Pushing Yourself to Scale as CEO with Steve Sloan

Intro: Welcome to the Daily Bolster. Each day we welcome transformational executives to share their real world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- founder and CEO of Bolster, and I'm here today with Steve Sloan. Steve is the CEO of Contentful. Steve, it's great to have you here.

Steve Sloan: Matt, thanks for having me. Good to see you.

Matt Blumberg: Yeah, good to see you. So you joined Contentful when the company was how big? Like employees or revenue?

Steve Sloan: We were right about 225 people. Doing almost$ 30 million in ARR.

Matt Blumberg: And what does the company look like today and how many years has it been?

Steve Sloan: So it's been right about four years, and now we are right around 800 people, and we are north of $175 million in ARR.

Matt Blumberg: All right. So four times the number of people, 6, 7, 8 times the amount of revenue, which by the way, congratulations. Tremendous growth.

Steve Sloan: Thanks. We've been very fortunate.

Matt Blumberg: My suspicion is that while you have had the same job and the same business card for four years, that it actually feels like you've had four different jobs. That level of growth means that every year, every few quarters, you kind of have to reassess what you're doing to think about how you're scaling yourself. So my question to you is, how have you done that? First of all, is my premise, right, and then how have you gone about doing that?

Steve Sloan: Oh, I absolutely think you're right. I think the way we think about a role as a CEO and the way we engage, it's one of the primary bottlenecks for the company, and the company has to be different every year as we go through these different phases. The way you operate at 25 million versus a hundred million versus 200, it has to be very, very different. The people are different. The way you work is different. And so, one of the challenging things, as you said, is my title's the same, the company's the same, literally my desk is the same. There are all these things that look the same around you and that can lead you down the wrong path. So there is an exercise that I've found really hopeful, inspired by the folks at Intel a long time ago. They were going through an existential crisis about whether or not to stay in the memory business. And I believe it was Andy Grove, who's probably one of the greatest CEOs of all time posed the question, well, if we left the building and someone else came in, what would they do? And clearly the answer when they posed it that way was get out of the memory business, which they ended up doing, which was a great choice. And so this is inspired by that idea. I call it the revolving door. And so the idea is once a year to do a process that has basically three steps. So the first thing is you sit down and you say, looking back at just the past 12 months, three things that went really well, and three things that I'm not proud of or went really poorly, or even were just really different than I thought they were going to be. So go to that retrospective place, actually write it down in kind of two columns. And then you have the second part, which is you write your resignation letter. So it's super important that you write it out in prose. I believe you have to print it out and literally sign it so that you have to go to that place really emotionally, like, no, I'm done. And for me personally at least I've found that having a piece of paper and signing my name, it just does at least this little extra trick. Don't send it, but sign it. And then ideally give yourself, maybe you do that on a Friday, give yourself a Saturday, go do something fun, get away, create a little bit of emotional space. And then there's the third part, which is you sit down and you're not writing your job description because you've left, you've resigned. You are writing the letter for the next person who's going to do your role and come back to it and say, okay, here are the three most important things for you, my successor, in the next year. And the three things that old person used to do, that you should definitely not do. And giving that space in the third person is, I think, more helpful, because we frequently give better advice to our friends than we give to ourselves.

Matt Blumberg: We do to ourselves, yeah.

Steve Sloan: And so, that can really reframe the notion of the job. And I found it to be clarifying, found it to be energizing, honestly, because it can feel like you're doing the same thing all the time. And there's one extra trick that's really important. If there are elements of that job description, and this should be the case, that are different from the prior year, you want to make sure you tell people about it. So I make sure to tell people I do this exercise and say, Hey, I actually went and said today I'm doing these things. I need to stop doing those things. And we either stop doing them entirely or it's delegated to somebody else on the team, which is honestly frequently. Frequently, they're relieved that I've realized that I need to stop doing something. So that can be a positive benefit.

Matt Blumberg: It's a great formula. Do you have other people on your team do the same thing? Do you all do it at the same time, or is this just for you?

Steve Sloan: I have recommended it to other people. Some people have done it, not everyone. I think it's incredibly helpful and clarifying, but it's not something that everyone likes to do.

Matt Blumberg: Yeah, I think it's a great exercise and I love your mental jujitsu of actually write the resignation letter, print it, sign it, get yourself in the headspace of someone who is handing something off. So that is great advice on scaling yourself as a CEO of a growth company. So thanks for being here with me today, Steve. I appreciate it.

Steve Sloan: Thanks, Matt. Really appreciate it. Great to see you.