Stop Creating a New SaaS Category and Start Positioning

Omer (00:09.760)
Welcome to another episode of the SaaS Podcast.
I'm your host Omer Khan and this is a show where I interview proven founders and industry experts who share their stories, strategies and insights to help you build, launch and grow your SaaS business.
In this episode I took to James Evans, the co founder and CEO of Command Bar, 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 quickly 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 managed to get into yc, but they struggled to get traction as they spent most of their time having to explain 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 would make loom videos for each potential customer showing Command Bar integrated with their app and how it could help Here.
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.
At one point James realized they were spending over 80% of meetings with potential customers just 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.
However, today Command bar 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 have 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 the Chrome extension significantly helped Command Bar demonstrate its value to potential customers.
We'll talk about the exact steps and process James followed to create a cold email campaign that achieved a response rate of over 30%.
And we talk about how the founders figured out how to turn around their struggling startup and grow into a 7 figure ARR SaaS business.
So I hope you enjoy it.
James, welcome to the show.

James Evans (02:45.420)
Thanks so much for having me.

Omer (02:46.780)
Do you have a favorite quote?
Something that inspires or motivates you that you can share with us?

James Evans (02:51.470)
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 a founder to choose.
I love this video so much that I quoted it in my wedding vows, believe it or not.
And I'll try to.
Yeah, no, right.
I'm a fun guy.
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 types of people in the world.
People who sort of play the game of life that's given to them.
So sort of the quests of like rising in the career ladder, saving a bit of money, going on increasingly nice vacations, giving their kids a good education, 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 items in this quest and the quest themselves were created by people who are no smarter than they are.
And really no different.
Fundamentally, maybe different circumstances, but fundamentally exactly the same type of person.
And it's not really like.
Of course, a lot of people see that as a call to arms, to be a founder, create products, create companies, influence the way people live, leave your mark upon the world.
I don't think it needs to be that.
I don't think everyone should be a founder.
But I think it is really empowering to realize that everything you experience, 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.
And you can be one of those people if you want to be.

Omer (04:22.180)
Yeah, yeah, I love it.
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 link to the video where we'll embed it, obviously after your video, that will come first.
Okay, so tell us about Command Bar.
What does the product do, who is it for, and what's the main problem you're helping to solve?

James Evans (04:47.250)
So we call Command Bar 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.
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 we have these things called computers that make us so much more productive and give us access to the entire sum of human knowledge.
Imagine explaining this to someone from 200 years ago.
We have these magical things But a lot of the time, the way we interface day to day with computers, the net experience we have is frustration.
Is the frustration of I want to make the computer do something, have some intent, and I have to translate that intent into the language of the user interface, the keystrokes, which file, which menu do I click on, which tab, what is the feature I want called?
And so we end up getting really frustrated.
So much so that sometimes we do this thing called Rage click where we jam on the mouse because we're so frustrated.
And that has always been a very weird paradox to me.
These computers are so powerful and so magical, yet so much of our experience with them is 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 think, you know, 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.
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 Command Bar with that context?
Command Bar 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 pop ups.
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 kind of a natural language copilot interface where a user can just sort of describe what they're trying to do and get a kind of personalized walkthrough or have the copilot actually just take an action for them to nudges that show up in the interface kind of guide a user to

Omer (07:16.490)
what they're trying to do 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.

James Evans (07:26.080)
Yeah, so we're about, I think 40 people.
We've raised like 24 million so far in a couple of rounds.
Seven figure ARR business been going for a little over three years.

Omer (07:41.120)
And in terms of users or customers,

James Evans (07:44.480)
hundreds of customers so far.

Omer (07:46.480)
Okay, cool.
So I think one of the things that when I heard about command bark, I should say command bar, my British accent is still can't shake it off completely.
But when I heard about it, I imagined you familiar with Alfred.
Right.
Or Raycast or something like that.
Right.
So I was like a command bar.

James Evans (08:07.240)
Right.

Omer (08:07.920)
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, if I had to describe it today, it sounds like you're kind of helping with some kind of user adoption type stuff.
It helps some with onboarding.
It can be helping help people with support.
So there's a whole bunch of use cases that Command Bar can help with.
One thing I wanted to try and understand was when you said that you interface with other software products and let's take the example of a chat widget or something like that.
Are you powering their chat widgets or are you the chat widget and everything else that happens behind there.
I was just trying to understand where do you draw the line in terms of what's their product and what's your product?

James Evans (09:11.160)
It's a great question.
Yeah.
So the physics of Command Bar, we are a layer on top of our customers products.
So most of our customers are software companies.
We work with web apps, mobile apps, desktop apps, some websites as well.
You don't have to identify as a software company to use Command Bar.
And we actually are.
You can call them widgets, we call them experiences.
Users interact with those directly.
Another way to think about Command Bar 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 should be built by engineering the kind of EPD team at a software company.
We're 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 Copilot interface, these are experiences that users interface with directly and then teams can shape without having to write code.
And we felt like there was an opportunity to, like I said, peel off this assistance layer that's relatively, or we think should be relatively consistent across products.

Omer (10:38.800)
And then tell us a little bit about Copilot because 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 think Copilot kind of took it a little further.
So Just explain that a little bit in terms of what end users can start to do.

James Evans (11:08.650)
Yeah, so Copilot is our newest product and it looks very much like a chatbot and like kind of the basic physics of it are very similar to a chatbot.
The key difference between Copilot and a chatbot in our view is that we refer to Copilot as a quote unquote user assistant, not a chatbot.
What does that actually mean?
We call our product a user assistance 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 chatbot, you ask a question like, how do I create TPS reports in some B2B app that your employer is forcing you to use?
The chatbot, There's a gazillion of these will probably answer with like a list of 14 steps.
In a good, in a good case, you know, 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 reading multi page manuals for doing kind of flows that they think should take like 30 seconds.
And so what does Kauf's Copilot approach to that problem?
If you ask that question to Copilot, yeah.
It can respond with a text based answer if that's how the company tunes it or if Copilot thinks that's the best way to respond.
But it can also wields other tools.
So one tool it yields are walkthroughs.
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.
And then it's going to.
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 in the product, what features they have access to, et cetera.
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 want to create a TPS report.
Okay, great.
What do you want to 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 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.
So it's basically more helpful than a chatbot.
The mental model we have for how a user assistant should work is imagine you had a human.
Imagine every company, every software company employed human user assistance, and they would send them as part of the package, you sign your 100k enterprise software deal or whatever.
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 is kind of leaning over your shoulder there to answer questions, you go off track.
Oh, nope.
Are you sure you want to go there?
That kind of mental model is how we want Copilot to feel for end users.

Omer (13:58.870)
So where did the idea for this come from?

James Evans (14:02.080)
Yeah, you mentioned, you mentioned our original product earlier.
The name Command Bar is kind of a vestigial name.
It refers to our original product, the Command bar.
So the context was we, my co founders and I, Richard and Vinay, we were working on a completely different product.
It's one of these classic, you know, working on one thing, dog food at something for yourself, and then decided that was a, you know, ended up being a bigger, could be a bigger company.
We working on an edtech product.
This was a tool for people teaching computer science to give students feedback on their code.
So completely unrelated to what Command Bar is 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.
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.
And so we pretty quickly, the product became really top heavy.
No one was using all the features.
People were struggling with basic flows.
We were getting a ton of support requests.
And so we really didn't want to redesign our UI from scratch.
We felt like that's what big companies do, constantly redesigning their whole ui, taking into account all the jobs we've done, et cetera.
We wanted a relatively quick solution.
And so at the time, there was this pattern called a command palette, which was sort of becoming popular in some apps.
It was most popular in dev tools like Sublime and VS Code.
There were some products like Superhuman and Linear that really leaned into this paradigm.
This is the interface you can trigger with Command K 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 escape hatch where if a user in our product 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.
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.
And we got just super fascinated by this idea.
But it felt like kind of a weird idea to turn into a company.
Are you really going to create a component as a service and put it in other people's front ends?
It just didn't feel like a normal company or normal software structure.
And so we basically treated YC as a good idea.
Oracle, which I don't recommend doing, by the way.
YC is not going to tell you if your idea is good, but in our case, we just needed a nudge to start working on the idea.
So we wrote up the YC app for this new idea.
Command Bar.
The Command Bar.
And then once we got into yc, we started working on it.

Omer (16:55.430)
Let's talk about the first 10 customers.
What did you do to try and one validate the idea?
So you said you were talking to users and adding a bunch of features.
So 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 sort of realize, hey, this isn't quite the right product or market or whatever, and we need to change things.
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 for sure.

James Evans (17:35.410)
So we entered YC with basically nothing.
Which, by the way, for people, I think sometimes there's a misconception that YC only accepts products or companies with meaningful traction.
Definitely not true.
We had zero traction.
We just published our YC app and the answer to the question of how much traction you have is awful.
It's like, oh, we have four companies committed to using Command Bar.
In fact, one of those four companies ever ended up using Using Command Bar and they didn't even pay us anything.
So, like, wanted to dispel that misconception.
So we showed up with nothing.
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, there's a bunch of software companies in yc.
We can probably get them to use Command bar.
And it went really well in the batch.
Like we got our first 10 customers were all came from RYC batch.
They weren't paying us very much.
It was like 50 bucks a month, 100 bucks a month.
But it definitely made us feel like, okay, this has some legs.
So the problem with these wedge products, they're great in the sense that they're narrow, clearly defined.
The problem is in our case at that time, summer 2020, no one was 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 head of product was delegating the task of assessing natural language search bar as a service vendors to someone on their team.
So we had to create both budget but also time for people to understand our thing and be like, yeah, this is something that I want to experiment with because at the end of the day every novel mousetrap company starts off in the mind of a buyer as an experiment.
Like I'm going to try this, see if it works because it's not a proven thing.
And we would have early conversations with people who found the idea interesting, but sometimes they wouldn't go anywhere.
This is sort of like towards the end of yc.
And the solution we found to this was actually it was inspired by a PG Paul Graham article where he talks about for his company, I forget what it was called back in the 90s.
I think it was basically like a Shopify, early version of Shopify.
He talks about how people didn't really want to pay them for the software to create a digital store, but they were happy to pay them to create a digital store and if they use their software then so be it.
It's kind of 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 Command Bar could look like in other companies products.
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, we're Command bar, we do X.
We noticed these three flows in your product that seem hard for users to do.
Seems like they're generating a lot of chatter on your forum or whatever.
Here's how easy they could be if you're using Command Bar.
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 our first 10 real customers besides the folks in the batch.
Not that they weren't real, but they were just much earlier stage.

Omer (20:47.990)
Okay, 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?

James Evans (20:59.510)
No, this is just the search bar.
We were just a single product company just doing that search bar through our Series A.

Omer (21:06.390)
Got it.

James Evans (21:06.830)
Okay.

Omer (21:07.830)
All right.
So you, you use this Chrome extension and you, you were basically, like, recorded.
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.

James Evans (21:25.510)
No, no, it was like a custom.
It basically allowed us to.
It's not that fancy for Chrome Extension.
It just allows us to.
Allowed us to embed.
Command Bar is basically just JavaScript.
And so it allows us to embed Command Bar 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.
So it would make it appear.
And then there's a bunch of things you can do in Command Bar.
No code today.
You can do a lot back then.
You could do a few things.
No code.
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 Command Bar and then seeing some result, whether that's like an action they can complete or it takes them, teleports them to the right page.
But yeah, we created, yeah, like 200 of these videos.
I think we whittled it down.
At my peak, I think I could do one of these in like 45 minutes.
Because 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, 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 mock up the command bar and then you do the video.
Got it.

Omer (22:34.080)
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.

James Evans (22:47.440)
Yeah.
And it was visual.
It was like, it kind of.
I can't.
Kind of made it seem like we had solved them.
Honestly, I think that was part of.
Of what worked was it made it clear that it was pretty easy to get a basic version of Command Bar going, which you can say, oh, it's only going to take a day to get Command Bar up and running.
But no one believes you because anyone who buys software is burned by claims that software is easy to set up that end up not being true.
And so I think it was a bit of a show me, don't tell me situation where if we could create this video, clearly we weren't spending days building one loom video for one cold email.
So I think there was a bit of a proof point that actually was like, pretty easy to use.

Omer (23:26.400)
So it strikes me that, you know, you're 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, that's a very visible point, 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 so I think that's, that's like super smart.
I mean, it's, it's a lot of work to, to do that.
Right.
It's not like, hey, upload 200 email addresses into some outreach tool and write a temp, you know, one email and whoosh, it's gone.
This takes a lot of work.
And, and I think that's probably why you got such a high response rate from people.
What did you do beyond that when you used that to start those conversations, get to the first real 10 customers, as you said, was that basically kind of your playbook for getting more customers?

James Evans (24:38.950)
Yeah, there was a second piece.
I'll actually circle back to something you just said about the time required.
Yes, this is not a kind of a quick marketing or sales hack.
Like, 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 spicy 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 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 an 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.
It's really easy.
We've already done like 80% of the work put into the product and see what results it drives 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 put in a lot of the work to get them ready to go.
And I think, you know, everyone's.
If you can credibly convince someone that you can move a metric they care about, that's like basically what sales is.

Omer (26:17.070)
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.
Initially, it's like, what exactly do you do?
What problem do you help solve?
Is this thing right for me?
And so you talked about a number of things in terms of using the loom videos as a way to explain very clearly in a very relevant way what the product does and how they can use it and what problems it helps solve.
And 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 whether it's JavaScript or some code I need to add to my web pages, or it's a Chrome extension.
Okay, that sounds pretty easy.
The second part of this would be, is like, well, what about all the information that you're delivering through this search bar?
How much work do I have to do to get that data for your product to access that data?
So what was actually involved and how did you make that easier?
So more people were willing to give this a try?

James Evans (27:39.830)
Yeah, I mean, the way it worked then is actually still the way it works now.
We just have more ways of packaging the things people are putting into Command Bar for users, and so we can show them in more situations.
But the basic principles are the same.
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 Command Bar does with it.
Is it surfacing the right things at the right times?
Is it picking up multiple ways?
Users might be describing some feature using our semantic search or natural language stuff?
And then there's also manual creation, because there are certain situations where when a user types in, like, how do I upgrade my plan?
Like, you really want to make sure that does exactly what you want it to do and is the fastest possible path to the user converting, because those are like, you know, real dollars at stake for that particular query.
So there's a way to curate kind of specific flows in Command Bar, whether that's when a user searches for something or asks Copilot a question, or if you really want to show a particular nudge on a particular page, a particular type of user, something like that.
And there's also kind of more of an autopilot mode where you kind of let Command Bar 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 the flows that, you know, really matter, you're really opinionated about, and let Command Bar 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 company, 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.
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.
And 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 get the dopamine loop of like, oh, this is really easy.
I should keep building this.
They might just never get there because something might come up.
And so the integrations and autopilot approach, I think really help with that.

Omer (29:57.960)
Okay, were there any other growth channels that worked for you?
Let's say beyond sort of first 10 customers, as you try to get towards the first million in ARR.
Beyond the cold email with Loom videos, which sounds like it was working really well.
And you shared that link with me with the Reddit ama.
You did.
I think we'll definitely include a link in the show notes to that so people can deep dive a little bit.
And there's actually.
You shared a Loom video with me as well, right?
An example of one of those videos.

James Evans (30:33.020)
Yeah, one of the ones I think it was.
I can't remember if it was successful or unsuccessful video, but it was definitely from that crop.

Omer (30:39.500)
Yeah, but people get the idea when they watch that.
So beyond that, were there any other growth channels that you tried that you got working or got working?

James Evans (30:51.260)
Not really for us.
Honestly.
We cruise 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 grateful for.
I still think might just have been like, dumb luck.
I think the product experience was pretty good, so I think the kind of referral loop was working, but we didn't really do anything to stoke it.
It just sort of happened.
1.
Learning from the early days on growth.
We tried a lot of content marketing in the early, early days.
And by tried, I mean like we would do two or three articles about a topic.
Like, we weren't 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 think 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.
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.
Are we getting comments when we post it on Hacker News?
Do people talk about it?
We don't really measure.
How many leads did we generate from each post?
Because it's so hard to determine, okay, this person read an article and then they went away for two months and they came back.
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 it and not measuring it.

Omer (32:41.850)
Right, right.
Yeah, yeah, yeah.
I had an experience with, with some founders who I think got into that.
I don't know what I, how I describe it, but it was like they, they wanted to do content marketing, would try a little bit of it for a few months and, and then want

James Evans (33:03.740)
to wait to see before they invest in it again.
Right.
What type of funnel does it drive?

Omer (33:09.140)
Yeah, which, which makes sense.
But the reality is, I think with content marketing is you either need to just say we're not going to 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're just going to keep doing it and we're just going to say this is part of the strategy.
This is a bet that we're making.
But you're right, it's a huge attribution problem because the chances of somebody going on, unless they're like, they have really high buyer intent and they're searching for one of your articles designed to convert them, start a trial, 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?

James Evans (34:08.040)
I don't know.

Omer (34:08.680)
Right.

James Evans (34:09.480)
I think you can do it at scale.
Like, I think there's, you know, plenty of companies that are doing a good job of that.
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 got to 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.
And I think this is how I used to think about testing out different channels.
They think of it as flipping over a card.
It's like either this channel is going to work for us or not.
And our job is just to kind of do the minimum viable exploration of the channel and see whether it works.
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.
Whereas content marketing, like you just said, like we've been talking about, like it's one of these things, or 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 bets, but just know their bets going into it 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 spewing 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.
Like, okay, yeah, then maybe there's something with your content, but don't abandon it just because it's not good.
It's not converting leads.

Omer (35:44.870)
Yeah, yeah, totally agree.
Let's talk about the category creation challenge a bit more.
So 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, chatbot onboarding, you know, in app stuff and whatever.
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?

James Evans (36:42.660)
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?
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 pop up companies.
So at the top of the show when I described Command Bar, I said like, we saw the same problem as those in product pop ups, but we're not annoying.
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 Command Bar, you can get rid of those vendors.
But like, we don't really have a take.
Like, that's old school, we're new school.
And we sort of just shrugged it off for a while.
And we were like, we're creating a category.
Our product is totally different.
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, 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 really helping someone understand what jobs did we do for them, what metrics could we move, what other tools we integrate with.
Who at the company would be using this tool?
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 there is something here.
Like, maybe we should start saying we are a replacement for X or substitute for X.
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 Command Bar to make it personalized for users.
One of the things you can do in Command Bar 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.
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 new way.
And that was a very challenging realization for me and the team because for so long we had been very dismissive of these old school tools.
And it was like, wait a second, we're going to build, like we're going to build a way to do pop ups in Command Bar.
For, for so long we've been talking about how we hate pop ups and now you're going to be able to create a pop up in Command Bar?
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 leaning on review sites like capture and G2 to really, like, create some social proof in the category and get noticed.
But if you compare 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 kind of have that signaled to anyone who encounters command bar, 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, and it's already done the job of educating the market about why it's important to help users.
Let's stand on the shoulders of that instead of starting from scratch.
So the tldr, I would say, is 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 changing the world.
How could you be a Me Too product?
But the dynamics of selling into an existing market are often far simpler than selling into a totally new market that might never exist.

Omer (40:46.890)
So you said it took about a large part of 2023 to figure that out.
What were you trying along the way?
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 nearly all the time trying to explain what their product does, what are some of the steps that they can take to make a similar transition?

James Evans (41:15.790)
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 think whenever you hear that, first of all, you should listen and identify trends.
If people are constantly comparing you to X, you should go look into X.
But if someone is trying to compare you to a tool, that's their basis of understanding.
And you should answer in a more of a yes and way.
And you should say, yeah, here are the ways where you're exactly like that tool.
Because at that point, you've created some groundwork for you to explain how you're different.
If you just jump into how you're different, they might be like, oh, okay, I just don't get this tool at all.
That's the first Thing I'd say is listen, listen to those comparisons.
Also seek those comparisons if you're not getting them.
One of my favorite pieces of advice for founders that is applicable in so many scenarios is ask open ended questions, especially in conversations with prospects.
How did you come across Command bar, let them talk.
A card I used to play in the beginning was like, people would ask, okay, can you demo the product?
What does it do?
And I'd be like, yes, I'm absolutely going to demo the product.
We just redid our marketing site.
I'm really curious what you think we do because we want to 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, whether they get it.
They might just get it, in which case amazing.
Maybe you don't have a category creation course 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.

Omer (43:04.320)
Yeah, I like the way you describe that.
If someone's saying, are you like whatever 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.

James Evans (43:25.820)
Right.

Omer (43:26.060)
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, it sounds so simple when you break it down now

James Evans (43:42.660)
I know right in the moment it's like a heat of battle.
It's really hard.
I think a little framework you can use in these situations is when someone compares you to X, you, you can start with the problems.
Be like, that solves this problem.
We also solve this problem.
However, we do it in a different way to X.
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.

Omer (44:03.230)
Yeah, yeah, that's pretty cool.
Okay, one kind of clarifying thing I want to just understand is you said that the cold email loom was basically the primary growth channel.
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.

James Evans (44:28.320)
We, I mean we do do outbound and we do do looms.
It's one of many channels.
We don't really have like one and if we did, I probably wouldn't tell you one like amazing channel.
I think the my mindset shift on marketing in B2B SaaS has been in the beginning like I described earlier.
I think I was playing this game of like, what channel is going to work for us?
Because you hear these things like you got to experiment, you got to focus, you have limited resources, you can't do everything at once.
Now I actually have adopted the perspective of you kind of just got to be everywhere all at once, always and try a lot of things and not expect any one marketing investment to 10x 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 going to 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

Omer (45:28.160)
your biggest growth channel in terms of being a founder.
What, and you look back over the last few years, what have been maybe one or two of the biggest struggles or challenges that you look back at on this journey?

James Evans (45:44.900)
For me personally, I think something I've struggled with a lot is how much to work, how much I should work, what is the right amount of myself that I should be pouring into the company.
I've tried a lot of different things over the years and I've sought a lot of advice and I've kind of just come to the conclusion and I'm sort of angel investing and this is what I talk 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.
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 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's doing well, like amazing, that's awesome.
Like there's no glory in like pouring hours into your company and for the sake of pouring hours.
And by the way, most people who say 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 getting lunch.
Like you may be in the office for 80 hours, but I doubt you're doing 80 hours of actual work.
That's really exhausting.
Some people can do it.
And so 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 got to work more.
And I think part of the advice here is like the answer can change.
And knowing when you should lean in or when your team should lean in is, I think, a superpower that some founders have and everyone should try to cultivate because it's even worse with the team because there's no way the team is going to sprint for 80 hours a week every week.
It's just not going to 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, like product trying to meet the deadline.
You kind of just have to apply this intuitive feel to your own work, but also the whole company and just realize there's no right answer and no investor is going to like yell at you or no one's going to yell at you because you didn't put in 80 hours a week.
I think hearing that is helpful for.
I certainly would have been helpful for me.

Omer (47:49.950)
So do you feel like you have a better control of that?
Do you feel like you found the right balance?

James Evans (47:58.350)
It ebbs and flows.
I think I tend to overwork just because like a lot of founders, I think I have an obsessive personality.
And by overwork I mean put in hours where the marginal utility is fairly low.
So I don't think I've 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.

Omer (48:36.090)
Yeah, my wife is a therapist and she's very helpful in keeping me under check.
And I remember when there was a lot of talk about the four day work week and there was a whole bunch of companies going on about that and I was like, oh, maybe this sounds really interesting.
Right.
Maybe that would be something I could try.
And I said to her, I've just been reading about this stuff and maybe that's what I should do.
And, and she was like so nice 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.
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?

James Evans (49:33.320)
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.
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.

Omer (49:52.920)
What book would you recommend to our audience and why?

James Evans (49:55.640)
It's a book called Never Split the Difference.
I wonder if it's come up before.
It's a book about negotiation that, that taught me to ask more open ended questions.

Omer (50:05.160)
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?

James Evans (50:16.040)
I call this like scoutness.
It's not a really clean word.
There's a book by Julia Galef called Scout Mindset that basically describes how there are two types of people or different situations.
You might be a soldier where you're trying to defend a point of view, or you could be a scout who's trying to uncover truths about the world, 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 had a vision of the future and just made it happen and not listened to signals that might have said it was a bad idea.
But more often than not, I think it's the scout founders who succeed.
Scouts who succeeded say I'm going to go build X.
And then they learned something about the market and said, you know what?
X was a terrible idea.
I'm now going to build X prime and exploit what I just learned about the market, especially at the early stage.
I think a lot of founders think they need to kind of pitch an idea to an 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 specific product that was in your seed deck.

Omer (51:20.160)
Yeah, cool.
By the way, I came across that book recently.
It's on my reading list, so I definitely want to get around to it.
It was when I was exploring this whole idea of rational thinking.
One of the books, the other books I came across was Harry Potter and the Methods of Rationality, which is also kind of a related thing.
I don't know if you've seen that.
It's kind of like this basically fan fiction thing on Harry Potter where it's all about applying rational thinking to the story.
So I've been trying to go through that and then I was like, yeah, scout mindset.
Definitely want to read that too.
What's your favorite personal productivity tool or habit?

James Evans (51:59.180)
I'm one of 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.

Omer (52:07.980)
I wish they would let me change fonts.
That's the only thing I don't like about Apple Notes.

James Evans (52:12.300)
It is.
I wish they had toggles.
That's my feature request.

Omer (52:15.290)
Who knows?
Maybe one day.
Maybe Tim Cook is listening.
I doubt it very much.
What's a new or crazy business idea you'd love to pursue if you had the extra time?

James Evans (52:25.290)
I feel like this maybe already exists, but it seems so obvious to me.
Like an LLM based accountability coach who can text me the same way my wife texts me to keep me accountable.
Did you work out today?
And then if I don't respond, pester me.
It just seems like such an obvious use case.

Omer (52:41.220)
Yeah, I love that.
What's an interesting or fun fact about you that most people don't know?

James Evans (52:45.700)
I'm a super boring person.
Like my team gives me about this all the time.
I think the two facts I think the most interesting fact 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.

Omer (53:06.270)
Love it.
And finally, what's one of your most important passions outside of your work?

James Evans (53:10.350)
I started angel investing.
I think 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 should I invest in this or not?
It's also just a really great way to meet other founders.
And I think there's this dynamic sometimes investing where it's like, oh, if you're the investor, you have to bring the knowledge and it's like a very one way relationship.
But I've learned so much from the founders I invest in.
It's a great hack for just getting.
A lot of times founders work in a vacuum.
You don't really see other founders at work, the strategies they use, how they write investor updates, what kind of progress they're making, what experiments they're running.
And angel investing is a great way to do that.
Cool.

Omer (53:54.140)
So thank you for joining me, James.
It's been a pleasure.
If people want to check out Command Bar, they can go to commandbar.com, and if folks want to get in touch with you, what's the best way for them to do that?

James Evans (54:05.590)
Twitter or LinkedIn?
Twitter on Dazzloid.

Omer (54:08.750)
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, thanks so much.
It's been a pleasure and I wish you and the team the best of success.

James Evans (54:21.270)
Thanks so much.
Take care.

Omer (54:22.550)
Cheers.