The idea for Appcues all started at the end of Jonathan Kim’s time at HubSpot, as he was having a conversation with his boss, David Cancel (the future founder of Drift).

Here’s how he describes the interaction:

“So David Cancel comes over to my desk and he’s like, ‘Hey man, I’ve been seeing you and you’re either at 110% and you’re super passionate about something, or you’re like you know, just not passionate at all. And for the past couple weeks, you’ve been not passionate.’

And so we caught up a little later and you know I started talking about this thing. I was like, ‘oh man, how’s about we crack this huge problem around user onboarding and check out this landing page I built and it could be like a real product.’

And he said like, ‘The way you light up about that, that’s what you’re really passionate about. You should go do that.’

And I said, ‘I guess you’re right. I guess I quit today.’ And I just kinda quit on the spot because I was so passionate about the problem.”

5 years later, Appcues has grown to nearly 70 employees and 1000 customers across SMB and Enterprise.

How have they managed to reach such fast-growth? We’ll cover it all in our interview with Jonathan!

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In This Episode You’ll Learn:

0:00 Introduction 
1:28 What is Appcues? How would you describe it?
2:43 What allows you to build a great company with great products? 
7:38 Growth strategy through inbound marketing
14:59  Pricing strategy as you move up-market
20:48 Jonathan’s thoughts on how companies should be thinking about onboarding
29: 03 Salty Six

Full transcript:

DR: Today I’ve got a new friend with me, Jonathan Kim, CEO and Founder of Appcues. And if you don’t know Appcues — it is a fast-growing company up in Boston. And they help other companies create really beautiful and delightful onboarding flows for their users and it works really, really well. We’re customers ourselves.

Before that, Jonathan spent a couple years at HubSpot, and before that was at Performable, which was the company founded by David Cancel — who was guest number one on Scale or Die.

So Jonathan, welcome to the show! I’m honestly super pumped to have you here.

JK: Thanks. Great to be here, thanks for having me, Dave.

DR:  Yeah, so we’ve been customers you know for a while now. We were just talking before this, we re-launched our Appcues just this morning.

I love the product and I think as I started to like, look into the company behind the product — we really liked what you guys were building as a company. You know we felt like we kinda had the same ethos, the same culture, and like the same idea behind what we’re trying to do with creating great products for people.

But I’m excited to dig into that, and I guess I’m just curious, from your perspective:

What is Appcues? How do you describe it? And then maybe like where are you today as far as some key metrics that you track?

JK: Yeah that’s a great question. And it’s a great question because the story has evolved a lot, the product has evolved a lot over time.

Appcues GIF

The Appcues flow builder in action!

We started out just trying to solve the problem of user onboarding primarily for B2B software products. And today we describe ourselves really differently.

We describe ourselves as really this experience layer that sits on top of your product and helps you grow your business by creating these amazing user experiences.

And the way that we came to that vision or came to that point was we, in building this product for onboarding. We saw the way that people were hacking the product, they were using it for feature announcements, they were putting surveys in there. And these people were not technical right?

So when we talked to them, their biggest benefit to it, it just made them feel empowered, made them feel like they were finally welcome within the product. And that’s how we really believe that companies create great products.

DR:  Interesting. And so you were just watching?

Well here’s a question, I’ve seen you talk about how excited you are about user onboarding. And I’m just curious are you really, actually passionate about user onboarding.

Or is that just kind of the thing that allows you to do what you’re passionate about and build a company and build great products and do that?

JK: Yeah. It’s funny I would say, the evidence that I go back to is the story of how I left HubSpot and started Appcues.

David Cancel came over to my desk and he’s like, “Hey man, like I’ve been seeing you “and you’re either at 110% and you’re super passionate about something, or you’re like you know, just not passionate at all. And like the past couple weeks you’ve been not passionate.”

And so we caught up a little later and you know I started talking about this thing, I was like, “Oh man, how about we crack this huge problem around user onboarding and check out this landing page I built and it could be like a real product.”

And he said like, “The way you light up about that, that’s what you’re really passionate about.”

He was like, “You should go do that.”

And I said, “Okay I guess you’re right. I guess I quit today.”

And I just kinda quit on the spot because I was so passionate about the problem. But I think as an entrepreneur, I’ve started to discover that I can get passionate about problems that are really close to me and that I feel every day. And so creating our own products right, having to onboard customers, get them to adopt new features, you know to collect NPS survey results. Those are all things that we actively feel, and so I can get really passionate about them.

DR:  Gotcha. So really passionate about solving problems, and you happened to stumble upon a really big problem that you knew how to solve — and that gets you fired up?

JK: Yeah.

DR:  Okay.

So where is Appcues today? How many people do you guys have? How many customers if you share those numbers? 

JK: Yeah so we’re just over 1000 customers, just under 70 employees, and we’re tracking to basically double this year in revenue. It should be pretty exciting for us.

DR:  That’s awesome. And you raised a Series A not too long ago? 

JK: Yeah back in August.

DR:  Okay, cool cool. How long has the company been around?

JK: Just over five years now. I left HubSpot technically at the end of 2013.

DR:  Okay.

JK: So just over five.

DR:  Okay, very cool man.

So I wanna talk about growth. I wanna go back to, so you leave HubSpot, you build a product.

How long does it take to build a product? And then how did you kind of launch into the world?

JK: Yeah so, again like another David Cancel influence. I’m a huge believer in charging money for a product before you build it. And charging money from day one.

And so after leaving HubSpot I did a lot of consulting, just to kind of, see if I could build the product or be the product.

And then I started pitching — I had this animated GIF that I made out of like HTML and CSS, and I recorded it and made an animated GIF.

Which I can send you, it’s kind of funny how simple it was. And I pitched it to a company in Boston called Nanigans. And I was like yeah, you know, this is kind of what I’m thinking, I’m gonna build it. And they were like yeah we could use that tomorrow — like we’ll pay for it.

And at the time I was like okay cool like $45/month seems like a fair price.

I got them to pay $45 a month via check on like New Year’s Eve and then I had to build the product, cause it didn’t actually exist. It took me about three weeks to build the first version, which was our STK web application to edit stuff.

And then it kind of got rolling from there. I mean product development now, we’re taking on bigger and bigger challenges and there’s also just a lot at stake now, and so we have to be a lot more careful.

DR:  Yup.

JK: But back in the day, I mean software’s so easy to create. Especially now, it’s like it gets easier every day.

DR:  And are you an engineer?

JK: Actually I have a degree in journalism.

DR:  Okay.

JK: I taught myself how to code to pay for school, and then I did that at HubSpot.

DR:  Okay. Cool. But you were the one who created the very first version?

ES: Yeah, yeah I wrote most of the code until … 2015.

DR:  Okay.

JK: Something like that.

DR:  Okay. Very cool.

And so you launch it there — what does growth look like past that?

What were some of the early growth channels or the growth channels that you had that really started to get adoption?

JK: Yeah. So day one, we started a blog right.

The user onboarding academy

Actually, we started this thing called the User Onboarding Academy, which was like an evergreen series of content. But really there wasn’t a whole lot of knowledge around how to do great user onboarding at the time.

And so that was really the pillar of our education strategy — which is our mission, right? To help teams create products their users’ love.

user test fest appcues

The view from an Appcues user test fest

There are multiple ways that we do that. And so one of those channels was the Onboarding Academy and content. Another one of those was a User Test Fest, which used to be called Drunk User Testing back in the day. We started that really early, I think we were five employees when we started that.

DR:  That’s awesome.

JK: It’s crazy. Yeah, we’ve done nine of them now.

DR:  We hosted one in our office here at Proof with you guys, which was awesome.

JK: Yeah. Our inaugural Austin one.

DR:  Yeah.

JK: It was really great.

DR:  That was a great time. It was an awesome, awesome team. It was fun meeting the team, Jack, and the girls, and yeah, everyone a part of what you guys are doing.

JK: Yeah. And to date basically, except for maybe a handful of customers, every single one of our customers has come through inbound. And so we are just now starting to do some of the outbound stuff — some of the more like traditional sales methodologies. But we’ve been really fortunate to really invest and be good at inbound marketing.

DR:  So when you talk about inbound, you know you had some of these like big assets the User Onboarding Academy and some of these other, you know, things.

Were you like spending a ton of effort on SEO and actually trying to rank? Or was it like ‘Hey, we’re going to create some of these assets? We’re going to build a good product, most of this is gonna be word of mouth?’

JK: Yeah. We’ve really focused on just like really high-quality content and topics that nobody was talking about.

And giving a very informed and unique angle on it. So the Onboarding Academy, for instance, we didn’t spend a whole lot of time focusing on SEO in the early days.

We really focused on like understanding the problem, putting together unique research that was out there. Nobody was really consolidating a lot of best practices.

And so just by bringing them together when we looped in people like Josh Porter, or Samio Hulik, Kristal Hagens — like these different people who were really niche experts in their space and we got them to write a section of that Onboarding Academy or different assets. And they started lending their expertise to it, and now that community marketing is actually a major part of our go-to-market strategy for content.

DR: Interesting, so what does that look like, to like build out and add some structure to like the community marketing? I’ve never actually heard that term before.

JK: Yeah it’s actually … I had never really thought of it before either. So we hired this woman named Margaret, she’s phenomenal. Came to us from InVision. And she essentially ran the same playbook when she was there.

And it’s so brilliant cause you know her whole take on it was like “hey I’m not a designer but I work at InVision. And so I’m just gonna ask other people, right?”

And she’s like but I’m in charge of marketing, or in charge of content. She’s like so I’m just gonna ask other people to write the blog posts for me. And it’s brilliant because you get them to share their audience and share their expertise.

The article ends up being really high-quality. Better than if you’re sort of a second-hand person writing it or interpreting it. And then you can sort of play with all of these unique different styles. Interview styles, first-hand account stories, case studies.

And so yeah it’s been a really cool way for us to compliment the stuff that’s written internally which we can now be a lot more specific about and curate. Versus the stuff that’s coming from the community which is kind of pulling it all together in one place.

DR:  That’s one of those things where it’s actually it’s easier and better. It’s like, wait, I don’t have to write the articles and they’re gonna be better than if I stayed up all night writing the articles. Very cool.

JK: We saw the same thing with the User Onboarding Academy which is like ‘oh man blogs are really hard to keep up, especially if you’re a small startup, right?’

HubSpot says you gotta be writing three times a week. It’s like you’re a small startup, no way are you gonna write three times a week. And so the Onboarding Academy, it’s just like I just wrote the first three articles, teased out what the titles were gonna be for the next six and said if you want to get the next ones to sign up and put your email in.

And it’s just way higher converting. You could write it at your own schedule, and then it’s Evergreen content. It’s like you win in every single way.

DR:  Amazing. And you get a lot of leads that come in through that?

JK: Yeah.

DR:  So you said kind of more recently things are starting to shift, as far as marketing and you know your channels and I think you guys are adding more sales into the mix, right?

Like how have the channels shifted as of late, and what does that look like to go from just inbound to maybe a little bit more sophisticated sales model?

JK: I would say that you know, the thing that I’ve really come to appreciate over the years is just how strong market forces are. Like five years ago, when we were getting started, the idea, right, like … If I were to come to you and say hey in five years this kid outta HubSpot’s gonna take your user onboarding experience and kind of own it in a third party tool, you’d be like no freakin’ way.

DR: Yeah.

JK: And now, now it’s one of the existential challenges we had and now we’ve got huge companies. We’ve got like amazing consumer brands using Appcues.

And all of those things make us feel like, just in the past couple years that the market timing is really shifting and people are opening up to this idea. And they need to just compete and move faster and create this personal experience. And so that’s why we feel more conviction to say like okay cool we’ve got an engine that works but you know the Microsofts and Googles of the world aren’t gonna necessarily be reading our blog and sign up for a trial.

DR:  Yup.

JK: So, how can we get to them faster? And that’s where a great outbound strategy and different types of marketing can really help.

DR:  Gotcha.

JK: So those two things are, I think are really at top of the line for us.

DR:  Yeah I remember when we first I think hear about Appcues probably two years ago, right around when Proof was starting.

We saw it, we really liked it, and we kind of came to JP our co-founder and our CTO. We’re like, “We gotta have this.” And he was like, he was like “No freaking way, are you gonna like install this code in the app, it’s gonna break everything.”

You know, we’re gonna build it ourselves. And it was just kinda this like the non-technical people are like “We need it, we need it. We need access, we wanna go in there and do stuff.”

And then only yeah, like over the last year he’s kind of been like “Okay, like, like, let’s try it, like let’s figure out how this thing integrates.”

And definitely we’ve seen like a shift culturally too where I think for us like we’re so much more … We’re not gonna build anything that’s not our core competency. Everything else will be a third party tool. And I think a lot of businesses are shifting to that which sounds like that’s opened up a lot of doors for you.

JK: Yeah can you ask, or can I ask you actually, why is that?

Why do you think, why is that mindset shifting? Because I think it does, it is really relevant to have companies now need to grow.

DR:  I think there are so many more amazing tools out there like, you know, five years ago it was like you guys were just entering the market. And so I dunno.

I just think there are like 10 options for every little thing that you want to do. There are like real companies behind little widgets. I mean we have a social proof notification that you know is pretty simple. And it’s like we’ve got a whole frickin company like around this one little thing.

I wonder if there’s just more cool tools in the market right now that actually solve a problem really well. And at the same time it’s like that means there’s so much more competition for us. Like we can’t like, we can’t dink around, on like for like a few weeks on like a user onboarding flow — it just has to be done because we’ve gotta build our core product as fast as we possibly can.

JK: Yeah 100 percent. I think that’s really the piece that I’ve started to latch onto too, is it’s so competitive now and if you’re working on something that has already been reinvented three times before–

DR:  Yeah.

JK: It’s stuff that you’re not, or time you’re not dedicating to your core product or core competency.

DR:  Yeah. I wonder if like just the flexibility of APIs and just integrating code together is like so much more … Available now. And it’s like every tool seems to have deep integrations into what we’re doing. And I feel like that’s like one of the number one things we look for in software.

Like first question is, how flexible is this? Are we gonna get locked in, are we gonna go down a road that we don’t wanna go down? And it seems like that’s just more table stakes now to have flexible APIs.

JK: Yeah although it’s always I feel like history’s a pendulum right.

And so I think we’re going to a very ecosystem type environment right now and maybe it’ll swing back where everyone is like too many tools right — I want all-in-one.

DR:  Yeah. Yeah, yeah, yeah, totally. That totally could be. So I want to talk about like moving up-market. I was talking with Jack Moberger when he was here in Austin, and we were talking about price, we were talking about Proof moving up-market.

Pricing for Appcues varies by monthly active users and plan type.

And he was saying that now you guys have some customers that are paying, you know, well into the six figures. And you’ve really made this shift, and are trying to make an even bigger shift. What does that look like for you guys to go up-market. I guess like what was your pricing? And then how has it looked like shifting into those bigger companies?

JK: Yeah. I would say …

One of the things that we’ve been really careful about — I’ve been trying to be really careful about too is how we talk about enterprise versus SMB. We call it commercial internally.

And there are two strategies right, out there. When I was at HubSpot there’s the HubSpot versus Marketo. And that’s your SMB player versus your enterprise player. More and more you start seeing companies that are spanning the gamut, right?

They’re no longer just an enterprise and SMB player. You look at Shopify, you look at Dropbox, you look at Slack, you look at Intercom. These are like selling $99 deals and also selling six or seven-figure deals.

And that’s the kind of companies that I think are now the future of, are really product-driven companies. And so when we talk about, we don’t really talk about it as a shift, we talk about it as an expansion.

So we still have customers paying us, some customers paying us $45/month, or $99/month. And our lowest client on, published on the website, is $200 dollars a month basically. And so it goes anywhere from that, all that way up to that six or seven figures. And they’re using almost exactly the same product.

To me that’s the part that’s like most exciting, is this is the dream of like a true product scalable-product company.

DR:  So what’s the difference then? Because you know, in my mind, I’ve got some of these limiting beliefs where I’m like you know, I think our most expensive plan is a couple people at a thousand dollars a month.

Most people are at you know a $100, $29, you know kind of around there.

And then it’s like, what’s the leap? Like how do you make that leap past just the inbound self serve, kind of low, lower ticket SMB market?

JK: Yeah so we’re, and we’re still trying to figure some of this stuff out.

But what I would say right now, or what we started to learn is that the biggest difference is what is true within their organization. Or how they can sort of like get their organizational dynamics.

Right, so from a sales motion, you know if you’re a small company and you’re the end-user and decision-maker, you can make the buying decision right then and there. If you are a senior PM and you need to get buy-in and you’re trying to buy it for the whole organization you’re probably gonna need help.

Especially if you need to go through legal and all of this stuff. And so that’s where a salesperson can really help, you know, one of our champions navigate their organization. You know make a case internally, really evaluate the options and feel like this is gonna be the right thing for them.

And so that’s an area where it’s like okay cool, we’re adding value and we can sort of like you know get value in return. And then the second is still organization related but … And you’re probably doing a lot of these same things. You know compliance, SSO, two-factor auth, you know provisioning and permissions and things like that. User roles, all of these like check the box enterprise-type features.

But they’re really solving organizational challenges, right?

Which is them afraid of something going wrong, you know our control or transparency into what’s happening. And these are all like organizational challenges that a small company just doesn’t have. You just have awkward visibility or less at risk.

DR:  Yup.

JK: So that’s when we think about what product features we are building for larger organizations — it’s almost always leading by the difference in the enterprise or commercial. It’s almost always based along like how can we help them as an organization, right? Creating team structures, role permissions, SSO, so that they can work together better.

DR:  And for you guys when you were started to land some of these bigger clients were you kind of pulled into it as in like they came knocking, you started talking with them, you said okay we can build a single sign-on if you’ll sign up? Or was it more like push like this year we’re gonna land these bigger clients let’s start building out these things and go do that?

JK: Yeah. In the same way that we started out like not building a product until we had some dollars committed, we do the same thing with enterprise too. To the chagrin of our sales team, or sort of like a begrudging sales team.

You know their whole concept, or mindset, is like I can’t sell a deal unless I have these enterprise features. And I was like just come back to me, it’s okay if you lose five deals, but like try to sell five deals, lose them, and that’ll be a good validation that we can figure out how much this is worth, right?

DR:  Yeah.

JK: And so they did that, we lost deals right. And it’s like “okay cool, now we know that there’s a real market and real appetite for this.”

But the last thing we’d want to do is invest you know, three months of effort, build all this stuff and then find out that nobody wants it, right. That’s the number one killer in startups is building something nobody wants.

DR:  Yup. Absolutely. And so as you guys think about continuing … Like do you continue, or do you want to continue, moving upmarket and continue shifting focus there? Or do you think of it purely as an expansion?

JK: Yeah we did this really helpful exercise where we mapped out — okay what does Appcues look like? What is our customer profile?

What does our customer base look like, at a hundred million in revenue? It’s actually a really great exercise I’d recommend everybody to do it.

And you just say like here’s how many customers are gonna pay us, you know, a thousand dollars a month. Or five thousand dollars a month. Here’s how many are gonna pay us ten thousand.

And we can now just go through and just fill in the percentages once a quarter, you know my co-founder and I, and just say like how are we doing towards this? Or do we need to do this?

Just like you would have a product roadmap or a product blueprint, we have a customer profile blueprint. And we can say okay, you know, we’re pretty good in this we feel like just naturally we’ll fill this bucket up. It’s time to move into the next bucket.

DR:  Very cool.

JK: Yeah.

DR:  So I want to talk about onboarding. And again you’re kind of the go-to guy in my mind.

It’s like Johnathan knows onboarding. Yeah, you know more than that, it’s the whole experience layer inside the product, but what do you see work really well?

What have been some of the experiments you have run, or seen customers run, that all companies should be doing?

JK: Yeah. The low hanging fruit.

So, you know, oftentimes we’re competing against nothing. And so if you don’t have anything in there I would say throw a welcome experience with your founding team or somebody in your company — that just has a video or a GIF of them waving and saying “Hi, welcome to the product “we’re so glad to have you here.”

And there’s a whole lot of psychology principals that you can lean on right. But that, that one simple thing, takes you 15 minutes and it humanizes your product right? It gets them to tie an identity of an individual to this like, you know, not a cold dead thing on the other side of a screen.

And it actually builds a little bit more momentum and commitment from the end-user. If you can take that a step further and tie in the information that you collected from the signup experience or from the landing page, what they are looking to do, and just saying hey like “Welcome to Proof. We hear you’re here to improve conversion rate. Let’s get started.”

Even that little thing, even though you don’t change anything about the underlying experience. It falls into what’s called the commitment and consistency principle where they signed up because they’re trying to improve conversion rate.

You now follow that up and say let’s get started on improving that conversion rate. They’re much more likely to do that.

The last one I would say is figuring out the invited user experience. Most especially B2B software companies today and even B2C are actually, you know, either leaning on viral mechanics or collaborative mechanics.

People spend so much time thinking about what’s the signup experience like and then they spend zero time thinking about what happens when you invite a person.

I bet you, you know, 99 out of 100 people — if they go back and look at their invited user experience, there’s nothing but the walk and you knock.

And so just kind of building that momentum helps you just have a stickier champion, open the organization, and that person is invited for a reason, right. And so help them to get what they’re trying to get done, so that they can build brand equity in your company.

DR:  Okay.

And how important are like the walkthrough. Where it’s, you know, highlight this button, and then you’re gonna do this, and then this. And then it walks you through the whole thing.

What do you see there? Does that help across the board?

JK: Yeah I love telling this one story.

When we first released that product right, Walkthrough?

So it’s actually the iteration of what was called Hot Spots. And it was like when Slack first launched you had these hot spots around right so we launched Hot Spots.

And I remember a couple months into launching that feature I kept getting this email … I put in this limiter of it right, so you can only have five hot spots on the page.

To me that was like plenty, I was like nobody’s gonna want more than five hot spots on the page. I got this email from this guy from a company called Sod Solutions right, they sold grass to like different contractors right, like they sold grass in bulk. Sod Solutions is a great name.

And he was like “Hey Johnathan, love the product I need more hotspots. And I’d be like okay here I’ll bump it eight right. And he just kept emailing me, more hot spots I need more hot spots. And I bumped it to 10 and bumped it to 14. And then after a point, I was like okay cool we gotta hop on a call. I need to figure out why you want more hot spots.”

And I got on the call thinking I was gonna tell him like hey you don’t need more hot spots. And he started out saying “Hey thanks for hopping on the call. My customers love this stuff. They are non-technical people, who maybe are using a computer, you know just in the past couple of years. And they also don’t have a whole lot of time right. They’re usually doing this after work when I’m not available to give them support and so this is really helpful to them.”

And then we recently did this analysis in our data and we found that believe it or not, the flows with the most, or highest completion rate actually are 14 steps long, if you look across our entire base.

And all of this to say like, we go in, or I went in, with this bias, that there’s an optimal number of steps and an optimal length because that’s how I perceived how I wanted to use the software.

And really like that’s, that’s a shortcoming of what software is doing today. It needs to be more intuitive, more data-driven to who that user is, not what the person designing it wants it to be.

And so like my mom would love a 10 step or 15 step walkthrough on how to set up our router. Whereas like you and I probably don’t want any guidance, we’ll figure it out.

DR:  Totally. I remember we had this exact same conversation when we were setting up Appcues ourselves. It was like, you know, we’re all early adopters, tech people, like I get into an app I click out of that instantly and I’m just gonna like navigate my way through like a pioneer.

And yeah we brought all this bias in and then we realized like that’s not who most people are. Like we are an incredibly biased section of like the tech community, who just want to do everything ourselves. And yeah as we kind of launched it, you know I was telling you before, I think we saw people were like 73% more likely to set up our first notification if they went through the whole walkthrough.

And that just blew my mind. Cause again I’m looking at it, I’m like this looks cool, it looks like what software companies should do. But personally, I wouldn’t go through this flow. But then everybody loved it.

JK: We’re gonna have you on a case site pretty soon.

DR:  Yeah man, dude totally. Last one, what about checklists? I saw you guys released checklists, kind of checklists as a service. And you were talking about how hey the data is showing that this is working.

What kind of data have you seen and results have you seen from having a checklist?

JK: Yeah so the checklist data, it’s still early. So we’re still analyzing it.

But yeah we’re seeing across the board, roughly about a 20% lift in people who complete a flows in terms of end-user retention. So it’s across all of our different patterns. And so especially if it’s in your first session right. We seen an app user experience in your first session, I think it’s even higher it’s like 24% retention rate. Higher than if you never see anything at all.

DR:  Interesting.

JK: And the checklist is one of those features that we … I mean people are just, they love it. End-users seem to love it because it’s very opt-in. And then also sort of feeds into your like completions–

DR:  Oh yeah.

JK: And it’s clear. It’s clear what you need to do. I think in the same way as the patterns that Proof puts together, it’s like, it sort of plays into your like your excitement around it. There’s sort of a randomness factor to it. But it’s also really clear what you’re seeing and what you’re getting.

DR:  Yeah.

JK: I think all of those like principals when we think about user psychology as we’re using products, like really help you drive action and help people find what they’re looking for quickly.

DR:  Yeah no I do love hopping in having a good checklist. Like I’m just filling it out, even if I don’t even know like what it’s for, or I signed up for a yesterday. We were gonna host some help docs there.

And it’s funny I was kinda going through just setting it all up and I’m like uploading the favicon and then I got to the integrations page.

And it had all these integrations that like you know, it was like put in your segment ID, and put in your Google analytics, your verification.

And I didn’t even know what we were gonna do with all this, but I’m instantly like filling every little box with like the integration ID. And it’s like I don’t need to be doing this. But it felt really good to just go in and like get some momentum in a product and feel like okay we have the tools like we’re hooking up to them the way that they expect. I think that’s like the same thing with checklists. Like, give them something to do where they feel like they’re getting momentum and they’re able to make progress.

JK: I’m super excited for us to continue to expand on this. In the same way that people have been hacking our core product. There’s a lot of research around like learning theory.

And checklist is one of those things. We see people starting to use it for, not just that new user experience but okay cool you’ve gone from a newbie to a basic user.

How can we take you from a basic to advanced strider power user? I’m sure there are a lot of things within Proof that are like, oh maybe I don’t want people to know about this in their first 30 days, but like if you’ve been using it for a couple months like you should really know about this stuff. And how can you create like a new learning experience for them later on?

DR:  Yeah absolutely, I love that idea. All right shifting into one question before we go into the salty six, which is six rapid-fire questions.

But you yourself, you guys are growing really quickly, as a CEO how do you keep leveling up? How do you keep advancing?

How do you kind of think about your own personal development through all these different phases?

JK: Yeah that is like really really hard. To be honest, I think it’s the hardest part of the job, is that is changes every three months.

And the second you get good at something you’ve got to give it up. I lean on a lot of other people in my network. Here in Boston, it’s been really great to have people who I’m close to and feel like they’ve gone through challenges, thankfully a couple years ahead of what I have. I’m reading incessantly, I’m a huge audiobook person, so I listen to a lot of audiobooks.

DR:  What speed do you listen to ’em on? Just super speed?

JK: Well it depends on the book. If it’s for pleasure like if it’s a science fiction book I’ll read it at one or one and a half. All business books basically at two X.

DR:  Yup. I’m with you man. I can’t even go back to one anymore.

JK: Yeah you get used to the chip on in your ear after a while .

DR:  And then like people will get into my car or something I’ll like listen to an audiobook and it’ll like turn on for a little bit and they’re like what was that. And I’m like I can hear it, I can hear it totally fine, but they can’t understand a word. But the brain catches up to it.

JK: Yeah, yeah totally. I think those are great sources. We’re also starting … We just hired our first VPs. And I feel like just being around other people who’ve run a couple plays at previous company I can see how they’re thinking and how they’re processing.

DR:  Yup.

JK: And start adapting my style in the same way.

DR:  Yup.

JK: Train myself with information as much as I can.

DR:  That makes sense. All right man, well we’re heading into the salty six. This is my favorite part of the show. Six rapid-fire questions to get to know you better. So question number one, what do you do for fun outside of building user experiences?

JK: Oh so I recently got married in October. And so spending a lot of time with my wife. We travel every once in a while here and there. And we just moved apartments so my for fun is putting together Ikea furniture.

DR:  Oh my gosh man, it just takes forever. But it feels good. Now do you throw away the instructions or do you actually like read those?

JK: Oh I absolutely throw away the instructions and try to put it together. I have a pretty high hit rate.

The Salty Six

DR: That’s me, that’s me too.

Okay, do you have a morning routine? And if so, what is it?

JK: Yeah so I wake up in the morning I actually make the bed which is a new habit that I’ve been doing for the past couple of months. I’ll usually throw on like an audiobook or some Drake and then brush my teeth. I always have coffee I almost always make it myself, and then I get started with my day.

DR:  Okay. Question number three.

How do you focus during the day with everything coming at you? Do you have strategies or tips about to get deep work done?

JK: Yeah so if I really need to get deep work done I’ll just work from home. I’ll be doing that this afternoon. Noise-canceling headphones huge help. And if I want to be really extreme I’ll actually put earplugs under the noise-canceling headphones, just to drown out all the sounds.

DR:  That’s awesome, very cool. Number four, what’s a book that has impacted you deeply in the last few years?

JK: Oh. Let’s see. I feel like it’s always just like the last book that I’ve been reading. I just finished Blue Ocean Strategy which I thought was really good. I would say actually Powerful by Patty McCord, that’s probably one that I read recently that I thought was just really really great.

Image result for blue ocean strategy

DR:  I haven’t even heard of that. What’s that about?

JK: It talks about, so she was head of culture at Netflix. And it talks about culture and team building. The one quote that I just like love and took away is we talk about empowerment, companies are trying to empower people, and what’s funny she said that you know people walk in the door with all the power in the world right. When they’re outside of the office they already are powerful. And they walk into the office companies take that power away. And great cultures, ones that really empower people, are ones that take power away from the least.

DR:  So how are you trying to implement that at Appcues?

JK: Yeah so it’s basically like what are all the processes that get in the way of somebody doing great work? Rather than putting in processes that like help people do great work because that’s actually counterintuitive, or counterproductive.

DR:  Yeah I think about that. I look out at our team and I’m like everybody here is so smart and talented. Like they’re all better at their job than me, like how can I just get out of their way as much as possible and just like let ’em run. It’s so easy to like strangle people or like add these systems in place that just kind of like throw people from doing their best work.

All right number five, what’s the best purchase you’ve made recently under 150 bucks?

JK: Oh. Under 150 bucks. I love this, so I bought this app for my computer, it’s called “Shotty.” It’s a little piece of software. If you take a lot of screenshots on your computer it actually just saves the screenshot right on your desktop and it’s really really handy. Probably saves me, I dunno, 100 hours a year or something like that. Just like a stupid amount of time. We’re always taking screenshots of user experiences that we see in the wild. And this little thing helps me like keep them all organized. It syncs up directly to Dropbox. Yeah.

DR:  Cool.

JK: I think it was 13 bucks.

DR:  S-H-O-T-T-Y?

JK: Yeah.

DR:  Okay very cool. Oh man, I take probably 200 screenshots a day. Just send ’em all over the place. All right man number six. What’s a trait or characteristic that you have that has led to your success today?

JK: Oh. I would say like my biggest strength is probably that I’m adaptable. You know I grew up in Hawaii, moved to Boston, adapted there. I have a degree in journalism, taught myself how to code to pay for school. You know became a software engineer, built the products, transitioned to CEO, and that’s just a constant iteration of change. And so changing myself as, to whatever the situation needs I think is one of my biggest strengths, and a necessity I would say for most CEOs.

DR:  Do you write any code now?

JK: Uh … No I am very tempted sometimes. But I’m trying to let the team do their best work. Instead I’m writing blog posts and I’m making pitch decks.

DR:  Yup.

JK: I’m making Excel sheets here and there, stuff that I never thought I would be doing.

DR:  Very cool man. Well, Johnathan, this has been hugely helpful. I feel like I’ve got a lot to chew on and a lot I wanna kinda go unpack and think about how we can apply here at Proof. And as I told you before, we just resigned back up for Appcues this morning to deploy into our new app, so we’re excited to get going on that man. But if people want to find you or you know follow what you’re doing, where you at?

JK: Yes I’m @hijohnathan on Twitter. I also have a website it’s Or you can find me at

DR:  All right, perfect man. Well thanks so much for being on. We’ll see you here soon. Can’t wait to get up to Boston and actually meet you in person.

JK: That would be awesome. I’ll do the same and go down there for tacos with you.

DR:  Oh man, tacos sounds sick, we’ll do it. All right cool well thanks for watching guys, we’ll see you in the next episode.

This interview has been edited and condensed.