SEASON 2 - EPISODE 196 - July 22, 2026

Start Here: Building a better onboarding experience

Getting a new customer through the door is one thing, but making sure they understand how things work is another. In this episode, Jason Fried and David Heinemeier Hansson break down how (and why) 37signals redesigned the onboarding experience with their latest version of Basecamp, why onboarding is one of the easiest things to overlook, and what it looks like when founders stay personally connected to that first impression.

Watch the full video episode on YouTube

Key Takeaways

00:09 - What Basecamp’s onboarding looked like before, and what changed with Basecamp 5
04:01 - Why onboarding is one of the hardest things to get right
08:33 - Why the people who built it are best suited to showcase it to customers
11:07 - Using onboarding to introduce who you are, not just what you built

Links & Resources

Transcript

Kimberly (00:00): Welcome to REWORK, podcast by 37signals about the better way to work and run your business. I’m Kimberly, joined by the co-founders of 37signals, Jason Fried and David Heinemeier Hansson. This week I want to talk a little bit about onboarding — onboarding customers to your product. We’ve done things a little bit differently with Basecamp 5, so I thought we would break it down just a bit. Jason, I’m going to start with you. I know HEY previous to Basecamp 5 was kind of our pinnacle for how to onboard a customer. Tell us a little bit about that and then what we’ve done differently in this new version.

Jason (00:30): Yeah, onboarding is something that’s always been really fun to work on, although Basecamp never really had a great onboarding. It was decent and there’s some things we did to make it better, but it was a little bit like pointing arrows at things and this is where this is and this is where this is and this is how this works. And when we did HEY a number of years ago, we went through a really nice process of sending you basically a bunch of emails and you have to screen them in because that’s the first step in HEY. And so I’m not going to go into all the detail, but it became this interactive thing that you work through the product to get to understand and learn the product. And we never really had that in Basecamp and now we do. So with Basecamp 5, when you sign up, we have a whole new approach and actually it’s very different. We have a picture-in-picture…

Kimberly (01:13): Wait, Jason, let me interrupt you for a second. Did we not have that in Basecamp before because the thought was like, “Oh, it’s so easy. We don’t need to take people through it?” Or was it just something that had just been overlooked? Why wasn’t it there from the beginning?

Jason (01:25): Yeah, I think that we just kind of hit a new high watermark with HEY actually, where we just had a new product. This is one of the beautiful things about making something brand new is you just like, okay, what can we do here that’s interesting and better? And you build it like, this is really good. I’m really, really… remain very, very proud of the HEY onboarding, the whole procedure and how it works. It’s really good. And so now then you’re shifted into a different orbit and you’re like, this is sort of our new bar and we should bring that kind of thinking to Basecamp. And now we have an opportunity to do that with Basecamp 5. With Basecamp 4, we are already in the middle of the product. It just didn’t feel like the time. We did play with onboarding and improved conversion considerably in fact with Basecamp 4’s onboarding in the middle of that product cycle, but we didn’t redo it really in a sense. This was an opportunity with Basecamp 5 since we’re changing so many things to kind of redo it. And so now what we do is we actually walk you through, it’s about a three-minute tour, like a picture-in-picture tour. And Kimberly, of course, is the star of the onboarding process.

Kimberly (02:23): I don’t know if star is the right word.

Jason (02:25): But what we do is we say, here’s a project, a fully fleshed out project. Play around with it. Click this, do this, leave a comment. It’s a real project. And before you get to make your own, you just walk through a real one and you really mess around with it. And there’s a little video of you in the corner saying, “Hey, try this and try that, whatever.” And you’re like, “Okay, I got that.” And you’re like, “Next.” And then the next step is now make your own first project. And you kind of make that and you get to learn that procedure and you’re using the product to learn how to use the product. And there’s no stakes here. That’s the other thing. You’re not making projects that matter and you’re not going to screw anything up if you play around. And then at the end it’s like, okay, now I’m ready to go.

(03:01): And then we bring the whole interface in and drop you basically to a sidebar. We have a few more notifications for a few more things you can learn. And at that point, we’ve sort of explained the whole thing with the product and also with your notifications so you learn how to use those too. It’s a really kind of a cool process and I’m proud of it as well. It feels really good. The product has not been around long enough to look back on it and see how it’s been doing compared to the previous versions of that, but we will at one point. And I don’t know, it’s always fun I think to explore onboarding because the ideal version of onboarding, the thing I’ve always tried to do or try to think about is what would it be like to sit next to somebody and walk them through the product?

(03:36): If you could literally sit next to every single customer and go, here’s what I want to show you, what would you do? And that’s the gold standard for me. And I think the current version of Basecamp is maybe the closest we’ve gotten to that. Like, hey, here’s a project, play around with it. Here’s how you make your own, play around with it. Now here’s this stuff, and then you’re off on your own. Anyway, that’s kind of what I’m always aiming for. And I think Basecamp 5 has a pretty good shot at being as accurate as possible to that vision.

David (04:01): I think one of the reasons why this is hard to do really well is that you don’t see it that often. We are not signing up for Basecamp every day because we already have Basecamp and we’re very engrossed in it and we have a lot of data in it. So one thing is the signup flow, you’re putting in your credentials and you’re getting onboarded. But it’s also what does the product look like when it’s sparse? What does it look like when it only has one project, when it only has two to-do lists? Those states, blank slates we used to call that when there was literally nothing and tried to do some stuff around that, but I think structurally why it’s hard for software companies to really get good at it is because there’s not a lot of iterations. Even for us, this required some very dedicated focus.

(04:47): Jason and the team around it sat down like, okay, we’re going to improve it. And then a lot of effort flows into that. But then by the time that’s over, it’s a little bit of, okay, that’s a closed chapter. We can of course return to that and work on it together. We’re not going to see it every day. Versus if there’s something that isn’t quite right about how the card table works or how you drag things about it, we’re going to be annoyed about it every day and we’re going to see it. So I’ve often found myself signing up for someone else’s product and go like, “This is obviously broken. This obviously outdated. How could they not know?” And then I would think back like, oh, I’m not sure I would know. When was the last time I just signed up for Basecamp? In fact, that was probably around Basecamp 5 when Jason and I went through that whole flow a couple times.

(05:31): But before that, it had been a long time. It’d probably been months, maybe in some cases it could even have been a year. There’s always opportunities for these things to drift so that your nice onboarding flow, yeah, it was nice when you designed it and then seven things changed in the product and things moved around and maybe you introduced new features or whatever and you just don’t see it or it just didn’t keep up. You kept evolving the product, you kept making it better and improving and so on. But the signup process is as it was on launch day because that was the last time you looked at it. So I think those are some of the structural factors of why it often seems weird because as a new customer, this is the thing you see. The first thing you see is the onboarding flow.

(06:10): So you of course assume that it’s going to be the best that that team has to offer. And that’s just not the case. In almost all cases, onboarding flow is going to be substantially worse than the rest of the product if someone had kept working on it because all the attention goes somewhere else. So having gone through that and then having seen it on the inside gives me a little more empathy when I go through one of those kind of mediocre or even shitty onboarding flows where I go like, “Wow, why can’t they just? How could they not see this?” And I go like, “Yeah, maybe I wouldn’t have seen it either.”

Kimberly (06:41): So Jason, you mentioned sitting one-on-one with someone talking through. I did notice on Twitter that you extended an offer to do basically that for a handful of customers. Tell us about that. How’s that going?

Jason (06:53): I just enjoy it. I mean, I’m really proud of the product. Basecamp 5 is really, really good and I just want to show people. And so I basically said, hey, I’ll take five customers under my wing, wherever the heck their language was. If you sign up for this plan over the next 90 days, we’ll do a call every couple of weeks. I’ll walk you through our account and we can do Q&A along the way. And immediately got five people who want to do that. And so I’m working with them now. We haven’t started yet, but we have some scheduled calls coming up. And it’s a joy to be proud of what you’ve made and to show it off. What better thing is there to do? And what’s really cool about Basecamp 5 specifically is that it’s gotten so good and it’s so flexible that I feel like there’s nothing it can’t do for somebody who’s like, well, how do I manage this and how do I manage that? And what about this? What about that?

(07:39): And people are like, “How do you hook in GitHub issues and all these things?” I’m like, “You don’t actually have to do those.” People come at software these days thinking you need a bunch of tools and a bunch of separate things and a bunch of separate places. People are confused and they think designers work in one place and programmers work in another. And so not only do we get to show them the product, but we get to show them the point of view and the philosophy of working that a team is two people. It’s a programmer and a designer. Those are the functional roles, but they work together in the same place on the same stuff. And that blows people’s minds and it’s always fun to blow people’s minds. That’s a fun thing to do. And to do it in such a simple way and you can show them how we do it, it really makes an impression and it’s just great fun. I actually really enjoy it. Aside from making the thing, I think demoing the thing is my second most favorite thing to do. It’s great to just hop on a Zoom and show people our account and walk them through it. And that’s open for anybody. Anyone who wants to do that, you can get in touch with me. I’m happy to set something up with you.

Kimberly (08:33): I think also what probably is blowing people’s minds, I mean myself included, that you were doing it. It’s not just like someone random. The CEO, the founder is doing it. I think that’s kind of unheard of for most companies.

Jason (08:48): Yeah, I don’t know. I mean, I just think of myself as a guy who likes the product and knows it inside and out and I’m happy to show it off. So wherever my role is my role. But the key is that someone’s available and I’m not a salesperson. I’m not trying to sell you anything. I don’t care if you buy it or not. I think it’ll leave an impression, make an impression on you and it’s up to you at that point. And I’m not making promises about adding things or it’s not like a sales thing where I’ll take that back to the team and we’ll make these three customizations. I’m proud to show the product off and it should be the job that I do. I should show the product off. We should show the product off. We’re proud of it. And we do a lot of things in it that people don’t know are possible.

(09:24): And how would they ever know? You can make a marketing site about all this stuff, but people aren’t going to even look at that. They want to watch something. They want to walk through something and it’s fun to show these things off. I think the other thing we try to do with Basecamp 5 onboarding is not only introduce people to the product, but introduce people to us. Like what are we like as a company? Who are we? Which is why you’re heavily featured. Look, we have friendly faces here. We talk in normal words. We don’t use ridiculous technical jargon. Also, the first thing you see when you sign up is a letter from me. Obviously it’s a form letter. I wrote it once. I’m not writing each person a letter, but it’s like, hey, here I am and here’s my email address. Write me if you have any questions.

(09:59): And I get tons of emails from customers every day and I answer them personally unless I can’t because there’s something I don’t know and I forward it to somebody else. But it’s like, here’s who we are. Here’s what we’re like. Here’s how we talk. Here’s how we act. Here’s how we present ourselves. And I think this is another important thing that companies can do to further differentiate themselves from other companies. Most products these days, most software these days looks about the same and a lot of it works about the same. And if you look at, especially in our industry across things like Monday and ClickUp and Asana and Notion and whatever, they’re all fully all in AI and they’re all big text boxes in the middle and you just type what you want. And I think it’s actually very confusing for a lot of people.

(10:40): I don’t think they really know what they want necessarily. And also the products become more and more alike, not more and more different from one another. And then it’s like, why do you exist? Why are there five things that kind of do the same thing? So I think differentiating yourselves not only in terms of the product offering, but also in terms of who you are, how approachable you are, presentable you are, open you are to communication is a fundamentally important thing that we try to do as often as we can. And I think the onboarding process is the first example of that.

Kimberly (11:07): And actually another example that you made me think of is our announcements that we send to customers within the app are now personalized. So it used to be just generically coming from the company, Basecamp. Now it is an avatar, it’s a message from Jason, it’s a message from me, it’s a message from Brian. So that is just that additional, we’re real people. There’s real people behind the scenes. It’s not just this generic company brand.

David (11:28): I also think it’s a very reciprocal process actually. Yes, someone is getting a tour of Basecamp, but Jason or I are getting a tour of how someone receives Basecamp. What they notice, what they don’t notice, this was one of the things, especially with Basecamp 5, where we changed quite a lot of things and some of the changes we thought before launching it, these were going to be the controversial bits. These were going to be the ones that get… And then you launch it and you’re like, that wasn’t it. Some of the things we thought were going to be a problem were a problem, but a lot of them either didn’t get noticed at all or what did get noticed was something we would never have thought of. It’s only that direct exposure to reality, to customers, that you realize what actually lands. It’s a little bit like standup comedy.

(12:13): You got to go work on the material. You got to go see if the timing is right and what gets the laughs. And sometimes it’s sort of a throwaway comment that kills that night and you go like, “Oh, okay. I didn’t realize that that would be the trigger point.” And I think you have that a lot in software development as well. We worked on, I don’t know how many features for Basecamp 5. There’s probably hundreds of small changes and trying to guess exactly what’s going to land is surprisingly difficult, but you get to see it when you sit down with someone and you experience them using it. Now, the other thing you get to see is just kind of the stupid things they can stumble over. This is all the way back to Jakob Nielsen back in the ‘90s. Usability, watching customers use your product.

(13:01): You say, Kimberly, like, oh, you’re surprised that Jason would do that. I can understand it’s surprised because most company CEOs, certainly the professional ones never do. And that’s why their shit sucks because they’re not actually exposed to it. It reminds me of the McDonald’s CEO. I’m going to take a bite of this tasty product here. And he takes this little nibble and he looks like a total fucking moron, right? Because he looks like someone who despises his own product, who would never in a million years eat a McDonald’s burger. He just takes a tiny little bite of a product. Not a burger, a product. Already there, just in that language, you know it’s all wrong. You know, here’s someone who doesn’t give two fucks about the actual burger, whether it’s tasty or not. And I think this is the magic in large part about founder-led companies, that someone who went from there was nothing here, I literally had to make every sale manually, is way more likely to stay connected to that exchange, reciprocal exchange.

(14:02): I actually care about the thing I’m selling. I’m not selling product. I’m selling burgers. I’m selling project management tools. I’m selling something specific. I’m not selling a category. I’m not selling content. And it’s surprisingly hard, I think, to create that connection, especially after the fact, and especially if you are a company who’s being led by professionals who could just as well sell burgers, that they could sell toilet papers, they could sell sugar water to invoke Steve Jobs again.

Kimberly (14:32): Well, you can check out our new onboarding with a new Basecamp account at basecamp.com. Check it out, sign up for an account for free, and you can see that in-app the video that we were talking about. We’re going to wrap it up there. Rework is production at 37signals. You can find show notes and transcripts on our website at 37signals.com/podcast. Full video episodes on YouTube. And if you have a question for Jason or David about a better way to work and run your business, leave us a video. You can do that, 37signals.com/podcastquestion or send us an email to rework@37signals.com.