The new PLG playbook | Arming the next generation of product-led companies | Oliver Jay (Asana, Dropbox)

Brett: Before we kind of drill into a lot of these topics about how you, how you set up to sort of successfully go after enterprise. I'm interested in the last 10 years. You've kind of had kind of 2 big chapters. The 1st, at Dropbox and then the last 6 plus years at Asana. Do you have, like, crystallized big ideas that you keep coming back to that kind of ties that last 10 years of building together?

OJ: I'll start on the people side. I think winning the enterprise is really And winning a more traditional sort of PLG motion, it's almost like two separate companies. I think it's a very different way you think about building product, different way you interact with customers, and certainly a very different way to go-to-market And as a result, I think even the talent is, it's usually quite separate across the whole company. Even how finance and legal and HR supports an enterprise company versus a more traditional bottoms up PLG company. I think it's very different. So the big idea here is like, it's really frigging hard, really hard because if it will feel like you got your, you're building two businesses at the same time.

I think the big mistakes companies make over and over again, one I see is when they try to blend. They think they can, they think they can just seamlessly evolve and as they scale and, into an enterprise company.

I think it's, I think it's a lot more complicated than that. If it feels like you're building two companies at the same time, I, I think you, that might actually feel, that might be okay.

Brett: Why do you think intuition is so wrong there?

As a thought exercise, you talk to the average founder. They, are not doing enterprise today. So let's just say mid market. It's more PLG oriented. ACVs are 20k they're growing from five to 12 million. And you bring up the topic of doing enterprise. Most founders' intuition is that you can blend it together.

 And the case I'm hearing you make, which very strongly resonates with me is that that intuition is actually incorrect. 

OJ: To me, there's, there's a short and long answer. Short answer is there's a, there's a lot of successful, I don't know a lot, but there's at least a dozen successful multi billion dollar private and public companies that started as PLG and From the outside, it looks like, oh, they morphed into being an enterprise company and they got to multi billion.

And so for most PLG companies that are like, you know, sub 10 million, 20 million in valuation, they're like, they see those as examples, prime examples, right? They see Slack, oh, people here talk about Slack all the time in the last five years but that's a great example. Look at that. Become enterprise and now they're in Salesforce.

So we can be the next, we can ride that wave. We can just take their playbook. So I think that's the short answer is like I think people, a lot of times, over index on precedents and without really thinking about what were the drivers for certain outcomes, um, that led to, like, for example, Slack's success. The second reason, I think, is because, like, a lot of founders I've met are phenomenal, super smart, and, and there's a lot of pride in being a first principle thinker.

And so being a first principle thinker, what you do is you look at the data in front of you and what information you're receiving. For a PLG company, this is how you build intuition. You first throw your product out there. A lot of people use it. And you're getting a lot of user love. Awesome. The next phase, your product is actually being adopted in enterprises, right?

Small teams or individuals within enterprises and a small subset of those enterprises actually reach out and say, Hey, I see that a bunch of people are using your product. I want many more people to use the product. And so instead of a $10k deal, you go from a $50-100k right? Now, a 50K deal from an enterprise is like, it's like a POC. If you're used to like selling individual 10 a month deals, suddenly companies, your own customers are coming. They're very happy. And they're saying, hey, I want to buy more, I will give you this money. If you build me all these like security features.

And you're like, well, I'm a first principle thinker.

That's very logical people love my product. They're one, like I just, it's pretty rare, right? You're coming from a world as a PLG founder where you're building a product and you don't even know if product market fit is there to now people are like saying, hey, you rebuild it, I will pay you. That's so attractive.

And so your intuition's like, oh yeah, of course let's, let's start building the security stuff. And then the next phase, what happens is like, as you build the security stuff, it does unlock major expansion in within your customer base, right? The companies where you have good organic usage, many of those companies will start paying you $25k $50k $100k $200k. And so you're taking in this data, and you're like, wow. It's working. Until you don't have enough accounts. Until you're scaling out the sales team, the marketing team, and you just don't have enough accounts that have that kind of organic bubbling up organic usage. And then you hit the wall and then you fall into the, what I call the PLG trap. But along the way, you see every strategic decision you've made is super logical. And so it's the, that's why I think the intuition is like, oh yeah, I can, this is a, this is a very linear way to build a and sequential way to build a, enterprise company starting from PLG. And I think that's why that where the danger is. 

Brett: Before we get into some of the implementation details, maybe you can kind of continue the line of thinking and talk about this idea of, if you're doing this correctly, it should feel like 2 companies.

OJ: Let's think about the mindset first. Enterprise, we always use the term customer journey. What's the customer journey? Who are the people in the company who receive different forms of value along the way, that eventually makes the right decision of buying your product, right?

And that takes a long time. It can take 12 months or 18 months for big enterprise, but it's a customer journey that you're designing everything towards. It's certainly on the go-to-market side. Sales, marketing, support. They're thinking about the customer journey. PLG, your mindset is not customer. It's user.

What is the user journey? How do I get them to show up, learn about me, consider me on the website, try my product, maybe freemium maybe through a trial, and then convert as a user. That's like a very different mindset. If you're from a product perspective, you would look at feedback, sort of aggregate customer feedback very differently, On the enterprise side, it is largely dependent on what's coming from the field. I would say 80 percent probably, and then 20 percent is like, what, with that feedback, how can you sort of do the, fulfill your customer's job in a better way with your product, with a more innovative way?

Whereas on the consumer side, you have to look at everything on a massive scale. It's much more like a consumer business. It's much more growth driven, and the same, same thing on the go-to-market side with a traditional PLG motion. It's about how do I, hey, at best, it's like, hey, how can I get that user to really love my product?

So there's a lot of questions around, hey, where, Where should the initial human touch and experience come in? Should I hire an inbound sales team or support team and intercept people midway through the onboarding journey to like really accelerate how they use the product?

that's sort of like the limit to which how you think about layering the human go to market motion on top of your self serve piece. And then obviously on the enterprise side It is it is completely different. You need a massive team approach from driving demand to outbounding to qualification and all that. Again, it is operationally, it is really very very very different jobs And so, because what you, what you end up doing is you have to be like, okay, I got to optimize for the users and for the, for the company.

And like that mindset is very different.

Brett: if the two of them are working symbiotically, what does that look like? Or do you generally think about the world separately? 

OJ: I think it depends on your product and your category and your audience. If you're fortunate and you pick the right category, can be pretty seamless. So let's, if I take a look, if I think about, certain dev ops tools, think about like a Datadog or in the infrastructure layer the PLG traction directly leads to an enterprise deal, right? A small team of engineers evaluate the products. They decide Datadog's, the right product to go with. You can even put Atlassian in there and Jira. And the next step is, okay, the CTO or VP of engineering says we're standardizing on this and next thing you know, procurement comes in and, and you got the, you got the, the six figure deal.

For those companies, it's very clear that it's actually a straight path and it's, it's, it's quite efficient. 

Brett: And in that case, do you, your sort of simplistic way of thinking about it as two companies, that is not the right framework? Or still, even in that case, you think about it similarly?

OJ: It's like a spectrum, right? So it's like, it will, it won't feel as much like it's two separate companies because your user value, but until we said just now that your user value and the and the company value is tied. It's the same. And so, in practice, what happens is like, you get really big and then you have, like, you have new customer versus existing customers on the enterprise side, you're trying to go outbound.

And so the motions will likely be different and need to be treated differently. Like, Datadog today at this scale, they can, absolutely, and I'm sure they do, build an outbound business. They can go in cold into a company and force that evaluation, even if it's not happening organically, bottom's up.

In those cases, I think it is less so of a feeling of, like, you got two different companies, even though, you know, certainly some of the motions would be very, very separate, when you get bigger. But for companies where your user problem is very different. The problems you solve for users is very different than the problem you can solve for a company.

Then it really is very, very different.

Brett: What are the best examples of those shapes of companies?

OJ: let me Asana as an example because I think it's, obviously one I'm very familiar with, right? The initial product, bottoms up, is phenomenal for smaller teams. Teams of 5 to 20 trying to get a product done, trying to get a project done, trying to plan an event, trying, that is an amazing, amazing product market fit.

We did a lot of things to sort of propagate that growth organically inside enterprises. It's not uncommon, you go look at an enterprise and you see hundreds and thousands of small teams using the product, getting value on that sort of user level or small team level.

But when you have a conversation with an executive, and you're trying to get them to like, go adopt Asana in a big way, the question is, what problem are you solving for me? because as an executive, all I care about is driving enterprise value. And really the only things that drive enterprise value are driving more revenue, lowering costs, risk mitigating, right, on that level. And so your pitch at that point is like, well look, uh, look, so many teams are being more productive. You see? Right? And so we can help you lower costs. Or you can say, oh, we can help you drive more revenue because you can launch more products in a year. It might be true, but as an executive, like, I'm benchmarking that option of forcing everybody in my company to use Asana.

Or I can go acquire another company and get more revenue that way. My job, as an executive, is to drive more revenue. And, pumping out more product with the help of Asana is a multi step process where I can just go buy another company. Well, I'm going to choose to go buy another company. And so the company level problem that Asana solves, if it's for the same as what it is for the small teams, it doesn't really resonate with executives.

Circling back to your question of is there any kind of symbiotic relationship here, I think there is yes, because You will start getting some glimpses of what enterprise value you can provide, enterprise scale value you can provide with some of your, more successful customers that started bottoms up.

So at Asana, what we realized was a lot of companies were starting to use Asana as the framework for goal setting and OKR setting. The reason is because all the work is actually already happening in projects and tasks in the product. And so you might as well set up a portfolio and that portfolio is basically your goal.

Each project is sort of like the, the project is tied to each of the KRs. We started observing that pattern, and that was a really interesting insight because goal setting and OKRs is an enterprise level, an enterprise scale problem. It's a decision that companies, you know, CEOs, or at least the head of HR, they make those decisions.

And so we found that out, not because we were just like geniuses, because our more healthy, organic PLG customers showed us the way, and that's why we ended up investing a lot in OKRs, because that gives us that conversation opens up that door to have that executive level conversation.

Brett: What was the story behind company value and user value in the context of Dropbox?

OJ: There was no company value, from the product side, except security. Dropbox is a really interesting case study. And it is one that I think too many people look to emulate, but they just can't because what happened with Dropbox, amazing product, perfect market timing. You can go to most, like I ran APAC and I remember our headline when we launched in Australia, it was one in three Australians use Dropbox. That's a very powerful headline. And it means that when you go into a company, 30-40 percent of employees are already using Dropbox. And, and Slack is similar, right? Slack will get all the developers on board first, and that's like 20, 30 percent of the company.

So then when you actually build your enterprise sales team, all you need to do is sell security for your own PLG product. Because when I have a third of employees using your product, and they might be using, there might be confidential information going, you know, going in, and I want to make sure I got the right access for a third of my company,

I'll pay up for the enterprise version. I'll sign a multi year, deal. I want to make sure your SLAs are enterprise grade. And so Dropbox and Slack, if you ask me what's a company value, Well, the company of value was securitizing, in a way, the bottoms up problem that we created for them. Which is all this rogue usage.

And, you know, Dropbox and Slack were phenomenally successful because they had such a large base. Most companies aren't able to pull that off, even if they wanted to.

Brett: Are there downsides to that or like local maxima problems you run into? When your primary company value is peace of mind and or fear mongering security? And not much else?

OJ: Yeah, this is, this is what I call the, the SAML, you know, SSO hostage play that many companies employ. Including my own companies in the past. Here's the downside. The downside is very likely your upside case is essentially you have securitized and stabilized your initial organic user base.

So at Dropbox, it was very common was we would see people pay like seven figure deals, right? For the enterprise grade of a version of Dropbox that has all the security bells and whistles, but it was primarily for just that 30 percent of employees. You don't really develop trust and the right relationships with the shared services and procurement and IT to really like deploy out wall to wall.

Of course you try right? And I would say maybe 5 percent of your enterprise customers are able to actually leverage that access to IT's interest in security to drive a bigger deployment. A lot of times you're basically trading seats for a discount. You know, traditionally, traditional enterprise software. You think of yourself as a company, as a strategic partner to the, to your customer. How can I help you actually achieve your company goals? And, the hostage play, you're not setting up yourself for that kind of relationship and so the local maximum, I like the way you framed it, oftentimes, the local maximum is your existing deployment and whatever happens organically and you don't get pulled. Like, the, the beauty of enterprise is you can develop that relationship with your customers and together figure out how you deploy the software, in which teams, when to solve a company problem.

You don't, you're not going to get that conversation.

Brett: is this the root cause of why Dropbox is call it a 5 or 10 billion dollar company and not a 50 billion company, or there's more underpinnings to what's kept it from compounding in that way?

OJ: I think you get different answers when you talk to different people. I think Dropbox is a tremendously successful company and generates hundreds of millions of free cash flow a year, which in today's market, I think a lot of companies would, would die for that. When I think back at our, our strategy, one component that we, I think we missed, which was the, which was sort of how do you move up the stack to deliver enterprise scale value beyond your own security, uh, the security of your own usage.

I don't think we nailed that. We tried a few, I mean a few different bets to get there. One can argue there, if Dropbox Paper, had, You know, maybe launch at a different time or a different way there would be no Notion potentially.

So there's, I think there's some execution potentially, uh, why that is. But for sure, I think Dropbox, like I would say, there's a scenario where there is no box. And I think that was Dropbox could have made that happen. But I think there were a lot, a lot of other bets that, that could have actually made Dropbox a lot, lot, lot bigger, but that's a full podcast.

Brett: You bumped up against this idea of the, the place to begin with company value is goal setting and or OKRs.

But I'd love you to kind of expand on that and just tell the story of, of what the Asana sort of enterprise narrative ended up being or what is the story that unfolded?

OJ: I think Asana started in a really fortunate time because a lot of the early unicorns like when unicorns were still a big deal 80 percent of them were sort of built on Asana. This all grew up together Airbnb, Uber, Pinterest, you know, so forth. And so that got us really into big enterprise deployments in those early tech unicorns.

Brett: There was no traditional sales at that point it was bottoms up adoption and you would see, you know, at Uber.Com or whatever that that was sort of the state of things where it began?

OJ: Yep, that's right. It would just organically grow. And then it was not an outbound play. So there, there's two steps. The first go to market motion we layered on was, was inbound, which was really taking and cherry picking the users that were coming in self serve and like enabling them, making sure they're successful.

So yeah, if we saw you're coming in from Uber, you'll probably get a personalized outreach, right? Because we want to make sure you're successful as a team. And more importantly for us at that point it was also like, we want to make sure that those teams are using the same conventions. As other people, other teams at Uber.

So that's how it started. The second team we layered on was expansion sales. 

Brett: So that 1st team is it feels more like CS?

OJ: It's a hybrid. I call it online sales when we started it. Many companies call it inbound sales. Some people call PLS product led sales. I've heard that. I think your question is right. Like I, the, the, the job is realistically is 70 percent CS, 30 percent sales.

If I had to do it again, I wouldn't call it inbound sales. And if I had to do it again, I might actually just make, just call that CS. Uh, but your job really is getting people really comfortable and in love with the product very quickly at their highest point of propensity but the, the sales component comes in where yeah, at the end of the day, you still have to like, have the grit and discipline to, to follow up and, and make sure people actually get you their payment details. And so it's a combo. but yes, that's a, that's a really good observation. It's really much more of a CS play up front. Once that's happening and you're starting to see momentum, then, then that's when we layered on expansion sales, and this is a team that cherry picked the most, let's call it the most healthy, larger companies that have a reasonable amount of usage.

We didn't have the dynamic that Dropbox and Slack had where you have 30 percent of the company using it, especially when you go outside of the, big tech companies. And so, A lot of times it would be like 5 percent of employee base, right? Well, that's, that's already pretty good. And, um, this expansion sales team would go and sort of take over and they'll give the white glove service to users and champions in those organizations.

Brett: But at this point, you're not going to the executive level. If they have a VP eng or VP product or CIO, we're not there yet. We're just trying to get more pods of people using the product.

OJ: Look, you always try, because if you can, we always say you got, you got to go high, you got to go low. And sometimes if you get a bite, you know, senior up, amazing. Then it cascades down. Later we can talk about how sometimes I think that can be a, um, that gets people into trouble in terms of how they think about champions.

But generally speaking, you, you get as many champions as possible. The more senior, the better. Usually you're looking at the sort of director level, right? The team for us, it's the people who are actually doing the job.

Brett: If you're kind of going in a multitude of directions, how does product strategy fit in? Because I would assume as soon as you're trying to go wall to wall, you're making an executive level case, a company value prop that you were talking about earlier. I would assume that there's product work to then be able to convert that into six or seven figure deals.

That product work is probably different than we have 5 percent and we're trying to go to 10 percent this year of the company?

OJ: The base activity is to just get as many teams as possible. And so whatever worked for the first team of 20 probably will work for the next 10 teams of 20. Then the question is, okay, how do I get not teams at 20? How do I get teams of 100 and 200 at a time?

And there is product work there. And, and, and this is where I think we had a really good alignment across the business. And, and, and so there were two things that needed to happen. One was we needed to build, we need, we got, we had to get the security roadmap along the way, that's a no brainer. But what we realized was we need to develop the product experience for, let's call it manager of managers, project managers of project managers. 

And so, uh, that's what led to eventually we even launched a whole SKU, that is targeted the ICP there was the folks who manage a portfolio of projects and it's a different, it's a different, experience. It's a lot more about reporting, a lot more about insights, a lot more about goal tracking. And this, this is how eventually we got the sign that, oh, this is how people are using the product for goal tracking, And so we, co created with our product team to target a, not executive, but somewhere between executive and like a manager level. And that persona was, was pretty key.

Brett: And when you think about the sort of this phase of selling and the go to market org and this phase of product work, was the team now starting to be split into two different worlds or what did the not sort of terminal case of org design look like, but as you're going from the 20 person teams to phase two, how has the team actually organized and who's running what at that period of time?

OJ: You know, when I think about the revenue team, the marketing team, and the product team, I think we loosely had in each of these groups, we loosely had, at this point, three different pods that targeted the different personas, right? The end user, the manager of managers, and then the, IT.

So, like, on the product side, we had a growth team that's working on monetization of really just optimizing the funnel, all right, of people coming into the product, getting people to buy within the first try. We had another team that was building the features needed for managers and portfolio managers.

And then we had another team that was building the enterprise SKU. That wasn't that different to how we set, we're set up on the revenue side. I also had a self serve team that was driving the optimization of all the different conversion points before they get into the product. And they work really closely with that monetization growth team on product.

I had a team that really focused on the online sales, which was really that hybrid CS sales role. And then I had another team that was carved out to, you know, we called it the enterprise team. And their job was to go after and hunt and expand, with the, the new portfolio SKU right.

And go after that, that persona - manager of managers?.

 That's right. That's right. So it's, it is pretty loosely like correlated, I'd say. Um, I don't think we did it by design. I think looking back, I think there was an opportunity to strategically actually align even more.

Brett: Now knowing what you know, was that correct? Or like you can go back and change anything you want with the incredible benefit of hindsight. Are there adjustments you're making to how that kind of emerged?

OJ: I think so or, or chart how you design it or chart. There's so many, so many factors and there's no right or wrong, right? You align one way. There's always a trade off. That's the only thing you can guarantee. So how we like figure out our lines, our lines, whatever is, I think it can go any way, I think there was an opportunity to, looking back, to be really, really laser focused on okay, what is the persona of that, that first project manager, and, and really think about that, the user journey in this case. From marketing, awareness and consideration all the way into when does that CS team get in front of them? I think for us we, and the same on the enterprise side, right? We, I think we did it more piecemeal, but I think we could have been even more clear on like designing that journey.

and, and it probably would have led to like faster progress.

Brett: As you're explaining what's happening in phase two, starting to build product and sell to a slightly more senior person in the org, did things immediately start to click as you're doing this, or was it wobbly in some way where the self serve was firing on all cylinders and you're kind of getting this new thing off the ground?

OJ: We essentially as a company, we layered on different motions, right? First it was 100 percent self serve. Then we layered on that CS sales experience. Then we layered on expansion sales. And eventually we layered on let's call it more traditional enterprise, executive selling.

And in the beginning, of course, it's rocky every time you add a different layer. we got through it pretty well, uh, until the executive side was hard, right? Uh, because that, that was one where I think the, the gestational period to build that play took us by surprise. It took, it just, it takes a long, long time.

And so I think, to your question around, were things rocky? I think things are rocky whenever the business and the product side are not fully aligned, in terms of timing. Let's assume, let's assume you get your strategy right. If your strategy is wrong, then you've got bigger problems. Assuming your strategy is right.

You gotta, you have to like time, the execution of both the product and the business side really, really well. And also the, the GNA side too. Making sure you have the right legal support, to drive enterprise deals is as important as the product, by the way. I think that's where things get difficult.

Brett: You talked about phase two, both on the product side, go to market side, sort of starting to carve out this product that was sold to managers of managers, and then enterprise, and enterprise selling, did anything happen in between those two phases or that's what you would define as the third phase is going now one, two, or three clicks above to an enterprise product and enterprise sale?

OJ: In retrospect, it was really clear those are two different phases. In the moment they, it didn't feel that way. Right? In the mo, in that moment, you're getting some traction, right? Some of your bottoms up plays where you get managers of managers to buy into your product, they happen to be really outspoken VPs, and they bring you to the CIO, and the CIO's like, oh, this Asana's great, right? You ask about like, how our messaging changed, like, our messaging, when we get to that level, we weren't selling projects, we were selling clarity. We were saying, like, we call it the pyramid of clarity, at that point.

Uh, which is like, Asana is how you gain clarity on what's actually happening in your company. If you ask executives, they don't actually know that. There's a whole series of reports that get created for them. I mean, Asana is like, gave you that kind of level of clarity. And so some enterprise accounts naturally, we were able to have those conversations.

And so it felt like, oh, this is the natural path, like we just keep, keep doing this. In retrospect, what I found, at least in retrospect, was that at a certain point in time, those kinds of accounts that you, where you can naturally migrate into that company journey is, is limited.

Because you may not have developed the right kinds of champions in those organizations. to actually get you, in front and have that right conversation. And, and so how do you create more of those opportunities is a very different play than the generic, generic expansion play that we were running. So that's where to me it's a different phase because you want to go after executives,

you got to find a different way to create that demand. You can't just rely on your organic user base to organically create, um, you know, create those opportunities.

Brett: How did you figure out this idea of selling clarity?

OJ: This is the genius of Dustin Moskovitz and JR, their co founders. From the start, that was what Asana was built for. Asana wasn't built to be a project management tool. A lot of project managers use it, but why do you use it? You use it to gain clarity over what's going on.

And so, I think I had the good fortune of finding, the best possible founders who got it right from the start.

I mean, the, the, the story of Asana was that it was the Dustin and JR built a version of it at Facebook and that's how Facebook built product so much so that it was, Facebook was one of the hardest enterprise accounts for us to crack because their V1 like non mobile version was still so widely used, right called tasks. And so they, they had a very, very clear idea of the problem at scale that companies have, which is lack of clarity, which is what I think when, when Dustin was managing all the engineers and the CTO, he, he knew that. And so for us, that was always part of like the, the true north is to get organizations clarity.

But in reality, in the beginning, people were just doing projects and tasks. And it wasn't until we started seeing large deployments, people started using Asana for goal setting. That's when we start, it started to click. We're like, hey, now's the time we can actually start pitching this idea that you can actually get clarity.

And I think that, it really was the genius of the founders.

Brett: Let's talk more about that phase three, the enterprise chapter. Sort of what was the order of operations to make that work?

OJ: I think it always starts with a user problem. So, identifying, right, the job to be done here. And it was really to help executives get clarity on where their hotspots are in a company. Like goal setting, as you know, like most executives when they goal set, they're not looking at the goals that are green, they're just looking at the ones that are red or yellow turning into red, right?

So that was the, a big part of it was, okay, that's what we want to solve because the alternative is usually spreadsheets and presentations that get rolled up, over the course of a week, two weeks, a month to get executives visibility on their most important projects. So number one was problem identification and also persona.

Number, number two, then it was, it was really about, okay, figuring out how do we actually. what's the motion? What's the go to market motion to get to these people?

Brett: How did you also figure out just before we keep going? This was the time to make a concerted effort to crack enterprise.

OJ: In retrospect, I can give you a really fancy answer. In reality, at that moment, I mean, I think you can ask anyone on my team, like, I want it all. I want it all. and so I think that's, probably the predominant, feeling here, which is that we want to win, and we believe that, I remember talking about this in my all hands, when you look at every single category that's been created, it's very noisy in the beginning, but there's a period of like, there's like a two to three year window where there's massive competition, but coming out of that, the category leader is kinged or queened.

And that category leader gets like 70, 80 percent of the market share. And I think I saw this at Dropbox. I saw this at, you can see this in the messaging world. You saw this, um, in obviously CRM, every category, like the thing about service now, like there is a there's like a two to three, four year window where like all the action happens, and then the leader is ordained. And so with that belief, and then another belief was all categories have to go through the enterprise. All winners have to win through the enterprise. There's very few, I really can't think of many, if any, companies that have become the category leader without, winning the enterprise.

So winning the enterprise was an imperative. Winning during a window when you feel like, this category is being created was important. And so I think that's why we decided to really, step on the pedal to the metal.

Brett: That's helpful context. So let's go back to sort of step by step what you ended up doing.

OJ: Yeah. So after you, after we gained confidence. in where, what product.Market fit could look like for us on an enterprise scale, then it's really about the go to market and it's about getting access.

Brett: For that first step, are you just spending a lot of time with customers, seeing how people are using the product, sort of doing more classic zero to one kind of work to land on where the product needed to go and how you're going to articulate value?

OJ: ABsolutely. That is, that is getting really close to customers. we had built a pretty sophisticated feedback engine between the, the field and product. And, and we had. you know, we call it voice of the customer, but it was, it was a really robust program to foster the right kinds of conversations and, uh, to, to ensure that that feedback was being had.

I had great, great partners on the product side, like all the product leads, including Alex, the head of product, Dustin, they were very, very. Very supportive in getting on calls with customers. And so I think as a CRO, a big part of my job was orchestrating that information flow. And I think that that helped a lot.

It's because then everybody was on the same page and saw the same opportunity. Now you still don't know, but you can. inch your way in and test and get customer feedback really quickly. That's a good thing about the enterprise side, is that you don't need to build a full, full fledged product to get confirmation of product market fit.

Brett: So yeah, share more about then the go to market side.

OJ: So at this point, the go to market is all about, Hey, how do you get access? How do you get in front of the right executives to have this conversation about providing clarity in the form of better goal tracking. We thought it was, it was hard to go just straight outbound. Straight outbound to some executive, get them to be interested.

Like I don't even know if that motion really works at scale anymore. When you, right, it's just, it's so overused now. And everyone's just like filtering out those emails. It's just, and like AI now is just going to automate that whole thing. W Hat we found was in most organizations we had champions. And the question was, how do we leverage our existing champions to get to that executive champion?

And in many organizations, we would say, like when we review accounts, account strategy, I want to see the champion, I call it the champion tree. Which is, who is the target executive we're trying to get to? All right, and who are we, who do we have a good relationship with now? Show me how we're going to connect the dots.

All right, what's the path to get there? And so a lot of our go-to-market approach was really executing on connecting those dots. And what we found was, in most organizations you have different types of champions. and you need them all to, to have a deal. So, let's take a step, let me, let me double click here.

A traditional enterprise methodology. It's like BANT, right, where A is like authority, or you use MEDIC or MEDPIC, right, which is like, basically there's two champions that you need, which is like, one is, who's going to advocate for your product. And the second is who's going to sign the paper, right?

That's traditional thinking. FOr PLG companies moving to enterprise, what we found was one, and kudos to my team for figuring this out. I didn't coin this, my team did. First we call them, we call them Intel Agents. Why are they Intel Agents? These are people who are pretty junior in an organization.

They're using your product, they love it. But they don't have any say in strategy for the company, And we call them Intel Agents because they can help you map out your tree. You're champion tree. They tell you where are the hotspots, right? They get, they tell you, uh, they're, they're intel agents.

The next level, we call them or change agents. So these are people who are, they could be junior to usually like one or two level more senior, but still junior, but they're they're change agents because they're willing to put their name on the line. I think this is traditionally the the champ the the type of persona that enterprise sales you would want to go after, It's like someone's willing to put their name on the line and they're in the way they're building their career by advocating for your product. And so those are change agents and those are really, really important because change agents are the ones who bring you to what then we call the executive agents.

They're the ones who connect the dots and, and open up that door to the right executive to have that conversation. The fourth champion is, centralized or procurement agent, right? That's like your IT security procurement. You got to win those folks over as well. And I think the big change in this phase is elevating that executive agent.

Because remember at this point, we've been building other security features. Those features are unlocking million dollar expansion deals, mainly just through IT and security and procurement. So you've, we have elevated in this, at this point in phase two, we've elevated that shared services persona, but now we need to, in addition to that also add the, that executive agent and find a way to make them successful.

Brett: When you started to do your first few, what you would define as enterprise deals, did you have one or two enterprise reps, and that was the go to market org? Or like, what did the people side of this look like?

OJ: The benefit of hindsight coming from Dropbox because at Dropbox, we, tried a lot of different motions. We went really big after with direct sales. We went really big with obviously, PLG. We also really went big with channel. And so when I, when I started, from day one, I launched, even though my focus was building out the online sales side, I always had a pilot enterprise team, and it was just three people in the beginning.

And I basically took the three more sophisticated, members of the team in terms of like handling deals. And that's the team that over the next five years really got built out. But it started with small team and the theme was always let's build that enterprise sales muscle. All right, figure out our playbook, figure out our messaging by really cherry picking the best enterprise accounts early.

And we like sort of manually said, all right, you three will work on these a hundred accounts. Over time, I realized that's too, even too many. It should have been just 50. And the idea was like, okay, let's start with a small team and give a small team that counts to have our best penetration already.

And let's see how, what kind of expansion can we do? Because if we can't even, if we can't even drive big expansion in our existing best accounts, then we have no chance going outbound and getting a more cooler account, right? Less hot account. And so that was always the case. So like, Nike was you know, as an example, I'm not saying like he was a customer.

I don't think I'm authorized to say that. But as an example, if Nike had a lot of users, Nike would be in the, in the enterprise book, but Adidas would not because Adidas, we didn't have enough people, uh, users, right? And so that notion we sort of maintain through the years. And so even as we're sort of now much bigger going after enterprise, we sort of had the same mentality, which is okay, which are like, let's, let's have a team that's carved away and their job is to figure out which are like, let's, let's find the, the companies that are like in the perfect ICP profile.

And, um, even if they, at that point, even if they, they weren't the ones that already have a lot of usage, let's see if these folks can crack it. and working with marketing to, you know, execute account based marketing and all that, all the, like the full, the full artillery. All right, let's see.

Can we crack open the best ICP companies, companies that fit our ICP? And as we did that, then we sort of expanded the radius.

Brett: And you did that long before you were ready to, to go hard at enterprise?

OJ: Yes, definitely. 

Brett: And knowing what you know now, that was the correct thing to do?

OJ: Absolutely. so we talked about phase one as like primarily online sales. Phase two is expansion sales. Phase three is like value sales, right? Going traditional enterprise sales. Phase three starts the same time phase two starts.

Because it takes much time to identify the problem, identify the path, and then start building the right team to execute that, that play.

It takes a long, long time. And so, yeah, the minute we were like building the security features, which is sort of like the launch of the expansion sales phase, absolutely was, we were already like dialed into figuring out, okay, how do we get to that executive sale where we can solve an enterprise scale problem?

And a lot of that came from like, a lot of that comes from the field and insights from the field. And when I, when I travel around to visit our offices and customers. I'm laser focused. At that point, I'm laser. Even though, the team is primarily driving expansion deals unlocked by security. When I talk to customers at that point, it is usually at a high level, and I'm, laser focused on trying to figure out what that problem is.

And then start to pilot and build the right motions to, to execute it.

Brett: We spent a lot of time talking about how go to market and product sort of changed as you wanted to go from having maybe 10 people at Nike to the whole company using it. Are there any sort of insights that you figured out around let's call it, you know, the 10 person arts and crafts store using the product in Nebraska versus the hundred person venture backed tech company versus the thousand person venture backed tech company versus the 50, 000 person technology company versus 100, 000 person, you know, packaged goods company. And how that sort of fits into this sort of topic of phases or go to market motion, sort of those types of things.

OJ: This is something that I see a lot of PLG companies get wrong, which is they, they, they, they confuse segments and motions. If you take a step back, traditionally enterprise companies are set up and they are split by segments, SMB, mid market enterprise, right? And of course, of course you have like big enterprise strategic accounts, but it's, it's primarily correlated with company size as a segment because the motion like Salesforce selling sales cloud marketing cloud to an SMB is a very different motion to that of mid market versus an enterprise. For PLG companies, that might not be the case. You may find yourself where, what it takes to get a 50 person, 100 person deal done in a large enterprise is the same exact motion to get a 100 person company use your product wall to wall.

And so, uh, this is something I learned at Dropbox when I remember looking at, our teams and we were set up at one, at one phase, we, we, we were split up by segments tied to company size. And what I noticed was it was really, really hard to get the enterprise sales team to actually do the right thing, which is hunt, because if, if you are enterprise and you get California.

It is likely that you have three accounts that have tremendous existing, you know, existing customers already that have tremendous expansion potential. And then you have like some lukewarm ones and you have a bunch of cold ones. What I find is that human behavior is very hard to change and so human behavior will lead you to spend most of your time on those three big enterprise accounts that are already healthy and you're just trying to milk more from them.

Makes sense. And you don't spend that much time prospecting into the other accounts. Where you spend time on instead is you spend time on working the inbound opportunities that come from those, let's call it cold accounts. Because history tells you that 1 in 10 of those inbound opportunities can lead to a much larger opportunity, right?

You might actually get a change agent from the start and very quickly you have a six figure deal. And I find that a lot of times the sales team will, will focus a lot of their attention on, expanding existing big ones.

the, the focus is on expanding and then let, and then the small deals, they're just, they're, they spend so much time on working the inbound opportunities they're not actually prospecting to the right, to the right people and the right personas. 

They don't actually hunt, they don't actually do the hard, the hard work of prospecting. And so for me, when, we're building teams at Asana, that principle of like, hey I do want people to specialize in motions, and there's a specific motion that I want you all to prospect.

These accounts are cold, we gotta find ways to, like, they won't organically grow. That's a very different motion than a company that already has large expansion opportunities and, uh, it would take another podcast to get into the details, but that's how we ended up segmenting in the company, which was, there's a team that's focused on the large expansion opportunities.

Those accounts were already ready. And some of those were mid market accounts. Some of those were enterprise accounts. And then there's another team that's focused on like actually getting the right types of usage and champions actually helping us land, um, in those organizations.

Brett: Can you explain that just in a little bit more detail, what you ended up sort of landing on? 

OJ: The framework was seed, land, and expand. 

Brett: And then you have like the two dimensions of ultimate company size and sector. So you have SMB, mid market enterprise, mega enterprise, and then you have healthcare, financial services, whatever. It's like the universe of all companies. So I'm trying to understand how, how that sort of clicks together with, this motion idea. 

OJ: So we ended up splitting our team into seed, land, and expand. Seed is very straightforward. That's the self service and the online sales component. The land and expand. The way I would think about it was, accounts that we were trying to go after, the universe of accounts we were trying to go after that fit the ICP we figured out, we carved out, let's call it a few hundred accounts, that we felt like were well penetrated, we had good use use cases already and they're ripe for a massive expansion play.

Those are the accounts that we put into the expand team and that team, some accounts were mid market some accounts were enterprise because what we felt was like the motion, once you're like, once you're already have the right champions in the organizations, the motion to close that deal is not that different. Over time, we actually found out that, okay, for the large, large enterprise, it is quite different. And we did carve out within expand and enterprise component, but all other accounts we put in this land bucket. And there's a team that was focused on getting us well, like getting us those initial use cases In these more, let's call it cold companies where we don't have traction. And again, like whether it's getting traction at a 500 person mid market company or getting 500 people in a 5000 organization to use the product, that was the same motion. That's how we segmented the 

accounts.

Brett: Oh, that's interesting. So, so you mentioned this a little bit, but so you, you tried to avoid it's a 5000,, it's Coca Cola. It's tens of thousands, hundreds of thousands. It was unlikely that you would go to the CIO and try to make a case to them. You would begin with, let's get 300 people at Coca Cola really starting to use this.

And that's kind of where it, because it's a cold account at this point, that's sort of where everything begins. 

OJ: The decision we made was we have a much better, our best path to that executive sale is through what we talked about earlier with a champion and that champion tree. And so we got to build that and connect the dots. We didn't have, I didn't have the confidence that we had what it took to just go straight to cold and go straight to AVP and have that conversation.

And so it was that motion is, we're basically thinking of it as we're building out and connecting the dots on the, on the champion tree. Whether it's a mid market company or enterprise company, it's the same process. Obviously for Coca Cola, you would, there would be more steps, right? The tree would be a little longer, but the motion is actually not that different.

You're, you're basically going from small team to get an awesome case study. To a number of teams that are interesting. You get IT to be in interested. And then you just need to find what is the most efficient path to an executive to have that conversation. It's like even at a Coca Cola, I mean obviously really huge enterprise, but it's like, it's probably only one or two other layers to, to get to the top.

Brett: Now that you kind of unpack the journey at Asana, if we go back to a place, we sort of started the conversation. And you're starting up your 20 or 30 people, you have your 1st few million in revenue. That's predominantly inbound or PLG oriented. You know, and you're getting together with the founder and they're trying to figure out what the next few years are going to look like and how do we think about enterprise and all the other types of things that we talked about? What are the most important things that you tend to convey or kind of most crystallized pieces of advice that you would tend to share with that founder?

OJ: It comes down to that user value, uh, conversation we had earlier, which is. So I think there's actually two junctions from some PLG companies, which is some PLG companies start as an individual. Their product is really good for the individual usage. And now they want to go into teams.

The value for a user versus the value for a team may require significant product changes and packaging and go to market changes. And then what we've talked about for the past hour is really going from small teams to big enterprise. Again, right, that value is very different. I always ask founders even early on, even if I'm like, uh, evaluating a seed investment.

I asked, like, what's your hypothesis, right? What is that, if it's an individual, if it's like a productivity app, like one of those email or calendar apps today, right? It's like, okay, what's your hypothesis of what that team level user value, team level value will be? What are the problems you're solving on the team level?

And then, what are the problems you're solving on the enterprise level? You have to start generating these hypotheses as soon as possible and as early as possible so you can test them test them and validate as you go. Otherwise you end up with company like, uh, like Evernote, Um, Evernote was a tremendous individual productivity app.

It was like one of the first PLG companies. It's like, I still have it. I think it's still on my tray. And like, one can argue if they executed better, there would be, there would be no Notion as well, right? But they just got stuck on the individual user value and the team user value, like they didn't really, it doesn't really, it didn't really resonate, the right, the product didn't really solve. a team level problem. I mean, to me, it's a tragedy. It's a company that's, man, I don't even know if it exists anymore. Uh, but at one point, remember it was like, it was super hot shit. It was super hot. Right? And I think there's, there's a lot of companies, that kind of missed that transition to go from individual to team, team to enterprise.

Brett: And so if that unit of value or user value is really important, what are some of the other things? Maybe as it relates to timing for any of these things, org structure experimentation kind of on what will be a 5 to 10 year journey for all of these companies, because to your point, there's there's almost no companies there's almost no existence proof of PLG inbound only only companies that can be worth more than 5 billion dollars.

OJ: You have to have hypotheses on how you move up this move up the scale in which the scale of problem you're solving in companies. 

I think a lot of companies now are trying to go horizontal. They see the previous generation of SaaS companies, right? From Dropbox to Airtable and even Notion, and they're, they're horizontal companies. and as you get into B2B and Teams, in today's market, I don't know if you have the runway to try that horizontal approach for too long.

You might need to abandon some of your idealistic product vision, to get traction, to get revenue, so that over time you can execute a more horizontal play, Um, so if we had to go back, if, if Evernote existed today I would say they should go after like the, the sales note taking app use case, right?

There's a lot of, that is a B2B use case. There's a whole bunch of companies that have started doing that. Like I would say, Hey, you go, you go build, build that, win that use case. It is just a vertical. It might not be as exciting, but you might need to do that just to get traction so that you can unlock other verticals in the future.

Brett: You've talked about a bunch of traps that you've noticed in building companies and working with a lot of founders. Are there other things in this world of, of bottoms up or PLG that you just constantly keep running into that tends to be tricky issues, problems, sort of those types of things.

OJ: I think a lot of PLG companies struggle with forecasting or PLG companies in the beginning, forecasting is actually quite easy because it's like, it's, it looks like a e commerce business, right? Like it's not your funnel. It won't. You're not going to get like 30 percent more traffic next month.

And so you're, you're optimizing your conversion, but it's, it's pretty stable, right? It's kind of a more of a run rate business. When you start adding on the enterprise piece, it's really hard because a lot of people, a lot of companies start, using traditional enterprise forecasting, which is headcount driven.

If I hire the people the deals will, the deals will come. But if fundamentally you don't have the product market fit, to have a cold outbound enterprise level conversation. At one point, at at some point you will run out of accounts and you'll, you'll start, you'll overhire. And I've seen this a lot in the, especially in the last two years, where investors and companies are just, they want in their head, they want to go back to the good old days. So basically they back into a plan based on what will prevent a down round. And that's the revenue that they got to get to. That's step one. Step two, they figure out their run rate of their PLG business and they know that it's not going to inflect that much. And they basically they plug the gap. Well, this is how much enterprise revenue we're going to bring in. on average, I see, you know, I did a Google search and ask a couple of people, ask some board members and they say, oh, what, you know what?

Sometimes people ask me like, what's your, what was your enterprise, uh, reps, uh, you know, attainment, average attainment? And the reason why they're asking that is because they're trying to figure out a benchmark to then divide the gap, which they want to close with enterprise revenue. And that now they know how many people they need to hire.

And I think for PLG companies, that are moving into enterprise. Your likely bottleneck is not number of heads, number of AEs. Your likely bottleneck is how many companies do you actually have real product market fit on a large scale? And I think asking that question first is the, is the most important question.

Because then how I would do forecasting is you would start with your run rate, right? And then you take a look at your base and say okay, of my healthy base, customer base, how much expansion is reasonable. And then you kind of add just a little bit for that outbound piece. that's going to be a good aggressive plan.

And it very well may mean that you're going to get a down round in 18 months. But at least it's something that you, that's aggressive, still aggressive and is reasonable. So I think, I think that that's where, to your question about like where PLG companies get wrong, I think it's this part. It's like they, it's very hard to plan and predict because of all these different conflicting motions.

Brett: Are there companies that you constantly come back to that you're just enamored by, like you think they've just navigated this stuff very beautifully, that are not ones that you've worked at?

OJ: No, I mean, and I would include like, they've been the ones that I've worked at. I think there's plenty of improvement. You know, and you can see, you can see the deceleration in their growth rates. And so, the short answer is no, I, I haven't seen it yet, which is why I went on this long thinking journey of why it is that it seems like so many of the most promising PLG companies seem to get trapped, right? Airtable. Who knows what's going to happen to Notion? I'm trying to figure out what is that enterprise level scale problem that they're trying to solve. And if it's not clear to me, um, will it be clear to others?

And, uh, I think that's where. I, I haven't seen it yet, so I'm, I'm hoping the reason why I'm, I'm, I'm doing this podcast and I did some writing on this is because I'm hoping people actually can figure it out. But right now I don't see it, and I don't think open AI counts for obvious reasons.

Brett: So do you think it's more likely that most companies would be better served to not start PLG?

OJ: I still think it's a phenomenal business model if you have the right product and you can actually get an edge on getting started. I think it's by far the best and most and has the best unit economics in the beginning. I mean, I just, the names that I just mentioned, whether it's Airtable or Asana or, you know, whatever Zendesk, like these are all somewhat PLG companies that I think over time you can see their growth decelerate. I think many companies would be really happy to have their outcome, right? And so I think it is still a very, very, attractive business model. But I think you have to execute a little differently if you want to break past the 10 billion market cap.

There really aren't many successful PLG companies outside of like the DevOps ones, like Datadog and Atlassian, that have actually really broken out. 

Brett: What's your take on Atlassian then? Because I, I, I think it is related to an infrastructure company or infrastructure monitoring company like Datadog, but it does feel like more of a SaaS tool style company. Is there versus AWS or some other kind of more classic infrastructure company? Is there something that you find intriguing with what they did, or you just chalk it up, you bundle that with AWS and all these other companies? 

OJ: What they did was really interesting. So I do, I do have a tremendous respect for Atlassian. I just think it's really hard for people to emulate what they did. So what they did, from my perspective, It was, it was really largely started with Jira, right? And Jira had a similar impact that Slack had, bottoms up, which is it quietly and organically crept into lots of organizations.

But at some point everybody woke up and was like, whoa, everyone's using Jira. Uh, we should use Jira. And and very quickly, you organically got at least a third of the organization, at least, right? All the engineers and PMs usually to be on Jira, and that dynamic is really hard to, to see happening, you know, again, but maybe there's an opportunity for others.

But what Atlassian did that was amazing around that was then they built a whole ecosystem around Jira, right? And they started, they played almost like the same game like Intuit plays or like SMB players play, which is like they started launching new product lines. And, and so. right Confluent was a great add on, Bitbucket was a great add on, and they bought or built lots of adjacent things on top of building the ecosystem, right, and, and the platform, they got that lock in, right, much like, and so, I think, I think what they did was amazing.

I just think the dynamic they got with Jira early on, it's hard to see working again. Um, certainly it will like, I think it will unlikely work in that same category. I think a lot of companies are trying to be like the better version of Jira. To me, that's like being the better version of Salesforce. It's going to be really hard to do and replace and win.

The question is like, what is that next category where there already isn't, there isn't a massive system of record, tool being used? There's probably an opportunity for someone to do that, and next thing you know, they're really well penetrated in many companies. And then they can like, build the ecosystem around it.

Brett: Yeah. They were also able to go multi buyer pretty interestingly, right? Like they started to build out the security use case for JIRA.

And you can start to sell into security ticketing, which I always found very interesting when you have to do very little product modification to then have a whole new both set of use cases, but also a new entry point into a company. We're now the security org can be adopting at first, and that's always kind of an interesting sort of dynamic.

OJ: Yeah, that's actually quite similar to Asana. They're basically selling the same workflow, but skinned and messaged differently to different, uh, folks. but the edge that they had was eventually the route to the CIO, the CTO, to then just, all right, let's just. deploy this across the whole organization.

That path is very short.

Whereas for many PLG companies like Asana, the distance was really long.

Brett: So I would love to end where we always do, which is who's someone in this journey of company building that's kind of had the biggest impact on you, the way you think about the world, the way you operate?

OJ: From a strategy perspective, my two mentors are Jay Simons and Dan Shapero. Jay Simons was president at Atlassian and, and, you know, Dan's the COO of LinkedIn. I've known them for years. And a lot of my insights, like Jay, because of his Atlassian learnings was like so good on the self serve and PLG side.

And Dan from LinkedIn was so spot on, on enterprise building. A lot of my, my own strategy development was like hybriding, like their two insights. So I think those two guys had a big impact on me from, a strategy perspective. Uh, from a management perspective, I, early on in my operating career, I met, Kim Scott, who had just ran AdSense globally at Google and, um, She was at Dropbox for a short period of time and we developed a, a strong relationship and she was, she really opened up my eyes on like how to think about people management, um, which, you know, Google did a great job at.

And so she had the first, she certainly saw a lot of that, and a lot, I took a lot from her. Um, and then later I worked for another exec from Google called Dennis Woodside. It was very, very different, uh, right? He was a president of America's, eventually ran Motorola as CEO when, when, um, Google bought it.

And he's, he's like an Ironman, triathlete. He probably wins Ironman's competitions today. And so he really taught me a lot about operating and cadence and driving results. And so when I think about my leadership, it's very much a function of the hybrid of Kim and Dennis. And that's what I executed at, at Asana.

Brett: Awesome Well, thank you so much for spending the time with us.

OJ: Awesome. Thanks, Brett.