Brian Casel: [00:00:00] Hey, it's Open Threads. It's my podcast. I'm Brian Casel. Welcome to it. Today. I'm talking to my friend, Tyler King. He is the founder of Less Annoying CRM. com. What a name, right? so as you might imagine, they are a CRM software company, customer relationship management, and they are Less Annoying than the, than the vast number of competitors in that super competitive space.

And that's actually what I wanted to talk to Tyler about today. They've been successfully running this SaaS company for over 10 years now, multiple millions in ARR. So they have figured out a thing or two or three when it comes to growth, but it's still something that all these years in, even a company of their size and experience still struggles with this idea of growth and finding the next growth [00:01:00] channel and even understanding.

Where the current growth is even coming from, like, believe it or not, like, when you look at these companies that are, that have been around and they're well established, you might be surprised to know that so many of them don't have growth completely figured out. And I mean, kind of ranting and raving and complaining about how difficult it is to do the work of marketing and to understand marketing strategy.

That's 1 of my favorite things to complain about every day. Um, so what better idea for, for a podcast episode to, to invite Tyler on, to kind of commiserate on that stuff. I should also mention Tyler is the co host of one of my favorite other podcasts called Startup to Last. You know, they're talking about bootstrapping behind the scenes, very similar to what I do on Bootstrapped Web with, with Jordan Gal.

So that's another one I highly recommend. for now, let's talk to Tyler about growth.

Hey, Tyler. How's it [00:02:00] going, man? Doing good. How are you doing? Good. Yeah. Great to connect. We were just talking offline that like. I feel like you and I have spoken a lot in the last year or so. And this is actually the very first time we're speaking live because everything else has been asynchronous on, on ZipMessage.

Tyler King: This is like a boomer conversation we're having right now where we're both actually present.

Brian Casel: Very cool. Very cool. So you're of course the founder of Less Annoying CRM. I mean. I think in this chat here, we'll talk a bit about marketing and growth, but one thing just right off the bat that clearly you guys have gotten really right is the branding and the name.

I actually think that that, that's got to like work wonders for you from a growth standpoint, you know, like. It's like marketing, positioning, messaging, right from the name itself.

Tyler King: Yeah. It's, I mean, some people hate the name, Less Annoying CRM. Like there are a lot of people who are like, I can't show this to my boss.

Like they're going to laugh me out of the room. So it works against us sometimes, but yeah, when you're doing the whole like jobs to be [00:03:00] done, positioning, messaging exercise. Like, we get to skip a step. Normally, you have some name that doesn't mean much, and then in your H1, you have to explain what it actually is, and our name kind of explains it, and then that gives us a lot of freedom to be like, well, Less Annoying CRM, you already got, you got the gist, what else is there to say, you know?

Yeah.

Brian Casel: And also it's a CRM. So you're in this like hyper competitive space. Maybe one of the most competitive spaces for SaaS. Yeah. The original SaaS. I feel like having a name like that, I mean, it's also like a conversation starter. So it like gets you into the conversation, right? Like if you're looking at literally like a list of 50 CRMs, the name Less Annoying CRM.

Stands out just from its uniqueness, you know,

Tyler King: yeah, when we've done customer interviews, like a bunch of people have said, like, okay, first I looked at salesforce, then I looked at HubSpot, then I looked at pipe drive and I was pulling my hair out and I was on CRM number 12. I scrolled through this huge list and we're like number, you know, 87 on the list [00:04:00] or whatever.

And they're like, I saw your name and I had to click. I think a lot of companies don't like, they don't brand themselves acknowledging the reality that they're like a really, really tiny fish. They like try to do this like Slack or Stripe type of branding where it's just, it means nothing and everyone knows who you are.

And like, yeah, I don't know. That's hard.

Brian Casel: Well, you know, in this chat, I thought we would talk about growth and marketing in general, and, uh, maybe both of us would just sort of complain about how, how hard it is. Yeah, one of my favorite things to complain about, but like, you guys have been around a while and you've figured out a thing or two, you know, you're at like several million ARR.

I do want to point folks to your mixer G interview that you did a few months back. I thought that was. That was really great. And you know, you get like the whole backstory, so we won't do all that here, but sure, but what I am curious about, like before we get to like the present day and how we think about marketing and growth here in 2022, I mean, maybe give us a quick, like what year did, did Less Annoying actually start and what were the [00:05:00] Some of the early wins or like key milestones, first customers, and then like the next hundred customers.

And then, you know, from there,

Tyler King: yeah, so we started in 2009 and we didn't really have an official launch, but we kind of retroactively said it was January 1st, 2010 is around when the product was in a state where someone could actually sign up and use it. So we're going on, uh, almost 13 years now. Yeah, the world was very different back then.

Like, there was Salesforce, and there was Basecamp, and I probably, like, the term SaaS barely existed at the time. So in the early days, I think we were basically like, where's the game now is there's all this competition and you have to stand out in the early days. It was trying to convince people like, oh, no, you can buy software online.

Like, you don't have to, it's like secure enough. So that was kind of the challenge,

Brian Casel: like, let alone subscription software, just putting a credit card for anything on the internet was like,

Tyler King: yeah, exactly. Like our homepage, I was actually just looking back at some of our old homepage mockups and they were like, They have this whole justification for monthly fees instead of, [00:06:00] uh, one time payments and stuff like that, and all that has changed.

But yeah, in terms of, like, early wins and stuff, it took us a few months to get our first, our first customer. And really, these were people who, the product was so bad, no one would ever buy it in today's world. It was just that there was not much else out there at the time. We only really have ever had one big marketing win.

And that was, do you remember the Chrome web store back in the day? Like not the current version of it, but when it launched, I don't remember when it launched. No. So like nowadays the Chrome web store, yeah. Like you use it or you have a Chrome extension.

Brian Casel: Yeah. Yeah. Yeah. And I use Chrome and extensions all the time.

I just don't remember when they started.

Tyler King: Yeah. Well, so that's what it is today. What it used to be was like Google was doing this anti. IOS play of like, let's make a directory of all web apps, basically. And so instead of installing native apps, let's use web apps. It wasn't about extensions at the time.

And that came out, you know, a year or two after we started and I got [00:07:00] listed on there the first day I was like, sure, let's be on there. And we just got a ton of free traffic from that. It's basically that and Google AdWords was kind of our early growth.

Brian Casel: Yeah. It seems like a lot of these bootstrapped SaaS that really had success in.

You know, starting from around 10 years ago, that's when the Google that was like, the heyday of Google adsense, right?

Tyler King: Like, or AdWords. AdWords, yeah. It was great. At the time, I thought it was very expensive, and now looking back on it, man, I would give anything to go back to those days.

Brian Casel: Yeah, yeah, exactly. So, I mean, I see how that can give you, like, the first launch and turn nothing into something, right?

But then, what did it look like, let's say, like, five years ago, right? Like, you must have still found some things that were working.

Tyler King: I don't necessarily know what they are. I'm spiraling where I keep kind of thinking one thing and then thinking another. And where I currently am is thinking A lot of stuff we've done has worked, it's just no one thing has worked well enough that any of them stood out.

You know, we placed a lot of small bets, but we've got [00:08:00] directory listings on like G2 and Captera and websites like that. We suck at SEO, but after 13 years you can't help but have some organic search traffic coming in. We advertise with probably like 10 different random little sites where we're paying.

Brian Casel: I wonder if you, you get any search traffic for people just typing it and not knowing your brand name or anything.

And they're just typing in like, like Less Annoying CRM. Is there one of those?

Tyler King: I've heard one person tell me that that happened before. So at least once that has happened and they were like, no way. Is there a company named this?

Brian Casel: Great. I mean, even Google is like smart enough now to know like. If you type, like, less frustrating CRM, like, they would, like, associate that with you, probably.

Tyler King: Yeah. The game I used to play, because we existed before Google did the, like, autocomplete while you were typing thing, and as soon as they launched that, I was like, how many letters of Less Annoying CRM, because it's a long name, how many letters do I have to type before it guesses it? It wasn't until you got to the CRM and then gradually, like, it's one point I typed like L [00:09:00] E S S space a, and it filled in Less Annoying CRM.

And I was like, we made it. We've done it

Brian Casel: very cool. I'm also curious about, so you're sort of like me and you're like a product first, right? Would you say like.

Tyler King: Yeah, formally educated in computer science, but like, kind of half design half programming. Really?

Brian Casel: Cool. Yeah. I'm sort of the same, except started as designer and sort of hacked together some back end.

Skills later on, but very much a product person. And I always felt like I figured a thing or two out with, or I've been lucky with marketing, I would say in the last 10 plus years, but I've never felt like it was a strong side of, of the tool belt for me.

Tyler King: That's funny. Cause you ran a basically marketing agency, right?

Brian Casel: And like, I ran a content marketing agency and like, we're doing a bit of content and SEO stuff with ZipMessage. And it's like, We actually have a strategy and it's like, we didn't even like do like the things that we're doing now in ZipMessage or not even things that we were [00:10:00] doing in audience ops, like, and, and, you know, actually on that note, what was interesting, it was part of this frustration with me when I was doing sales calls for audience ops over the years, it transitioned like in the very early years, it was like.

We will sell you content marketing because content marketing will work to get you customers and, and that's the right strategy. Right. But it sort of very quickly shifted toward like, we don't know what's going to work. If you're convinced that you need content done, then we are a production shop that we will produce content for you.

And we're very efficient at that, but we're not here to do the strategy or get you customers, quote unquote. We're just here to write the articles that you believe will get you customers.

Tyler King: Yeah, because I mean, that's 1 thing that I keep telling myself content marketing has to be like, it fits our price point, our skill set, all that.

And that's 1 thing that just, I've never really been able to prove a connection between writing content and getting customers in a meaningful way.

Brian Casel: [00:11:00] Yeah, I mean, we're investing in it right now, but I think that my basic understanding from what I can gather from, from some folks is really most of it happens like bottom of the funnel.

Intent, you know, so you want to like optimize your product pages and things like that, but you're probably not, that's going to be super competitive, hard to get links pointing to your product pages. So the next best thing is to write articles that are like comparing tools, including yours. I'm like torn on this, like, I don't want to publish articles that list my competitors, you know?

Tyler King: Right. Well, especially cause you're kind of in a new space. Like we're on opposite ends of the spectrum where. With us, when someone comes to us, we don't need to tell them what a CRM is. We don't need to pitch them on the value that they already know with you. You're kind of saying like, Hey, here's this new thing that maybe you've never heard of before, which yeah, talking about competition and stuff like that, like that's how we were in the early days.

We got a lot of customers cause they didn't know about other options if I'm being honest. [00:12:00]

Brian Casel: I think there's a lot of that. It was in my previous businesses, like they just weren't aware of the competitors. And I think that with content, like the one thing that I've started to really separate now is investing in article writing content versus investing in audience or brand.

Like those are completely different things now. I think a few years ago, people used to think of them as the same, but I think they're very different now.

Tyler King: Well, and like, what is the difference in your mind between SEO and content marketing?

Brian Casel: Well, content marketing could be pretty broad, but when I think of SEO, we're going to be creating content that's like text based, you know, articles essentially.

But SEO also includes optimizing your homepage and your product information pages and your comparison pages, right? Like there's SEO in that too.

Tyler King: I was reading the book Traction by Gabriel Weinberg, not the Traction everyone thinks of, but the other book called Traction. It differentiates between the [00:13:00] two and kind of the impression I get by the book's definition is that like content marketing is meant to be enjoyed by people.

And like it succeeds by, you know, people might share it or whatever, whereas SEO is like meant to be enjoyed by Google's algorithm, basically, and not that they're mutually exclusive, but like, it is kind of a different approach. I think,

Brian Casel: yeah, I think that content is also pretty broad and it couldn't include written articles in terms of just written articles.

I think of some that are like, bottom of funnel, like, you're about to buy a tool like this. Here's an article about buying tools like this. And then there's more top of funnel, which is like how to run a sales team. Cause you're a sales manager and maybe there's some SEO juice for that. That's not necessarily buying intent, but then there's like another class of content that's like, I think more like thought pieces.

It doesn't matter at all about the SEO value of this. It's just interesting, or it's like taking a stance on something and yeah.

Tyler King: And that's more the audience side you were talking about.

Brian Casel: That's more on the [00:14:00] audience and even content marketing too. It's like. Meant to be shared or meant to convince your people of some thing, you know?

Tyler King: Yeah, you said like you're making a big difference between audience building and like I forget what the other one is like getting conversions or something like that. What are you focusing on?

Brian Casel: I think of it as like, there's like audience and brand stuff, and that could be a number of different projects.

And then there's just pure SEO driven article development.

Tyler King: Right. Okay. But you said you're doing content stuff now, which are you doing both of those? Are you focusing on one or the other?

Brian Casel: Both. Yeah. The SEO article stuff is like up and running. I have a writer, a separate like SEO keyword strategist who he just researches keywords and creates briefs that we then hand to the writer.

And then I have a marketing coordinator sort of manages that, but then she's also involved in the audience brands. I'm curious to ask you about that, actually. So like with over the years, right? Because you have a team of like, what, what's your team size now? 19 people now. [00:15:00] 19. So when it comes to hiring people to work on marketing stuff, what's been your approach to that?

Like, were you, or are you ever like, you're going to be hands on in it, or I'm going to hire like a head of marketing to figure it out and run with it or outsource to an agency, what are your thoughts on that?

Tyler King: Yeah, I'm happy to share, but let me preface this by saying, like, this is my greatest weakness, or like the thing that we've probably done worse, just a terrible job at.

In the early days, like, I did most of the marketing for a long time myself. My brother, who's the other co founder, did some as well. One of my weaknesses is outsourcing. I'm just, like, terrible at quick transactional relationships. So I've basically never effectively hired anyone that's not a full time employee, which is, I think, the opposite of most people in our space.

The good side of this is like, I think we've got a really good culture and all this, but the bad side is like, it's not, I've never been in a situation where it's like, oh, we need some quick copywriting. Let me pay someone for 20 to do some copywriting. I just would do it myself. [00:16:00] And. I'm okay at it, but I'm not an expert at any of this stuff.

We didn't have a real marketing person until two years ago.

Brian Casel: Like no person who was working on any sort of marketing.

Tyler King: The biggest team of the company is CRM coaches, which is basically customer service. They get 20 percent time. So one day a week they can do other stuff. So we've had a lot of CRM coaches, like.

Enjoying writing is a common characteristic of people who like customer service. So a lot of them have chosen to write help articles, to write blog posts, to create content like that.

Brian Casel: I like that model of content marketing essentially, right? Like having your subject matter experts Create some content.

Tyler King: The problem is we're not subject matter experts. Like, you know, close the CRM with Stelly's. So Stelly is like this uber sales guy, right? He knows everything about sales and that's like, CRMs are consumed by salespeople. I look at his content. I'm like, wow. I wish anyone at Less Annoying CRM had that kind of understanding of how, like, we have no salespeople.

None of us have ever done sales before. We're selling to salespeople. We're [00:17:00] experts on how to build software and how to provide customer service, which is not what our customers want to know. I agree with you. That would be a great model, but this is one of our great struggles is. We can write interesting content, but it is interesting to people who would never use Less Annoying CRM.

Brian Casel: It just made me think of like my friend, Brad Tunar, who ran Delicious Brains. He just recently sold it. It's like a big, it's a software dev shop and they make developer tools, right? So all of their tools are very, very technical only for developers. One of the things that they've had success with is having their in house software developers write technical articles.

They're too technical to be able to outsource content. That's great. And that's been working well for them. I hear you like, you guys are basically like a software shop first. You're not like a sales team first.

Tyler King: Right. There's like that classic co founder pair of like, you know, this person was a travel agent and this person builds software and now they can build really good software for travel agents.

We don't have. That domain expert at all, [00:18:00] really. I'm curious how you're, cause you know, you're doing this pivot to coaches and consultants. I think you're probably closer to that world than I am to the world of sales, but like, you're not a deep domain expert in that, right?

Brian Casel: Yeah, no, I'm not. And this is one of the things that made me a little bit.

Nervous about starting to focus on coaches because probably for the first time, although I use that message every single day, I'm a user of it. You know, we're finding that our best customers are coaches, but I don't identify as a coach and I never really have, I've dabbled in a couple of years ago when I was doing product high stuff, but like never as like a real business thing, and I don't do any of it today.

So this is definitely the first time where we're doing marketing things. Speaking to people who are not like me. So I have a little bit of a harder time writing an article or an email, knowing that it's going to resonate because I can't put myself in their shoes necessarily. You know, but I would say that one of the other reasons I'm excited [00:19:00] about going after coaches here is because.

It is one of those verticals that is pretty broad and it's not impossible to like outsource writing on topics. And I feel like everyone has some sort of experience with coaches, even me, like dabbling in it. But like Claire, our new marketing coordinator, like she does coaching on the side too. And she's well connected to many other coaches.

She's in other communities. So that, that sort of helps. Even our, our writer cat, like she's not necessarily a full time coach, but she's familiar with it, familiar with the territory. And I mean, the subject matter, we've done a ton of interviews. So we really have a lot of like voice of customer data and like actual stories from actual coaches that we pull from, but the things that they're talking about are not like super technical, like we're not speaking to developers, we're not speaking to doctors or lawyers where we have to have like really technical industry.

Accuracy, right. We're basically talking about business [00:20:00] topics in the context of building a coaching business, you know? So like, I guess like what we're doing is from a SEO article standpoint, we're doing a mix of bottom of funnel, like you're shopping for tools to run your coaching business. We're in the mix there.

We have articles about that. And then we have more top of funnel articles that are more about like how to start a coaching business, how to grow a coaching business, how to do group coaching, like things like that. And then on the content side, and we're just getting started with this right now, we're going to soon be launching like a community for coaches, like a private.

Tyler King: That's been my dream for a long time.

Brian Casel: I mean, I think that's another interesting area with marketing. I think this is one of the things today that is really hard to pull off and do well, and it won't happen quickly. It'll definitely be a long term play, but if you can get this right, that like this community thing.

Some form of community that's like the most effective if pay per click ads are way too [00:21:00] expensive like a non starter these days. And even content marketing and is just extremely competitive. And Google is showing half the front page of just ads anyway. Building a community with your ideal customers like that to me, I'm thinking of that as like a product in itself.

Give them an experience. That's that's great.

Tyler King: It's word of mouth on steroids. Like everybody wants word of mouth. And I hear a lot of people say, Oh, you know, that's not even a real channel. Don't call it that. I think it is. And I think like Less Annoying gets most of our customers from that, but. Once in our past, there was a Facebook group created by one of our customers who was a travel agent.

So it was like Less Annoying CRM for travel agents was the group. And it got a few hundred members. And like, again, we didn't even create it, but like they invited me and I joined it. And like once a month I would go in and answer a question in there and it kept growing and growing and all this great goodwill would build up and someone would post a question.

And it'd be half about the CRM, but half about how to use it as a travel agent. And I'd be like, I didn't [00:22:00] even know travel agents still existed until six months ago. I don't know the answer to this, but someone else would go in and answer the question for me. And, uh, yeah, I, if you could do that, but instead of it being this weird, tiny niche of your customers, be the main core group, that'd be huge.

Brian Casel: Yeah. And I mean, think about all the different communities and whether it's like Facebook groups or Slack groups or. Other places online where people are like, Hey, what do you all use for your CRM for your business? And then there's a thread and hopefully you are mentioned in there, probably alongside all of your competitors.

But I'm sure like how many customers have, have you gotten just from someone in a comment thread in a community somewhere answering the question of like, which CRM do you, does everybody here use, right?

Tyler King: Yeah, probably a bunch. We were dabbling with doing a community, but A, I keep getting scared off by, like, moderation, and, like, it's just a big responsibility, but B, our problem is we're not as niche, like, we haven't found an industry or some other niche the way you have, so we're, like, for small [00:23:00] businesses, and, like, we did a little dipping our toe in the water, and we were like, that's not actually a community.

Like coaches, that's a community small businesses is not no one like thinks of themselves as a small business owner. They think of themselves as a coach or a travel agent or an insurance agent or whatever. So that's why we haven't,

Brian Casel: we're still, uh, in the process of dipping our toes in the water here and like, starting to niche down and even starting to do this community thing.

So I have no idea if, if it would be the right strategy, or even if we'll be successful with, with executing it, but it is hard, you know, because I think. I don't think like the mod, like moderating is one thing, but I think just making it good, you know, cause like it can't just be, we're this product company and come join our community all about our own product.

It's gotta be like actually valuable, which means you need to basically hire at least one person to, to be the one to really drive the energy and like talk to people every day and run many workshops in the [00:24:00] community and keep them engaged and all this different stuff, so.

Tyler King: Yeah, I feel like most marketing attempts in my experience that have failed like at the end of the day, you could look back on it.

And it's exactly the problem. You just said it's like, we put effort into it. We tried to make a good, but we were doing what we wanted. We weren't given anyone anything they wanted. And it really sucks when you have to market your marketing. Like, you make an ebook and then you're like, okay, now I have to, okay, how does anyone hear about this ebook?

And it's like, if they're not already looking for it, like, this is Justin Jackson's whole thing about like, writing an existing way, right? Yeah. If you're putting something out there, even if it's good, but if nobody wants it, now you've got a second marketing challenge of getting people to your, the top of your main marketing funnel.

Brian Casel: I was going to like send you a private ZM about this. I don't know if you're open to talking about this kind of like future marketing ideas for Less Annoying, but like. You know, I was hearing you talk about it on your podcast the other day and like trying to sort of brainstorm new channels that you can unlock.

I'm sure you're probably already thinking about this because you're what? Over, over 10 years in now on this [00:25:00] business, right? We talked about how you have the Less Annoying CRM brands. So, well, like, have you thought about just firing up new products?

Tyler King: Yes, we have a few misadventures in this in the past.

Brian Casel: Like Less Annoying invoicing and Less Annoying whatever else.

Tyler King: So our name as a company is actually Less Annoying Software LLC because this has been kind of the idea, like no one grows up and dreams of starting a CRM company, like it's a pretty boring thing to, to make. But the idea was like, what is the core thing that everything else would build off of?

And so yeah, that has been the plan and we've every once in a while we start going down that path and then coincidentally the main business, like, starts doing better and we're like, it's hard to justify putting resources into this side thing when, you know, you could put the same resources into like, you've just got a lot more leverage focusing, I think, but I'm conflicted about that.

Brian Casel: Well, one argument to make for it, I think. Is that you already have a huge [00:26:00] customer base and an even larger audience, like email list, right? All right, at least people who have tried it in the past, maybe didn't fully convert, but then you still have all these paying customers, right? So you instantly have an audience, like whatever new product you launch, as long as it's in the same set of needs, you can instantly launch to over 10 K MRR, right?

Like within a few weeks of launching it, you're at a huge headstart against every other new SaaS startup.

Tyler King: Yeah. So how do you decide whether to build it as a new product versus build it into the existing one is one question I've struggled with. What you're saying makes absolute sense from like a revenue standpoint.

If we build it into our existing product, then it's like. Providing value to people and it gets a lot of usage, but you don't make any money off of it.

Brian Casel: Yeah. It sort of depends on what kind of product it is. I would think that the breakdown there would be, it goes in and we're about to build a bunch of new features, which maybe should be their own product, but I don't, I don't know.

But the breakdown I would [00:27:00] think is like, if it's still in CRM land, but just bigger, more powerful CRM land, or maybe like a super automated CRM, like that's like a new, more expensive plan on the existing product. But if it's an adjacent product that like some customers might find valuable and use and other customers might not be interested at all, spin off a separate product, but I really do think that like, you also have the branding advantage too.

Like. You could literally call your line of products, like Less annoying, this Less Annoying that, you know?

Tyler King: Yeah, I think that's a good idea. So sometimes I like feel this weird FOMO about like, when you listen to true impressive entrepreneurs on podcasts or follow them on Twitter or whatever. And they're like, well, all I did was I.

Took out a 5 million loan somehow and hired a bunch of people and like super leveraged myself and built it very quickly every once in a while. I'm like, I should do that. Like, yeah, we've got this equity, we could leverage it and we could grow faster and do more. And then I'm also like, Oh [00:28:00] man, it's hard enough doing one thing.

Brian Casel: Yeah. For me, like sitting here with a, with just a tiny team and I'm always like struggling to figure out like which resources I'm going to put on which things. Which things can we not do? Cause we don't have the resources right now. You know, I always look at, at these other companies and friends, companies that have teams, you know, that have really built out.

And I'm like, Oh, you can do everything. You know, like two of your employees.

Tyler King: Well, actually you might be right. Like if we were starting a brand new Greenfield project, I guess we could probably move roughly as quick. I mean, you never move as fast as the founder does, like no employee ever moves as fast as the founder.

Cause like. They're not going to put in nights and weekends and all that stuff. We could move a lot faster if we did that. The thing that I didn't appreciate until we got bigger is just how slow everything moves on the main business now. Because we've got five software engineers and two DevOps engineers and We're shipping stuff faster than we ever have before, but like our NPS score is actually dropping right now, which suggests to me [00:29:00] that the competition is moving faster than us.

And it's hard to justify slowing down the pace that we're trying to improve our current product. Yeah, so I don't know, it's, I think you're right, but also it's, it's a tough set of trade offs.

Brian Casel: I'm curious about this because again, like at several million ARR, you're at a very different landscape than what I'm looking at.

You know, I'm still in total like startup land here. And so like, yeah, like what metrics are you generally looking at in terms of like deciding where to focus the energy? It sounds like, I mean, correct me if I'm wrong. It sounds like lately, you've been thinking about, we need to find some new marketing channels.

Right. So like, what is it about, what like metrics or numbers are you looking at that, that tells you like, well, that's the thing to focus on instead of reducing churn or whatever else it might be.

Tyler King: Yeah. So we looked at this and basically, you know, we've got whatever amount of traffic hits our website and like, who could say, is it a lot or a little, I don't know, like in a vacuum, it's hard to say we looked at, okay.

How many of those [00:30:00] people sign up for free trials? Key thing here. You got to filter out people who are going to your site to log in. When we looked at it, 90 percent of our traffic to our homepage is current customers going to log in. So it looks like we had a really low conversion rate and we kept AB testing everything and we couldn't get it to go up.

And then we realized 90 percent are already customers. When you filter those out. Yeah.

Brian Casel: That's a really tricky thing for ZipMessage too, because we use our own domain for, for the whole app, including our marketing site. And so like. I actually have like different versions of analytics installed with code built in to see a, if they're logged in, but then we also have ZipMessage conversations that can be shared publicly, right?

So you don't have to be logged in to just be looking at somebody's conversation. And so we like filtered the, we had like a different view just to filter that stuff out.

Tyler King: Yeah, well, and then also, like, let's say you, so our most successful blog post ever was my brother, who's a, like, he's basically has a PhD in data science, more or less, and he wrote this [00:31:00] post about like baseball statistics, like advanced sabermetric stuff has nothing to do with Less Annoying CRM.

But he wrote it. He wanted a place to publish it. So we put it on our blog like 11 years ago. I guess a ton. And it got a ton of traffic. You shouldn't like beat yourself up over having a bad conversion rate, because people looking at Sabermetrics blog posts aren't signing up for the CRM afterwards.

Brian Casel: Well, I mean, now you guys have to go, go build a Sabermetrics SaaS app.

Tyler King: Yeah. Yeah. That's the Less Annoying baseball statistics. Yeah, there you go. But anyway, so we tried to filter out like, who are the actual people who are potential Potentially might sign up for a free trial, what percentage of them convert? And I tried to compare those to industry benchmarks and who knows what, I think we're at one and a half percent conversion.

And I don't know, is that good or bad? But I think that's okay. It's not great. That gets them to a free trial. This is where our numbers all get good. So 25 percent ish of free trial accounts pay, which for a no credit card trial, [00:32:00] it's not like the best in the world, but it's, I think, pretty strong and then.

If someone comes back a second time after signing up for the free trial, that number jumps to like 70 or 80%. So basically they're either dropping off immediately or they're going to pay us. So, and then our, if you look at our churn, it's 1. 5 percent per month or something like that, which more than half of our accounts are single users paying us 15.

So pretty low value. 1. 5 percent churn is pretty good for that type of customer. So we looked at all of this and we basically said, if someone comes back to our site a second time, they're going to pay us and they're not going to churn at a high rate. So we're just like, yeah, we could optimize that, but like, that's not what we're going to worry.

Getting people to come back a second time after they sign up for the free trial is like one of our top priorities. And then the second one is just more traffic because I think all our other numbers look okay.

Brian Casel: Do you do any sort of a sales like phone sales or whatever?

Tyler King: Historically, very little. What we do is we buy, it's called PPL, pay per lead, um, where you kind of [00:33:00] buy a lead that's, there are all these websites out there that say like, we'll help you pick the best CRM, and then people go to those websites, give them their contact info, talk to them, and then they basically sell that lead to people.

Sounds real slimy, but actually we've found. You can get some pretty qualified leads that way, even with them being that qualified, it's like arguably not worth the time. Cause again, our average deal size is so small, but that's the only way we've really gotten it to work. We don't do any like outbound sales or kind of cold outreach to anybody.

Right, right.

Brian Casel: So hard, man. Cause it's like tracking it, just getting visibility. Like we were talking about the logged in users versus not logged in, but even anything else, like it takes so long, the thing that really kind of. Kind of pisses me off about all the marketing advice out there. It's like, Oh, just do this or just test this.

People always say like, well, just test this testing. This means probably hiring someone. And if you're not hiring someone, then you are stopping everything else you were doing, and you're going to work [00:34:00] full time on this little idea. And it's not going to take a day. It's going to take a month just to launch it.

And then you're going to need three, five, six months before you even know. Is there a meaningful data coming from this channel? I think there's no version of like, do just enough to test it, to know if it's worth investing in. I think that you just need to strategize and pick a couple of big channels and take like huge bets, like spend F your year on these bets.

Tyler King: I a hundred percent agree. I used to like really buy into the data driven mindset and like when it works great. Like when something's easy to measure and it's very quantifiable, fantastic, but. I keep looking at my business and saying we're at three and a half million ARR and I can't really point at a single marketing success.

If you follow the data, we aren't a three and a half million dollar business. Like what happened? Where's the disconnect? And the disconnect is like a lot of stuff's hard to track. Like it's so hard to attribute because you do something over here and then 18 months later someone who saw that comes and signs [00:35:00] up and how could you ever know?

So yeah, I agree with you. You just have to kind of have a hypothesis and commit to it longer than it probably makes sense to you sometimes.

Brian Casel: Yeah. And then I think the other thing, and it's like, again, we're like product people, so it's so the opposite of like, okay, these are the specs for a new feature, we're going to build it.

We're going to test it. It's going to pass these tests. We're going to deploy it. And then green light, like it works great with marketing. It's like, you do all that work. And then it's like, maybe this might work someday. I don't know.

Tyler King: Yeah. And the competitive side of it, like I could write a really great blog post and HubSpot has a team of a hundred people writing blog posts.

Like my great blog post on page five of the Google search, it isn't going to do anything. Whereas yeah, back to the product thing. It's been years since I've built something and not been a hundred percent confident it would provide a lot of value to customers. It's pretty easy to de risk that, especially as you get more mature and you get a lot of customer feedback.

But with marketing, it's like, who knows? I kind of hate it.

Brian Casel: And, you know, and then there's this other [00:36:00] thing that like. As product people, at least for me, like I start to feel this like guilt around like, Oh, maybe if we just build these features or start to build for these customers, we'll do better. And I'm hearing in, at least in my head, like all the marketing people on Twitter saying like, Oh, don't just build features.

You have to market. You have to, you're not working on marketing. It's like, well, yeah, I think I am.

Tyler King: I hear that voice. It's like a pendulum though, where you, you probably want to be in the middle and like right now. All the conventional wisdom is like too far on the marketing side, I think, because it used to be too far on the product side, where like a lot of people would have you think the product doesn't matter.

You're wasting your time if you're building a product. I tried this once in my life where I kept hearing this advice, like, Just like come up with an idea for product build, like not even an MVP, just like maybe a prototype or maybe not even that just mock ups or whatever. And then go sell it. And after like five or 10 people pay for it, then go build it.

No one buys software like that.

Brian Casel: Yeah. I mean, it's so competitive on the product [00:37:00] side now, because it's like. You not only have to solve a micro problem, you have to solve a whole problem. Like there's so many table stakes features in every category that if you don't have these things, you're just a non starter, even if you do one thing better than the competitor.

And then the quality, like if it's clunky again, like that alone. It would definitely turn me off from a product. And I know many customers are looking at that, you know,

Tyler King: The standards are so much higher. I wouldn't use my products today. If I'm being honest, like I will in three months after we launched this redesign, I would sign up for it and take a look at it and be like, Oh, absolutely not.

And that's not through lack of trying. It's just hard. Like, you know, you get bigger, it's hard to just change. It's harder. Everything you change, you have to be like, okay, there's 25, 000 people I might piss off with this. Got to be very careful about it.

Brian Casel: Well, if folks take anything away from this podcast, I guess it's marketing and growth is just hard.

Yeah, that's all we got.

Tyler King: Good luck.