The following interview is a conversation we had with James Evans, Co-Founder and CEO of CommandBar, on our podcast Category Visionaries. You can view the full episode here: $24 Million Raised to Build the Leading AI-Powered User Assistance Platform

James Evans
Yeah, pleasure to be here. 

Brett
So before we begin talking about what you’re building there, could we just start with a quick summary of who you are and a bit more about your background? 

James Evans
Yeah, I studied computer science, worked investing in private equity for a couple of years, but then I started working in startup land. Always wanted to start a company, always very interested in web development. I’m old enough to remember when CSS was new. The first thing I started building was an ed tech tool, actually kind of like a classic first startup project for someone who studied computer science. Kind of solve your own problem as a student. So that was for about a year, and then I’ve been working on CommandBar for the last two years of change. 

Brett
Nice. We’re going to dive deeper into the company in a second here, but one question we like to ask, just to better understand what makes you tick, is what book has had the greatest impact on you as a Founder and entrepreneur? And this can be one of the classic business books or just a personal book that’s influenced how you view the world. 

James Evans
Yeah, so many potential options. There’s this book called Never Split the Difference, which is like an incredible book that I think everyone should read. It’s about kind of negotiation, which may feel like kind of a weird topic to or kind of a zero sum topic to kind of inspire a Founder, but something that it helped me realize early on in kind of Founder journey is the importance of open ended questions. The Mom Test is another book that talks about kind of early customer interviews and things like that and also stresses the importance of open ended questions. But I think when I first started working on startups and doing customer interviews and just talking to people day to day, I didn’t ask a lot of open ended questions. I was someone who wanted to ask smart questions, and I always felt like open ended questions were kind of dumb and disrespectful. 

James Evans
If you’re going to talk to someone, you should take the time to read what they’ve put into the world and ask them a specific question about problems they have or whatever. But this book talks about how essentially you can learn a lot more about a person, whether it’s someone you’re thinking about hiring or potential investor or a customer, by just asking them open ended questions that let them talk about what’s on their mind. And so I now deploy this in all aspects of both work and life. Try to kind of tee people up to share what they’re feeling as opposed to kind of showing how smart I am or how much research I’ve done by asking them like a real singer of a question. Kind of like the Joe rogan tactic. 

Brett
Nice. 

James Evans
I love that. 

Brett
Can you share an example of an open ended question you asked in the early days of CommandBar? 

James Evans
Yeah, it’s a good question. Something know what are your priorities for this quarter or what are you most excited about on your roadmap? Things like that. That doesn’t take me any prep. I can ask those questions to literally any product manager and have no idea what they work on. But you’d be amazed at the quality of answers you get. And it’s so much more interesting than asking are you excited about X? Or I saw you wrote about Y, how’s that going? Because that’s just a much narrower conversation. 

Brett
Makes sense. And could you share with our audience the Mom Test? Can you walk us through that framework? 

James Evans
Yeah. So Mom Test is a great book, kind of an unfortunate name, but basically the kind of key takeaway from the Mom Test, at least as I saw it, was essentially when you’re doing kind of idea validation and it kind of relates to, I think the central topic is when searching for an idea or testing product, market fit. But I think it applies to a lot of stuff about startups, from specific feature launches to new product launches, et cetera. Basically the idea is like, you should never ask people, would they want to use something if I built it? So hey, if I built this cool new mousetrap that kind of a morbid example, uses lasers or something that’s going to catch mice better, would you use it? And the premise is like, that’s a terrible question because people are really bad at actually thinking through whether they would use it and also they’re likely to not want to offend you. 

James Evans
And so it’s really easy in that situation in a customer interview like that to be like, oh yeah, I would totally use it. That sounds amazing. And then you go off and build it and then you come back and they’re like, sorry, not going to happen this quarter. There’s just not enough mice running around. Or we’re happy with our existing mass trap vendor. And the book talks about instead, you should do two things. One, just sort of ask people those open ended questions that were talking about to try to understand what excites them, what problems they have, what do they pay for what’s on their mind. And then instead of asking people for a very loose commitment of basically non commitment of like, would you use X? Or does X sound exciting? You instead ask for concrete commitments. So instead of would you use X, be like, hey, yeah, I think I’ll have a prototype ready in a month. 

James Evans
Could you introduce me to five people? That’s kind of like extracting a social commitment, the person that’s putting their reputation on the line to introduce you to them or hey, would you put down a deposit for $1,000 for my new mousetrap? That’s obviously a much higher intent commitment than just saying, yeah, it sounds cool. So we apply that all the time, basically in every customer interview we do. 

Brett
How many do you do customer interviews? Is that something that you’re doing on a daily basis? Weekly, monthly, quarterly? What does that look like? 

James Evans
I try to do it every week. We do have kind of like ongoing meetings with a lot of our customers and so I try to attend as many of those as possible and try to do a mix of new folks. Some of our long term customers so don’t get to it every week. But when I’m not actually doing the actually in those conversations, we record basically all of our sales calls and customer calls. And so I try to listen to as many of those as possible. 

Brett
Nice. Love that. Let’s talk about the origin story. Can you take me back to the early days of the company? 

James Evans
Yeah, sure. CommandBar is kind of a weird company and product, especially in the early days. So as I mentioned, first thing that Richard Bennett and I are my co-founders started working on was an Ed tech tool. So for the sake of this conversation, essentially kind of generic. You think of it as like a generic sort of B2B SaaS tool. What it was is a tool for helping computer science instructors kind of teach and provide feedback on student work. So were building this it was something that we had wanted in college and essentially, long story short, six, nine months in the product became really complicated. Turns out people who teach computer science have a lot of feature requests and our strategy was basically respond to every feature request as fast as possible. So the product became super top heavy. Very kind of hard to use. 

James Evans
No one was really using all of the features. New users were having a really hard time getting started. We were doing a lot of manual handholding and we sort of needed to solve this problem and I think also very reflective of problems that a lot of SaaS tools fall into. And so our solution we didn’t want to do like a big redesign and it was just three of us and we’re not really basically no design talent. So our solution was this UI pattern called Command Palette, which is basically a search bar for actions so like in the ed tech context, say you want to duplicate a course, or remove a student, or create a new rubric item, stuff like that. There were entry points for all of those actions in the product, but they were often nested or they were hidden behind words that users didn’t associate with that action. 

James Evans
And so we built this command palette and we didn’t come up with the idea like it existed in tools like Sublime and Vs code and Superhuman had a really popular command palette at the time and they were definitely an inspiration. So we built this command palette and it just worked really well. Users could search and if you’re a user, you could just search for what you’re trying to do. And if you were using the tool a lot, it was like a really turns out it was a really fast sort of index into all the functionality of what were building. As we kind of had this moment where were building this and seeing it work so well, were just kind of like why doesn’t every app have this? It just seems like such a universally useful building block should be as commonplace as chat. In fact, it’s often a better user experience than chat because it’s so much faster and always available. 

James Evans
And essentially, we concluded that we wanted to take this pattern to all of software and that the reason perhaps it hadn’t taken over was A it’s kind of hard to build well, B it’s hard to maintain. And so if it doesn’t keep up with your app, then it’s not going to be that useful. And C, kind of our other insight was that we thought it could be really useful for nontechnical users as well as technical users. Like at the time it was kind of mainly in DevTools and productivity oriented tools and so essentially we set out to kind of bring this one pattern to the world. Like we wanted to build a new building block for software and that’s basically all we did for the first two years of the company is kind of go really deep on this one building block. Since then we’ve kind of expanded the product to be more of kind of a toolkit to help users get more out of software generally. 

James Evans
And so the command palette is still one of our most important widgets. We have a bunch of others, but the origin story was we really just wanted to build this one building block really well. 

Brett
Nice, I love that. And talk to me about market categories. So I’d introduced you as a developer tool. Now I don’t know if that was the right category. UX optimization platform. So what are you how do you define that category? 

James Evans
Yeah, I think we’re still trying to answer this question. I think when were kind of the only people doing this command palette as a service thing, so for a while were just kind of that and people would ask us like hey, are you an alternative for Product tour? Are you like a search company? And we kind of used to describe it as we’re our own thing but we kind of exist in the orbit of customer success tools like Zendesk, intercom search companies like Algolia and Elastic and then this sort of amorphous category that’s sometimes called Digital adoption. And I’d say if we had to fall into a category it would probably be the latter, digital adoption which sounds very web 1.0 but basically includes all tools that make other software easier to use. There’s a lot of those tools and I think we’ve basically just as we’ve grown our customer base, we’ve just had a lot of customer pull to help users in multiple ways. 

James Evans
Both kind of when they have intent, which is what our kind of search widgets are really good at and also when they don’t have intent which is when you want more of a proactive experience like a product tour. 

Brett
And looking through the site, I see some really impressive logos. We have Angelist, Gusto, Freshworks and I’m sure there’s many more. How did you go about landing those logos? I think that’s every Founder’s dream is to have logos like that on their website. But what happened behind the scenes? How did you pull that off and what do you think you got? 

James Evans
Know, sometimes honestly it just feels like luck and kind of path dependence. I think once you get some really high quality software companies to use your product, that’s kind of the best business card is you just kind of say, yeah, these other really high quality teams are using us. And then even if someone doesn’t really understand how they could use your tool or they don’t grock it yet, they think there must be something there, because these other teams that they respect have used it. I think in our case the logos are kind of even more meaningful because for us to put a logo on our homepage it means that the company has put us into their product and exposed us to their users, which is like the highest compliment and also like a risk on their part, right? Like we’re a startup and they want to put their best foot forward and so we really need to nail the user experience if we’re going to be exposed to users directly. 

James Evans
And so I think that has definitely helped us because people, when they see those logos, they both respect the teams and they also kind of know what it means for us to have those logos. In terms of how went about getting companies like this, I don’t think we did anything kind of particularly arcane. I think it was just a matter of having kind of like a differentiated take on a problem that a lot of people had. And so like I mentioned earlier on, people would often ask us like, are you a replacement for these other onboarding adoption patterns? And what we’d usually say is, no, we’re not a replacement. Maybe we’re solving a similar job to be done. But what you should do is you should try us out. And this is I think what worked really well is we would position CommandBar as kind of a no brainer experiment where we’d say, look, we have examples of situations where we’ve kind of moved metrics really meaningfully for other companies. 

James Evans
We usually like to focus on conversion and sometimes retention because they’re kind of really close to the P L. For a software company, sometimes we focus on ticket deflection because obviously that’s a cost argument, which is also close to the P L. And so we say, look, we’ve moved these metrics before. We think we can move these metrics for you. And the cost on your side is relatively minimal to try us out because you don’t have to invest kind of much, if any, engineering investment to get started with these experiments. Like, that’s why we exist. And if you don’t like us, then if we don’t generate results, just no harm done. And the other question that sometimes people would ask in the early days was build versus buy. Why should I use CommandBar instead of kind of building these experiences myself? And the answer was just like, you totally can build yourself. 

James Evans
Just don’t build before you run the experiment using us. Because you really don’t want to waste resources running the experiment. Use us to do the experiment and then if it works, but for whatever reason you want to DIY, then go ahead, rip us off. And so I think that experiment ROI oriented framing resonated with a lot of teams. 

Brett
And is that your biggest competitor then? Would you say it’s just companies building it themselves or what’s the competitive landscape look like? 

James Evans
We started off hearing that a decent amount. I think it’s something that people bring up and they think about because they know it’s always an alternative. But I think the software economy has become a lot more modularized and I think people have started to realize that it’s often a lot more effective to peel off part of your product and outsource it to a specialized company like us just because we’re putting all of our resources behind it. We’re amortizing the learnings we get from all of our customer base into the product. So people ask about it, but we don’t actually see it as kind of a competitor. I’d say like the main competitor, there’s going to be two kind of axes. Digital adoption category definitely has a lot of other vendors in it. And so we see folks there sometimes we’re one of the only players in that space that’s kind of trying to differentiate on strategy versus execution. 

James Evans
So I wouldn’t say we get into bake off situations very often because we’re a pretty unique product. I’d say the kind of biggest competitor and I think this is true for a lot of startups, is just no action time trying to make it so that, yeah, CommandBar is an experiment, but do you have time to run that experiment this quarter? Is it the highest priority experiment? And I think to stand out as the highest priority experiment and not be on someone’s someday section of some product manager’s to do list, we just really focus on the ROI. We show examples of similar companies for whom we driven ROI and just try to make it as low cost to experiment with the highest upside. Pick a metric that really matters to the company and try to create a convincing case for how they can move that metric without a lot of effort. 

Brett
Are there any examples of maybe, like, the top one or two metrics that you see companies measure? 

James Evans
Yeah, there are so many different ones. We always try to start with something that’s close to the PNL, because every software company has PNL, and every software company is trying to convert users, retain users, and spend less to support them. So we usually start there. I’d say sometimes teams have a specific kind of maybe a list of five areas of product friction that they kind of know are contributing to bad things. And sometimes we’ll choose to start there, but usually we try to focus on kind of things that are we know that if we move them, people will want to adopt us and want to pay us a piece of the value we’re creating. We try to stay away from metrics like engagement and things like that just because they’re harder to interpret and harder to assign a value to. 

Brett
Yeah, that makes a lot of sense. 

Brett
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Brett
And what about internal metrics? Are there any numbers that you can share that just demonstrate the growth, traction, and adoption you’re seeing right now as a company? 

James Evans
Yeah, I think my favorite vanity metric is just the number of end users we reach because obviously we’re embedded in our customers products, and so that’s how we kind of gather end user exposure. And so I think we passed 10 million end users a little while ago, which is a pretty cool number. 

Brett
What did you guys do to celebrate that? 

James Evans
I don’t really think we did anything. I think it was like a slack message or something with a lot of emojis nice. 

Brett
I love it. And in terms of rising above the noise, is there anything else that you think you’ve really done right or really nailed in your efforts here to get that type of growth and to be able to reach 10 million years? Anything else that you can reflect on that was unique or different or just insightful along that journey? 

James Evans
Yeah, I don’t know about unique, different or insightful. I don’t really have a good answer to this one, to be honest. Maybe this is the answer. I try not to think about fundraising too much except when we are fundraising. I think that’s like the common advice. It’s like a binary switch. Like you’re either not fundraising or you’re fundraising. I think there’s definitely a lot of noise, especially at the early stage, but if you have a differentiated product with a big opportunity, a good team and evidence that you’ve been executing, I don’t think you really need to do anything especially unique to stand out. I do think sometimes people make the mistake of trying to tell VCs what to hear or at worst, trying to goal seek their company to fundraise, which if you’re running out of cash, that could make a lot of sense. But I think especially at the early stage when you’re just getting started raising seed, I think that’s kind of exactly the opposite approach you want to take. 

James Evans
When were raising our seed, we didn’t know were going to broaden the product suite and we thought were just going to focus on the search widget for the foreseeable future. And we’d often get questions from investors that were like some permutation of kind of what’s the big vision here? What’s beyond this for kind of initial thing? There’s an open ended question for you. And I think when we got questions like that, usually it felt like the person on the other side of the table was kind of like fishing for something more exciting than what we’d presented and so it was really tempting to say, oh, this is just the start. Once we take this command palette widget to all software, that’ll be a stepping stone for us to actually build the thing we want or a wedge to do X, Y and Z, but we just stuck to our guns and was like, no, that is the vision. 

James Evans
We think that’s a really big vision. Adding a new building block to how humans interact with software is something we’re really excited about. And if we can do it, we think it can be a cool business. And I think that is actually kind often that conviction is appreciated and more what investors are looking for at the early stage and also helped us find partners who were excited and believed in that vision. Specifically, we really didn’t want to shape our story for VCs and then end up in a situation where we’re at a board meeting and the VC is like, oh well, yeah, it’s time to do part two. And you’re like, oh, but I just told you that because I wanted to raise money. That’s obviously completely untenable. 

Brett
Yeah, not an ideal meeting to be. 

James Evans
Part of probably totally. 

Brett
In the go to market journey, is there a specific challenge that you experienced and overcame that you can share? 

James Evans
I think the figuring out how to create urgency on the B, two B side like were talking about earlier and positioning your experiment or your tool as something that is solving kind of actually urgent pain point is something we kind of already talked about. That’s probably our biggest learning. I think one thing that’s been interesting about our go to market journey is we’ve kind of really let the market dictate where we should take the product beyond that sort of initial bet on this command palette widget. When we got started, we expected our ideal customer to be basically one of two things developer tool or a productivity tool. The thinking was that develop command palettes are already a fairly established pattern in DevTools. Like developers want these experiences. It’s really just a build verse buy and we felt really confident about our case on build verse like we talked about earlier or productivity tool because that’s what the power users are and power users like tools like Superhuman, they’ll appreciate the productivity gains. 

James Evans
What ended up happening was we certainly got customers in those domains, but we ended up seeing a lot stronger pull from companies with non technical users or companies where users actually weren’t spending a lot of time in the product. And this is just inbound, right? We were just seeing a lot of companies like this. And we kind of finally when we took a step back and looked at all the companies were talking with and where CommandBar was creating the most value, et cetera. What we realized is this pattern is kind of almost more useful for users who, either because they don’t have a lot of experience in software or they’re just not spending a lot of time in the tool, aren’t masters of the tool. Because search is such a familiar pattern, basically everyone knows how to search. It can often be easier to search than use the underlying tool. 

James Evans
And so we started getting a lot of traction in domains like HR software where users tend to spend less time using software tools and also don’t spend a lot of time in the tools themselves. And so they never kind of take the time to understand the topography of the tool. They’re just like they get in, they’ve got a job to do, they want to set up a 401 for their employees and that’s just what they want to do. And we definitely, I think, started paying attention to that early and started kind of building specifically for that use case. And that’s definitely why that’s one of the reasons we decided to kind of expand the product portfolio to kind of cater to user experience in general and kind of being that last mile delivery for UX overall because we saw that those were the kind of jobs were being hired for. 

Brett
Interesting. Now for the last question, I’m not going to ask you about the vision given what you just said previously, not having this big next step that’s going to come. So let’s just end with some aspirations around the numbers. So you’re at 10 million users that you touch today. What’s, like the three year goal? Have you thought through that at all? 

James Evans
I’d say our big goal or kind of North Star is just to be in every big grandiose statement but we just really want to be in every software, every piece of software that’s serving users that’s not just like SaaS, that’s also know your bank account. I think our final boss is probably the DMV. We can get into the DMV site. We’d probably help a lot of people. We want to be a layer in every app and serve as that last mile for user experience. Just think there’s so much human energy that goes into creating tools or creating features and capabilities and software tools and those features and capabilities are just often hard for people to access. I think it’s pretty crazy to me that I think I’m getting this right. I’m pretty sure there are conflicting data on whether computers have actually improved worker productivity in most domains, which is really shocking if you think about it. 

James Evans
We have these magical calculating machines, pretty horrifying if they’re not actually yielding productivity gains. So I think if that’s the case, clearly the interface between us and those computers isn’t wide enough and we want to change that. We want to peel off these pieces of user experience that are common across pieces of software and be that last mile that connects all the great work these development teams, product teams are doing with users. And I think the really exciting opportunity for us is once we go beyond the 10 million and get into the hundreds of millions, we can build experiences that take advantage of the fact that we can follow users across apps. Today, most people who interact with CommandBar are only doing so in one app. But that’s slowly starting to change and we see the value of CommandBar to a user is way higher if they use us in multiple apps because they know how we work, they’re familiar with the search bar works, they know how to set custom shortcuts, they know how to snooze a nudge, et cetera. 

James Evans
And so we’ve got big plans that depend on us having a lot of end user density and excited to just improve the day to day of more user. 

Brett
Amazing. I love it. James, I’d love to keep you on and ask another 20 or 30 questions here, but we. Are up on time, so we’re going to need to wrap. If people want to follow along with your journey, where’s the best place for them to go? 

James Evans
commandbar.com. We’re on Twitter and LinkedIn as well. And I’m on Twitter as at Dazzle. 

Brett
Yeah, I’m sure there’s not too many. 

James Evans
Evans either, so, yeah, don’t search for James Evans. 

Brett
Awesome. James, thanks so much for taking the time to share your story and talk about what you’re building. This is all super exciting and look forward to having you back on in a couple years to talk about everything that’s happened. 

James Evans
Awesome. Thanks for having me, Brett. 

Brett
All right, keep in touch. 

Brett
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