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The SaaS Podcast

James Evans - CommandBar

CommandBar: Mastering Cold Emails to Grow a 7-Figure SaaS – with James Evans [385]

CommandBar: Mastering Cold Emails to Grow a 7-Figure SaaS

James Evans is the co-founder and CEO of CommandBar, a user assistance platform that makes your software product easier to use.

In 2019, James and his co-founders were working on an EdTech product to help teachers give coding feedback to students.

They got frustrated with their product's complexity, so they built a search bar tool to help users find features and complete tasks more easily.

And then they realized, the search bar tool was a more interesting product.

Despite having no customers, they got into YC. However, they struggled to get traction as they spent most of their time explaining what their product did.

The breakthrough came when they made a Chrome extension that visually showed their product working in potential customers' own websites.

James made Loom videos for each potential customer, showing Command Bar integrated with their app and how it could help. His cold emails had a whopping 30% response rate and helped land their first 10 customers.

But the team kept struggling to explain their unique product and its value.

James realized they were spending over 80% of meetings with potential customers explaining how Command Bar was different from other options and what exact issues it solved.

It made it incredibly difficult for them to grow the business more quickly.

Today, CommandBar is a 7-figure ARR SaaS business, with over 20 million end-users across hundreds of customers like Hashicorp, Freshworks, and Hubspot. They've grown to a team of 40 people and raised $24 million.

In this episode, you'll learn:

  • What specific strategies and insights the founders gained at YC that helped them improve their go-to-market approach.
  • How developing a Chrome extension significantly helped Command Bar demonstrate its value to potential customers.
  • The exact steps and process James followed to create a cold email campaign that achieved a response rate of over 30%.
  • How the founders figured out to turnaround their struggling startup and grow into a 7-figure ARR SaaS business.

I hope you enjoy it.

Transcript

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This is a machine-generated transcript.

[00:00:00] Omer: James, welcome to the show.

[00:00:01] James: Thanks so much for having me.

[00:00:02] Omer: Do you have a favorite quote, something that inspires or motivates you that you can share with us?

[00:00:07] James: I don't have a quote, but I have the modern equivalent, which is a YouTube video. it's a Steve Jobs interview, very on brand for founder to choose.

[00:00:17] I love this video so much that I quoted it in my wedding vows, believe it or not, and I'll try to Yeah, I know, right? I'm a fun guy. I'll, I'll, I'll try to summarize it. I'll probably butcher it. Everyone should just go watch the video, but basically. Steve Jobs talks about how there are two people, two types of people in the world, people who sort of play the game of life that's given to them.

[00:00:38] So sort of the quests of like rising in the career ladder, saving a bit of money, going on increasingly, you know, nice vacations, giving their kids a good education and stuff like that. And then there's another group of people that sort of pushes against the walls of the game and realizes that. All the stuff, like all the, the items in this quest and the quest themselves were created by people who are no smarter than they are and really like no different fundamentally, you know, maybe different circumstances, but fundamentally exactly the same type of person.

[00:01:10] And it's not really like. Of course, like a lot of people see that as a call to arms, to like be a founder or create products, create companies, like influence the way people live, leave your markup on the world. I don't think it like needs to be that, like, I don't think everyone should be a founder, but I think it is really empowering to realize that like everything you experience, like the wallpaper, the, you know, the rewards program on your credit card, like all that, all those things are created by people that are no really different than you are.

[00:01:36] And you can be one of those people if you want to be.

[00:01:38] Omer: Yeah. Yeah. I love it. I, I, I know the video you're talking about, I haven't seen it for a long time, but when we publish this, we'll include a, a link to the video where we'll embed it obviously after your video. That will come first. Okay. so tell us about CommandBar.

[00:01:54] What does the product do? Who is it for, and what's the main problem you're helping to solve?

[00:02:00] James: So we call CommandBar, a user assistance platform, which is a three letter or three word phrase that we've agonized over and we've used a lot of different ones over the years. User personalization platform, UX optimization platform.

[00:02:13] But we've stuck with user assistance platform. But I realize it doesn't actually describe what the product does. The context, oh, I'll get into that. But the context for why we exist is. I think it's pretty crazy that like we have these things called computers that make us like so much more productive and give us access to like the entire sum of human knowledge.

[00:02:30] Imagine explaining this to someone from like 200 years ago. We have these magical things, but a lot of the time, like the way we interface day-to-day with computers, like the net experience we have is frustration. Is the frustration of like. I want to make the computer do something, I have some intent and I have to translate that intent into the language of the user interface, the keystrokes, the, you know, which file, which menu do I click on, which tab, you know, what is the feature I want called?

[00:03:01] And so we end up getting really frustrated so much. So sometimes we like do this thing called rage click where we like jam on the mouse 'cause we're so frustrated. And that has always like been a very weird paradox to me. Like these computers are so powerful and so magical, yet so much of our experience with them is.

[00:03:15] Frustrating and the best solution that has existed for a while to sort of help users use software and help users learn how an interface can be useful to them are pop-ups, those thinking of those things that show up in interfaces that are like, we just launched a new feature. Or like, you seem new here, take a tour.

[00:03:33] Those never really felt like the pinnacle of user experience to me. So much so that I think like most users just dismiss them. They have, you know, fatigue or blindness for those types of experiences, and so they don't end up actually being very helpful. Okay, so what is CommandBar with that context?

[00:03:48] CommandBar is basically a platform for other software companies to make their products easier to use. That are, through the form factors that are not just annoying untargeted popups. So we have a variety of ways that. Product teams, customer teams, marketing teams can embed experiences into their products that can help users in a personalized way, all the way from a kind of a natural language co-pilot interface where a user can just sort of describe what they're trying to do and get a kind of personalized walkthrough.

[00:04:19] Or have the co-pilot actually just take an action for them to nudges that show up in the interface, kind of guide the user to what they're trying to do.

[00:04:27] Omer: And give us a sense of the size of the business where you, in terms of revenue, size of team, number of customers and all that.

[00:04:36] James: Yeah, so we're about, I think 40 people. We've raised like 24 million, so far in a couple of rounds. Seven figure a RR business. been going for a little over three years.

[00:04:51] Omer: And in terms of, users or customers?

[00:04:54] James: Hundreds of customers so far.

[00:04:56] Omer: Okay, cool. So I, I think one of the, the things that, when I heard about CommandBar, I should say CommandBar, my British accent is still can't shake it off completely, but when I heard about it, I, I imagined, are you familiar with Alfred?

[00:05:13] Right. Or RaYCast or something like that. Right. So I was like, CommandBar. Right. And I think it might make a little bit more sense when you talk about the story of how you guys started and what the first version. Was, and I think basically with, if I had to describe it today, it, it sounds like you are, you're kind of helping with some kind of user adoption type stuff.

[00:05:42] It helps some with onboarding, it can be helping help people with support. So there's a whole bunch of use cases that CommandBar can help with. I one thing I wanted to try and understand was when you said that you, you, you interface with other software products and let's, let's take the example of like a chat widget or something like that.

[00:06:03] Are you, are you powering their chat widgets or are you the chat widget and everything else that happens behind there? Like, I was just trying to understand like where, where, where do you draw the line in terms of what's their product and what's your product?

[00:06:15] James: It's a, it's a great question. Yeah. So the, the physics of CommandBar, we are a layer on top of our customer's products.

[00:06:24] So most of our customers are software companies. You know, we work with web apps, mobile apps, desktop apps, some websites as well. You don't have to like identify as a software company to use CommandBar. and we actually are, you can call them widgets, we call 'em experiences. Users interact with those directly.

[00:06:43] So another way to think about CommandBar is it's a product for any team at one of those companies to shape user experience without having to go through the kind of standard engineering flow. We're not trying to be like a no code app builder. There's tons of stuff that. I think, you know, should be built by engineering, the kind of EPD team at a software company.

[00:07:09] We are trying to peel off what we call the user assistance experiences. So that could be a nudge, that could be Spotlight Search. We actually call, we've started calling the original product that you alluded to, spotlight. so similar to Alfred, our co-pilot interface. These are experiences that users.

[00:07:26] Interface with directly and then teams can, shape without having to write code. and we just feel like we felt like there was an opportunity to kinda, like I said, peel off this assistance layer that's relatively. or should we think should be relatively consistent across products.

[00:07:42] Omer: And then tell us a little bit about Copilot, 'cause I watched, a little demo you put together about that, and I think people might hear what you're saying and say, well, that sounds kind of similar to some other products that maybe I've used for onboarding support, blah, blah, blah, whatever. I, I think Copilot kind of took it a little further. So just, just explain that a little bit in terms of what end users can start to do.

[00:08:09] James: Yeah, so Copilot is our newest product, and it looks very much like a chat bot and like kind of the, the basic physics of it are very similar to a chat bot. The key difference between. Copilot and a chat bot in our view is that we refer to Copilot as a quote unquote user assistant, not a chat bot. What does that actually mean?

[00:08:36] We call, we call our product a user assistant platform. So it's like pretty high praise to call one of the products a user assistant. The big difference is, we don't think responses. The most useful responses are often not textual in nature. So imagine with a chat bot, you ask a question like, how do I create TPS reports in some B2B app that your employer is forcing you to use the chat bot, there's a gazillion of these.

[00:09:03] We'll probably answer with like a list of 14 steps in a, in a good, in a good case. First you go here, then you do this. A bad case. It might just say like, oh, here's an article you should read about that topic. Well, that's like a lot of work. Like in our experience, users really don't enjoy like reading multi-page manuals for doing kind of flows that they think should take like 30 seconds.

[00:09:25] And so what does cos co-pilot approach that problem? If you ask that question to co-pilot, yeah, it can respond with a text-based answer if that's how the company tunes it or if co-pilot thinks that's the best way to respond. But it can also, it wields other tools. So one tool it wields are walkthroughs.

[00:09:43] James: So instead of here's steps one through 14, oh, it sounds like you're interested in creating a TPS report, click here. I can show you how. Then it's gonna, it's, it looks and feels very similar to a product tour, but it's initiated by the user asking a question and it's personalized for them where they are on the product, what features they have access to, et cetera.

[00:09:59] Another thing it can do is take action on behalf of a user. And that could mean completing a flow end-to-end, or it could mean starting a flow. So going back to the TPS report, example. I wanna create a TPS report. Okay, great. What do you wanna call it? Do you want to copy the one you made last week? And then that could either take the user where they need to go to fi, you know, finish completing the report, or it could just ask them a series of questions to complete the report for them using the company's API.

[00:10:22] So it's basically like more helpful than a chat bot. The mental model we have for how a user assistant should work is, imagine you had a human, like imagine every company, every software company employed human user assistance. And they would send them, you know, as part of the package, you sign your a hundred K enterprise software deal or whatever.

[00:10:39] As part of the package, every user gets a human user assistant who shows up at your house or your office. And whenever you're using the product, it's kind of leaning over your shoulder there to answer questions. If you go off track, oh nope, are you sure you wanna go there? That kind of mental model is how we want Copilot to feel for end users.

[00:10:56] Omer: So where did the idea for this come from?

[00:10:59] James: Yeah, you mentioned, you mentioned our original product earlier. The name CommandBar is kind of a vestigial name, it refers to our original product, the CommandBar. So the context was we, my co-founders and I, Richard and Benet, we were working on a completely different product.

[00:11:16] It's one of these classic, you know, working on one thing, dog food is something for yourself. And then decided that was a, you know, ended up being a bigger, could be a bigger company. We were working on an ed tech product. This was a tool for people teaching computer science to give students feedback on their code.

[00:11:32] So, completely unrelated to what command ours today, we were a team of three. We were really good at talking to users and we basically built anything they asked for, for that product. You know, there was a ton of feature requests and we saw our only competitive advantage was just like speed. And so we built everything users asked for.

[00:11:50] And so pretty quickly, like the product became really top heavy. no one was using all the features. people were struggling with like basic flows. We were getting a ton of support requests and so we really didn't want to like, redesign our UI from scratch. We felt like that's what like big companies do constantly re you know, redesigning their whole ui, all taking into account all the jobs we've done, et cetera.

[00:12:11] We wanted like a relatively quick solution. and so, at the time there was this pattern, called a command pallet, which was. Sort of becoming popular in some apps it was, it was most popular in dev tools like Sublime and VS Code. There were some products like Superhuman and Linear that I really leaned into this, this paradigm.

[00:12:31] This is the interface you can trigger with CommandBar in these products. And we thought this was like a really great idea for our situation because. It would allow us to create one interface, one like escape hatch, where if a user on our product is trying to do something, they could just like type what they were trying to do and then we could route them in the product where they could go to complete the thing they were trying to do.

[00:12:52] They could use their own words as well. They wouldn't have to learn like our vocabulary. And so we built, a command palette for our product. And it worked amazingly, and it had all these like cool side effects. Like for example, we started getting all this amazing data about what users were trying to do in our product because they were telling us in our own, in their own words, in the search bar, their intent.

[00:13:13] And we got just super fascinated by this idea, but it felt like kind of a weird like comp like idea to turn into a company. Like are you really gonna create like a component as a service and like put it in other people's front ends? Like it just didn't feel like kind of a normal company or normal software structure.

[00:13:31] And so we basically treated YC as like a good idea. Oracle, which I don't recommend doing by the way, like YC is not gonna tell you if your idea is good. But in our case, like we just needed a nudge to like start working on the idea. So we wrote up the YC app for this new idea. CommandBar, the CommandBar, and then once we got to YC, we, we started working on it.

[00:13:50] Omer: Well let's talk about the first 10 customers. What did you, what did you do? To try and one, like validate the idea. So you said you were talking to users and adding a bunch of features. So you, you, you joined YC. At what point, for how long did you keep selling this kind of version of the product and at what point did you, you sort of realize, hey, this isn't quite the right product or market or whatever and we need to, we need to change things. So just, just tell us about that process in terms of figuring that out, validating the initial product and kind of on the path to those first 10 customers.

[00:14:28] James: For sure. So we entered YC with like basically nothing. which by the way, for people, I think sometimes there's a misconception that like.

[00:14:34] YC only accepts products or companies with like meaningful traction. Definitely not true. We had zero traction. We just published our YC app and like the answer to the question of like how much traction you have is awful. It's like, oh, we have four companies committed to using CommandBar. In fact, like one of those four companies ever ended up using CommandBar and they didn't even pay us anything.

[00:14:55] So like. I wanted dispel that misconception. So we showed up with nothing. We just started, we just started building quickly and like trying to get other people in our batch to use it. That was one of the things that excited us about YC is we were like, oh, it's, there's a bunch of software companies in YC.

[00:15:08] We can probably get them to use command. And it went really well in the batch. Like we got, our first 10 customers were all came from our YC batch. They weren't paying us very much. It was like 50 bucks a month, a hundred bucks a month. But it definitely made us feel like, okay, this has some legs. So the, the problem with these wedge products, they're great in the sense that they're narrow, clearly defined.

[00:15:26] The problem is, in our case, like at that time, summer 2020, no one was like waking up. No product manager was waking up in the morning going, today I'm going to look for a vendor that makes a natural language search bar as a service. No, like head of product was delegating the task of assessing natural language search bar as a service vendors to like someone on their team.

[00:15:48] So we had to create both budget, but also time for people to like understand our thing and be like, yeah, this is something that I wanna experiment with. Because at the end of the day, like every novel mousetrap company starts off in the mind of a buyer as an experiment. Like, I'm gonna try this, see if it works, 'cause it's not a proven thing. And we would have like. Early conversations with people who found the idea interesting. But, sometimes they wouldn't go anywhere at this is sort of like to the, to the towards the N of YC and the solution we found to this was actually, it was inspired by a PG, Paul Graham.

[00:16:23] Article where he talks about for his company, I forget what it was called back in the nineties, I think it was basically like a Shopify, early version of Shopify. He talks about how people didn't really wanna pay them for the software to create a digital store, but they were happy to pay them to create a digital store.

[00:16:39] And if they used their software, then so be it. It's kinda like sell the work, not the tools. and so we took inspiration from this and we started doing. We'd always been doing cold outbound to other founders, especially YC founders. But we changed it up and we started, we built a Chrome extension that let us actually sort of mock up or semi spoof what CommandBar could look like in other companies products.

[00:17:06] And so instead of like a cold email where we would describe the product and its benefits, we would just include these loom videos and they would say things like, Hey, work CommandBar, we do x. We noticed these three flows in your product that seem hard for users to do. It seems like they're generating a lot of chatter on your forum or whatever.

[00:17:23] Here's how easy they could be. If you're using CommandBar, let me show you. And I think we sent like 200 of those emails and got like a 20 to 30% reply rate. And that's how we ended up getting out our, our first 10 like real customers. The, besides the, the folks in the match. Not that they weren't real, but they were just, you know, much earlier stage.

[00:17:39] Omer: Okay. Let, let's unpack that a bit. So when you had that Chrome extension, what exactly. Was that doing, was this when you introduced kind of like a chat widget or were you still in this?

[00:17:51] No, this was just the search bar. We were just a single product company just doing that search bar through our Series A.

[00:17:57] Got it. Okay. Alright, so you, you use this Chrome extension and you, you were basically like recording, like did you record like 200 videos? Like it was, was it like a video per website? You, it wasn't just some. Generic thing that you were sending out to everybody of like

[00:18:17] James: No, no. It was like a cus it basically allowed us to, it's not that fancy of Chrome initiative.

[00:18:20] It just allows us to, allowed us to embed CommandBar is basically just JavaScript and so it allows us to embed CommandBar on any site for the person who's currently browsing. Obviously we can't make it available to companies users. They have to install us for that. And so it would make it appear. And then there's a bunch of things you can do in CommandBar, no code today, you can do a lot back then you could do a few things, no code.

[00:18:42] And so we could set up some use cases and mock up others of users encountering a problem in the product. You know, typing something into CommandBar and then seeing some result, whether that's like an action they can complete or it takes some, teleports them to the right page. But yeah, we created, yeah, like 200 of these Zoom videos.

[00:18:59] I think we whittled it down. At my peak, I think I could do one of these in like 45 minutes. 'cause there's stages to it, right? Like you find the company, you gotta log in, create an account, which, you know, we all know onboarding flows are super painful sometimes. Like you gotta fill out the 14 questions or whatever.

[00:19:13] Get, get an account. Become acquainted with the product. Identify like three. We always did three, three things that could be better. And then you create the you, you mock up the CommandBar and then you do the video. Got it.

[00:19:25] Omer: Okay. And so you were using the product, each of these products yourself identifying like potential points of friction. And then showing them how they could solve them.

[00:19:37] James: Yeah, and it was visual. It was like, it kind, I kind of made it seem like we had solved them. Honestly. I think that that was part of what worked was it, it made it clear that it was pretty easy to get a basic version of CommandBar going, which, like you can say, oh, it's only gonna take a day to get CommandBar and running.

[00:19:54] But like, no one believes you because, you know, anyone who buys software is, is burned by claims. That software is easy to set up. That ended up not being true. And so I think it was a bit of like a show me, don't tell me situation where if we could create this video, clearly we weren't spending like days building one loom video for one cold email.

[00:20:12] So I think there was a bit of a proof point that it actually was like pretty easy to use.

[00:20:16] Omer: So it, it strikes me that, you know, you basically creating a new category here and the Loom video is pretty smart because you don't have to try to figure out like. How do we explain this in an email in a way, right?

[00:20:36] It's a very visual that doesn't understand what the product does, right? Like, we'll show them a video, but rather than just a demo video, we'll actually show them what this could do on their website, right? And, and so I think that's, that's like. Super smart. I mean, it's, it's a lot of work to totally to do that, right?

[00:20:54] It is not like, Hey, upload 200 email addresses into some outreach tool and write a temp, you know, one email and wish it's gone. This takes a lot of work and I think that's probably why you got, such a high response rate from, from people. What did you do beyond that? When, when, when you used that to.

[00:21:17] Start those conversations, get to the first real 10 customers, as you said. Was, was that basically kind of your playbook for getting more customers?

[00:21:29] James: Yeah. There, there was, a second piece. I'll actually circle back to something you just said about the, the time required. Yes. These, this is not a kind of a quick marketing or sales hack.

[00:21:41] Like it, it definitely requires a bet, but I'll go as far to say that. I love recommending this strategy to founders, not because it's efficient, but I believe maybe this is somewhat of a spice take. I believe if you try this and it doesn't work, like you don't get replies or the replies are tepid, I don't think your product is good, or at least you are.

[00:22:03] Maybe it's good, but you're really bad at talking about it, or you have the wrong. Audience, if you really put the work in to identify pain, show how your product is solving that pain in a extremely customized way. Like this isn't about sequence writing. This is like one-off emails and it doesn't work, something is deeply wrong and I think that makes it worth it because being able to assess I don't have product market fit in 200 hours is way faster than most companies determine they don't have product market fit, I think can save a lot of like. Wasted building. But to answer your question about what we did after that pretty simple process, we got the meeting with this, this loom, and then our whole pitch was like, try us.

[00:22:41] It's really easy. We've already done like 80% of the work, put it into the product and see what results. It tries us from users. And I think, and then we did that, did that, and I mean ultimately you have to create value to convert those. Into actual contracts. But I think people like that, we were confident they saw that we'd put in a lot of the work to get them ready to go.

[00:22:59] And I think, you know, everyone's, if, if you can incredibly convince someone that you can move a metric they care about, that's like basically what sales is.

[00:23:07] Omer: Yeah. Okay, great. So when, when we're trying to go out and sell. A product like that, there's, there's a number of questions or objections people have in initially.

[00:23:20] It's like, what exactly do you do? What problem do you help solve? Is you, you know, is this thing right for me? And, and so you, you talked about a number of things. Things in terms of. Using the Loom videos as a way to explain very clearly in a very relevant way, way what the product does and how, how they can use it, and what problems it helps solve.

[00:23:41] So I think that takes away a bunch of those issues. But then the next part of it is, what's the integration like? How much work do I have to do to actually get this to integrate with my product? And I think you've described that, you know, whether it's JavaScript or, you know, some code I need to add to my, my, you know, webpage or it's Chrome extension.

[00:24:00] Okay, that sounds pretty easy. The second part of this would be is like, well, what about all the information that you are, you are. Delivering through this search bar, how much work do I have to do to get that data, you know, your, your, you know, for your product to access that data. So what was actually involved and how did you make that easier?

[00:24:22] So more people were, you know, willing to, to give this a try?

[00:24:26] James: Yeah. I mean, the, the way it worked then is, is actually still the way it works now. We just have more ways of kind of packaging the things people are putting into CommandBar for users. And so we can show them in more situations. But the. Basic principles are the same.

[00:24:40] It's just a mix of sucking stuff up via integrations and manual curation. I think probably the insight we had is like, you kind of need both, because some people really just want to import all the content they've already created and sort of see how CommandBar does with it. Is it servicing the right things at the right times?

[00:24:57] Is it picking up multiple ways? Users might be describing some feature using our somatic search or natural language stuff. And then there's also manual creation. 'cause there are certain situations where when a user types in like, how do I upgrade my plan? Like, you really wanna make sure that does exactly what you want it to do and is the fastest possible path to the user converting 'cause those are like, you know, the real dollars at stake for that particular query. So there is a, there's a way to curate kind of specific flows in CommandBar, whether that's when a user search for something or asks Copilot a question or if you really wanna show like a particular nudge on a particular page, a particular type of user, you know.

[00:25:36] Something like that. And there's also a kind of more of an autopilot mode where you kind of let CommandBar decide when it thinks it should, interact with the user in certain ways. Some people do all of one, some people do all the other. Our recommendation is a mix of both kind of curate that the flows that you know, really matter, you're really opinionated about.

[00:25:55] And let CommandBar kind of pick up the long tail. And it's obviously iterative, but to answer your question specifically in the beginning, the integrations and the autopilot focus are really helpful. Even if the customer is ultimately going to do a lot of manual creation, those integrations make it so they can get into a sandbox and experience like what the product is going to be like quickly.

[00:26:15] Time kills all deals. It's even worse with trials. We started a bunch of trials in the early days where people just like would never even use the product. We were like, what the hell? Like we thought we were like doing something wrong. I think the learning there is honestly just like people are busy. and if you don't make it like super easy for people to get that initial kind of 10% and, and get the dopamine loop of like, oh, this is really easy, I should keep building this.

[00:26:38] They might just never get there 'cause something might come up. And so the integrations and autopilot approach I think really helped with that.

[00:26:45] Omer: Okay. With any other growth channels that, that worked for you? Let's say, you know, beyond sort of first 10 customers, as you try to get towards the first million in ARR.

[00:26:56] Beyond the cold email with Loom videos, which sounds like it was working really well. And you shared that link with me with the, with the Reddit MA you did. I think we'll definitely include a link in the show notes to that so people can deep dive a a little bit. And there's actually a, I. You shared a Loom video with me as well, right? An example of one of those videos?

[00:27:17] James: Yeah, one of the ones, one of the, I think it was, I can't remember if it was a successful or unsuccessful video, but it was definitely from that crop.

[00:27:24] Omer: Yeah. But now people get the idea when they watch that. So, so beyond that, were there any other growth channels that you you tried that you got working or got working?

[00:27:35] James: Not really. For us, honestly, we, we cruised through our initial revenue milestones with the Loom videos and just word of mouth, like basically all of our big customers, in the early days just like came inbound, which I'm incredibly great before. I, I still think might just have been like dumb luck. I think, you know, I think the product experience was pretty good. So I think the kinda referral loop was working, but we didn't really do anything to stoke it. It just sort of happened. One learning from the early days on growth. We tried a lot of content marketing in the early, early days, and I tried, I mean, like we would do, you know, two or three articles about a topic.

[00:28:09] Like we, we weren't, you know, investing months in these things. Our approach was like, let's sort of try to uncover the channels that work for us. And with content marketing in particular, I. Unless you can invest in it and feel okay about doing it and not worry about measuring ROI, you probably just shouldn't do it at all.

[00:28:27] You know, write the few blog posts that you want to refer your customers to over and over again, and leave it at that until you get to a stage where you can do content marketing and not care about the ROI. Because I think at the early stage, probably through like series B. Measuring ROI on content marketing is fruitless and instead we talk about it internally as measuring it. Right? Today at our company's stage, we measure success of our content marketing basically by vibes. Like, are our customers telling us, oh, this is a cool article. Like are we getting comments when we post it on Hacker News? Like do people talk about it?

[00:29:00] We don't really measure like how many leads did we generate from each post. Because it's so hard to determine like, oh, okay, this person read an article and then they went away for two months and they came back like, yeah, you can try to torture HubSpot and other tools to kind of figure it out. But my thinking today is just don't measure it and don't do it if you're not prepared to be okay investing in it and not measuring it.

[00:29:22] Omer: Right, right. Yeah, yeah, yeah. I had an experience with, with some founders who. I, I think, got into that, I dunno what I, how I'd describe it, but it was like they, they wanted to do content marketing, would try a little bit of it for a, a few months and then wanna wait to see

[00:29:46] James: before they invest in it again. Right. What top of funnel does it drive?

[00:29:49] Omer: Yeah. Which, which makes sense. But the reality is, I think with content marketing is you either need to. Just say we're not gonna do it. And you, like you just said, we just put some core pillar content out there that we think is useful and relevant, or we are just gonna keep doing it.

[00:30:09] And we're just gonna say, this is part of the strategy. This is a bet that we are making. But you're right, it's a huge attribution problem because the chances of somebody going on. Unless they're like the, the, you know, they have really high buyer intent and they're searching for one of your articles designed to, you know, convert them, start a trial.

[00:30:32] The chances are most people are going to visit your site multiple times. They might go and come across you on social media. They might talk to somebody else and whatever. And so what do you give attribution to, okay, it's you. I don't know. Right.

[00:30:50] James: I think you could do it at scale. Like I think there's, you know, you know plenty of companies that are doing a good job of it.

[00:30:55] I've just seen so many early-stage founders, they hear the advice, like, you should run experiments. And then they're like, okay, great. I'll run experiments. I gotta measure the results to run the experiment. And it gets so lost in the sauce of the measurement that they, first of all, it takes away from actually investing in the quality of the content they kind of think of.

[00:31:16] And I think this is how you just think about testing out different channels. They think of it as like flipping over a card. It's like either this channel is going to work for us or not. And like our job is just to kind of do the minimum viable exploration of the channel and like see whether it works.

[00:31:31] And I think for some channels, like you can approach it that way, like ads. Good, good way to, or a good channel where you can actually be extremely rOI oriented from the beginning. I would caution like most early-stage companies from doing any ads at all or even trying to experiment with it. But if you do, you can be ROI-oriented.

[00:31:49] Whereas content marketing, like you just said and like we've been talking about, like it's one of these things. Our SEO is another good example where like it's a bet, and it's okay. You can be a good founder who runs experiments. And still make some marketing betts, but just know their betts going into it.

[00:32:05] And don't be dismayed when three months in you've generated no leads. By the way, it doesn't mean you can abandon, you can't abandon it. If you've been speeding out content and you're getting no signal that it's useful, like no one is reading it to your knowledge. You're not getting any upvotes on Hacker News.

[00:32:20] Like, okay, yeah. Then maybe there's something with your content, but don't abandon it just 'cause it's not getting, it's not converting leads.

[00:32:25] Omer: Yeah. Yeah. Totally agree. Let, let's talk about the category creation, challenger a bit more. So you were, you were initially in this position where it's kind of a new category. You're having to spend a lot of time and effort explaining it to people, like what does the product do? Then you moved into sort of digital adoption world where people start to get, get what you do more easily, but, now you're also being compared with a whole bunch of other products, like I was doing when we started this conversation, I was saying, oh, chat bot onboarding, you know, in-app stuff and whatever.

[00:33:09] How easy or hard has it been to make that transition and what are some lessons you've learned about how to stand out from the crowd?

[00:33:20] James: Yeah, so context was, we were a single product company through our series A. And what we kept hearing over and over again from our customers was, are you a replacement for x?

[00:33:33] And x could be a number of different tools. Most frequently, X was a tool from this category called digital adoption. That is, they're basically the popup companies. So at the top of the show when I described CommandBar, I said like, we solve the same problem as those in-product popups, but we're not annoying.

[00:33:52] So we kept on getting compared to these other companies and we would sort of just like shrug and be like, we don't really care about those other companies. We don't really, maybe we kind of do the same job, but we're both trying to help users. Maybe if you help users so much with CommandBar, you can get rid of those vendors.

[00:34:06] But like we don't really have a take, like that's old school. We're a new, new school. And we started just shrugged it off for a while and we were like, we're creating a category. Our product is totally different. Like you can't compare us to anything else. But we kept hearing this over and over again. And like you said, it wasn't lost on us that although we were growing well.

[00:34:22] We were spending a lot of time explaining what our product did to people. Like in a 30 minute discovery call, we might spend 20, 25 minutes, like really helping someone understand what jobs did we do for them, what metrics could we move, what other tools we integrate with? Who would the company would be using this tool?

[00:34:40] Who would be the champion? Would it be them or someone else on their team? And eventually we were like, okay, maybe we should take a look at this digital adoption category. Like maybe this, there is something here, like maybe we should say start saying we are a replacement for X or A, you know, substitute for X.

[00:34:56] and we took a look at it and we basically came up with some ideas for how we thought we could make it a lot better. We were like, oh my God, there seems to be like a lot of opportunity here. And it kind of made sense structurally, like people were already doing things in CommandBar. To make it personalized for users like you.

[00:35:10] One of the things you can do in CommandBar is you can create audiences which are basically like cross-sections of your user base, defined by like what things they've done in your product, what plan they're on, what channel they came from, et cetera. If you're doing that for the purposes of personalizing the search bar experience, you can reuse those audiences in other ways to influence user experience.

[00:35:29] So we were like, okay, let's actually. Let's lean in to what the market seems to be telling us. And instead of talking about ourselves as a totally novel mousetrap, let's talk about ourselves as a better version of this existing category that's trying to solve the same problems, but is doing it in a, in a new way.

[00:35:46] And that was, a very challenging like realization for, for me and the team because for so long we had been like very dismissive of these old school tools and it was like, well, well wait a second. We're gonna build, like, we're gonna build a way to do Pop-ups in CommandBar for, for so long we've been talking about how we hate Pop-ups.

[00:36:02] Now you're gonna be able to create a Pop-up in CommandBar, like that's blasphemous. but I have to say like, it took a while for us to get noticed and there are some kind of nitty gritty tactics that we employ. Things like, cleaning on review sites like Capterra and G2 to really like create some social proof in the category and get noticed but if you compare like one of our discovery calls from this week to one of our discovery calls, say last January, so we went on this position journey basically all of 2023 started in December. Today we probably spend like four minutes of that product explanation part because the people we've kind of have that signaled to anyone who encounters CommandBar, this is what we do. This is who buys our product. These are the jobs we do. If you know anything about digital adoption, digital adoption is like a pretty mature category. It's already done the job of educating the market about why it's important to help users. Let's, you know, stand on the shoulders of that instead of starting from scratch.

[00:36:58] So the T-L-D-R would say is for most, in most situations, and for most founders. Creating a category is vastly overrated. It feels really fun. It feels like a grand intellectual adventure, and you're like changing the world. How could you be like a me too product? But the, the, dynamics of selling into an existing market are often far simpler than selling into a totally new market that might never exist.

[00:37:23] Omer: So you said it took about a large part of 2023. To figure that out. What, what were you trying along the way? I, I'm trying to sort of think about if somebody is in that situation today where they're getting on discovery calls and they're spending all the time trying to explain what their product does, what, what are some of the steps that they can take to, make a similar transition?

[00:37:48] James: The first thing I would say is always listen to product comparisons. I think founders are really eager to talk about how their product is new and special. And so when someone says, oh, are you like X? The default answer is like, oh, sort of. But here's how we're different. And I, I think whenever you hear that, first of all, you should listen and identify trends.

[00:38:08] If people are constantly comparing you to X, like you should go look into X. But I would often, if someone is trying to compare you a tool. That's their basis of understanding. And if you should answer in a more of a yes and way, and you should say, yeah, here are the ways we're exactly like that tool.

[00:38:23] Because at that point you've created some, you know, groundwork for you to explain how you're different. If you just jump into how you're different, that might be like, oh, okay. Like I just don't get this tool at all. So that's the first thing I'd say is listen, listen to those comparisons. also seek those comparisons if you're not getting them.

[00:38:40] One of my favorite pieces of advice for founders that is applicable in like so many scenarios. Ask open-ended questions, especially in, conversations with prospects. How did you come across CommandBar? Let 'em talk A card I used to play in the beginning was like people would ask, okay, like, can you demo the product?

[00:39:01] Like, what does it do? And I'd be like, yes, I'm absolutely gonna demo the product. We just redid our marketing site. I'm really curious what you think we do because, you know, we wanna make sure our marketing site is doing a good job. And then you have to deal with the awkwardness because people thought they were showing up for a demo and now they're showing up for a quiz, and you get them to explain what's in their head about your product, and that will tell you what they're attaching it to.

[00:39:26] Whether they get it, they might just get it, in which case, amazing. Like maybe you don't have a category creation problem. But if they don't get it and they're constantly comparing you to something else, then maybe you should consider leaning into that comparison.

[00:39:37] Omer: Yeah, I, I like the way you, you described that, like if someone's saying, are you like, whatever?

[00:39:42] Starting by, instead of jumping straight into why you're different, starting by saying, yes, we also do X, Y, and Z, but in addition to that. This is what we also do, which is different or whatever. Right. So I think, okay, great. So now I understand you're similar to that product. I understand. What are the things that I would still be able to do if I was using your product, and then I understand what's different on top of that.

[00:40:12] It sounds so simple when you break it down now.

[00:40:15] James: I know right in the moment it's like you heat a battle. It's really hard. I think a little framework you can use in these situations is when someone compares you to x. You can, start with the problems, be like that, that solves this problem. We also solve this problem, however, we do it in a different way to X.

[00:40:31] Here's how we do it. So at least, you know, they probably understand the problem and care about the problem. And so you can attach to that.

[00:40:35] Omer: Yeah. Yeah. That's pretty cool. Okay, 1 kind of clarifying thing I wanna just understand is you said that the cold email loom was. Basically the primary growth channel.

[00:40:46] Nothing else really worked. Today, you're doing a bunch more content marketing. And is is the, is the email loom thing still the biggest growth channel for you today?

[00:41:00] James: We, I mean, we do do outbound and we do do Looms it's one of many channels. We don't really have like a one, and if we did, I probably wouldn't tell you one, like amazing, channel.

[00:41:13] I think the, my mindset shift on marketing and B2B SaaS has been in the beginning, like I described earlier, I. I think I was playing this game of like, what channel is going to work for us? 'cause you hear these things like you've gotta experiment, you've gotta focus, you've limited resources, you can't do everything at once.

[00:41:30] Now I actually have adopted the perspective of you kind of just gotta be everywhere all at once, always, and try a lot of things and not expect any one marketing investment to 10 x your top funnel, but just do it all. Whether that's the content marketing, whether that's ads, whether that's SEO, like. Do it all, have a perspective on how you're gonna do it different and faster and cut things that clearly aren't working, but don't cut things just because they're not, they don't have the potential to be your biggest growth channel.

[00:42:02] Omer: In, in terms of being a founder, what, and you look back over the last few years, what have been, you know, maybe one or two of sort of the biggest struggles or challenges that you look back at on this journey?

[00:42:14] James: For me, like personally, I think something I've struggled with a lot is like how much to work, how much I should work, like what is the right amount of myself that I should be pouring into the company.

[00:42:26] And I've tried a lot of different things over the years and I've sought a lot of advice. I've kind of just come to the conclusion, and I'm sort of angel investing and this is what I talked to founders who I work with as well about is like, there's just no right answer to this question and like, you just gotta feel it out.

[00:42:42] I'd say if you're someone who like wants to work 120 hours a week on your company and like that works for you and you've structured your life in a way that that's like I. Reasonable. Like I think that's a beautiful thing and like, don't let anyone shame you for doing that. I think if you're a 40-hour person and the company is doing well, like amazing, that's awesome.

[00:43:00] Like there's no glory in like I, pouring hours into your company and for the sake of pouring hours. And by the way, most people who say, you know, these grind set people like, who say they're working like 80 hours a week, they're probably doing like 15 hours of like actual work. There's a lot of like get lunch.

[00:43:16] Like you may be in the office for 80 hours, but I doubt you're doing 80 hours of actual work. 'cause that's really exhausting. Some people can do it. and I think just sort of like letting go of trying to optimize this and just like. You know, intuitively working, and sometimes that means you gotta work more.

[00:43:31] And I think part of the, part of the advice here is like, the answer can change and, and knowing when you should lean in or when your team should lean in is a, I think a superpower that some founders have and everyone should try to cultivate. Because it's even worse with the team. 'cause there's no way the team is going to sprint for 80 hours a week every week.

[00:43:50] It's just not gonna work. and so you have to know when to push and when to rest. And that could be team wide. It could be when a specific team needs to push, whether it's like sales trying to meet a number or like product, trying to meet the deadline. You kind of just have to apply this intuitive. Feel to your, your own work, but also the whole company and just realize there's no right answer and, and no investor is gonna like, yell at you or no one's gonna yell at you 'cause you didn't put in 80 hours a week.

[00:44:14] I think hearing that is, helpful for I I certainly would've been helpful for me.

[00:44:18] Omer: So, so do you, do you feel like you have a better control of that? Like, do you feel like you found the right balance?

[00:44:27] James: It ebbs and flows, I think like I tend to overwork just 'cause like, like a lot of founders. I think I have an obsessive personality and by overwork I mean like put in hours that where the marginal utility is like fairly low.

[00:44:42] So I don't think I've like nailed it. My wife is very helpful. Biggest life hack, founder hack is like, get a partner who can support you and check you and we go on hikes all the time where I, you know. Our topic of conversation is like a work problem. It's like really useful. You can do like a mix of, a mix of leisure and work, but no, I definitely don't think it's like a problem you solve because it's such a dynamic one.

[00:45:04] Omer: Yeah. No, my, my wife is a therapist and she's, she's very helpful in, in, keeping me under check. And I remember when there was a lot of talk about, the four day work beat week, and there was a whole bunch of companies going on about that. And you know, I was like, oh, maybe this sounds really ex interesting, right?

[00:45:24] Maybe that will be like something I could try. And I said to her, you know, I've just been reading about this stuff and maybe that's what you know I should do. And, and she was like, so nice and, and kind of sweet about it. And she just said. I think that sounds like a great idea, but maybe you could start by going from seven days a week to five days a week before you do the four day thing.

[00:45:48] And I was like, oh, okay. All right. we should wrap up. Let's get onto, the lightning round. I've got seven quick fire questions for you. What's one of the best pieces of business advice you've ever received?

[00:45:59] James: Ask more open-ended questions. I think people tend to see question asking as an opportunity to sound smart and show like the integral of all the research they've done.

[00:46:09] But whether it's like a candidate or a prospect or a customer asking a super open-ended question, that requires like zero research often gives you way more insight than the smart question.

[00:46:19] Omer: What book would you recommend to our audience and why?

[00:46:22] James: It's a book called Never Split the Difference. I wonder if it's come up before.

[00:46:26] It's a book about negotiation that taught me to ask more open-ended questions.

[00:46:31] Omer: I think. it's Chris Voss, right, who wrote that book, so I think he did a masterclass as well. What's one attribute or characteristic in your mind of a successful founder?

[00:46:42] James: I call this like scout ness. It's not a really clean word.

[00:46:46] There's a book called Ju by Julia Gale called Scout Mindset that basically describes how like there are two types of people or different situations. You might be a soldier where you're trying to like, defend a point of view, or you could be a scout who's trying to like uncover truths about the world.

[00:47:03] Forming hypotheses, disproving them, forming new ones. and I think there's a time and place for being a soldier as a founder. Certainly there are plenty of successful founders who've like had a vision of the future and just like made it happen and not listened to signals that might've said it was a bad idea.

[00:47:15] But more often than not, I think it's the scout founders who succeed, scouts who say, I'm gonna go build X, and then they learn something about the market and said, you know what? X was a terrible idea. I'm now gonna build X prime. Exploit what I just learned about the market, especially at the early stage.

[00:47:30] I think a lot of founders think they need to kind of pitch an idea to investors and then go like, realize that idea. And if they don't do that, they'll be considered idiots. In reality, like at the early stage, investors are betting that you're going to make a company work. Not, or a product work, not the, the specific product that was in your seed deck.

[00:47:46] Omer: Yeah. Cool. by the way, I, I came across that book, recently. It's on my reading list, so I, I definitely want to get around to it. It was when I was exploring this whole idea of like rational thinking. one of the books, yeah. the other books I came across was, Harry Potter and the Methods of Rationality, which is also kind of, I dunno if you've seen that. It's kinda like this basically, fan fiction thing on Harry Potter where it's all about applying rational thinking to this, the story. So I, I've been trying to go through that and then I was like, yeah. Scout mindset. You wanna read that too? What's your favorite personal productivity tool or habit?

[00:48:23] James: I, one of these, these people who thinks we spend too much time on. Productivity tools and strategies. So I'm just like an Apple Notes guy, write everything down, triage layer. I wish they would let me change fonts.

[00:48:34] Omer: That's the only thing I don't like about Apple Notes.

[00:48:36] James: It is. I, I wish they had toggles. That's my feature request.

[00:48:39] Omer: Who knows? Maybe one day, maybe Tim Cook is listening. I doubt it very much. What's a new or crazy business idea I'd love to pursue if you had the extra time.

[00:48:48] James: I feel like this maybe already exists, but it seems so obvious to me like an l LM based accountability. coach who can text me the same way my wife text me to keep me accountable.

[00:48:59] Did you work out today? And then if I don't respond like pester me, it just seems like such an obvious use case.

[00:49:05] Omer: Yeah, I love that. what's an interesting or fun fact about you that most people don't know.

[00:49:09] James: I'm a super boring person. Like my team gives me about this all the time. I think two facts. I think the most interesting facts about me is that I, used to be, play bass in a heavy metal rock band, like not a good rock band, like in high school. And my wife thinks the most interesting fact about me is that my favorite dessert is, raw marshmallow.

[00:49:27] Omer: Love it. And, and finally, what's one of your most important passions outside of your work?

[00:49:31] James: I started angel investing.

[00:49:32] I think like the topic of, founders angel investing, kind of controversial, I think. More founders should do it. It's really fun and therapeutic to step outside of your own business and think about someone else's business in the context of like, should I invest in this or not? It's also just a really great way to meet other founders and like I think there's this dynamic sometimes investing where it's like, oh, if you're the investor you have to like bring the knowledge and.

[00:49:57] It's like a very one-way relationship, but I've learned so much from the founders I invest in. Like it's a great hack for just getting, I think a lot of times founders like work in a vacuum. You don't really like see other founders at work. The strategies they use, how they write investor updates, what kind of progress they're making, what's what experiments they're running.

[00:50:13] Angel investing is a, is a great way to do that.

[00:50:14] Omer: Cool. so thank you for joining me, James. it's been a pleasure. If people wanna check out, CommandBar, they're can go to CommandBar.com and if folks wanna get in touch with you, what's the best way for them to do that?

[00:50:26] James: Yeah, Twitter or, LinkedIn, Twitter @dazzeloid.

[00:50:29] Omer: Okay, great. So we'll include links to those in the show notes. We've got a lot of things to add to your show notes. It's cool. Well, thank you so much. It's been a pleasure and I wish you and the team the best of success.

[00:50:42] James: Thanks so much. Take care.

[00:50:43] Omer: Cheers.

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