The REWORK podcast

A podcast about a better way to work and run your business. We bring you stories and unconventional wisdom from Basecamp’s co-founders and other business owners.


In the Market for a Marketer

Like what we've got to say about business? You'll love Basecamp >

As part of a mini hiring boom at Basecamp this year, CEO Jason Fried went looking for a position that had never existed before at the company: head of marketing. Over a thousand people applied for the role. In this episode, Jason explains how he narrowed a very competitive pool of candidates to find the right person.

The Full Transcript:

Shaun: [00:00:00] Before we get into today’s episode, I’d like to remind you that we are gearing up for another mailbag show. If you have a question for Basecamp co-founders, Jason Fried and David Heinemeier Hansson or anyone else here at Basecamp, leave us a voicemail at (708) 628-7850.

Wailin: [00:00:17] Rework is a podcast by Basecamp. When you’re working with a group on a project, everything gets scattered across email, chats and whatever you use to track tasks and things slip through the cracks. Basecamp centralizes it all and it’s easy to use so everybody sees everything about the project in one place. Sign up free at

[00:00:37] Broken By Design by Clip Art plays.

Shaun: [00:00:39] Welcome to Rework, a podcast by Basecamp about the better way to work and run your business. I’m Shaun Hildner.

Wailin: [00:00:43] And I’m Wailin Wong. Basecamp recently did something for the first time in company history. We hired a Director of Marketing. You heard about the early part of the hiring process in a previous episode we called Hire When it Hurts. I’ll link to that one in the show notes. 1400 people applied for the marketing position. And because it was a brand-new role here at Basecamp, we didn’t have a playbook for how to find the right person.

Shaun: [00:01:08] On today’s show, I sit down with Basecamp CEO Jason Fried to talk about the process of choosing a Director of Marketing and the surprises that came along the way. This is the first of two episodes about hiring a Head of Marketing. Next week we’ll talk to the person who got the job. But first, here’s my conversation with Jason.

[00:01:27] Jason, you have been looking for a Marketing Manager fairly recently. Why is that?

Jason: [00:01:34] We’ve never traditionally done any marketing, and we’ve just turned 20 as a company, and I felt like it was time to do a few different things. So one thing is we’re working on a new product that we said we weren’t going to do, again. One thing as we just changed our logo, which we hadn’t really changed, we kind of changed it, but not really much for 15 years. And we’re still going to talk and still gonna write books and still going to do that sort of thing. But let’s get more intentional about how people find us. I found that we were basically just sort of doing our thing and crossing our fingers and hoping people find us. And many, many people do, but we shouldn’t leave that to chance anymore.

[00:02:12] So we’re out there looking for someone who can own this kind of work. And we’ve done some of this, sorta kinda. But no one’s ever owned it before. So those projects always kind of faded away. So I want someone focused on this all the time.

Shaun: [00:02:22] And during interviewing and accepting applications, what kind of people were you talking to?

Jason: [00:02:27] Well, we got a bit over a thousand applications. We narrowed it down. The way we did it is went from like a thousand, whatever it was to a few hundred to less than that to I think about 11 or 12 finalists. And then down to six and then down to four, then down to three and then down to two and then down to one. That was kind of the, those are the breaks. And the majority of people we talked to were professional marketing people. So their titles were, you know, VP of Marketing or Head of Marketing or Marketing Manager or Brand Manager, those of folks that’s been there.

[00:03:01] Most of them had been in that job for quite a while, but they all pretty much had a marketing title.

Shaun: [00:03:06] Going into it, did you think that was the kind of person you were looking for?

Jason: [00:03:09] Whenever you hire for a position you’ve never had before, you don’t always know what you’re looking for. Like you think you know what you’re looking for and then you talk to a bunch of people and actually the shopping process helps you figure out what you want to buy, essentially. It’s similar to, you know, you might go into a car dealer thinking you want a huge SUV with three rows of seats. Like, we need three rows of seats, you know. And you go test drive one and you’re like, this thing is enormous. Like, I thought I wanted this—

Shaun: [00:03:36] I can’t park this.

Jason: [00:03:36] But I can’t park this. Like this won’t even fit my garage. Like okay, maybe we want something different. That’s still an SUV, but maybe something a bit different. And I kind of feel like you have to go through that process sometimes to really figure out what you want.

Shaun: [00:03:50] So at some point during this process you did figure out what you were actually looking for. When did that change?

Jason: [00:03:56] I don’t know if it changed so much as certain things came into focus perhaps. We still wanted somebody with marketing experience, obviously. It shouldn’t, this person shouldn’t be a newbie. We need someone who’s done this sort of thing before. And when we got down to the final four, we didn’t know what to do actually. Cause we had four really, really good candidates. And so we took a book or took a page out of our book for hiring designers, which is that we give everybody a project.

[00:04:25] Whenever we hire designers, we give people a project for one week, it’s $1500 and we ask them to design something for us. And the main reason we do that is because we want to see their actual work. The hardest thing about hiring a marketing person was that you can’t really see anybody’s work. You don’t really know what they did. It’s just, it’s sort of a hard thing. It’s—when you look at a coder or programmer, like you can look at code and when you look at a designer, you can look at design, but it’s very hard to like look at marketing. Marketing is a very big thing. It involves a lot of things that are out of individual people’s controls. Could be large campaigns that involve a whole whole team or other people. It gets, just, it’s hard.

Shaun: [00:05:00] Even the timelines are longer.

Jason: [00:05:02] The timelines are longer.

Shaun: [00:05:01] Two weeks. How much traffic did you drive to the website, right?

Jason: [00:05:05] Yeah. And you’ll, you’ll see people in their resumes, they’ll be like, we know I improved ROI on this 43% or we increased sales 32% and it’s not that I don’t believe them, it’s that it’s hard to connect the dots, really.

Shaun: [00:05:17] Mm-hmm. It’s murky.

Jason: [00:05:17] I’m sure the work that you did had something to do with that, but it also might’ve been a price change or it might’ve been some other thing that you don’t have control over or the market changed. It’s hard to know, really. So what we decided was with the last four we would do a marketing project exercise where we gave everybody the same project, which was like kind of put together a campaign. Like, don’t interview anybody, don’t do research. Like what does your gut tell you we should do as a brand, as a company, and you have a week to do it and we’ll pay you 1500 bucks.

[00:05:43] So, the final four went and did that. And that’s when something became clearer for me, which was, can I imagine myself seeing these ideas play out? And, by the way, it was, you know, this hiring process involved, four other people. I was leading it, but there were four other people. So we had some vigorous debates about this and in fact, at different times in the process, each one of these four people was the leading candidate in a sense.

[00:06:11] So it bounced around a lot. But the work was interesting because the work kind of showed some contrast. What eventually drew my interest was ideas that I could see from start to finish. And I was attracted to the ones, to the projects that were about things that we could do ourselves that didn’t rely on a lot of outside help.

[00:06:31] So, for example, a few of the projects that came back were like, we’re gonna partner with six or seven different brands and we’re going to get this kind of media coverage and we’re going to do… Oh, and by the way, these aren’t bad ideas. It’s just like these are enormous ideas and some of the brands listed, are brands like I know the CEOs of these other brands and I’ve tried to do partnership deals. It’s like partnership deals are very hard to pull off because you’ve got to depend on another brand doing something for you. And the timing’s got to be right and they’ve got to have dedicated resources and you’ve got to have resources and they’ve gotta be some sort of alignment between like what they’re getting out of it and what we’re getting out of it. And so to say, like, we’re going to partner with all these brands, or these are the brands we could partner with and then we’re gonna get this media coverage and we’re gonna do this and do that.

[00:07:12] I started to get a little bit nervous about actually executing this stuff and we were relying so much on other companies be able to follow through on these things. Of course these weren’t, this was just a proposed idea they each had a week to put together. But still, I wanted to see where their gut went. And most of the guts went towards like these big, broad, let’s get a lot of people involve a lot of things happening at once, a lot of coordination, a lot of complexity and it’s going to be this big huge splash. And like I appreciate the dream but I couldn’t confidently wrap my head around how are we truly going to execute that. And, as a company here, we’ve always been pretty practical in terms of taking on things that we know we can do and relying on ourselves to do those things.

[00:07:55] So, for example, we have big ideas for how to pull off like a new product idea. So, like big idea, but like we’re going to break it into small pieces that we know we can handle. We can see the start, we can see the end, we know what the scope is, we know how we can do this. We don’t have to rely on third parties left and right to make sure that they do their part right at the right time. And every time we’ve tried to do that, it’s always a little bit murky. And so I just started to feel like I was angling towards the still creative projects, but the ones where we were in full control and we could see them from start to finish and that sort of thing.

[00:08:25] So anyway, that’s where I began to [inaudible].

Shaun: [00:08:29] So, you sorta changed directions a little bit. Who’d you end up with?

Jason: [00:08:32] We ended up with somebody who is quite a bit different from the other three finalists. The other three finalists were very, very good professional marketers. Excellent. Wide range of experience, perfectly competent, could do the job well, no question. The person we ended up going with was not a traditional marketer in the sense of job title. This person had never held a marketing position. They sort of kind of only worked for a few other people here and there, but this person was actually an entrepreneur. It turns out that an entrepreneur is someone who has been doing marketing their whole lives because even though they don’t have it in their title, like, that’s what they do.

[00:09:14] What I found was that the entrepreneur in the group, in the bunch was a very practically minded. Scrappy because he had to be. Had done a whole lot with a little, had made a lot of sound from a small stage, and had put together some really interesting projects over the years. Some of which had gotten significant publicity, significant press, and he just gutted it out and figured out how to do it and he’s kind of a roll up your sleeves, let’s figure this thing out with like no resources whatsoever. And in fact, what was interesting was, in the project that we gave out, for each one of them to do, which was the same project, I threw a budget in there. I said, like, you have $1 million to spend.

[00:09:57] The three marketers spent all of it and they explained how they would spend it, like totally professional and solid, like 300 here and 200 here and 50 here. Like, totally solid. He didn’t spend hardly any of it. His whole thing was like, I don’t think we’re going to need to spend any amount near that to figure out what we want to do first. Let’s validate some stuff and then we can spend as much as we want. But like, I just don’t think this is going to take a lot of money to do what we need to do here. And it wasn’t that like I was like, “Oh, he’s gonna save us money, because I was happy to spend the million.” It was more of the perspective, which is like, just because you’re given a million doesn’t mean you need to spend a million. Like what do we really need to do here? And I just appreciated that perspective.

[00:10:36] And that was more of an, that’s an entrepreneurial thing, because people in marketing positions are given budgets and they typically will spend the budget as they’re expected to.

Shaun: [00:10:43] Absolutely.

Jason: [00:10:44] An entrepreneur is like, well this is my money and I have to be scrappy with it because I might not have any more of it and I don’t want to spend it on something that’s not gonna work. And I might not get a second chance. So there’s this natural tendency to be careful in some respects, but also, I think, very thoughtful about the spend and trying to sort of edge their way into figuring out if they should go all in or not. And I just appreciated that. I appreciate the other angles too. But like when it came down to this, I felt like that was the right attitude.

[00:11:09] So this fell on Andy as who we ended up going with. Andy has been running this thing called the Detroit Bus Company for a number of years. I think it’s maybe been, I don’t know, six years, seven years, maybe actually longer. So Andy is a Detroit guy who was very frust—Detroit went bankrupt, basically. And even, this was a problem even before that, and bus schedules were not running on time. Buses were not available. People had to wait an hour to get a bus to get to work. You can’t like, you know, wait for a bus that’s totally unreliable and get to where… If you have to be at work at eight, you gotta be at work at eight. And like if the buses don’t come, you’re screwed. Kids couldn’t get to school. It all started falling apart.

[00:11:48] Because just a concerned citizen is like, this is crazy. People can’t into the city, they can’t get to school. Like fuck it, I’m just going to buy a bus and like I’m going to start driving around and help people get around. And so that’s essentially what he did. He bought an old school bus, painted it kind of fun and just started this bus line. And they also adopted sort of the TOMS philosophy, which is that a few buy a ride on a tour, you’re actually buying a ride for a kid to get to school or to an after-school program.

[00:12:12] So they kind of did this really nice thing there. And he did this because he cared about the problem and he pulled that together and he’s done a number of other things. But I was really intrigued by his ability to go from absolutely nothing with just an idea that just he felt like he had to do and just figure out how to do it with no experience whatsoever in the thing itself. And is sort of at the point now where he’s able to step aside and join another company.

Shaun: [00:12:42] Can you tell me about the sample project?

Jason: [00:12:44] What I liked about where he was coming from was that he saw, or he sees Basecamp not as just a software tool. He sees it as sort of an elevated way to work. And what’s interesting about Andy is that Andy is an entrepreneur who’s also a Basecamp customer and has been for many years. But he’s also left Basecamp a number of times over the years. So he had Basecamp. He couldn’t get people to use it. They tried some other stuff. Asana, I think. Trello.

[00:13:10] And that experience to me is priceless, because that’s—he’s our customer and that’s what our customers deal with all the time. So the other part of it is like when I’m thinking about marketing and thinking about reaching customers, and many of our customers are small business owners, who’s better than a small business owner who’s gone through the exact same struggles… Like, who would better understand these struggles than someone who’s actually had them themselves? And I think that that’s really valuable.

[00:13:10] On the other hand, by the way, the other marketing people, we had, the finalists had all used Basecamp, were huge fans of the company. They knew the company just as well as he did. But I liked that he had the extra dose of reality in terms of he actually paid the Basecamp bill. He had to get people to use it, the whole thing.

[00:13:47] What he’s realized is that Basecamp is not just a product, it’s actually, it’s an elevated way to work. It’s a different approach to work. It’s not just about how to get people to like switch from this product to that product. It’s about how to actually make companies legitimately better.

[00:14:00] The other thing I thought was very interesting was some of the tactical stuff he came up with ,and he’s the only person out of a thousand to just say this. Look, it’s not that hard to get a list of LLCs, new LLCs every year who start up. Like, they’re small businesses. They’re new businesses like let’s get to them before anyone else does or let’s talk to them. We understand what struggles they’re going through. Growing a business is hard. Let’s get that list and work off that list kind of thing.

[00:14:25] So there’s this, this real specificity that he came to every discussion with that felt very concrete to me, which I have to say was very attractive because it’s not hard to throw out big ideas, but every time we talked about ideas, he always kept coming back to like, practically, here’s how we can get there. Here’s the, here are the tactics, here are some specific things we can do. And they were all things you could see us doing versus like things you had to imagine us may be doing and figuring out. So I, I really appreciated that about his, his overall application.

Shaun: [00:14:57] What is your philosophy on measuring this kind of work?

Jason: [00:15:02] Yeah, I think David and I have historically butted heads around this a little bit. Understandably, because like you’ve got to be able to measure something, you know, you can’t just like blow money on stuff.

[00:15:12] I’m more like looking for the feel. Do we feel like things have changed? One of the candidates asked us, because we said like, any other questions for us, you know, at the end of the, and she said a year from now, how do you know if this worked or not? And Ryan, who was on the call said like, that’s a great question. I think the way we know is if we feel like we’ve done a lot of work and we haven’t made any progress, then it’s going to feel like it’s not working. Like we can, we can be busy, but if it feels like we’re in the same place we were when we started, then this hasn’t really worked out. And that’s not necessarily about like measuring, it’s just, it’s also about like how does it feel? Do we feel like we’re in the conversation? Are we hearing from more people? Do we feel like we’re saying the right things? Do we feel like we’re in the right places? Do we feel like we’re getting in people’s heads? Do we feel like we’re sponsoring the right events?

[00:15:59] Even if we don’t see the right returns. Are we getting behind the right kind of people? Are we helping companies, are we hearing from customers? And are those customers telling us different stories than they told us before? Like, at the same time, I think there’s a lot of tactical things we can do that we can measure and we should measure to make sure that some of these things are working.

[00:15:59] The other thing about marketing is, is that marketing is also internal. How do we all feel about what we’re doing, too? Do we feel like we’re cheering ourselves on some more? Do we feel more confident with what we’re doing? We have a new product that we’re launching next year, so like that’s going to be a big part of this too. Like, are we explaining that well enough? Are we getting the word out about that well enough?

[00:16:30] I’m not, I’ve never been big into measuring things. I just think about like how we started the business. We didn’t measure anything. And I feel like sometimes you can get to the point where you have a lot to lose. So, you begin to be very careful about those things and you then you have to justify everything. And I think there’s some things we want to justify for sure, but I don’t want to lose the instinctual, intuitive things that we’ve always done because that’s also what we have the most fun doing. And I think that’s another big important part of this. You just don’t ever know what’s going to happen and so you can measure yourself out of an opportunity as well. So, anyway, we have to be prudent, though, at the same time.

Shaun: [00:17:05] Can you talk a little bit more about the idea of having a lot to lose? Like what do we have to lose if this doesn’t work out? We’re back where we are this September.

Jason: [00:17:13] I mean, more broadly, the companies as they’ve been around for a while and they’re more successful and now you have a history and now you have to live up to certain things. And you feel like you have more to lose because when you have nothing, you’ve got nothing to lose, right? And now we’ve got a lot. So we’ve got a legacy, we’ve got tons and tons of customers and lots of money coming through the door and 55 employees and whatever it is. And there’s a lot to lose. So, if we get a lot of things wrong, we have a long way to fall, basically.

[00:17:41] And that’s kind of what I mean. So then you end up in this preservation mode, companies tend to switch into preservation mode—

Shaun: [00:17:45] Taking less risks.

Jason: [00:17:46] Taking less risks, yeah, fewer risks, and also smaller risks, which is not a bad instinct, but also I think it can lull you into this sense of being afraid. And I think we’ve maybe fallen into that a little bit over the last few years. And I feel like we’re now working our way out of that, actually. The fact that we’re going to launch a new product. The fact that we just like decided to rebrand stuff. Like this, the fact that we’re hiring someone in marketing, probably start working on Basecamp 4 next year, perhaps. And it’s a lot of new stuff happening, which feels good. And a 20th anniversary. It’s just like kind of the right time to kick things off again.

[00:18:21] And the way I sort of explained it internally is, not to think of the next year as our 21st year, but as our first year of our next 20. And that’s kind of how I want us to start thinking about things.

Shaun: [00:18:29] This is every midlife crisis ever.

Jason: [00:18:31] It is.

Shaun: [00:18:31] Like we just bought the sports car—

Jason: [00:18:34] The red corvette.

Shaun: [00:18:34] We’re feeling young again.

Jason: [00:18:35] Yes, totally. I mean, it’s funny because it’s so true.

Shaun: [00:18:37] Yeah.

Jason: [00:18:38] And like I feel like I’m in that in my life. I’m 45, like, okay. I’m like, technically past halfway.

Shaun: [00:18:44] You don’t own a red car, do you?

Jason: [00:18:45] No, of course not.

Shaun: [00:18:46] Thank God.

Jason: [00:18:46] Of course not.

Shaun: [00:18:47] I couldn’t see you in it.

Jason: [00:18:47] No, no, no red cars. But, maybe it’s funny, maybe it is tied up with my own existential whatever thing going on, being 45 and having two kids and the whole thing. But like it also just feels like the right time for a company to do something like this. And we’ve even talked internally, I mean we haven’t talked about this publicly, but like if we’re going to have a second product, does the name Basecamp still make sense for the company? Do we go back to 37 signals? Like, I don’t know. This is kind of an interesting time and Andy might help us think that through a little bit.

[00:19:18] It’s sort of fun that we’re in this position where we can just decide to go in a different direction if we want. And I like that kind of lightness and that flexibility and it’s hard to do that as you get bigger. But we’re trying to prevent us from, calcifying and staying flexible.

[00:19:35] Broken By Design by Clip Art plays.

Wailin: [00:19:37] Rework is produced by Shaun Hildner, and me, Wailin Wong. Our theme music is Broken By Design by Clip Art. Next week, Basecamp’s new Head of Marketing, Andy Didorosi, will tell the story of how he started the Detroit Bus Company. Make sure you’re subscribed to Rework in your favorite podcast app so that you get all our new episodes as soon as they’re released.

Shaun: [00:19:57] And in the meantime, you can visit our website at or follow us on Twitter @reworkpodcast. Again, if you have a question for Jason or Basecamp CTO, David Heinemeier Hansson, leave us a voicemail at (708) 628-7850.

Wailin: [00:20:13] As always, Rework is a podcast by Basecamp. Basecamp is an online tool that helps you communicate and collaborate with other people and contains most of the features most people need to organize whatever they’re working on. Try it for free