A framework for finding product-market fit | Todd Jackson (First Round Capital)

Todd Jackson (00:00:00):
Finding product-market fit is the single most important thing that your startup does in the first three years, and it's just underexplored and it's just underexplained as a topic.

Lenny Rachitsky (00:00:08):
You've been working on a product-market fit framework.

Todd Jackson (00:00:11):
We've published dozens of articles on the First Round Review, and we have found a very consistent set of patterns, demand satisfaction, and efficiency. But the interesting thing is that you don't go for all three of them from the very beginning.

Lenny Rachitsky (00:00:22):
There's essentially four levels of product-market fit: nascent, developing, strong, extreme.

Todd Jackson (00:00:27):
Roughly, 60% are never going to get past L2.

Lenny Rachitsky (00:00:29):
These four Ps is essentially what you should try to change if you're stuck.

Todd Jackson (00:00:34):
You've got the persona, the problem, the promise, and the product. Lattice kept the first one but changed the others. Vanta changed all four.

Lenny Rachitsky (00:00:41):
Hearing level three tells me level two is basically your pivot from: I'm just grinding, selling, pitching.

Todd Jackson (00:00:47):
This is where it starts to get fun.

Lenny Rachitsky (00:00:53):
Today my guest is Todd Jackson. Todd is a partner at the legendary VC firm, First Round Capital. I rarely have VCs on this podcast, but as Todd shares at the top of this episode, Todd is a very special VC. Prior to moving into venture, he was product lead for Gmail for four years. He was product manager of Facebook's newsfeed, photos and groups, including leading a major redesign of the newsfeed. He's also a director of product management at Twitter and VP of product and design at Dropbox.

(00:01:21):
He's also a founder and sold his company to Twitter. This episode is a very different and special kind of episode. Todd and the team at First Round have spent the last year looking at all of their data and the journeys of the hundreds of startups that they've worked with over the years. And through that, have put together a very practical and very actionable framework to help founders find product-market fit. They're turning this framework into a three-month program for founders, and in this conversation, Todd shares an exclusive peek into the program, in particular, the stages of product-market fit.

(00:01:55):
We talk about how to know which stage you're in, what to do if you're stuck in that stage, and also what you can change in order to get unstuck. If you're a founder or building a new product within a company and feeling like you're not making as much progress as you'd hope, you will find tremendous value in this conversation. With that, I bring you Todd Jackson after a short word from our sponsors. And if you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing feature episodes and it helps the podcast tremendously.

(00:02:26):
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Todd Jackson (00:04:56):
Lenny, I'm excited to be here. Thank you for having me.

Lenny Rachitsky (00:04:58):
So first of all, just to mention you're a VC, which is very rare for this podcast. But you're a very special VC, you have a deep background in product, and I thought it might be helpful just to give a little bit of context on your product background, your product bona fides so people will get a real sense of just how legit you are as a product thinker.

Todd Jackson (00:05:17):
Yeah, you got it. So I am a VC. I'm a partner at First Round Capital now, and I've been at First Round for four years. But I was not a VC before First Round. So I started a company in 2013 called Cover, and that was actually funded by First Round 11 years ago. That's how I got to know First Round. And before that, I had worked on Gmail as the product lead in the early days, early 2000s and at Facebook.

(00:05:39):
And then I started Cover, and we ended up selling Cover to Twitter in 2014. And I worked on a bunch of different products at Twitter. And then I was the VP of product and design at Dropbox. That was 2015 to 2018. So I have always loved product, and that's actually the reason now that I love being a seed stage VC because I love investing at the early stage founders who are pre-product-market fit and then helping them get there. And I just love doing that over and over again.

Lenny Rachitsky (00:06:07):
I feel like we could have a whole other podcast episode on why you decided to move into venture versus staying in product.

Todd Jackson (00:06:12):
We can do it.

Lenny Rachitsky (00:06:13):
But we're going to stay focused. So the reason we're here is that for over a year, you've been working on a product-market fit framework, essentially, a framework to help founders and product teams find product-market fit, which we should talk about this. But this is the most important thing you've got to get right as a founder in a product team is finding product-market fit. I got a peek at this framework. I love it. I love the way you've structured it, the way you're thinking about it.

(00:06:36):
So what we're going to do today is walk through this framework in depth. First, I just want to spend a few minutes on setting a little context just so people understand who this is for and how to think about this. So maybe a first question is just why do you believe people need a framework for finding product-market fit? And just also, if you want to touch on why is product-market fit so important? Why is that something people should even be thinking about?

Todd Jackson (00:06:57):
The thing about product-market fit is that I find it's mysterious to a lot of people, and people tend to think about it purely as an art rather than a science. And all the advice that you find out there on the internet is very general when it comes to product-market fit. You'll know it when you see it, you'll know it when you have it. It's not specific. And there's so many other startup topics where there is good content on the internet like hiring your first salesperson, running board meetings, stuff that is specific and tactical. But there isn't that much content around product-market fit that is that specific.

(00:07:33):
And so I think that's actually why Rahul from Superhuman is well-known for his approach to finding product-market fit. That was published on the First Round Review in 2018, and it was immediately popular and interesting to people. And I think the reason is because it was specific and because it was tactical and it brought a little bit of the science to something that people thought was just an art. And I think it's why your content is really popular too, Lenny.

(00:07:57):
You and I worked on this product validation article together a little while back, and the seven part series that you did on B2B SaaS companies and the PMF benchmarking data that you had, I think it was how long it took to get to a product and a customer and to product-market fit, that was super well-read. And there just isn't that much good specific content about this. But like you said, product-market fit is the single most important thing that your startup does in the first three years and it's just underexplored, it's underexplained as a topic.

(00:08:28):
So we felt this was a very important thing to do, something worth focusing on. And I've personally talked to hundreds of founders about this topic. We've published dozens of articles on the First Round Review. We call this our Paths to Product-Market Fit Series where we interview founders about the early days. And I'm just always interested in what are the patterns. If you talk to enough successful founders, and in this case, it can be enterprise founders, and you ask them, "What did you do in the first six to nine months of running your company, of starting your company? What patterns emerged from that?" And we have found a very consistent set of patterns, and that's what we decided to base our framework around.

Lenny Rachitsky (00:09:07):
Amazing. And I think you're at such an interesting Venn diagram of exposure to develop something like this. One, you have a deep product background, you started a company, you see tons of startups going through the journey, many succeeding, many not. So I get why one, you wanted to do this and why I think this is going to be so valuable to a lot of people. You talked briefly about why product-market fit is so important, and maybe it might be helpful just to share a little bit more just why is this something people should be so obsessed with and why did you spend so much time developing this?

Todd Jackson (00:09:40):
I think as a founder, there are so many things you have to do. You have to pick a market, you have to find a co-founder, you have to hire a team, you have to raise funding, you have to build a product, you have to sell a product. And so sometimes it gets lost that actually, the only thing that matters in the first couple years is finding product-market fit and actually, what we define as extreme product-market fit, and I'll go into that. Because if you find extreme product-market fit, the momentum just carries you, and the market pulls you along. And it's easy to know what to build because you're building the thing that your customers want and it's motivating as a team. It's easy to hire people, everything becomes easier if you find product-market fit, it is the thing that propels the company.

(00:10:25):
And so we are a seed stage venture firm. We tend to work with very early founders who are pre-product-market fit. And the hard truth about it is that most of them don't get past the first couple levels of it. The majority of startups do not get past, what we call, level one product-market fit or level two product-market fit. And I'll go through and define all that stuff. They get stuck at one of those first couple levels. And if they can unlock the right product and the right way to explain it to a customer and make a customer deeply satisfied, and there's enough customers out there like that, it just pulls the whole thing along.

Lenny Rachitsky (00:11:02):
Who is this framework for specifically? And for people that are listening, how do they know if this is for them or not?

Todd Jackson (00:11:07):
This is for early B2B founders, and specifically founders who are doing something that is more sales-led than bottom-up. I think bottom-up is its own world. It's closer to consumer product development in my mind. And I have done consumer products. Consumer product, I think there is a little bit more alchemy involved. It's about having great taste and finding the right thing at the right time and it's like catching lightning in a bottle.

(00:11:36):
I think the good thing about enterprise, and specifically sales-led B2B, is that there is more science to it. And so it is for sales-led B2B founders who are in, let's call it, the first six to nine months of starting their company and want to set the foundation for product-market fit right from the beginning.

Lenny Rachitsky (00:11:53):
Awesome. Okay. So B2B founders, sales-led in the first six to nine months of their journey. Awesome.

Todd Jackson (00:11:59):
That's right. Yes.

Lenny Rachitsky (00:12:00):
You talked about the science of this. I imagine you don't want to overpromise this is going to help you find product-market fit, step one, two, three profit. How do you think about just what the benefits of this are and how people should think about the chance that they will find product-market fit at the end of this journey following this framework?

Todd Jackson (00:12:16):
We can't guarantee success here. I just want to contextualize that finding extreme product-market fit is very, very hard. And what we are trying to do is increase your odds, increase the odds, reduce the role of luck, give you a framework and way of thinking about the things that you need to do. And I think that that can increase the odds. Like I said earlier, the majority of startups are getting stuck at these first couple levels. I think if you know what the path looks like and you know what the levers are at your disposal and you know what you need to aim for, I think we can get more of these companies to level three and level four product-market fit, which is where you really want to be and where you have a very valuable company.

Lenny Rachitsky (00:12:54):
Perfect. Okay, final question. You launched a whole program for founders to go through and learn all of this in depth, many week kind of program. We're going to be covering a lot of it here for folks that want to go a lot deeper and actually go through this program. Talk about how they find this and how this program works.

Todd Jackson (00:13:11):
So we launched a new program, and we call it Product-Market Fit Method. It is designed, like I said, to help early B2B founders increase the odds of finding product-market fit. It's totally free, it's a very intensive program. You can see all the details at pmf.firstround.com, and the application deadline is May 7th. The program starts on May 29th. And we actually ran a beta version, a test version of this late last year with 11 founders, I think probably some you know, Lenny, from Stripe and Plaid and Airbnb and Twitter. And the feedback, it was great. It made me feel very good.

(00:13:47):
One of the founders was like, "I feel like these 14 weeks saved me two years of time in what would've been wandering through the desert." And so there's eight sessions in the full program, and the first one is the one we're going to do today. So the first session is on what we call the levels of product-market fit. The second one is on customer discovery, and we actually refer to it as dollar-driven discovery. We get very specific about not just the normal way of doing customer conversations and customer discovery, but how do you find that a customer is willing to pay money for this thing and a lot of money?

(00:14:22):
We talk about market validation, product positioning. We do a section on design partners because I think a lot of founders have questions about that. How do I find the right design partners? What's the right way to structure an agreement with them? How do I convert them to paying customers? All that stuff. We talk about product iteration and pivots, and I refer to this stage as the grind, the grind of product iteration. And then we spend a ton of time on founder-led sales.

(00:14:47):
And the reason that we do that is we really like working with very technical founders, builders, people that are either engineering background, product design, data science, people who are builders. So that's the program in a nutshell. And like I said, any founder working on a new B2B SaaS company, welcome to apply. And then bonus points if you are technical, like I said, if you have a clear product idea or a hypothesis, but that you're less than six to 12 months into building the company.

Lenny Rachitsky (00:15:19):
I love how incentives are so aligned here. You help companies find product-market fit. If First Round does great, everyone does great. It makes so much sense to build something like this. One thing I can't help but mention or ask about is you said it's an intensive program. How do you find founders have time to do something like this and also be building their company? I know this helps them build, but how do you just think about they have so much to do, they have time to do a program like this?

Todd Jackson (00:15:41):
The way that we think about it is that the program roughly takes about 10 hours a week for each founder, and it's 10 hours of work that you were going to be doing anyway. It is literally you're talking to customers, you're improving your positioning, you're doing critical thinking about your market and what you should be building. And so the way I think about it, and the way I've heard from the 11 founders that went through it is it just added structure to what I was doing anyway and it actually made me more efficient.

Lenny Rachitsky (00:16:10):
Last question, you mentioned that it's free. How does that work? How does that work for everyone?

Todd Jackson (00:16:14):
So it's 100% free and literally, it costs you $0. We give you $0, we own 0% of your company. And it's pretty different than I think a lot of other programs out there. And this is just something we do. Over the years, we've run First Round Angel Track, which I know you were in, Lenny. We've run the First Round Review for 10 years. We make these things free and our belief is that you have to create value in the ecosystem.

(00:16:36):
You have to put stuff out in the world that is useful, and if you can create that value, create enough value with the audience, then you'll be able to capture that value at some point. And so we think there's a win-win here. We get an inside look at some of tomorrow's great companies and they get an inside look at First Round.

Lenny Rachitsky (00:16:49):
Got it. So companies don't have to take money from you guys to be a part of this program.

Todd Jackson (00:16:53):
That's right.

Lenny Rachitsky (00:16:54):
Okay, let's get into it. Let's talk about this framework. Maybe just as a broad strokes overview, how does this framework work? How do companies find product-market fit?

Todd Jackson (00:17:03):
So the framework starts with a very simple idea that is product-market fit is not a one-size-fits-all thing, and it doesn't just happen overnight. And for B2B companies, specifically, it does tend to follow a repeatable pattern. And so we start with defining the ultimate goal. The ultimate goal is to get to extreme product-market fit. And we have a precise definition for this. Let me read it to you. So extreme product-market fit is a state of widespread demand for a product that satisfies a critical need and crucially can be delivered repeatably and efficiently to each customer.

(00:17:40):
And so there's three key ideas in there: demand, satisfaction and efficiency. And I think efficiency is worth highlighting because that's what most people would leave out of their definition. You talk about like, "Oh, it's a product, people like it. That's good, that's product-market fit." But if you look, there's products out there. I was a big fan of WeWork, as a customer of WeWork. And I'm a fan of Casper and these other products. Those products managed to achieve customer satisfaction and demand, but they never got the efficiency right, and so the whole business just never worked at scale.

(00:18:18):
And my partner, Brett Berson, at First Round, he gives this example of the $100 vending machine, and I really like this example, which is imagine I built a vending machine and I stuck it in the middle of San Francisco. And you walk up to this vending machine and you put a dollar in and $100 bill comes out. And that's the product. That would have insane demand. There would be a line at that vending machine. I think people would be extremely satisfied. They'd be like, "This is awesome." The retention would be very good. I'm sure they would come back tomorrow. But the whole thing is it's ridiculous. The whole metaphor is ridiculous because it's just not viable to do something like that.

(00:18:59):
And yet you see a lot of startups kind of do this. They're basically with their products, giving away $2 for $1 and it gets them pretty far. But that's not real product-market fit. And so that's one of the reasons that we think efficiency and how you think about the economic model of what you're doing is very important. And then this other aspect that I like, which is we have this concept that we call the marginal customer, and the next incremental customer you're going to get for your company, for your product. And if you have product-market fit, and as you are progressing along this journey, the marginal customer should be getting easier and easier and easier to get, easier to acquire them, easier to give them good service with a good product.

(00:19:42):
And that means your efficiency is increasing along the way and your product-market fit is strengthening. So you've got to have all three of those things: demand, satisfaction, efficiency. But the interesting thing is that you don't go for all three of them at once from the very beginning. And so product-market fit, it happens in the sequence of levels, it happens over multiple years. And for the best enterprise companies, I would say they tend to reach extreme product-market fit in roughly four to six years. There's some variance, but roughly four to six years. And so we label these four levels. We say level one product-market fit is nascent product-market fit. Level two is developing, level three is strong, and level four is extreme. And that's where you want to get.

(00:20:26):
And along the way, you're trading off these three dimensions: satisfaction, demand, and efficiency because they're intertwined. You could spend a bunch of money on marketing, and that's going to increase your demand, but you're decreasing your efficiency if you do that. You can invest a bunch in efficiency and automating a whole bunch of stuff, but that actually might harm the customer experience and you're reducing satisfaction. So that's an interesting thing, I think, is you're actually making trade-offs at each level and what you should optimize for at each level is different. And so we talk about all these signs, whether you're getting stuck at a given level, how do you get unstuck and how do you progress along this path.

Lenny Rachitsky (00:21:01):
Amazing. And we're going to go through each of these. And the idea, as a listener, what I'm thinking is you're probably in one of these buckets. What we're trying to do is help you out of that bucket and help you move further up the ladder to the next level. So just to summarize, I have my notes here. So there's essentially four levels of product-market fit, basically, the strength of product-market fit that you have: nascent, developing, strong, extreme.

Todd Jackson (00:21:24):
Yes.

Lenny Rachitsky (00:21:25):
Okay. And then you have three dimensions within each of these levels: satisfaction, demand, and efficiency. We're going to talk about what all these mean and how you use these. Let's talk about level one, nascent product-market fit. What does that look like? What do you do when you're there if you're stuck? And what are some examples of companies that felt nascent product-market fit?

Todd Jackson (00:21:44):
Yeah. Okay, level one, nascent. So at this point, you're probably like a pre-seed or seed stage company. You've got less than 10 people on your team. And at level one, your job is to find three to five customers that have a particular problem that is worth solving and to deliver them a satisfying solution. And you got to pick a problem that is both important and urgent to them.

(00:22:08):
And the solution that you deliver needs to satisfy some kind of promise that they care deeply about. So of the three dimensions that you just recapped, Lenny, it's satisfaction first, demand second, efficiency last when you're at level one. It's actually okay to be inefficient at this stage if it helps you uncover something that delivers an insanely good customer satisfaction. And so I think that one of the best examples I can think of that is this company called Vanta.

Lenny Rachitsky (00:22:37):
Love Vanta. Also, a happy sponsor and I'm an investor. What a great example.

Todd Jackson (00:22:42):
What a great example. So Vanta was founded in 2016 by Christina Cacioppo, and she had come from Dropbox and we got to work at Dropbox together, which was awesome. She was the PM of Dropbox Paper at that time. And so Vanta, it's a company that does compliance automation, continuous monitoring. And most startups think of Vanta is how you get a SOC 2, but they didn't do that at first.

(00:23:03):
And I remember in 2018, Christina and I went on a walk around the South Park neighborhood in San Francisco. And this was the first time I heard the idea of Vanta. And she had actually, in 2016, 2017, tried a few other ideas. She had this smart speaker that would record meetings and it would send meeting summaries over Slack.

Lenny Rachitsky (00:23:24):
B2B Alexa is what she called it. I remember.

Todd Jackson (00:23:25):
B2B Alexa. And she had this other idea, something about dropshipping, but she didn't know anything about dropshipping. And she had just been in this mode of like, "We're building stuff and then we're seeing if anybody wants it." And then she realized that wasn't working and she changed what she was doing. And she started talking to potential customers, and she was very interested in the idea of security and why a lot of startups didn't use any security products.

(00:23:48):
And she was talking to security engineers and CISOs and just CTOs and startups. And she would ask them, "What is the thing you hate most about your job as it relates to security?" And over and over and over they would say, "I hate filling out the security questionnaires. I hate doing the compliance audits. It's so much grungy manual work. I'm in there filling out spreadsheets and taking screenshots of my AWS account. And the whole thing just doesn't make sense." And she had actually felt this herself when she was on Dropbox Paper and the experience of getting a SOC 2 was onerous.

(00:24:26):
And the reason that she needed to get it is because we wanted to start selling Dropbox Paper into enterprise. And so she said to me, "There's this pain out there, I think I can solve it, and I think there might be a revenue unlock." And I was like, "What do you mean by that?" And she was like, "Well, I've got these first few customers or design partner, pseudo customers. It's Segment and Front and Figma." And this is 2017, '18. So these companies were smaller at the time, not the big companies they are now. And she was like, "Yeah, they're trying to sell into Fortune 500 companies. One of them is actually trying to land a Fortune 10 right now. And they said the thing that's holding them back is they don't have compliance certification, they don't have a SOC 2.

(00:25:08):
"And I told them, 'Hey, what if I do that for you?' And they were like, 'Oh, you can just do that?'" And she was like, "Yeah." And she did it, and they landed the deal. And it's one of the clearest examples to me of a product that satisfies a promise, but this product is going to unlock revenue for you. You are going to be able to land this enterprise deal. And so I think they just did a phenomenal job of that. And that's what you're looking for when you're at level one, a problem that really matters to three to five customers.

Lenny Rachitsky (00:25:41):
That specific example, I think she delivered a spreadsheet. There was no product, she just manually filled out a spreadsheet and gave it to them.

Todd Jackson (00:25:49):
Completely manual. She was the one behind the email address posing as the AI, but doing it herself. And I think that's revealing of it's okay to be inefficient at level one, as long as you are delivering incredible satisfaction.

Lenny Rachitsky (00:26:03):
Yeah, I was just going to say that. This is the ultimate example of efficiency is not important, which I love, is what you're pointing out at this step. I know you're going to share another example, but just to summarize what this stage feels like from earlier when you talked about, essentially, of less than 10 people, you're trying to find three to five customers. I think that's so important. You're not trying to find tens or hundreds, you're just like, "Three to five people." And the customer element, I imagine, you're implying they're paying you money.

Todd Jackson (00:26:29):
Yes, they're paying you money and you're delivering a product that solves a problem for them.

Lenny Rachitsky (00:26:33):
And the product could be potentially a spreadsheet or super Wizard of Oz at this point even.

Todd Jackson (00:26:37):
Yeah, that's okay at this level.

Lenny Rachitsky (00:26:39):
I know RAMP actually had barely a product when they started selling. Initially, they had someone just updating things behind the scenes on these dashboards. And then you talked about the problem needs to be important and urgent, which connects to people paying attention to a startup that they don't trust or know anything about because the problem is that important and urgent. And you also mentioned it has to satisfy a promise you're giving them, "We'll solve SOC 2 for you," and then you actually accomplish that.

Todd Jackson (00:27:03):
That's right.

Lenny Rachitsky (00:27:03):
Is there anything else maybe as a benchmark that tells you you're at this step of product-market fit?

Todd Jackson (00:27:10):
Yeah. So like I said, you're pre-seed less than 10 people. Probably, your demand source at this stage is mostly people you know. It's friends and family, it's your network, maybe it's VCs. You haven't probably done a lot of cold outreach at this point, and it's hard to find customers. You're trying to get three to five. It probably takes you 20 warm intros to get one, something along those lines. So maybe to get to three to five, it's at least 50 conversations. That's very normal at this stage because you're just trying to find the right problem and find customers who have it. You're probably in the $0 to 500K ARR, somewhere in that zone. I would say that you're at level one.

(00:27:48):
And then there are metrics to track efficiency, things like burn multiple, gross margin, NRR all of these things. All of them are just not applicable at this stage. It's too early and you shouldn't be worrying about that stuff. And so you want to be feeling this sense of progress that there are customers who need what you are building and the thing you're building works. And so conversely, the signs that we see a lot of founders get stuck, and this is a very common level to get stuck. And so if you're hanging out here for six months, nine months, 12 months, and there's yellow flags that are appearing, you're starting to feel stuck.

(00:28:24):
And so the yellow flags are something like, let's say, your product disappeared overnight, your customers wouldn't be super disappointed. Let's say you have a handful of happy customers. Let's say you've got four or five customers, but the most important feature is actually different for each one of them. That starts to look a little bit more like a consulting business than a product business. Or it just feels incredibly hard to find the marginal customer, the next new customer. Or your usage is low. The product is in their hands, but the usage is low, it's not growing that much. It lasts for six months.

(00:28:55):
And I think, there's a really good example, Jack Altman, who's the founder of Lattice, he founded Lattice in 2015. We've talked to him a bunch on the First Round Paths to Product-Market Fit and other things. So for those who don't know, Lattice is a people management platform, but it didn't start that way. And most people don't know about this, Lattice actually started as an OKR tool back in 2015.

Lenny Rachitsky (00:29:15):
Oh, didn't know.

Todd Jackson (00:29:16):
Yeah. And so Jack had just seen this at other companies. He's like, "Okay, companies are doing OKRs, but they're not very good at it and it causes a lot of arguments among the executive team and employees are noncompliant. They think the whole thing's dumb. So I can fix that with software." And so the original version of Lattice was for managing OKRs. And he was able to sell it. And so his buyer was the head of HR, and they said, "Okay, yeah, we'll give this a shot." And he had a couple companies using it, and they would use it for one quarter. And then the next quarter would come around, and they were like, "Didn't go that well last time. I don't know, the employees don't seem to like it. I don't know."

(00:29:59):
And then the quarter after that, they were like, "No, we're not buying this, we're not using this." And so Jack pulled off the pivot to people management. And the way that he did it was he actually kept the persona. And so this gets into the ideas of the four Ps, and I'll talk about this a little bit more. This is our version of the four Ps. You've got the persona, the problem, the promise, and the product. And all four of these things have to line up. Your product has to deliver a promise that solves the problem of your persona. And so Jack actually kept the persona. He was like, "I've gotten to know these heads of HR really well over the last six to nine months. I text with them, I go out to coffee with them, I'm friends with them, I know them really well. This OKR thing just doesn't seem to be a big deal for them, but they've got other problems that I could look at solving."

(00:30:53):
And the interesting thing was that timing, it was mid-2010s, performance management had started to come back in favor. It was like this pendulum. There was a period of time where performance management was really important, and then all these companies were like, "We're not doing this anymore." And then the pendulum swung back, and around 2015, 2016 was that time. And so Jack literally showed them Figma mock-ups. There was no product, but he's like, "What if I could solve performance management for you in a way that is much more modern and much more employee-friendly and manager-friendly and the whole thing's just going to work better?"

(00:31:25):
And the response was off the charts. And people wanted this thing. And I believe he sold his first five or 10 customers with Figma mock-ups. Before, he hadn't built anything really. And so that, I think, is an interesting example of he was stuck in the zone of people didn't love what he was doing. He kept the persona, but he changed the problem that he was solving and the promise he was delivering through the product. And we do a whole section on pivots and when to pivot and how to pivot. And I think this is actually the best framework for this, is the four Ps. Lattice kept the first one but changed the others. Vanta changed all four.

(00:32:08):
There are other products like Plaid that actually kept elements of the product they were doing. So I don't know if you know the story of Plaid, but Zach Perret was building... Plaid started out not as like a API for bank accounts. It started out as a consumer budgeting app. It was a consumer app. And it just was supposed to help you save money and budget and stuff. And it just wasn't that popular. And the founders were frustrated, but they had built this part of the product that enabled the app to connect to your bank accounts, and had solved all the nitty-gritty issues with that. And then they found that their friends wanted to license it from them.

(00:32:46):
So Zach had a friend at Venmo who wanted to license this, and they got Robinhood at some point, they got Coinbase at some point. So that's an example of they actually kept a lot of the code that they had written. They kept the product, but they completely changed the other three Ps. Instead of solving for consumers who have a problem with budgeting, we are going to solve for developers at fintech companies who have a problem connecting to bank accounts. And it was a total flip of the four Ps. But that's why I really like this framework because I think it really helps founders think in a structured way about this.

Lenny Rachitsky (00:33:15):
Todd, this is amazing. I'm so happy we're doing this. I think this is going to help a lot of people. I want to move on to level two, but first let me try to summarize some of these key elements. So these four Ps is essentially what you should try to change if you're stuck in this level or any level. And just to summarize, you can change who you're targeting, the persona, you can change the problem you're solving, you could change the way you're pitching it, which is the promise is how you describe it, basically positioning. And then you could also just change your product. You mentioned Vanta changed all four, some companies change just one. Any advice for how to know which of these to change? What points you to change this versus change that? Is there anything that you've seen?

Todd Jackson (00:33:55):
I think different founders approach this differently. And I've seen a lot of founders who are build first and then sell, and I've seen a lot of founders who are sell first and then build. And they can both work. I tend to gravitate towards the, "I want to sell it before I build it," because I really want the signal from customers and I want that to be the guide and the oxygen that drives what I'm building. I find that very motivating. I also find it easier, honestly.

(00:34:25):
Rather than guessing like, "Oh, I'm going to write 50,000 lines of code and then see if somebody wants this thing," I think it's better to talk to a bunch of customers, know that, "Hey, if I had this thing, if I could build this thing, I know it would sell. I know these people want this thing." So I tend to approach it from that point of view and therefore, I focus on the persona and the problem and the promise. What is the promise that is really going to click for that buyer, for that persona? And then the product's job is to satisfy those first three Ps really.

Lenny Rachitsky (00:34:55):
And obviously, those are much easier to change and play with versus rebuilding your product. So if nothing else, you should probably start there. I actually have a post with a bunch of awesome examples of changing the positioning, changing the persona, and so we'll link to that in show notes if people want more examples. Finally, let me try to summarize the stage. So I think it's important to note at this nascent stage, it's not roaring product-market fit. It's, as you described, very nascent. You're getting customers, but it's hard. You said it's 20 introductions to one sale, but you're getting them.

(00:35:25):
I know Retool has a great quote. David has this quote of, "Every customer he got early on, he felt it was the last customer he was ever going to get. No more people want this thing and it's always a struggle." So I think that's very normal, is what you're describing. The beginnings are rarely off and to the right. And it's okay if this takes a while. You said that if you spent 12 months at this stage, you're probably stuck in the stage, and signs that you're stuck in this nascent stage versus this is actually normal. Signs you mentioned are if you ask people if this went away and they wouldn't be disappointed, they'd be like, "Nah, all right. It's cool."

(00:36:01):
You have many customers, but they're using different features of the product. So to you, the way you described it, essentially, you're professional services for them. You're not actually building a product. You consult a lot of people. And then they're actually not using it often. They're buying, they're paying for it, like the last example, but they're not necessarily using it and they're going to churn pretty quickly.

Todd Jackson (00:36:19):
That's right.

Lenny Rachitsky (00:36:20):
Anything else you wanted to touch on there before we get to level two?

Todd Jackson (00:36:23):
The last thing that I'd add at level one is there's this founder from a company called Persona, his name is Rick Song. He's super awesome. Persona is a First Round company. They do identity verification. And Rick's analogy, I just love it for level one, is you don't want to get friend-zoned by your customers, where your customers like you, but they don't love you and they don't need you. And he was super paranoid about this in the early days of Persona. And his technique for doing this, which I really like, is super simple, was he was very close with his first five or 10 customers.

(00:37:00):
And he would go to them and sit them down one-on-one and say, "I need your help. It is very important to me that this company succeeds and does not fail. So I don't want you to be nice to me. I want you to tell me is Persona a necessity for your company? If we went away, how painful would that be? If a competitor came along that charged half as much as us, would you switch to them?" And he's really trying to get to the essence of: is Persona critical for you or am I in the friend zone? And I just think that's a really great way of thinking about this.

Lenny Rachitsky (00:37:35):
I love that story. It's like in a relationship, it's the talk.

Todd Jackson (00:37:37):
It's the talk.

Lenny Rachitsky (00:37:38):
"Are we a thing?" I love that. That's so good. The sooner you know the truth, the better. And it's hard to hear bad news, but I love that, just advice of just sit them down one-on-one. Let me tell you about CommandBar. If you're like me and most users I've built product for, you probably find those little in-product pop-ups really annoying, "Want to take a tour?" "Check out this new feature." And these pop-ups are becoming less and less effective since most users don't read what they say. They just want to close them as soon as possible.

(00:38:08):
But every product builder knows that users need help to learn the ins and outs of your product. We use so many products every day and we can't possibly know the ins and outs of everyone. CommandBar is an AI-powered toolkit for product growth, marketing and customer teams to help users get the most out of your product without annoying them. They use AI to get closer to user intent. So they have search and chat products that let users describe what they're trying to do in their own words, and then see personalized results like customer walkthroughs or actions.

(00:38:36):
And they do pop-ups too, but their nudges are based on in-product behaviors like confusion or intent classification, which makes them much less annoying and much more impactful. This works for web apps, mobile apps and websites, and they work with industry-leading companies like Gusto, Freshworks, HashiCorp and LaunchDarkly. Over 15 million end-users have interacted with CommandBar. To try out CommandBar, you can sign up at commandbar.com/lenny and you can unlock an extra 1,000 AI responses per month for any plan. That's commandbar.com/lenny. Let's talk about level two. So what does level two look like? And what should founders be focusing on when they're in level two?

Todd Jackson (00:39:19):
Yeah. So level two is developing product-market fit, and your job at level two is now you've got to go from five satisfied customers to 25 satisfied customers. And so now you've got to start thinking about demand in addition to satisfaction. Because it is very hard to just grind your way all the way to 25 customers with sheer willpower, but you can do that to five, maybe 10. And we see some founders who just have phenomenal willpower and grit and grind their way to five or 10 customers. To get to 25 and to get beyond 25, the product has to be doing a lot of the heavy lifting for you. And so that is the essence of this level.

(00:39:58):
So if you're at this level, now you're seed or Series A style company, maybe you've got up to 20 people at the company. And you're starting to work on this demand source where you have the early signs of a scalable channel, and it's not just warm intros from your VCs or from your friends. You're maybe investing in cold outreach and getting that tuned and humming. You might be investing in content, you might be doing community events, but the whole idea is you're trying to scale the demand source. It's still not easy. A benchmark, we would say, is that your sales conversion without a warm intro is still probably 10%, something like that.

(00:40:38):
First call to close one is around 10%. If you get higher than that, that's great, but that sort of benchmark for this level. You're in anywhere from the 500K to five million ARR zone, that's a hallmark of level two. And you're actually starting to think about efficiency metrics and sales metrics. You might starting to be thinking about magic number, which is a new ARR that you take in in a period divided by the CAC you spend in that period, so something in the 0.5 to 0.75 range. You want to get higher eventually, but that's pretty reasonable for this level.

(00:41:10):
You're just starting to think about retention. You've been around for a year, so you've got renewals and you want those renewals renewing. Maybe something like 10%, 20% regretted churn is okay. You don't want to be higher than that, and you want your NRR to be at least 100%. And then things like gross margin and burn multiple, they're still not the focus. Those are the classic efficiency metrics. They're not the focus right now.

(00:41:30):
But we would say you want your gross margin to be not worse than 50%, and you'd want your burn multiple to be not worse than five X. Your burn multiple, by the way, is just how much you burn in a current period versus how much new ARR comes in. So if you burn $5 million and you take in one, then you've got to burn multiple of five. And you don't want to be worse than that at this stage.

Lenny Rachitsky (00:41:51):
Amazing. There's a lot of these benchmarks which I love. I imagine not everyone's going to hit each of them exactly. These are just rough guidelines of like, "You're probably in this stage if you're in this level," right?

Todd Jackson (00:42:03):
Yeah, exactly. There's some wide bars around these metrics. It's just representative of, generally, the stage of five to 25 customers.

Lenny Rachitsky (00:42:10):
I love it. And it's so interesting that people think of product-market fit, as you said, as this binary, "I have it or I don't." And the way you're talking about this is in this level to developing product-market fit, a company has 25 satisfied customers, they're over five million in ARR, a lot of cases they have 20 employees.

Todd Jackson (00:42:28):
Between 500K and five million. Yeah.

Lenny Rachitsky (00:42:31):
500K and five million. They have 20 employees. In theory, you would think this is a roaring success. They're killing it, they have all these customers, they're growing. But it's still just level two of product-market fit. So I think this has a really interesting insight, and it reminds me of when I did a bunch of research on product-market fit.

(00:42:49):
So many founders are like, "I never felt that product-market fit. I didn't have it. It was always, 'I don't know, maybe when we get to 100 million ARR, I'll really feel like we got this.'" So I think this is a really good reminder that a lot of times you're not actually going to feel so confident this will last, and you're going to get to lasting durable product-market fit. So I think that's a really great insight here.

Todd Jackson (00:43:12):
Yeah. And the thing that's really, I think, the hallmark of level two is you've got a product that a handful of people like. It's satisfying a critical need for them. Now you've got to open the demand floodgates so that we can get to 25 customers and beyond. And different companies do this in very different ways. It's much easier said than done. Looker is an example. So Looker is a First Round company founded in 2012 by Lloyd Tabb. They do business intelligence. And Looker is interesting because they spent actually a long time at level one, but then flew through level two. And the reason is because Lloyd, the founder, the first five customers of Looker, he was basically going in and doing consulting for them.

(00:43:59):
And the reason is because of the nature of the product. People don't get Looker until they see their own data in it, and their data is modeled and they see the dashboards and they're like, "Oh, my God. Wow, I didn't realize these insights." So Lloyd understood Looker is not a product you could sell with Figma mock-ups. And so what happened was Lloyd would go into these customers, spend 20, 30, 40 hours before they were even a customer, modeling their data, teaching them how to use it, showing more people within the organization the power of the data and the dashboards.

(00:44:32):
And later, they called this their forward deploy process. This is how they figured out sales. And so it actually took them a long time in level one to get this right, but then they were able to do this repeatably. And so they went from five to 25 fairly quickly, and a lot of amazing... 75% close rate because they were only selling customers who were already using it. There was zero churn. And Lloyd explains once he got to 20 customers, he's like, "I know I'm onto something. And I think I figured out a model."

(00:45:03):
And the model stayed the same until they ended up selling to Google. And so they did these other things too. They started focusing on demand channels. They got a couple SDRs who were prospecting. I think they did some partner marketing with AWS Redshift. They did these look-and-tell customer events in San Francisco where they got Looker customers together to talk about what they were doing in Looker and how they built the product. But really, the groundwork was set at level one and then they moved really quickly through level two.

Lenny Rachitsky (00:45:32):
So again, the way to think about this phase, is this is when you're starting to scale a way to drive demand. You're not just grinding sales, cold outreach. There's a way you're starting to bring in customers that are more efficient. And in Looker's case, they just started coming because I imagine there's word of mouth and people started to talk about it.

Todd Jackson (00:45:50):
Yeah. Let me do another example. A really different example is a company called Ironclad. Ironclad, it's legal. It's a legal tech company founded in 2015. Jason Jason Boehmig is the founder. AI-powered contract management software. So this was interesting because Jason, he started out calling this an AI legal assistant. And in 2024, people are like, "Oh, AI legal assistant. Yeah, that's awesome." But in 2014, people were like, "What?" And he found it really hard to sell. No one was looking for an AI legal assistant. And so he told us this story.

(00:46:29):
There was an email address on the Ironclad homepage, hello@ironclad.com. This is in 2015. And he doesn't get very much email, but Jason is checking the email. And one day he gets this one line email, and he almost archives it because he doesn't know who it's from and it's one line. But he sees that it's from a person at a publicly-traded company, and so he's like, "Oh, maybe there's something here." And the one line email is just, "Are you a CLM?" And he was like, "What is a CLM?" And he Googles for it. A CLM is a contract lifecycle management platform. And he's reading up about CLMs, and he's like, "Oh, we do that. Yeah."

(00:47:08):
And so he replies to the email, "Yes, we are a CLM." And the customer gets them on the phone. And the customer says, "Oh, I'm in the market for a CLM. I'm looking at 10 or 12 different vendors, but you guys look pretty cool because there's some automation and some AI stuff going on. Can I check this out?" And Jason's like, "Of course." So he and his co-founder take the train from San Francisco down to San Jose. And on the train, Jason is telling his co-founder, Cai, "Hey, I need you to code this up right now to make it look like what this customer is expecting."

(00:47:42):
And they get to the meeting, and they do the demo. And the customer has no idea that they just made this demo on the train, and they're a very small company. And they win the contract against these 10 or 12 other established bases, because Ironclad, it's more modern, it's automated, it's got this AI stuff. It's just a better product, or the demo looks like it's going to be a better product. And so Jason reflects on this and he's like, "Yeah, the thing for us is we had been trying to create this new category of AI legal assistant, and it was just a slog.

(00:48:10):
"And instead, when we changed our positioning to play in an existing category of CLM, but a much better CLM, but customers are already looking for a CLM, they're already looking to spend money on a CLM, and just expand the definition of what that category is, things just started to click." And that's how they got through that zone of 10, 20, 30 customers. And even if you look at the Ironclad website today, it says AI-Powered Contract Management Software. That really is the key idea still.

Lenny Rachitsky (00:48:38):
Awesome. So this is an awesome example of positioning/promise is the lever they pull here. I love the point about category design. That's one of the ongoing debates on this podcast, whether you should try to create a category.

Todd Jackson (00:48:50):
I know, it's a hot topic.

Lenny Rachitsky (00:48:51):
Hot topic. Sounds like you're in the boat of probably better not to create your own category.

Todd Jackson (00:48:56):
I think it's hard to create a category. It certainly works in some cases, but if you actually have a really interesting spin on an existing category, there's already buyers spending money on that thing. They're already looking for something to buy. So if you can do it, I do actually think that way is easier.

Lenny Rachitsky (00:49:13):
Before we get to level three, what are signs that you're maybe stuck at level two, and what should one do about that?

Todd Jackson (00:49:21):
Yeah. So the whole idea of level two is this thing that the marginal customer is getting easier. And so you've got to be focusing on demand and the repeatability of demand while you maintain satisfaction. So the yellow flags are things that are the opposite of that. Your current customers are pretty happy, but you're just having trouble opening the floodgates. As you're getting to the top end of level two, you should start to hear some startups know who you are like, "Oh, you need a SOC 2, you're a startup. Oh, Vanta." "Oh, you need AI-powered contract management software. Oh, Ironclad." You start to get known for a thing.

(00:49:59):
And so if you're having trouble opening those floodgates, and you're sitting there for, I don't know, 12 months, 18 months, that's a problem. Or you have things like your regretted churn is greater than 20%. That's a satisfaction warning sign. And again, you have to maintain the satisfaction as you work on these other things. Every level just gets more things you have to do. Or you could be finding that the sales cycle's taking too long, you're losing deals late in the funnel, you're losing the competitors. You're just not feeling the urgency from customers or you're struggling to hit the price point that you want.

(00:50:33):
And the way that customers will say this to you because customers are nice, right? They'll say, "Oh, we don't have the budget." Or, "Oh, it's just not the right time for us. We'd love to talk again next year." That means no, when you're hearing that from customers. You want customers who are like, "Oh, of course. Yeah, this is expensive, but I'm going to make this work because I need this." And so if you're seeing any of those signs, those are the signs that you maybe are stuck or plateauing at this level. And I really think it's important to think about the four Ps and think about: how am I going to pivot my way out of this? Jack Altman, who I mentioned earlier from Lattice, he's got a great quote on this.

(00:51:14):
It's up in a video on the website. What did he say? He said, "Most founders do a 10% pivot, and what they need to be doing is a 200% pivot." Jack didn't say this, but I think part of my interpretation of this is it's psychologically hard as a founder. You've gotten to this many customers, you're starting to plateau, but you're like, "I don't want to throw this whole thing away." But you have to be willing to let go and really focus on nailing the four Ps at this point.

Lenny Rachitsky (00:51:46):
And in your experience, do you find, essentially, pivoting is the answer if you're stuck?

Todd Jackson (00:51:52):
I think sometimes it's nice when it's the Ironclad thing, right?

Lenny Rachitsky (00:51:56):
Yeah.

Todd Jackson (00:51:57):
It's nicest when it's the Looker thing of you don't have to change anything. It just starts working and basically, the whole thing works the whole time. That's not common. It's nice when it's the Ironclad thing when you just change one of them, or maybe two of them. Starting over with all four of these is hard at level two, but oftentimes, it's what's required. I was mentioning earlier, level two is the second most common level to get stuck.

(00:52:20):
A big chunk of companies are going to get stuck at level one, and the second biggest is at level two. So sometimes it's hard. I think the trap is not doing enough to realize that you're actually not progressing to product-market fit in the way that you need to and just starting to burn money and not make progress. And you've seen many startups struggle with this. I think it's the hardest part of it.

Lenny Rachitsky (00:52:42):
Yeah. Especially once they're a million, two million, three million ARR and they're like, "Look, we're making all this money." And they don't necessarily realize that they've been stuck at this stage for so long. So just to summarize flags that something is wrong and that you should probably think about changing your persona, your problem, your promise or your product, is it's been 12 to 18 months at this stage of product-market fit. You are churning about 20% of customers. And these are logo churn, I imagine, just like businesses stop using you.

Todd Jackson (00:53:14):
Yep.

Lenny Rachitsky (00:53:14):
Your sales cycles are really slow. Is there a sense of what slow means? Just a rough heuristic. What should it...

Todd Jackson (00:53:20):
Well, some sales cycles are slow. If you're selling to companies that are big, you're selling to government, that type of thing. I don't know. Rough rule of thumb is... There's different ACVs also. If you're the kind of product that is 20K, 30K annual contracts, that was Looker, right? But they were able to do the sales cycle very repeatedly because they closed so often. There are some contracts that are 100K, 200K, six figure contracts. Those can take a long time. Those can take three to six months. You can't basically be in the worst of both worlds where you've got a slow sales cycle and a low ACV. That is the quadrant of death basically.

Lenny Rachitsky (00:53:57):
Awesome. Okay. And then the other sign is just you're not finding demand starting to come to you. You're not finding a channel to drive demand. And is a big part of this inbound? You're supposed to start seeing more inbound coming at you? Or is it more just sales becomes easier?

Todd Jackson (00:54:12):
It's both. So sales becomes easier, but I think if you are starting to get to level three, which is where we're getting to next, you've probably got 10%, 20% of your inbound coming or completely organic inbound.

Lenny Rachitsky (00:54:25):
Awesome. Okay. So again, if you're stuck at this stage, and these are signs that are like, "Oh, man, this sounds familiar," your advice is find one of these things to shift the person you're going after, the problem you're solving, the way you position it and/or your product if you have to.

Todd Jackson (00:54:41):
Yeah. And probably just look for something that is a lot more of a burning pain. It's usually that the problem is not significant enough, important enough to people, or the promise is not valuable enough. It's usually one of those [inaudible 00:54:54] assuming you have a reasonable persona.

Lenny Rachitsky (00:54:56):
Awesome. And the reason I am spending so much time here, as you said, most companies get stuck here, like B2B SaaS companies. So I think it's really important to make sure people have something to go with. And in the course and in the post you put out, there's more examples of companies going through this and what they did. Let's talk about level three. What does level three look like? What should you be focusing on there?

Todd Jackson (00:55:16):
Yeah. So level three is strong product-market fit. This is where I think it starts to get fun. This is where all the product-market fit adages come in, "The fish are jumping into the boat. The rock is rolling down the hill and I'm trying to chase it instead of pushing it up the hill." And keep in mind, for most enterprise founders, we're now three, four or five years into the company, so it's not easy to get here. And to get to L3 here, you are looking for repeatability. The marginal customer has become much easier.

(00:55:48):
And so you mentioned, Lenny, this quote from David Hsu from Retool, which I love too, and I'll read it again. He said, "We talked to someone who said that finding product-market fit was so visceral, you immediately felt it like a geyser." And we honestly never felt that in the first couple years. At Retool, every customer we got, whether that was number four or number 14, felt like the last customer we were ever going to find. It felt like rolling the stone uphill, and if you stop pushing, it's going to roll back on you and crush you.

(00:56:15):
And that's how it felt until we had a few million in ARR. That's when the boulder went down the other side and we had to chase it to keep up. And you mentioned earlier, founders were like, "I'm not sure I ever felt product-market fit." This is when you start to feel it. And Jack Altman, again, from Lattice said, "The biggest shift was in the ease of getting leads." I remember thinking, "I don't even know where these leads are coming from, just more and more of them are showing up each month."

(00:56:43):
But that is a great feeling. That is a great feeling. Filip Kaliszan from Verkada, he's in some of the videos on our website too. His quote, I'll read it, was, "After our first year of sales in 2018, those next two years were crazy. We were barely keeping up with production. We had to scale all the systems. A lot of things had to happen in the span of 12 to 18 months in order to deliver on everything that customers were hoping the solution was going to do for them. And that in itself was a very formative and tricky part of the journey."

(00:57:11):
So the benchmarks when you are at level three are now you're probably 30 to 100 people inside your company. You're probably at Series B-ish territory in terms of venture, maybe late Series A, maybe early Series C, but probably around Series B. You've really cracked a demand channel. You've cracked marketing and sales. You've got at least one channel that is very scalable. And probably 10% or more of your inbound is coming from just referrals and word of mouth and you're getting known, like we talked about.

(00:57:45):
ACV ranges are very high. Very wide, I should say. I'd say where you want to get to with level three is 100 customers. And so if you're approaching 100 customers and maybe you have 75K average ACV, that would be strong. You're in this wide zone of five million, all the way up to 25 million ARR. That is very level three. And you're actually starting now to think about some of these efficiency metrics. Remember, we've been punting efficiency. We were saying it shouldn't be worse than a certain number, but it's not a focus. Now, it's got to come into focus.

(00:58:20):
Because the way that we get to level four is we keep ripping on the satisfaction and the demand, and we tune this thing to get very efficient. So we're talking about our gross margin needs to be above 60%, hopefully above 70%. Our burn multiple is now below three. Ideally, we're close to one. Burn multiple in the one to three zone is where we want to be at level three. Regretted churn's less than 10%, NRR is greater than 110%. These are good benchmarks for this level.

Lenny Rachitsky (00:58:50):
Hearing level three again tells me level two is basically your pivot from: I'm just grinding customers, selling, pitching, constantly trying to find new people, to level three, where it's coming at you and basically, it's the way you always hear about it, as you described. It's rolling downhill. Fish are jumping in the boat. I haven't heard that one before, but I love this.

(00:59:11):
So essentially, you found a demand channel. You found a way to get people to come to you. A lot of them are just hearing about you from other people, you don't even know where they're coming from. 10% you said are coming from referrals and you're getting to 100 customers. I actually have another quote from David Hsu at Retool, and he actually said even at 100 customers, he still felt like every customer he was getting was the last one.

Todd Jackson (00:59:33):
Oh, wow.

Lenny Rachitsky (00:59:33):
He's like, "I can't believe we got DoorDash. That's incredible. Okay. I think there's no more. That's it."

Todd Jackson (00:59:39):
He is a critical person and critical of himself, but a very high expectations person, let's say.

Lenny Rachitsky (00:59:43):
Yeah. Actually, another quote from Ali Ghodsi from Databricks actually said even at 100 million, he wasn't sure they had product-market fit.

Todd Jackson (00:59:50):
I mean, come on.

Lenny Rachitsky (00:59:54):
Because he's like, "I don't know." I don't know. He felt like, "This is it. Okay, we're done. We're going to cap out here." And I get that.

Todd Jackson (00:59:58):
I think if you told many, many pre-seed founders that they'd be able to get to 100 million and not know whether they had product-market fit, they'd probably take that.

Lenny Rachitsky (01:00:05):
But I think that's maybe an interesting insight. It's often good to be really paranoid and not feel like, "Okay, we're on our way. Let's start pouring in money. Let's do it."

Todd Jackson (01:00:13):
I think that's what makes a lot of the best founders the best.

Lenny Rachitsky (01:00:16):
Indeed. Okay, so level three, anything else that would be useful here? Maybe what are signs that you're struggling at level three, you're stuck?

Todd Jackson (01:00:25):
Yeah. So level three problems. And again, it's hard to get to level three, so awesome work for getting here. But the problems that might start to emerge are you've got a leaky bucket, your NRR is below 90%, or your regretted churn's greater than 10%. Maybe growth is just slowing down. You grew three X each of the prior two years, but you're struggling to do a two X this year. At level three, or five years into the company or so, there's probably a lot of competition. If you've gotten here, you've got something that's working, and people are starting to notice and there's going to be competitors.

(01:01:01):
And they could be the big competitors, they could be the new startups, but you're going to have to figure out how to navigate probably a tougher market than you entered five years ago. And so maybe you found your first scalable channel, but it's getting saturated, you got to find a new channel. These are the level three problems. Or you're growing, but like I said, with efficiency, you're spending too much money to grow. So you feel like, "Okay, yeah, we can grow at three X year over year, two X year over year, but that's going to push our burn multiple above three again." And that's a little bit of a pickle to be in when you have to trade off growth and spend like that.

Lenny Rachitsky (01:01:37):
You make it sound like life's great, level three people are coming at us. I think it's important to note never is it easy, never is it like, "Okay, we're good. Let's just ride this wave. Life's going to get so much easier from now on." It's never easy. As you said, there's all these things, you're always still juggling, you still aren't sure it's going to keep going.

Todd Jackson (01:01:55):
No, I agree. It's like you're spinning plates, and the higher levels you get, there's more plates. You have to keep spinning. And so at level three and getting to level four, we've got to maintain satisfaction and demand. We cannot let them regress in a market that's getting harder, and we have to really start focusing on efficiency. And the companies that can maintain satisfaction and demand and continue to grow and become really efficient, now we're at level four.

Lenny Rachitsky (01:02:21):
Let's talk about level four. What does that look like? What are some problems people run into there?

Todd Jackson (01:02:26):
So first of all, congrats. If you get to level four, you have a valuable company. You are probably already a unicorn, and you're starting to think about, "Can I become a decacorn?" And so you've reached the highest levels of satisfaction, demand, and efficiency. And so the benchmarks at level four are like, "Okay, now your team is probably bigger than 100 people, you're Series C, Series D or beyond. You've got more than 100 customers and you're starting to figure out, 'How do I get to 200, 300, eventually 1,000 customers?'" You're beyond 25 million in ARR, so 25 million and up, I think in ARR, it qualifies as level four. And your other metrics are looking really good too. Your sales conversion first call to close one is probably better than 15%, your magic number is greater than one, your tax payback is less than 12 months.

(01:03:13):
All these things are super awesome. And finally, now you've got your gross margin above 80%. Your burn multiple's ideally less than one at this point, you've got less than 10% churn. You've got greater than 120% NRR. And so now the whole thing is like, "Well, how do I keep growing?" This thing's gotten pretty big. And this is generally when we get to 100 million, especially and beyond, the stage that founders are thinking about, "How do I keep growing by expanding TAM, by expanding total addressable market?" And to expand TAM, I can usually take my product and bring it into new markets, or I start to think about multiple products as a way to expand TAM.

(01:03:55):
And so this is where you see all the truly great companies, the legendary companies are all able to do that. Vanta has begun to do this. They have the Vanta trust management platform, they've got security questionnaires, they've got vendor risk management. So they're starting to do this. You think of Verkada, who I mentioned before. They started with cloud security cameras, now they do alarms, now they do smoke detectors, now they do badge readers. Stripe has classic Stripe, but they've got Stripe Radar, Stripe Atlas. Square has the Square Stand, Cash App, Square Checking, Square Loans. All the companies that are tens of billions of dollars of value have figured out a way to do this. And it's like the never-ending journey that you said before, Lenny. Like, "Congrats, you got to level four."

(01:04:40):
But there's just this endless thirst for continued growth. And the interesting thing about that is that it requires finding product-market fit over and over again. Just because you got to level four on your main product doesn't mean product-market fit is free on all these new products. And you've been inside Airbnb and I've been inside Dropbox and Twitter. Getting new products to be successful is hard and it requires this mindset of like, "Yeah, we've got a little bit of advantage because people know who we are, and we have a customer set that hopefully we can layer on new products to. But it's not easy." You have to get into this mindset of product-market fit is never easy, and if we want to continue to grow, we got to find it again and again and maintain that mindset.

Lenny Rachitsky (01:05:22):
Casey Winters has this great point also that expectations of customers ever increase. And so you have product-market fit today, but there's going to be better products coming out, they're changing, the world changes. And so not only do you have to worry about competitors, there's just expectations continue to rise. So it's a never-ending battle. To give people a little bit of a broader sense here, what percentage of companies do you find make it through each of these stages in your experience, what are rough numbers you may have in your head?

Todd Jackson (01:05:52):
The majority of companies, so greater than 50%, probably closer to 60 or 70%, are going to get stuck at L1 or L2. And so that leaves, roughly, let's say, 30% make it to L3 or L4 just in our experience looking broadly. And that's our entire goal. Because again, once you get to L3, you've got a real shot, you've got a real shot at building an awesome company. And so if we get that number, help founders get that number above 30%, imagine if that was 50/50 and half the companies that we were working with at seed were able to get to level three strong product-market fit. I think that would be epic. And I think our founders would... There'd be incredible benefits to the ecosystem from that.

Lenny Rachitsky (01:06:36):
Okay. So essentially, 60% ish of companies don't make it past L2. And I love the way you're framing it of just, "If we can just get a few more companies further, that makes a massive dent both in the world and the lives of founders and people that want to use products." Another question I wanted to talk about briefly is just again, the timelines of each of these levels. Just in your rough experience, how long do each of these levels roughly take so people can get a sense of like, "Oh, it's taken a lot longer. Maybe there's a problem"?

Todd Jackson (01:07:10):
So again, this whole thing probably takes four to six years, and so let's just pick five years as the number to get to level four. I think the way this works, ideally, is you probably take 12 to 18 months to do level one, because that is the most important level, honestly, in my mind because that's where you're really choosing the right persona and the right problem to focus on. And I think just that choice is one of the most important choices that founders make. And the interesting thing, my partner, Josh Kopelman, talks about this all the time, is that founders spend 99% of their time building because that's what they've done.

(01:07:53):
And they spend 1% of their time picking, in picking the market, picking the problem, picking the customer. And in reality, it's that pick that determines the constraints and the boundaries of where you're going to be working for the next, hopefully, 10 years of your life. So there's a real imbalance there. And I actually think that that pick is the most important thing. So I would actually like to spend, let's say, somewhere 12 to 18 months in level one, just really figuring that out and figuring out my four Ps. And then, hopefully, I move very quickly. It takes me a while to get to my first five satisfied customers, but they love it.

(01:08:28):
And then I go quickly through L2, maybe that takes about a year. This is like the Looker path, the happy path. And then L3 is long just because we're going all the way from five million in revenue up to 25, and that might take a year or two, probably two years even in a good case. And then getting from 25 to 100 million is hard, obviously very hard. And then that probably takes a couple years. And then you're figuring out all of these things.

(01:08:53):
You're growing your team and your company's got a lot more moving parts and functions, and there's a demand generation side of the house and sales and there's engineering and the whole thing just gets more complicated with a lot more people. But I think that if you set the foundation really nicely at level one and level two that hopefully the whole thing... The boulder is rolling down the hill and it's carrying you forward and you don't just feel like you're pushing this rock uphill for five years. That's not a fun place to be.

Lenny Rachitsky (01:09:22):
There's a lot of founders in that place and I know a few, so this is really interesting. So you're roughly saying that maybe spend a year, year and a half on level one, which is you're just grinding, cold emailing, reaching out, selling customers, and maybe getting to five customers in the first year and a half. That's at the extreme, but that's a good outcome. And then maybe another year trying to get to... What was it? 20? 25 customers.

Todd Jackson (01:09:45):
Going from five to 25 quickly. Yeah, if I see a company go from five customers to 25 in a year, that is almost always a sign that there's some pretty strong product-market fit there.

Lenny Rachitsky (01:09:56):
Awesome. So many companies don't go through that, and they have the funding to keep iterating, exploring, trying to figure things out. I don't know if you have the answer here, but just what's your advice of if it's been four years and demand is not starting to come to them, they don't have 25 customers? Is it, "Wait until you run out of money, just give it a shot"? Or is it, "Let's just give the money back and move on to something else"?

Todd Jackson (01:10:21):
Well, that's a personal decision for founders. I do think if you've been going at it for four to five years and you haven't started to find anything that you're really feeling pull from the market on, I don't know, you've done it for four to five years, what are the chances that you're going to magically find something? I think there are probably a handful of startups that do it that figure it out and get back on an amazing growth curve, but that's the exception rather than the rule.

(01:10:46):
So if a founder wants to return the money to investors, if a founder wants to look for a soft landing, there's no shame in that. Product-market fit is very, very hard. That's why we're doing this. It's why we're trying to increase the odds. And we're also trying to make it clear what it looks like and what it doesn't look like. And everybody knows when they do a startup that the odds are that you will not get there. So there's no shame in that, and I would completely be supportive of any founder who wants to take that path.

Lenny Rachitsky (01:11:18):
I love that advice. I think that was a really important point to make. Let's quickly summarize the levels and then I want to also summarize the four Ps again, because I think that's the thing you can actually do. And so I think I just want to reinforce, "Here's the four things you should play with if things aren't going in the direction." So first of all, let's summarize the levels, what it looks like and what you should be focusing on there.

Todd Jackson (01:11:38):
Okay. So level one, nascent product-market fit. You're just trying to get three to five customers and you're focused on satisfaction first and foremost. Level two is developing. This is where you're going from five to 25 customers, and you're really starting to focus on demand. Level three is strong product-market fit. You're going from 25 customers up to 100 or more, and you've got to start thinking about efficiency at that scale. And then level four is extreme, you're more than 100 customers, your company's awesome. You got to keep doing all three of those things well, and you have to start looking for ways to expand your total addressable market.

Lenny Rachitsky (01:12:14):
Okay, perfect. And then let's come back to the four Ps. I have the draft. I have your post up here, so I have the detailed version of each of these things. But could you just talk through these four things? What is it you should be thinking about changing if things aren't working, the four Ps basically?

Todd Jackson (01:12:30):
Yeah. So the four Ps again are: persona, problem, promise, and product. And the persona is interesting because in some ways, it's synonymous with the market. A lot of people think of the market in this macroeconomic way where it's like, "Oh, it's this category of ERP software or whatever." I think it's much more tangible for a founder to think of the market as a collection of people. Jack Altman was thinking about his market as all of the HR leaders out there, and he was thinking about how many of them are there and what are the problems they have and how much money are they willing to spend on solving those problems.

(01:13:12):
It's a collection of people who have money to pay for a product or pay for a service. And so that's really the first piece, find the persona and really try to get into the mind of the persona. That's another thing I was amazed about spending time with Zach from Plaid, and Lloyd from Looker, and Jack from Lattice. They had all of these people, they were text messaging with all of their customers and they're meeting them on the weekends and stuff. They really, really knew their customer well. They were friends with their customers.

(01:13:45):
And so you've got to get so deep into the mind of the persona and: what are their challenges? What are their goals? How do you help them succeed at their job? That's the stuff that earns you the right to get the rest of the Ps right. And so the problem, obviously, comes next. And I think about this, and I can actually get into, Lenny, a little bit if you want to get into some of the customer discovery stuff because that's the second session.

Lenny Rachitsky (01:14:13):
Perfect segue.

Todd Jackson (01:14:14):
And I was talking a little bit about we think of it as dollar-driven customer discovery. And I think a lot of founders are familiar with customer discovery. I think they at least talk to customers, which is good. I don't think most of them do it in the highest signal way because again, the customers, they're people, they're nice, they're going to be polite. They're also not good at predicting things that they will use or buy or want.

(01:14:41):
They're very good at talking about their problems, but they're not necessarily good at predicting their own behavior. So we think about it in terms of dollar-driven discovery, which is how do you test the dollar potential of a hypothesis? And this is a whole two-hour session, but I'll try to do it briefly here just to give you a sense of it.

Lenny Rachitsky (01:15:00):
No, let's get into it. Let's keep going. I'm just joking.

Todd Jackson (01:15:02):
So you've got to identify extreme value. This is independent of what I'm building, Lenny. I want to hear about your problems and your challenges and what is most important to you. And so I need to do it in this non-leading way and I need to avoid the trap that we call happy years. Because I found a lot of founders, "I want to build this thing, I want you to like my thing." And so I look for the things that you say that support what I'm doing. That's the trap. And so I could just try it on you, Lenny. Yeah, I might say...

Lenny Rachitsky (01:15:35):
Let's do it.

Todd Jackson (01:15:36):
Okay, Lenny, so you're doing Lenny's Newsletter and you're building Lenny's Podcasts. When you think about we're sitting here in April, over the next three months, let's say, what are your top three goals for Lenny's Newsletter and Lenny's Podcast?

Lenny Rachitsky (01:15:53):
Oh, wow, interesting. I'm trying to find a more scalable way to do this newsletter long-term. It's basically something I have to do for the rest of my life, in theory. I don't know if there's an exit path for this newsletter career, so I'm trying to find ways to scale this over time. That's one. Two is just up-leveling the quality of each podcast episode in terms of visuals and audio and trailers and things like that. And then three is make the community more valuable to everyone that listens that's in the newsletter community. Those are top of mind.

Todd Jackson (01:16:26):
Okay, awesome. And so what's hard about those three things? You said you want to scale the newsletter, you want to increase quality, you want to make the community awesome. What's hard about those things? Or what's standing in your way of doing those?

Lenny Rachitsky (01:16:39):
I don't have the answer yet, I guess is the answer. I don't know exactly how to do this yet.

Todd Jackson (01:16:44):
You don't know how to do it. Okay. It's probably a service in this case, not a product. What if I was able to give you a service that said, "Lenny, you're going to be able to scale this podcast. We are going to help you find the 500 best guests in the world that are really excellent. We're going to guarantee they show up. You're going to have endless content on your podcast, in your newsletter"? What do you think about that? What do you think about that idea?

Lenny Rachitsky (01:17:16):
I'd pay a lot of money for that.

Todd Jackson (01:17:18):
Okay. So that's an example of a wow statement. And you probably had in the back of your mind, "How are you going to do that? Is that actually going to work?"

Lenny Rachitsky (01:17:27):
That's right.

Todd Jackson (01:17:28):
In my experience, that's a good thing and an exciting thing. If I'm pitching a product idea to somebody and they are like, "Wow, does that really work? And if that thing works, I'd sign up for the wait list today." That to me is like, "Okay, now I got to figure out how to build that thing, but I know if I am able to build it and deliver on that promise, they are going to want it." Or you would maybe say signs like you would demonstrate a behavior that shows that you're interested in. You'd be like, "Oh, Todd, can we meet again next week to talk about this?" Or like, "Hey Todd, I actually would love to show this to the people I work with. Can you send me the deck?"

(01:18:06):
Those are the signs that I'm looking for. If you had reacted like, "Yeah, that sounds kind of interesting," that's a no, right? That is a no. The word interesting is a polite way of saying no, right? And so I'm either looking for wow statements or I'm looking for demonstrated behavior that shows interest. I then would probably, if I want to keep going with this, and this is all in the identifying extreme value, I'd ask you, "Well, what stands out as valuable here to you?" And I want to hear you answer quickly. You mentioned it's either going to make my products so much better, it's going to drive success for my business, or it's going to save me a bunch of money or something. Save me a bunch of risk." But something where you would very quickly be able to identify why that's valuable to you.

(01:18:51):
So that part one is extreme value. Then I got to figure out ability to pay and willingness to pay. And for you, this is easy because you're not a 5,000 person company and you're the boss. So this is probably pretty streamlined. There's no procurement function at Lenny's Newsletter. So let's say I'm going after a bigger company. The questions I'd ask on confirming the ability to pay are: are you currently looking for a product like this? Or are you building something internally?

(01:19:24):
This is the Ironclad thing where Jason was like, "Oh, you're looking for a CLM already." Another way I think about it is if a customer has a problem, and I really think they have a problem, and they know they have the problem and they're looking for a solution for the problem. Or they've even tried to build their own solution to it and failed, that's the best customer. They want this thing badly. They've demonstrated that and they've actually failed at building it because they underestimated how hard it was. So are you currently looking for building a solution here?

Lenny Rachitsky (01:19:57):
Essentially, there's a budget. You're looking for, "Is there money to go towards this problem"?

Todd Jackson (01:20:01):
That's the next question I was going to say is where would a budget for this come from? And the best answer is that there's an existing budget. Either we already spend money in some way for a competing tool, or something that can be displaced by you, or we're spending, we put five engineers together to help build this thing. There's some source of budget that I can get. Then the question is, "Well, how does your team make decisions on third-party tools to bring on?" And you're never going to get the cleanest answer here. In larger companies, you might get semi-clean answers, but it's something like, "Okay, this manager can approve it directly up to a certain dollar amount. If not, it goes to this next level up of manager. And if we're going to spend more than 50K on it, we actually have to compare three different alternatives."

(01:20:47):
But whatever, there's some known process. That's what I'm looking for rather than just a bunch of ambiguity. So that's ability to pay. And then I'm going into willingness to pay. I don't want to try to quantify that. That's where I go, "What's your budget for solving this? What are you paying for this other tool? Let me show you mine. You think that you'd pay less for that or you'd pay more for that? Can you replace this other thing with the thing I have?" And then I love this question. I think you've had Madhavan Ramanujam on the show, right?

Lenny Rachitsky (01:21:16):
Mm-hmm.

Todd Jackson (01:21:17):
He has this question, he's from Simon-Kucher. I love his thing of like, "Lenny, what is a fair price you would pay for this thing that I just described to you?" And then you say your thing. And then I go, "Okay. Well, what would be an expensive price?" And then I say, "Okay, what would be a prohibitively expensive price?" And you ask those three questions. And generally, when people tell you the fair price, it's a little bit of like they're trying to get a deal. And if the product's good, the expensive price is the one that they would actually pay.

(01:21:47):
Where they're saying it feels expensive, but you put it in front of them, and you say, "It costs this much," and if it's really good, they want it. And the prohibitively expensive one is the one that's too expensive and they'd have to just, "I just can't do that." So I love these style of questions. I think they're just a lot more specific than what I see most founders doing, which is just chatting with customers. You really want to try to put them to some questions where you know they're going to answer honestly because you're asking them questions. You're not asking them to speculate and you're asking them fairly concrete stuff.

(01:22:18):
Oh, and the thing I should say is it's a two-hour session, like I mentioned. It's one thing to explain this stuff, but it's another thing to see it. And so we show tons of Zoom recordings from founders who have gone through the program, and we actually do this thing where all the founders who are going through the program, they recorded all their videos, their customer discovery videos, and then our team watches all of the videos and creates highlight reels.

(01:22:45):
And we sit around in a room and watch them together and we say like, "Oh, look at these questions that Lenny asked. And did you see how the customer responded? Wow, that's an eyes-light-up moment." Or, "Todd asked these questions, he's leading the witness a little bit and the customer didn't seem that interested." So the thing that's interesting is as a founder, you never see anybody else's version of this. You only have your own experience. And so just seeing how other founders do this in a real live setting is super. People love it.

Lenny Rachitsky (01:23:13):
And it's always easy to hear these things. It's much harder to be the person asking these questions to a potential customer you're trying to sell. And it's just asking, "How much would you pay for this?" So I love that you kind of force people through the actual practice of it. Todd, you're going to get a lot of applicants for this program. This sounds amazing. I know you're giving a peek at the stuff that we haven't really talked about. On this point you just shared, which is essentially trying to get real skin in the game insight into how big of a problem this is, I love that you just basically shared a bunch of questions.

(01:23:43):
Someone could just rewind right now and just write down all these questions that you shared and use them when you're talking to customers. Obviously, the classic problem is they tell you they're going to buy it but they don't. And all the stuff you shared is, "Here's ways to get at: will they actually buy it before they have the actual product?" Is there anything else you want to say on that? Just tips for not being tricked and people just saying, "Oh, yeah, I love this thing"? I know you talked through a lot of this, but anything else?

Todd Jackson (01:24:06):
Yeah, I think there's a couple of things. One is you have to know what to show people when you're actually showing them something. Lattice is the kind of product I mentioned that could be sold with Figma mock-ups. Looker couldn't be sold that way. Looker, you actually had to do a demo with their real data. So it required a lot more work to do that. Vanta was neither like a demo or a mock-up, it was actually doing the work. And Pilot was like that. There's a bunch of companies like that. So you have to figure out what is my product and how does it solve the problem? And therefore, what fidelity does my early product or early demo have to be at in order to land the sale?

(01:24:44):
And then I think you have to know when you've talked to enough people. It takes time to talk to people. And the rule of thumb is if you talk to enough people and you can predict 70 to 80% of what the next person is going to say to you, because you've just talked to so many people and you've heard the pattern so clearly, that's when you've talked to enough people. But these are all things you got to learn. And that's why doing it experientially in the way that we do the program we think was best.

Lenny Rachitsky (01:25:10):
Is there anything that we haven't covered that you wanted to touch on before we let you go?

Todd Jackson (01:25:15):
No. If you're listening, if you're a B2B founder in those early days of starting your company, or you know anyone who fits that description, and you have an appreciation for just how hard it is to find product-market fit and you don't want to go it alone, then please apply to this program or share the application. Like we promise, we will review every single application. And I'm just really looking forward to working with a group of 20 or so amazing founders, and helping them navigate these early days of product-market fit finding. It's what I love to do.

Lenny Rachitsky (01:25:43):
So just to make sure the right people apply, remind people who is a great fit. So it's B2B founders, and you said they've been at it for six to nine months, something like that?

Todd Jackson (01:25:52):
Yeah, something in that zone or earlier. You have an idea of what your product is. You have a hypothesis about what it is and who it's for, but you probably haven't started writing any code yet.

Lenny Rachitsky (01:26:01):
And if they've been at it for four years and haven't found success, this is not a fit.

Todd Jackson (01:26:07):
I could try to help them one-on-one, but no, that's not a fit for this program.

Lenny Rachitsky (01:26:10):
And then how do they apply and when are their applications due?

Todd Jackson (01:26:13):
Yeah. So you go to pmf.firstround.com. Applications are open. They're going to go till May 7th, and then the program starts on May 29th. And if you want to reach out to me specifically, you can find me on Twitter. I'm @tjack, T-J-A-C-K. You can follow me, DM me. And yeah, I'm looking forward to working with some amazing founders that I know are listening right now.

Lenny Rachitsky (01:26:34):
Amazing. I'm so happy we did this. I feel like this conversation is going to help a ton of founders, and they're going to come back to it again and again. Todd, thank you so much for being here.

Todd Jackson (01:26:43):
Lenny, it's been a pleasure.

Lenny Rachitsky (01:26:44):
It's been my pleasure. Bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.