Going Upmarket, And How Things Have Changed in a Decade, at Trello, with Founder Michael Pryor

OK, everybody, it's SaaStr. I'm with one of our, our all-time favorites, Michael Pryor from Trello, who joined us live several times at SaaStr Annuals on stage on his own. We had one of my favorite sessions where we did almost a board meeting for Atlassian with Michael Cannon-Brookes, which I promote all the time. If you want to watch two CEOs together, there's really nothing better than that. And one of my favorites, because I've used— Michael's built many products over the years. He's been building software I think since he was 6 or 13 or young, but I've used many of his products. Many of you won't even have heard of before Trello. And then I had some fun looking up, I actually, in the first 2 months of SaaStr back in 2012, the first and only product review I ever wrote was about Trello. I said it was great. And I had been exposed virally. So I don't know in 2012 how many Trello users, we have 50 million today, how many do you think we had in 2012, Mike? Michael?

Yeah, I don't know, a couple thousand, maybe a couple thousand.

That's pretty cool. So I'm old school. I'm OG Trello, I guess.

There's a special URL you can go to that will tell you which— what you're like, what user number you are.

Is that right? They have that for LinkedIn too. Wow.

Okay. I've got to look.

Yeah, maybe. Hopefully I'm in the quadruple digits. Probably not. Definitely in the, the 5 digits. My first and only software review: Trello is cool. And So one star, right?

You were like one star.

No, five stars. Just, I didn't, I realized quickly after that I don't think anyone wanted to hear product reviews from me, but I did, I did, I did do the one. But anyhow, it's always been one and it was interesting to me, you know, I got exposed virally, which we'll chat about. And so much has changed. But let's chat about that. Before we get there, the genesis of this is I want to talk about going enterprise, right? And we, and I'd seen a little thing that you guys had achieved FedRAMP authorization, which which we'll talk about maybe second, right? Going upmarket, 'cause it takes a while to start doing some of that stuff, right? And we think of the old days of a cool developer-focused project management Kanban tool, now selling to the federal government. It's a lot of change, but we're 8 years into Trello, right? 10 years? How many years are we into Trello and where's it going in the next decade?

Yeah, I mean, I think from the genesis of the idea, we're probably coming in on a decade. And I think that's a, it's been a great time for us to sort of step back and think like, how do we evolve do we want to do to change it? And I think within that backdrop, you have to understand what are the things that people love about this product? Why did they decide to use it in the first place? What's gotten us to that 50 million number, which at this point is a really old number, but you know, because big companies, but yeah, public companies, so there's some schedule to when you can say these numbers, but it's 10 years old. It's a lot higher than that now.

50+. Yeah.

You know, you have to take the essence, the product principles that made you succeed, the brand, and you can change it and evolve it. And I think that's for a lot of products, the general journey is they talk to their customers, their customers tell them about more problems and they create features, they create, sort of geography of their application that solves more problems for those people. And essentially you build a product that is more powerful, it's more customizable, it does more things, but it also becomes heavier, right? In the, in the sense of what is the affordance that I use this product for? So, you know, I think like there's a lot of productivity apps, there's a lot of project management apps, there's like, the space is really big. And while you could use a lot of them, you know, to plan your board offsite, or you could use a lot of them to run your financial quarterly close for your company, like people tend to gravitate to different tools for certain jobs. Like I think of, you know, why would you use PowerPoint for something versus just putting Word in landscape mode? Like they both let you put pictures and text and A lot of the features of apps are very similar, but there's sort of a space that people go to, where they gravitate to, and they realize that they want to use that app for those types of activities. And I think that what goes into that is those product principles that you're using and how you're applying them to your product. And so there's this kind of special place where it's like, how do I add power while keeping the simplicity? It's almost like— this holy grail, and it's almost an impossible thing to do. And we spend a lot of time thinking about that and trying to keep the mental model of what Trello does simple, but add a lot of power to the way people organize things. And I can go into that if you want to talk about that, but it's—

Well, let's— can we tease into one vector of that? Keeping it simple as the feature set expands, it's a classic challenge we've all talked about for a long time. Yeah, but I actually think that is easier than a related challenge because, look, if you have a core UI that's easy to use like Trello. Right. And you, and you stick to that, which, which is hard to do. Right. But if you stick to it and you have a good team, I think you can keep an easy-to-use product for a while. What, what I find more interesting is as you compete more broadly. So as you said, there's a lot of project management tools out there. Right. And notwithstanding that, maybe you're approaching 100 million users. People use other tools. So I would say I'm not an expert. I do use Trello. I haven't used a lot of other tools, but they're more complicated. Many tools are more complicated. But as you get pulled into that, how do you, how do you handle that balance of actually building a more complicated app intentionally so that you can close that million-dollar deal or attach to that big Jira deal or Confluence deal? How do you think about that piece?

Yeah. And this is just one way to think about it, but I think about it like grammar. What are the words that you're using in your application and what's the dictionary that somebody would have to have in order to understand what your app does? And the smaller the dictionary is, the easier it is for people to understand. So I sort of focus on the words that you're using because obviously you could just create a list of pages in your app or new places to go. You'd be like, we added OKRs to Trello. You go to the OKR page.

That's the traditional way to do it. That's on the admin page, right?

Sure, exactly. And then the problem becomes your PMs struggle because they're like, we don't get any people going over to this other place, right? Like that, it's very, it's easy to create these other destinations where you can kind of put those features. And I think that that is one way to solve it, but it's, there's sort of a question of design and an artfulness to like try to figure out how you can do that within the framework that you already have, or what's like the minimum set of inventions that you can come up with or new words in order to to do it. So, so let me, I'll give you an example here. So we in, in Trello, we have boards, which you're very familiar with, and boards hold cards, right? And above boards are these things called teams. So boards live inside teams, but it's actually probably not the best word for it. We're probably gonna name it workspaces because everyone uses that term for that. Type of thing, the container for your items. I think a lot of apps have solidified on that. So imagine you have workspaces. Inside your workspace, you have boards, and within your boards, you have cards. And that's pretty much like the gist of Trello. Like, if you can understand those sort of 3 things, you can really figure out how to, how to use Trello. Um, and one of the things that we were trying to understand is people are using their cards to represent all these tasks that they're working on or mini projects, and they're expressing them in different ways, and they want to look at them by, you know, their due date, or they want to look at them on a map, or they want to look at it in a calendar. They have all these just sort of pivots of the information, and you've probably seen this in a lot of applications where you can kind of take your board and you can go through these different views of the board. So you can look at it in the typical Kanban view, you can switch to the calendar view, you can switch to the timeline view, you can switch to the map view, you know, there's sort of like this extension of views at that board level, right? And I think anybody that's familiar with Trello or familiar with apps that compete with us has probably experienced that and understands that. But one of the things that we're going to do this year was to sort of extend that view metaphor up to the workspace level. So if you imagine it, it's, it's, um, you're down at the board, you're sort of looking at your project at the, you know, 5,000-foot level, and then you go up to the workspace. Now you're up at this 10,000-foot level and you want to get, you know, you're looking at more information, you're looking at multiple projects, a whole portfolio of things that's happening. How do you extract information from that? And so we're going to use that same metaphor that we use at the board level, which is, hey, you want to look at the timeline or the calendar or the, you know, the map or the canvas of all those boards, right? Not just a single board, but you're zooming out, you're getting the 10,000-foot view and you're looking down. And then That's great because it gives you this high-level overview, which you were talking before, like how do you kind of create more advanced use cases or kind of like people are using it for higher quantity of information or more, you know, complicated tasks, which you can add automation in there. We have an automation engine in Trello, so you can do a lot of things there. But then I think the one thing that, that is sort of inventive that we're doing is if you go down to the card level, We're also going to give people new views of the cards as well, which actually I don't think I've seen anywhere else. And, um, you know, it takes a little bit of an explanation to, to, to explain what I'm doing there. But if you think about Trello, you know how there's like the card and you can write some text on it and you can click and open it and you get the card back, which has all these conversations, attachments, it's got files, it's got pictures that you can add to it. It's sort of like a big project. There's like a lot of information. When you close the card, you just see the front. When you're looking at the board, you're just seeing a summary of the project. And it's within this context of all the other work that you're looking at, but it kind of gives you a hint like, oh, behind, you know, behind the other back on the back of the card, there's like all this density of information. And so one of the things that we're going to do is add new views to those cards. So for example, a card could actually be another board, or a card could be a mirrored card from another board, right? So a card could be a checklist from the back of the card, could appear on the front of the card, or a card could be like a Jira ticket from another application. You can make that card a piece of information from the other, from the other app. You could even make like—

is that part of managing bigger accounts and integrating broader with the Atlassian Suite? Are those the drivers?

It's kind of— we're thinking about the jobs to be done and what people do. So one thing that we've been experimenting a lot with lately, because we're all working distributed, has been, you know, everyone's on Zoom, you're using your communication tools, you're in Slack. But one thing we've been trying to do is use asynchronous video a lot more. So things like Loom or just recording Zooms and then distributing to people so that they can consume them at a different time. And you realize if you're ever in a Zoom and there's like 20 people, but like one person's talking the whole time, it's like, you probably could have just recorded that and then put the link in Slack or, you know, distributed some other way. So that async video, I think, is a really cool new opportunity for distributed working, right? It's like, it's somewhere between that real-time communication and Slack. And I think you even see this with Slack, they're adding, What do they call it? Stories. It's kind of like TikTok in Slack, right? So they're adding this and we've had this debate internally of like, whether, you know, is that, is async video like Loom, is that a product or is that just a feature that every app is going to kind of have?

Isn't that what people at big companies think about?

Yeah.

While Loom races to 50% of the internet. Yeah.

But then you ask the question, like, why, what is the, what's the interesting thing here? What are you unlocking? By giving people this technology. And so we ran this, we were talking about that internally and you're thinking about like, hey, we, you know, when we do a standup for Trello, like you do a standup in the morning, a lot of teams they'll have the Zoom on and there'll be screen sharing the Trello board, right? And they'll go through and people will talk about what they're working on or whatever. And you'll go around the room on the Zoom and you'd sort of start to think like, oh, async video, that's a cool use case. For a standup, actually. If everyone records their little status update, then you can just consume that whenever, you know, you don't have to do it real time. You can kind of like just—

Especially as the organization scales.

Right. And so we were like, oh, could you do that with Trello? Like, can you solve that job with a list and a card for, you know, every person on your team? And they just make a video card, right? And they just record the video and it shows up in the list. And then there's like a play all button at the top or something, and people can just watch them down. So thinking about, I think the, the reason that we thought about different card types or card views is because we realized that the sort of behaviors that people were doing inside Trello, we could kind of solve new jobs to be done. But the trick was, how do you do that without kind of just making a whole bunch of new nouns in Trello, right? And just complicating that dictionary of terms that people would have to understand. And like, you know, your help docs are basically just this giant nested, you know, thing of all these new, these new terms that you made up and people have to learn it. I think like, you know, there's a lot of tools that are very vertical tools that are super powerful, but that onboarding into that tool becomes a really high hurdle. And so you're only going to do that if it's like part of your job, right? Like you're only going to figure out how to use Salesforce if it's like, that's you're a salesperson, so you have to do that. Right. And so people that are just like, hey, I just need a little CRM. I'm running a little business. I, most of the time you're not going to jump into one of those vertical tools that has that huge hurdle to jump in order to understand it, because the amount of work that you have to do is, is disproportionate to like what you need to do to get your job done. Right. And so that's the balance. I think when you're building a horizontal tool like Trello, That's our job, is to keep that dictionary really small and make sure that the, the ramp to understand the application is as low as it can be for people to onboard.

Well, that's interesting. With this new expression of cards, you want to make it as sophisticated as you can with no training, no— the minimal onboarding headache, right? So that anybody can use Trello like back 10 years ago or 8 years ago. That, that's the— that may be the most existential trade-off, right? Is how can you add this complexity and add no additional burden in terms of usage and onboarding, right? Because I'm still trying to figure out how to use Salesforce. It's been a few years. And, and it's powerful, but it is powerful, no question, right?

But I think the behavior that happens a lot of times is PMs get in there, they, um, add the feature because they just need to do it, and so they just build it. They build it in a new, you know, space, they give it a term. And so then this problem comes where it's like, well, people don't understand it or they can't learn it. So they see that as an education problem. Right. And they're like, well, I guess my job is to, I have to explain it to you and I have to like make you watch a video or I have to put a bunch of words on the screen. And like, you know, people don't read, right? They don't read.

It works in the enterprise if you have to use it. Right.

But if you need a wiki, you do the training. Right. So then it's like, okay, yeah, now you're going to do the training. But if you're an app where your pitch is like, no, there is no training. You're just going to understand this. It's just going to be innate in, in the way that you use it. And you're kind of going to, oh yeah, it works the way I expect it to work. There's more sort of a burden on the design and how you think about what you're doing versus just, hey, just, I need to get 3 engineers to build this video feature.

But I have a new challenge I do with founders, which is no matter how enterprise your app is, it should have a self-service component. Because if it does, you will be able to figure out how to get to the atomic element of this app without training, right? If you have no self-service, You can, you can skip, you could have as many explainers and trainers and I don't care. People think self-service is a marketing tool or a viral tool. No, it's just a usability tool. Build a self-service. Even if 3% of your customers use it, your product will be twice as good.

Yeah, I think that that's a funny, um, that's a debate. I, I agree with you. Um, I've had this debate before and been on both sides of it, which is like you're, you're sort of saying like, oh, if you build this self-service enterprise funnel, but then, you know, the retort is, but no one's going to use it because anybody that was trying to buy an enterprise tool, you know, if they're going to spend 5 figures or 6 figures on a deal, they're not going to like stick their credit card in to buy it. So you're always going to be human to, um, but, but it, but it comes back to this thing where it's like, but if it's there, it forces you to get rid of all the friction in your process. So you sort of have, you're, you're almost like forced to deal with it, whereas if you don't what happens inside your organization is just use humans to—

humans, right?

You're just like, well, it's complicated. So we just have an onboarding engineer that walks them through it. And it's just like, you can do that, right? And it works. And I think then the only risk there is that you end up building— you build a more sales-led organization than a product-led organization, right? There's two types of enterprise companies. There's the companies that are like, I build enterprise software, and then 60% of the people that work at the company are enterprise salespeople. And then there's other companies where you have a tiny percentage of the company is the sales team, but they still sell enterprise software. I think Atlassian is in that latter group.

What if you could do both?

Yeah. And that's something that's iconic, right? Right. I mean, I think that's the idea. It's doable.

It's doable.

Just enough sales, because certainly people do expect, they do want a human to be there. They do want somebody to reach out to. They do want to talk to those people. And so it's like, okay, well, what's the, what's like the minimum margins we can have in order to, for the maximum revenue, I guess, is sort of the goal.

But can I go back to something you talked about on the morning standup where they're firing up Zoom and looking at Trello and going through the cards and all that? What, 'cause I don't know this, what has changed, if anything, in terms of where people wanna interact with Trello? Like back in the day, I think like portals have died and blogs have died. And I think to some extent standalone apps are dying because now we all, most enterprises have over 1,000 cloud apps deployed, right? Most departments have over 100, and that's a secret of Slack, right? Is you can run your apps inside of Slack. So where are, Are the majority of Trello folks still logging into trello.com to manage projects, or how has that changed over the years?

I think probably the majority, yeah. I think you still end up with like a kind of land, you know, in the app itself. But like, for example, Microsoft Teams has a design where you can add tabs into Teams. So you can have like your chat window in the channel. So you're in a channel and then you have your chat and then you can add a tab that's the Trello board, for example. So it brings it right into Teams. Slack has much more of a messaging interface. So you kind of like, your app kind of exists within the timeline. So it's kind of like posting updates or it's sort of within the feed of messages. So people definitely have that kind of interaction too, where they're coming from their messaging app, which I think is probably the bedrock of that distributed communication, the distributed way of working, right? Like is the tools that are at that communication layer, Teams and Slack and Zoom. And then on top of that becomes, you know, next you get your work management tools like Jira and Trello and, and the others. And then you kind of have other tools like your collaboration tools where you're talking about documentation and those things, or like brainstorming tools. Like, I think you've seen a lot of people, you know, picking up things like Mural and Miro, tools like that where you're kind of whiteboarding and investigating and ideating and doing those sorts of activities. So I think probably the change over the last couple of years has been an increase, certainly, in the way that people are interacting with information from other tools. To your point, I think there's this term Cambrian SaaS, just kind of like there's all these SaaS apps, and in order to compete, you want to make sure that you play really well with all of them, and especially at that communication layer, it's really important. 'Cause that's just, I think that's like the place that people go is that like the talking layer, right?

That's the part we probably underestimated a little bit, right? Is how much that would explode. It seemed like it was always there, but it was a side, it was a window before, it was a side part.

Yeah, I think it was like, I used to describe it as a triangle, right? Where I would say like one piece of the triangle was communication, one piece was work management, and one piece was documentation. But I think really it's more like Maslow's Hierarchy of Needs, right? And at the base layer is the chat communication layer. It's the bedrock. That's where people just start and they need that. And then they start to layer on top. So I think it's probably actually really— and I think that was Slack's— that was their pitch, right? And that was the idea behind the app. And part of their success and also Teams, trying to do the same thing. And I think like that's pretty compelling 'cause it does become that place that you go to first in order to then go to these other places and do the work.

Yep. So one of the things I wanna just go back to the past and then I wanna stay connected to some of these things in the future, like distributed companies and going upmarket. But it is with cloud being bigger than ever. And this is a rough term during a pandemic, but having a viral app is so critical, right? It's not the only path to success, success. I, when I discovered Trello, if you look at that Saastr post, it was viral. I don't know if it, how much is viral today, but what have you learned about viral growth in productivity apps and cloud apps? And has it changed over time how viral exposure works?

I don't think it's much different than it was, you know, 10 years ago. I think like any kind of collaboration app that you have is subject to like the weakest link, I'll say, you know, it's like in order for it to succeed, everyone has to buy into it or it's not gonna work. So if it's just becoming this system of record where every Friday you log into it to post your status update so that your boss can read it because it's their tool, right? You know, like it's like they're like, I require that you put your weekly updates in here, then it's not, Yes, you might be using it, you might count as a monthly active user, but you're not really adopting the tool into your workflow. So people had to be able to see how they can use it themselves in order to really, um, kind of be able to propagate within an organization, right? So you have like, hey, this little, this team uses it. It can spread virally to these other teams within the organization. You know, people can take it from work to home. They can use it for things at home, and then they go to a new job because they got fired, and they bring it over there. Um, that's been the nice thing about Trello is I think it's a tool that you can kind of— can stay with you throughout your life because you can kind of see how you can use it for stuff in, in your home life. You can use it for stuff at work. You could leave that company, go to a new company, and you're like, I'll just take my boards. And, you know, there's sort of this like— it's not—

you can take your boards.

It's not like, um I don't know what I mean. It's not like there's, there's a category of tools that's very much driven by the, the company has decided to standardize on this tool.

Salesforce isn't viral, right? Salesforce is not viral.

Yeah, right. Exactly. And it's like, um, the company's decided, it's like, you know, company decided to use Workday. So you, you go into Workday and log all your stuff. Like it's this sort of, it's one of those things you're not really bringing it into an organization. Yeah. So we benefit from that. I don't think that that has really changed that much.

But for the next, but if you're north of wherever you are, I know at last since public company, you're north of 50 million users, you know, 100 or whatever it is, has that roughly speaking, the viral contribution to growth, are there no limits? Can that stay consistent with your user base as it grows? I mean, at some point you have every user on the planet, but does it fail or does it actually accelerate over time? Does the viral component for Planet— I don't know.

I don't know yet. I mean, I don't know if there are limits.

You're only 8 years in. Yeah.

I mean, and I think like what you see is actually, you know, from a year ago, the total addressable market just grew, right? Like, it just went nuts back in March. So, you, you've, we've always been talking, it's funny, because like, you talk to the journalists, and I think the hot topic like 3 years ago was what's the future of work, right? And yeah, we're in it, like, it's like, it just came like a boom.

5 years turbocharged.

Yeah, like it would, it was happening, people are adopting it, people are playing with it. And it was like, nope, everyone has to do it. You have to figure out how to work in a distributed way. And so it just accelerated that for the companies that could, right? Like not everyone is in an industry where you can do that, but for the companies that could, they figured out how to make it work. And it was just like, you know, this March versus last March, I think signups were like 75% higher this March than they were the prior March from the year before. You know, it was just like this super big influx. And then people, you know, kind of found how they were working and, you know, it started interesting because there's also these macro trends where the economy is doing different things, right? Like a lot of small businesses are out of business. Like there's restaurants that are shut down and you see them every day shutting down. And then there's other places that are doing great. Like I bet Instacart is crushing it right now. You know, it's sort of like, so there's both winners and losers and obviously you could not have planned for a pandemic-proof business. Like, that wouldn't be— I don't think many people were thinking about it like that. Um, but, but, uh, I do think that the, that future has come, and, and it will probably— you know, many people will go back to the office when we can. There's just great things about working together in person. There's great things about being able to work from home and not having to commute. And yep, I think the nice thing is people kind of got a taste of what are the good things about working remotely, and we'll be able to kind of keep some of those things to get around the nonsense of, um, you know, things that just weren't really causing productivity, but they were just the way that we did things. So we just kept doing them that way. Right. Like, it's like, you know, this, you know, you just, it was just a behavior that we had adopted and the way that we worked. And so now we're able to develop new behaviors and people can be like, oh, actually, I'm getting more done this way, you know, or I have this— I used to work in an office where people are sitting right next to me and now I have a whole room to myself, you know, and I can concentrate and write a ton of code or draft documents or whatever it is that you do. I have some lawyer friends and I think like there was definitely a sense of you can't work from home when you're a lawyer, right? And I'm like, but why? And they're like, you just can't. Like, they just don't want you to. But then, you know, it's like now They have to. And it's like, of course they can work from home. Like most of what they're doing is like looking at documents, emailing clients. Like it's all distributed. Like it's all asynchronous type of work or ability to do it, not in a central location. And it's so, it's like, I think there's certain industries that'll be, it'll be really interesting to see what happens when they can go back to work.

I want to chat about that one sec, but there's one thing that I think a lot of folks are thinking about. You talked about how you had a step up in reg, GRV of about 75%, whatever the number is. Do you see it as a step function? What I mean is, especially folks in e-commerce, which you talk about Instacart, but other times, what we saw in productivity software was crazy. What we saw at Shopify broke the mold, like Zoom. But if the future is pulled forward 5 years, is it a new normal? Will growth return to normalcy after this? I mean, have we stepped into 2025 and now we should have normal, or are are we still seeing acceleration? Do you have a sense if the boost is over from COVID I don't, I don't.

I mean, I think it's too early to tell, because I don't know. There's probably a cohort of people that are just working like this because they're forced to, and when they can go back to working the other way with the old tools that they have, they will.

Yeah.

And there's probably a cohort that is new, and I definitely think there was Because it was a moment in time, I do think that there was a kind of front-loading, right? Like you pushed a whole bunch of people very quickly into— April wasn't 73% over the previous April. So it was sort of like— it was definitely higher, but March was like this huge surge. But the growth, it's kind of like If you took COVID out of the picture, you've definitely stepped up higher. And I don't know if the growth rates are faster now, right? Because the question is, and we were talking a little bit about this before, but it's like, how many people are starting businesses now? I don't know, right? Like, has that sort of slowed down? Are you able to just like recruit people if you can't see them in person? Like, you're like, oh, I'm gonna do a startup and I'm gonna hire 10 people. Is that— has that influx kept going? Are there as many small businesses that are being created? And I'm not— I don't know. But I would guess— my guess is there's some restriction on that flow in of— I don't know. It's hard. I guess there's probably a lot of people with great ideas and seeing problems that are happening right now. And they know how to solve them. So they're like, yeah, like you said, the Shopify thing where you have a whole bunch of merchants. I wonder if the thing is that those are people that didn't previously have a business versus people that had a brick-and-mortar business and needed to get online, right?

Yeah, I don't know. We should know. I mean, the e-commerce thing is substitution, right? I have no store anymore, right? I have to be online. And entrepreneurship is up, the new, the Trellos, and the Adobe signs that are being started, that's up. Whether small business across the country as a whole is up, I'm skeptical, skeptical, given the macro effects. I think, you know, brands have benefited. It's not just the Atlassian Trello, the KFCs and others have benefited, and the non-brands have been hurt, right? The non-brands, it's a flight to not— it's a flight to what we trust during a pandemic, right? Every trusted brand has gotten a boost. Right.

It's hard to create a new source of trust within the pandemic, right?

It's hard. It's hard. It's hard for recruiting. Like, even in venture capital, you see these incredible rounds, but they're all still with known people, right? Everyone that's getting the big rounds are all going, you know, if Trello was a private company now, you'd raise $400 million because they knew you, right? They've known you for 10 years. You'd be like, I can't believe this deal. I'm taking it.

But, uh, and it's sort of, it's, it's sort of interesting because then that means that there's like, there's capital there. I'm sure there's tons of people with ideas, but then that kind of says that there's something about the fabric of how we, we, you know, live that's so social, right? Like, that's such like reliant on us being in like kind of, you know, like if you're trying to figure out like what's the difference between before and now, it's like, well, people just can't get together as easily in person. Um, they can't travel. So you wouldn't, you're like, well, but we have Zoom, we have Slack, we have all these tools that let you work asynchronously, but some piece of that relationship forming, you know, whatever it is, making a new business, trying to like build excitement or whatever, must— something in there must be, um, at some stage being restricted by the inability for us to get together in person.

Well, it's funny, I moved my office, you know, we have an office in San Francisco for Saastr, which is basically abandoned, right? Because San Francisco is abandoned, but we took these little offices in downtown Palo Alto, which is very cute, and they're safe. Everyone has their own office. There's no shared door. We have these pods bringing downtown Palo Alto, and so I'm there a lot. And there's a lot of founders pitching VCs, walking around, and at lunch. And I think what's changed— well, I do know it's changed even with my own investments— that for a while there were no physical meetings. Now they're further down the funnel, and we may stay in that world to some extent. We may not need to meet as much, the first time we meet, right? Michael and I might not need to meet in person. We can meet on Zoom, and maybe it's the third or fourth time.

Yeah.

But that's so— that may still be critical that we meet. We just may not need to do as much, you know, first time, first, you know, knocking on the doors piece. And maybe— but maybe the human piece is still there. Maybe that's more efficient. Maybe that's great that we can do 3 Zooms before we meet in person instead of 3 meetings and then Zoom afterwards. I don't know.

I'm going to sound like I'm probably like a crazy person to say this, but I think that with the place where we've only begun to discover the capabilities here, and maybe this only works while we're all stuck in our houses, but I started playing with VR with like the Oculus Quest and just playing like mini golf with some friends. And that experience is so much fun. Like the difference between being able to see someone in VR versus on a Zoom, there's just something about the spatial representation that makes it feel totally different. So we tried the other day, for example, at work, I got a couple of the people together and we did a meeting in this app called Spatial with the VR goggles. But like, we spent the whole time, like, you can, you can kind of summon these objects, like you could summon a cat. Or a pencil or like an airplane. And so the problem was the whole meeting was everyone was just like summoning things and making them really big in the room. And like, you know, it was just, we were just playing, but it was, it was interesting because we actually brought up a browser and we were actually talking about a real problem that we have. We brought up a browser and we were like going through these charts. And one of my coworkers was, you know, pointing at the chart with his hands and like pointing stuff out. And I was like, I kept turning my head to look at him, you know, and he's like looking back at me and we're just, we're not, you know, we're all in this VR world and it was something, there was something there. Like, I don't know what it is. I don't know if people are going to want to put these headsets on once COVID goes away, but right now at least, um, I don't, and I don't think that this has really gotten mainstream, but there's something very cool that does capture some of what's missing from the very two-dimensional, like, computer screen interaction.

Um, yeah, there's something about presence that we're still in the early days of on the internet, right? That presence, that, that, that green dot in Slack or Teams is not enough, right? That's not presence, is it? Uh, and you're teasing at a piece of it. When we can cross presence, um, maybe, maybe in the old days of, you know, ICQ and Yahoo Messenger, it felt more like presence. Now we're surrounded by this stuff. But when we do that, maybe that's the hurdle. I don't know. Maybe for all collaboration and other tools, it's presence. Maybe. I don't know. Let's hit one— just maybe one and a half things related to this before we run out of time. But let's talk a little bit about that distributed world. And you noted when we were chatting before, I guess I knew this, but I forgot that Trello sort of led Atlassian to being distributed, right? Because you were distributed from the beginning and helped the company. And you made a comment, which I— which is I've heard different versions of different people that a lot of things are better distributed, but mentorship's harder, right? And sometimes for junior people, things are harder. And the more senior folks I talk to, the more they're doing fine here. And the more junior folks I talk to have just taken their first job, they're struggling to have that experience. So what have you learned around mentorship and having everyone distributed at Atlassian?

Yeah, I think that there's— everyone, we used to pitch this as like, is remote better or is in-person better? And it's like, the answer is, you know, it depends, right? Like, of course, obviously. And there's a lot of great things about working in a distributed way, and there's a lot of great things about working in person. And so I do think when you start talking about people that— and I don't know if it's always people at the beginning of their career or Or, you know, if they're just new to the, the, that particular job or role, but it's, I think it's definitely harder to start at a new place and form the trust and connections with, um, the people inside the company without some of the serendipity that, uh, an office provides. So for example, you might form deep relationships with, with, with the people that you work directly with. So it's like there's some set of work that you have to do and you have to, you know, you're in the chat rooms talking to your direct team and trying to figure out what you're on the Zooms with them. And you sort of develop a relationship with those people and you can make time to even, like one of the things we tell people is like, make time to even meet with those people, not about work, right? Like just to talk about random stuff, because that would happen if you were in the office, you know, you talk about, with the TV shows you're watching or whatever. And there's some, there's some camaraderie and trust that develops from those conversations that aren't directly related about work. Um, but the, I think the really difficult part is how do you form that with people that you don't work directly with? Cause now you're not even going to see them, right? The visible. Yeah. And they might be in your Slack workspace, but you're not in the channels with them. So, and you're not in a Zoom with them. So now, It just, it feels like it's, it's harder to form those kinds of connections. So if you're starting at a new company, that would be hard. And if you're, you know, earlier in your career and you're trying to kind of pick things up, like imagine a new salesperson. I think like we saw this a long time ago at Stack Overflow when we were hiring salespeople. If we would put Physically just put a junior salesperson next to somebody that was really good. Like just sit them seated at their desk next to somebody that over time, the junior person would ramp better than if you put all the junior people together.

Yeah.

If you sat them together, right? Like there was some, there was serendipitous conversations.

Brain by osmosis in sales has been known, right?

It's been known, right?

Yeah.

You, you, they'd overhear it, right? They'd overhear the, the more senior person, the pitch that they were making, or maybe the senior person would overhear their pitch and be like, you know what you should do? Is maybe talk more about security or whatever, right? Like, you're just— there's this sort of informal conversation going and learning going where it's not, it's not a formal training thing. It's an informal thing. It's like a critiquing that's happening throughout the day. So I think in a mentorship situation, like, there is a lot of that, and that happens to have to take place better in person because you can't necessarily plan it out. If you can plan it out, if you're like, oh, I'm going to call a customer and I want you to listen and then give me feedback, it's like, sure, you can do that. Right? Like, and that's probably what you do right now because we're distributed. But having that sort of flexibility to just be seated next to somebody and it's like, oh, I overheard you talking and you said this thing, but maybe if you had said it this way, you know, like you're not going to be present for those kinds of conversations. And so I do think that some of that mentorship probably is easier to do in person than it would be distributed.

Yeah, the sales change is— it always seemed like the very last frontier to change. I remember when I met back at Trello, your head of marketing, JD, said, my whole marketing team's distributed. I said, that's not possible. I said, I get that the rest of the company is.

But knowing your revenue team is like, yeah, this guy Michael, he makes us do it.

But team sales, but you know, we have a pandemic and it's fascinating to watch tools you may not use like Gong and Chorus, which Gong just raised $2 billion because every single person now that they can't, they're not in the pit, they listen to the Gong and Chorus calls of the top sales reps. But you need a slightly different DNA. You need to have a more curious mind, don't you, to listen to the calls rather than sip your coffee coffee and hear Laura next to you. So you need a different rep, but it's— we're just beginning to see how sales and marketing have changed. And it's crazy because engineering already— whether engineering teams were distributed or not, our whole careers we've had different offices for engineering, right? Whether they work from home, we've always been globally distributed, right? Just not always working from home, but sales and marketing. So, and the last thing I want to— oh, sorry, go ahead.

Well, just, I was just going to say that it's sort of interesting. You brought up that behavior where you can kind of like, now it's actually, in some sense, it's even easier because you're forced to use these tools that are digital. We can record things, right? Like, it's just like, well, naturally, like you and I are talking and the Zoom is recording, right? Like, it's just like, that actually becomes, now there's a behavior that we're doing that's much easier. Than if we were having a meeting in person. Um, because now if we record it, we can distribute that to way more people whenever we want.

Communication. It's just audio here. It can video too. Yeah.

So it's, to your point, like some of the salespeople could do better in this case because now if you had tried to pair up one junior person with one senior person, maybe what if for whatever reason those two people, that mentorship wasn't happening, but now it's like, hey, I recorded my call. I can reach out to like anybody that wants to give me feedback on this call and you can listen to it and it's like there, you know, for anyone to grab.

So everyone just sends out the best calls to their whole sales team. This is the best. Michael closed the biggest deal today. Here's his call. Listen to it.

Yeah.

For homework.

Yeah. So if you change the— so maybe ultimately when you change that behavior and the tools are there to support that, then maybe the things that we did in person aren't actually the most efficient, you know, like in the scheme of things. So, so there's, I think there's—

that's what I think. I think this is going to last too long. And guys like you and me think that mentorship in person matters, but in person is going to matter a different way when we go back. It's going to take too long. Right. It's going to be a different in-person. Yeah.

Yeah. Right. Totally. I, and I, I agree with you. I think that that's probably right. Like, it's like, as you started talking about those tools that are available for salespeople and started triggering my memories of us playing with those things before, I realized, oh yeah, if you start from scratch and you're using those things, like, you don't experience any of the pain that I was talking about, right? That mentorship pain. You're right, like, it's actually even a better, um, so it's, it's about— yeah, we're the old farts now. Sorry about that, stuck in our old ways.

But all right, last thing I want to hit before we run out of time, because we hit about this period— we, we started with Trello going into its second decade.

Right.

And this is the biggest surprise for me is how long brands last in software. Right. That, that, that Trello is coming. I mean, Atlassian is coming up. When was Atlassian founded? 2002 or something like that. Something like that. Right.

Yeah. Like 20 years ago. Yeah.

And it's just getting going. Right. As a brand. Right. And so these software, we used to think things would come and go, but brands, at least in software, can last 30, 40 years, which is stunning to me. So how do you How are you— what have you learned there? What are you thinking about that for Trello for 30 years or other products? How long should we go as founders? Should we go forever? Should we be building software when we're 100? Should we stick for— are you still excited about building Trello as a product?

Yeah, as long as there's— I would say you keep going as long as there's cool problems to solve. And I think that there's— I see a lot of opportunity over the last year, a lot like we were just— I mean, that was the whole podcast, right? We were talking about how people's behavior changes, what's like the future going to bring, and there's so many more people coming into these tools and these markets. Like, you remember, you know, years ago where the sophistication of like an average person, like we used to call, I think we say like techies or something like that, right? We have this term where, you know, and it's like everyone's a techie now, right? Like, it's just like technology is just so pervasive. So the software did eat the world, right? And it's like, it's just everywhere. So it's a different question now. It's sort of more of a question of How much time and energy is this person going to spend in order to figure out your tool? And then what are the benefits that they get? So I think, you know, back to your question about like, can the brand last for decades? And it's like, yeah, of course, right? Like, that's the connection with the customer is what's inherent in the brand, not necessarily the tool itself. And something that jobs that you solve for people today might be completely different jobs that you solve for them next year. Right? Like if you took a lot of tools that have been around that long, go back. Like I did this, I've done this occasionally where you go find the old screenshots of Facebook.

Yeah. Right.

And you think about what it did when it was first started and who it did it for. And, you know, just sort of the evolution of, and there's a lot of dead ends there, right? There's a lot of things that they added and they just realized Actually, people don't want to do this in Facebook. And even things that Facebook already did, but they weren't just really delivered in the way that people wanted to do them. We've seen that with Instagram and TikTok. And so I think that what you're talking about is more about the longevity, is the relationship with the customer and the type of people that you're going after and how you talk to them, right? Like what's the tone of your brand?

Yeah.

Is it, is it fun? Is it, you know, getting shit done? Is it, you know, we're efficient or whatever? And that's the, that's the audience that you're going to continue to talk to for, um, and as long as that audience is growing, then your business is growing because the pie is just getting bigger. And if more people are entering it, like, that's awesome. That's good news for you. And I think you've seen that, like, productivity software and project management software has been around for longer even than 20 years, and I still don't even see like an end in sight for how big this can get, right? Because it's just every year there's more and more people that are changing the way that they work and entering the space and picking up new tools, and it's just creating new industries right around it. I mean, like, I think this, even this pandemic is creating new business opportunities that will persist after after we go get back to what will be the new normal, right?

Yep.

It won't be the old normal. It'll be the new, new normal.

So let's just wrap this one up with maybe just two super easy questions for founders that maybe are a few stages earlier. They're hitting, they're having some challenges, right? It's 2020 now. What are the odds that Trello is, as a product, around in 2030? I already know the answer, but what's the odds it's around in 2030? 100%. 100%, of course. What about 2040? What do you see in 2040? What are the odds? Yeah, well, that's it.

Then, then you get into the question of, is it a product or is it, is it the—

what are the odds Trello is around in 2040?

Trello, the, the product or the brand?

I don't know, whatever. I just— that's why I say Trello. I'm not, I'm not adding anything after it. I don't know if it's a gerund or a noun or an adjective.

I don't know. I mean, I, like, I don't know. It's so like, am I around in 2040? You know, like, this is a very existential question.

It is an existential question. It's the journey we're on in life, isn't it? Should we build 4 Trellos in life or should we build 1? Should we call it a day and move to the Caribbean or should we push on?

The world got turned upside down this year and that ended up being not that In fact, it was probably in some ways kind of brought new customers into the space. So, you know, we benefited from that change, but then some years, you know, there's probably change that you never saw coming. And I guess the only way that you survive as a software product where every year the barriers to entry are getting lower and lower and things that you— I mean, I remember 10, 10 years, 20 years ago, I remember spending like years building a payment gateway system to process credit cards. And it's like, if you did that today, you would spend zero time because you would just go to Stripe and—

Well, it's 3 to 4 minutes.

—just use it, right? And so that will just— like building software and creating solutions is just getting easier and easier and easier. And so the challenge is, it's a different challenge now. It's like, what's the— How are you doing it? Or how will you stand out? Right? Like, it's not like, did you write a blog? Now it's like, everyone writes content on the internet. It's like, how are you going to get anyone to read it? So the challenge is always new. And I'm still excited about what we're doing now. So I think I'll give you 90% in 24 hours.

Jason M. Lemkin: All right, Michael. Well, thanks for all this time. It's always great catching up. And it's exciting. It's exciting. I hope You're gonna send me the URL, and I hope I'm a 4-digit Trello user. That's my— 3 digits, I'm worried, I'm not gonna, but 4 digits, we're gonna do some sort of a VR celebration if I am, which is gonna be excited. All right, thanks, my friend. Thanks, Jason.