paid pilots versus no pilots? What are your thoughts on T for C or term for convenience? How do you find that balance between getting new folks signed up and creating actual real durable revenue?
Free vs. Paid Pilots and Why Skin in the Game Wins
David: There’s a lot of tension there. I think the most important thing, whether you’re talking money, not money, is some form of skin in the game. And if I have an executive that’s involved or something that’s specific, I think that feels better. I tend to like some amount of money changing hands even if it’s very small because someone had to go through some hoop in order to do it, and the buyer takes it more seriously. So free, I don’t love. It’s not to say that you can’t or shouldn’t, but free usually means you’re dealing with someone who’s junior because someone who’s senior, if they want it, they can find a few dollars. So I would strongly look for opportunities where someone is willing to put some skin in the game. Even if it’s just to cover your costs, they should have enough respect for you. I think if that’s too much friction to get a small amount of dollars, I think it’s… I haven’t seen as much success on the free pilots.
Anna: I think just be careful we are hearing where people are trying multiple things because they can because they’re free. And if they didn’t have intent to buy something, they were experimenting. And so we’ve talked about, is there intellectual curiosity or actually a budget-paying curiosity? They’re coming to you because there is a problem they’re trying to solve, to all the points Dave made earlier. So please make sure when you guys are watching your funnel, I’ve seen bloat of pipeline with people thinking they had deals in play, and it was just people trying to understand what was out there versus any intent to actually buy.
This was phenomenal, Dave. I think you’re spot on with so many of the things that Lauren and Eric and I are also seeing in our portfolio.