Dean Mathews - OntheClock

OnTheClock: Bootstrapping a $5M+ SaaS Without Talking to Customers – with Dean Matthews [403]

OnTheClock: Bootstrapping a $5M+ SaaS Without Talking to Customers

Dean Mathews is the founder and CEO of OnTheClock, a time-tracking software that helps small businesses manage their employees' hours.

In 2004, Dean was sitting at his kitchen table with his laptop one day, browsing through small business and accounting forums.

As he scrolled, he noticed a trend: people were constantly complaining about not being able to find reliable, easy-to-use time-tracking systems for their companies.

Dean, who was working as a software consultant at the time, had a lightbulb moment. He thought to himself, “You know, I can build that for them.”

Dean spent the next few months building the first version of OnTheClock. He launched it in June 2004, while still maintaining his consulting work.

For the next decade, OnTheClock remained Dean's passion project. He'd dedicate about 20 hours a week to it, squeezing in time between client projects to improve the product and learn about marketing.

Despite the limited attention, the business grew steadily through SEO and word-of-mouth referrals. By 2015, OnTheClock had hit a major milestone – $1 million in annual recurring revenue (ARR).

The following year, Dean took the plunge. He handed off his consulting clients and brought his brother on board to develop a mobile app for OnTheClock.

Focusing full-time on the business accelerated growth, but it also brought new challenges. Dean had to shift from being a hands-on developer to leading a team – something he was initially reluctant to do.

Along the way, Dean faced other hurdles. Paid advertising didn't work well for them, and he had to learn how to be an effective leader. But he persevered.

Today, OnTheClock serves about 18,000 customers. The company generates well beyond $5M in annual recurring revenue and has a team of 22 people. And Dean's business is fully bootstrapped he's never raised any external funding.

In this episode you'll learn:

  • How Dean validated his product idea and acquired his first customers without talking directly to them.
  • What strategies Dean used to grow OnTheClock as a side project for over a decade before going all-in.
  • How Dean overcame his initial reluctance to hire employees and built a strong team culture.
  • Why Dean believes making your product easy to use can be a key differentiator in a competitive market.
  • How Dean transitioned from a solo founder to a team leader and the lessons he learned along the way.

I hope you enjoy it.

Transcript

Click to view transcript
[00:00:00] Omer: Welcome to the show.

[00:00:01] Dean: Thank you Omer for having me. And I wanted to say it's I've been a long time listener. I actually looked at my podcast just a couple weeks ago when, when we set this up and it took a lot of scrolling, but I got to the, got towards the bottom and it was 2016. It was the first episode that I listened to you.

[00:00:16] It was episode 119. So, and I also wanted to say congrats. I looked today and I saw you had 400 episodes. That's a big deal. So, congrats.

[00:00:25] Omer: Thank you. Awesome. So you're, you're you've been around for a while and, and I think 2016 was about the time that you went, like that's when you shifted, right?

[00:00:35] That went all into the business.

[00:00:36] Dean: Just a little before that, like that 15 ish era. So, and, and that's when I started to have to learn, right? So so I started watching you and a few other podcasts and so you have really helped you and your guests have really helped shape my career OnTheClock and I.

[00:00:53] In our trajectory. So thank you for that.

[00:00:55] Omer: Awesome. You made my day. Thank you.

[00:00:57] Dean: No, you're very welcome.

[00:00:58] Omer: Do you have a favorite quote, something that inspires or motivates you that you can share with us?

[00:01:03] Dean: I do. I do. I, I was actually looking the other night for the source of this, I couldn't find it. But it's, if you wanna go fast go alone.

[00:01:11] If you wanna go far, go together. So. That's something I've really learned over the years. I used to think about it, the inverse, but I really think about it that way now.

[00:01:20] Omer: Yeah, I, I think that's an interesting part of your story that will probably make more sense by the end of this episode when people know what you the journey you've taken.

[00:01:30] So tell us about OnTheClock, what does the product do? Who's it for, and what's the main problem you're helping to solve?

[00:01:37] Dean: So OnTheClock is we, we do employee time tracking. End result is for payroll. So it is online app, phone, app based. So an employer or manager can open an account with us.

[00:01:48] It's self service, so it's very easy to use. They add their employees employees clock in and out. And then the end result is I'm, they can use their phone or the website. We do have GPS controls and geofencing. And it's very modern. And the end result is timecards that could be sent over to your payroll provider, so, so your employees can get paid.

[00:02:09] We do have some additional features like I mentioned, the Geo GPS and geofencing. We also have PTO management, so employees can request PTO and managers can approve it, and then it ends up on time cards. You can also set up a lot against Accruments for the employees as well. Quite a few options there.

[00:02:26] We do automatic overtime calculations as well, so that's a really great feature for e especially if for somebody who's doing it manually, you know, that's a lot of work and a lot of errors as well.

[00:02:36] Omer: So typically like what, how big are the, your, your. How big is your average customer?

[00:02:42] Dean: Sure. We service SMBs mostly the Ss, it's in that below 20, 25 range is really our sweet spot.

[00:02:49] 25 employees up or less. But that's, we definitely have accounts that have hundreds and even some of 'em, some accounts that have, I think the highest account. It is right around three to 4,000 employees.

[00:02:59] Omer: And give us a sense of the size of the business. Were you in terms of revenue, number of customers, size of team and that stuff?

[00:03:05] Dean: Sure. So we are we're 22 team members right now, so 22 of us run OnTheClock. Revenue is we don't disclose the exact number, but it's between five and 10 million. And as far as customer count, we're at right around 18,000 customers. And those are mostly here in the United States.

[00:03:22] Omer: Great.

[00:03:23] And the business is bootstrap. You've never raised money,

[00:03:26] Dean: correct? Yes. Yeah, bootstrapped I was a consultant back when we started. It was more of a passion project in the beginning, so I had a source of income so I could work on this as much as I wanted to. And. It was bootstrapped by, by me really, you know, so it was funded, but by, by myself.

[00:03:42] Omer: So I think you launched the product OnTheClock. I think it was like 2004, but it, it sort of continued to be a passion project for like another 10 or 11 years. So you didn't go all in with the business? Until about 2016. Is that right?

[00:04:04] Dean: Correct. Yeah. Right in that 1516 era it got to the point to where it was, at that point it was profitable.

[00:04:11] It, it had it, it was to the point to where I really couldn't ignore it anymore. So really just decided, like you said, to go all in. And I had a consulting company here in the metro Detroit area computer consulting. So I would go and, and write various, software for customers custom software.

[00:04:29] And right about that time it was just like, you know, if we're gonna do something with this, now's the time. And I rehomed all my customers. There was a couple other small businesses that I was working with that I, I got went ahead and, and moved those off and really put 99% of my effort into OnTheClock.

[00:04:47] Omer: Great. Okay. So, first of all, let's, let's go back to 2003, 2004. Where did the idea for this product come from?

[00:04:59] Dean: Yeah, so I'm kind of a nerd. So I still remember the moment actually. I was sitting at my kitchen table with my laptop and I was reading through some small business accounting forums. You remember those?

[00:05:10] They're still around actually a lot. But yeah, I was noticing this trend. Trend. They were all complaining. They couldn't find a reliable and easy to use time tracking system for, for their company or for their, you know, their, their clients if they were the accountants. And I was like, you know, I, I can build that for them.

[00:05:29] And I was a software developer by trade, you know, consultant entrepreneurial spirit as well. So I literally the next day started doing my research and. Within a few months had the, the first version out. So that would've been, we actually just celebrated our, our 20th anniversary here, just last month.

[00:05:50] So that would've been right around June of 2004.

[00:05:53] Omer: Okay. So most developers if they get excited about an idea. They often jump to building the product and differ talking to customers later. How did you approach this? Did you do the same? Pretty much did the same thing.

[00:06:15] Dean: I, I did validate though I surveyed competition just to see what the competition was out there per potential competition.

[00:06:23] 'cause I didn't have a product. Definitely looked and found that there was definitely a few players out there, so that there was some validation there, that there was a market. Also did a lot more research in the forums and other areas and found that there was a need. So I didn't talk to actual customers, but you know, also just using logic, right?

[00:06:42] So small businesses that have hourly employees have to track time. So it, it, those three elements really went into it and. Even back then, you know, I said it was, it is a pa or was a passion project. It was almost like if it didn't work, it wasn't the end of the world. I wasn't gonna dump millions of dollars into it.

[00:07:01] It was my time, which, you know, is valuable, but it would've only been my time.

[00:07:06] Omer: Okay. So a few months you got the product built. How long did it take you to find the first customer?

[00:07:13] Dean: So, first customer came in we had to do a little paid at the time. And paid search, PPC Google AdWords mostly, I'd say within a couple days we had a couple signups, but the, the funny, funny story, feral Hare is they signed up with us in, within the first month.

[00:07:33] They're still with us. So they, they do hair replacement, I believe they're down in Florida. So, so, and they're still with us, so they've been paying us for 20 years is pretty awesome.

[00:07:41] Omer: Wow. You said we had to do. Some PPC was it, was there a we or was it just you at that point?

[00:07:50] Dean: There was an I I, I've morphed into the we scenario because there was, there is a we, there's been a we now for a lot of years.

[00:07:57] So it was I,

[00:07:58] Omer: alright, and then, so first customer in the first month. What about the first 10?

[00:08:03] Dean: So we were receiving at that point I would say two to three signups per day. You know, not a whole lot at least compared to now. And the first 10 actual customers, meaning that they chose us, right?

[00:08:16] Signups are different than somebody adopting or converting over to a paying customer. That would've happened roughly within the first I. Probably two months. We had the first 10.

[00:08:26] Omer: And

[00:08:26] Dean: where were

[00:08:27] Omer: these people coming from? Was this

[00:08:28] Dean: was this little PPC. So we did PPC for about a month. And then SEO started kicking in.

[00:08:34] So, so they started just doing Google searches or, or, you know whatever search engine they used back then.

[00:08:41] Omer: Yeah. Two two, 2004. When. SEO was a little bit different to, to today.

[00:08:48] Dean: Yes. Very different. It was a lot simpler back then.

[00:08:51] Omer: Yeah. Okay, great. So you've got, you've got some SEO traffic, some organic search traffic.

[00:08:57] You're getting these signups and getting to that first 10 didn't take that long.

[00:09:04] Dean: Yeah. Two, three months maybe at most.

[00:09:05] Omer: So for many founders, that's a, a, a, you know, great sign that. You know, basically strangers are coming along and they are signing up and you, you were charging people, right? There was, this wasn't like a free plan or something like that.

[00:09:21] People are actually coming in and paying.

[00:09:22] Dean: We did have a free, free plan for two employees or less. So, and we still have that plan today. So, you know, it's really designed to help really small businesses. And the idea is, is that. As your business grows, you use us for, you know, a year or two, and when you hit that third employee, then you start paying.

[00:09:40] So, but those first 10 customers, I would've called the paying customers.

[00:09:43] Omer: So again, so I think that's a great sign, right? I mean, for, for many founders it can take them much longer to get those first 10 customers. So great signal. It almost feels like, okay, you, you've validated the idea found problem, solution fit, got the first 10 customers that we all, you know, talk about.

[00:10:03] Great. Let's let's just focus on this business double down. But that's where it, it just continued to be, you know, as you said, a passion project. For, for many years you were still doing the consulting work. I. And you started building other products as well. So just, just tell me what was going through your head at the time and why you, you sort of left it as this passion project for a while.

[00:10:29] Dean: So, yeah. I, I'm, I'm a builder, so I like to build things. There's nothing nicer than just sitting down with a clean slate and building something. So that entrepreneurial spirit really fuels that, right? It, it really. You know, so OnTheClock was probably the second or third product that I had built the one.

[00:10:51] But right before that was a check drafting solution, like a payment solution. It involves, it's, it's not electronic, it's, it was a little more old school where you end up with a paper check draft. That was one that, that is actually still in existence today and, and still actually somewhat profitable.

[00:11:06] I don't run it anymore. We built a, I built a database like kind of a glorified Excel database type product where customers could go ahead and create these database tables with different field types, you know, maybe phone number, name, that type of stuff. And they might use it for like a contact list or something like that.

[00:11:26] That didn't go too far. So I, I ended up shutting that one down for after a year, a couple years. And then we did a survey very similar to like a survey Monkey, simpler though than it is now, at least, so you could survey people for various things. That was actually up until around five or six years ago and it was, I had given it away for free, so it, I expected at some point to just charge for it.

[00:11:52] But it really, that one I just kind of let stay free for a while and it, without really proper SEO and proper maintenance, if you will, it, it, it just kind of faded off.

[00:12:05] Omer: Yeah. Okay. So let's let's kind of fast forward to 2014 or 2015. Which is around the time that I think you said you hit your first million in a RR so you know, a a, a pretty long time.

[00:12:25] We're talking about a decade to get to that first million. But even at that point, it was still a passion project. You was still doing consulting and, and other stuff, right. So you, you're seeing this business grow, but you know, it's, it, you know, it almost sounds like you're reluctant to. Kind of jumping in with both feet on this, on this business?

[00:12:44] Dean: Yeah. I don't know if it was reluctance so much. You know, I, I tend to have my, my hands in three or four or five different things at a time. So it, it was really just, I saw that it was one of, one of my projects that I had but I saw that it started to really accelerate, right? The, the growth. And it was probably the, it not probably, it was the, the, what would you say?

[00:13:10] I put my most attention on that particular project. So that obviously that's probably why it grew. Right? So it got to the point to right around that 14, 15 time where I just had to make a decision, okay, I can, I can, you know, let this kind of stay accelerating at its current rate or I could really focus on one thing and try to make it awesome.

[00:13:30] So. So that's really the decision. And I was at a point in my career where I just really wanted to focus on one thing. I just wanted to like make one thing really big and and that's, that's why we focused, that's why I focused on that at that point.

[00:13:42] Omer: Yeah, and, and I think especially once you get to the point where you, you've hit a million in a RR with small businesses, we're talking about a, a, a good number of customers.

[00:13:58] Who are gonna need help with onboarding, who are gonna need help with support. There might be bugs. There's, you know, you know, requests for new features and stuff like that. So just letting it just kind of exist organically and it becomes harder and harder. And I think maybe that's probably the situation you were in.

[00:14:18] Was there a we at that point or was it still just you?

[00:14:20] Dean: So, right around 15 my brother Mark, who was also a, who is also a software developer and entrepreneur. He was looking to, to build apps and we didn't have an app at the time OnTheClock. Didn't have an app at the time. And so, you know, at that point I had really started to pivot towards going all in on it.

[00:14:40] And he wanted to build apps and he was kinda looking to go in all in on something too, I says, so I said, well, why don't you come on board, we can both focus on this and you can, you can build the app and, and I'll continue just focusing on, on the website. And so he came in and he actually did the same thing I did.

[00:14:58] He had a consulting company as well, so he, he rehomed all of his clients. I rehomed all of my clients and we really just went all in. And about a year or so after that, we hired we brought on Samantha. She's still with us today. So she's, she's awesome. She's now moved up to customer success manager.

[00:15:19] So that's, that's a really cool thing to see. And from there we just you know, as we scaled, we, we, as we grew, we just kept scaling. We, we hired brought on more people and really continued to build out the product. And that's, that's where we're sitting on now with 22 people and about 18,000 customers.

[00:15:38] Omer: When you and I were talking earlier, you said. That you didn't really wanna hire people, it just seemed like you just had a whole bunch of, you know, negative, you know, kind of thoughts about what that would mean for the business, for you, your time and all that stuff. So just, just tell me what, what was going on there and, and why you wanted to just go alone.

[00:16:04] Dean: Sure, absolutely. So I'm a people person. Yeah. And so it's not anything against people in general, but in the consulting world. I, I worked with people in the, in the front, you know, the, sometimes the CEOs, the owners and such. And then I would also work out, work with people out in the back if it was like a shop environment.

[00:16:24] And I'm friendly, so I got to know everybody. And there was always this like, war going on between management and people, you know, the, you know, the, the you like hourly employees. And I was, I was like, you know, I don't want that, you know, I, I don't. It, it, yeah. I do not all work environments were like that, but all of the, a lot of the ones that I saw were so, I really had to make a decision that when, when we did expand and as we did scale, that I was gonna do my absolute best to not have that environment.

[00:16:57] So yeah, I am a people person people first, you know, I love to see people move up into the right in, in any dimension that they're looking to move that move in that direction. It always had been, but really just had to adjust my hence the quote earlier. Really had to adjust my business philosophy on bringing on a team and made that decision.

[00:17:18] And so far we've been really good. We have an extremely low turnover rate at OnTheClock. And we, we view our support people, we call them our specialists. We view that as an incubator, so you can come in there and, and like I said with Samantha earlier, she started in product support and now she's moved up for customer success.

[00:17:38] So we've had a few of those instances over the years and, and that's really awesome to see.

[00:17:42] Omer: Great. So one of the things I, I wanna clarify is this journey to the first million in a RR, it, you know, people might be listening to this and thinking, okay, Dean built this product. Did a bit of PPC for a month, then SEO kicked in and you know, yes, it took 10 years to get to the first million, but it almost sounded like you weren't really doing that much.

[00:18:12] Like people coming in, signing up and you know, kind of becoming customers and stuff like that. Was it, was it a a difficult thing or, or did you just get lucky and, and you know, the thing started just growing on its own without, you know, a huge amount of effort?

[00:18:31] Dean: No, I did put a lot of effort into it. But it wasn't full-time and, and it was only me for that first 10 or so years.

[00:18:37] You know, being a consultant, I definitely had customers that required my time. Right. So if I had to estimate, I'd say I probably spent you know, maybe 20 hours a week on, OnTheClock. And that was continuing to build out the product, right? So you know, talking to customers, listening to their needs and learning, SEO learning marketing and just learning every other part about running a SaaS company.

[00:19:06] That you have to learn and, and really just continued to build it. So, yeah, it wasn't a hands off by any means. But it, it wasn't a full-time either, so you might call it like a halftime. So that was probably, but I am, I also work really fast, right? So it, it's, you know, even though it was only 20 hours.

[00:19:27] You know, it was still, you know, be when you're just hence the quote again. I was moving fast because I was alone. Right. And I could just veer off and, and, and do these things really quickly.

[00:19:40] Omer: How easy or hard was it to, to sell the product? I mean, you, you know, we, we talked about the first 10 weren't first 10 customers weren't that hard, but.

[00:19:52] It's still a relatively new product. It probably didn't have all the features it does today, and I'm sure there were already incumbents there in the market that maybe you know, these businesses were more familiar with. So what were you doing to, to differentiate yourself and, make that decision for people to choose you an easier one.

[00:20:20] Dean: Sure. So a lot of it I would attribute to learning, marketing and learning, SEO and talking to customers, right? So talking to customers reviewing the, their, their requests, you know, what they're asking for. And then taking that and building it into the product for one but also listening to their pain points.

[00:20:43] And then bringing that into marketing and really just showing them that you know, they have, if they're doing a search for, you know, online time tracking or whatever it is, so as soon as they hit the homepage the idea is for them to say, oh, yeah, that, that is something I'm struggling with. And if I try this product I should, I should, that struggle should be alleviated.

[00:21:06] So, and then. They would try, right? It was free. It was a free trial. Typ typical SaaS type, at least a of our type SaaS product. And they would try it. And if you could get them to an aha moment quickly, meaning they could quickly see, in our case it's seen timecards calculated that was a, a no brainer for them, right?

[00:21:28] So they're like, you know, back then. There wasn't a whole lot of online time tracking systems and anything that was in place was a software based, right? So you have servers and wires and, you know, punch clocks all over. And they didn't do a very good job at it either. And there was a lot of manual calculation where we did it all automatically.

[00:21:46] So as soon as they kind of cut to that aha moment, they, it sold itself basically.

[00:21:51] Omer: I, I think it's interesting that you point out the, the talking about customer pains on the homepage when people arrive there. You know, most of the times you'll see websites and they'll talk about benefits and features and all that stuff, and sometimes the pain gets lost in this somewhere.

[00:22:16] It was not even mentioned anywhere. Why, why did you do that? Why was that important to you to. You know, it almost feels like you know, there was some level of like edu, you know, education going on there. That, or, or was it about, like, I, I again, just kind of take, take us through the thought process in terms of why, why you took that approach.

[00:22:39] Dean: Yeah, so I mean, it's definitely, it's for sure bringing the pain points to the surface. So generally it, it, well, you may be able to affirm this as well. If you are searching the web for something, or the app store, or talking to a friend or whatever it, whatever it is in particular like a, a product, a software product, you probably hit an event in your, in your day or your life where you're like, you know, I, I, I've had too many in our case, say time cards.

[00:23:10] I had had too many bad payroll runs. You know, I am, this is a pain point, right? My employees are getting underpaid, overpaid, so I'm gonna search for an automated solution or I'm spending too much time doing this, right? It, it, it, we calculated it's several minutes per employee per pay period. So you could spend hours a week calculating timecards.

[00:23:31] So that's a, that's an event that happened and you're just fed up with it. So if you can bring that to the surface from a marketing perspective. You, you tell the customer, potential customer that this product solves your problem. So if you make that direct connection, that's really important. The other thing that's really important too, is letting them, letting them know like what your product is.

[00:23:52] We were searching for, this is a few years back to replace our project management software. And I was just helping doing some searching and I found, you know, you type in project management. You know, online or whatever, it's you app store. And and I was finding so many non-pro management softwares.

[00:24:12] It was just amazing. You know, there's, there were these softwares that weren't even close to project management that were, were doing not only SEO but paid PPC as well that we're showing up at the list. So it's also really important to identify what your product is and, and what it does. Like for us, it's employee time tracking, right.

[00:24:33] So, so that's the other element along with the pain points that, that I would definitely have have people look at,

[00:24:38] Omer: You, you also told me earlier that, word of mouth has, has been a, a, a a, you know, a decent driver of, of leads and, and new business. Most of it coming from, from SEO, but, but word of mouth is also important.

[00:24:57] And you, you also mentioned this idea of like the Purple cal, right? That Seth Godin talks about. So. May maybe just explain for people who don't know what the Purple Cow thing is, just explain in very simple terms what that means, and then I want to, I'm trying to understand like how you went about trying to be a purple cow with your product.

[00:25:18] Dean: Sure. So the Purple Cow is a concept by Seth Godin. So he is this is marketing is one of his books. So the concept is, is that, and I will probably. Butcher this, but it, the concept will get out. The concept is, is that, you know, if you're driving up and down a road by a farm every day of your life, there's cows, you stop, you, you don't notice them anymore as you're driving by every day.

[00:25:46] And then when you see a purple cow, you stop, you get out of the car, your kids get out of the car. You're taking pictures, you're taking selfies with it, with the purple cow. You're sending it to your friends, you're putting it on social. So the concept is, is how do you stand out? Right.

[00:26:02] Omer: And I would, I would just add to that, that in the, in the context of, you know, SaaS startup, it's really about how do you make your product outstanding?

[00:26:14] How do you make it unique? Right. And that is often a very difficult question. To answer. Right. So how did you do that? I mean, was it about focusing on unique aspects of the product or features? Or was it about we're gonna, we're gonna just have outstanding, you know, customer service or whatever. What was the first thing you picked to, to kind of become remarkable in this, in this market?

[00:26:44] Dean: So the first thing actually goes back to that original story when I was sitting at the table where they were asking for two things. The pattern I saw was they were looking for an easy and reliable online time tracking system. I'm really good at making things easy. That's what I did as a consultant.

[00:27:01] I could take somebody's idea and make it as easy as as possible. So that was one of the, one of the founding principles that we built into OnTheClock was that it has to be easy. Right? So, and we actually, funny thing, we did a we took all of our customer reviews. Thousands of 'em, and we put 'em in a word cloud generator and right in the middle was easy because everybody was saying easy.

[00:27:26] So I thought that was really cool, but really just making it easy. So, so when you get in there, you just know what to do. It's, it's self-directing to the best of your ability. You don't have things hidden, you know, underneath menus and behind tabs and such, at least the main features. So for us. It was making it easy.

[00:27:46] That was, that's really our probably biggest purple cow.

[00:27:50] Omer: And, and how did you do that? Was this, did you interview customers? Was it looking at usage data? Was it just using your own hunch on how to make software easier? Like how did you figure out how to make it the product easier to use?

[00:28:06] Dean: I think it really goes back to my consulting background.

[00:28:09] You know, I, I I'm a problem solver by. But it's the way I am. So, you know, it's really about the things that you're, that are important to you, putting them in a place that is easy for you to get at. So, you know, for instance even just earlier today my product owner, Steve and I were looking at a form and there was a checkbox there and I was like.

[00:28:36] But 99% of the people won't need that checkbox. So why are we putting it right there? Or, you know, what? If we moved it over here where the 1% do need it or button clicks, right? A fight over one button click and you know, and if you do that a hundred times, you've, you've gotten rid of a hundred button clicks, right?

[00:29:00] So it's, it's things like that and it's just intuition really. Just placement of things on a, on a elements, on a form or on, on the app. You know, making your navigation like in your website or your app. The top level pe top level items, like the main things that people wanna do. I've seen so many products where.

[00:29:23] One of the main things I wanna do is bury two or three menus deep, and it's like really, I mean, think about it for a minute.

[00:29:29] Omer: Yeah. Okay. So, so it was mainly just about your experience of designing software and just, you know, constantly looking at how to make the product easier to use.

[00:29:45] Dean: Correct. And just a lot of intuition, you know, and I use, I'm, I'm, I use technology a lot, so, you know, I'm always scrutinizing products when I'm using 'em.

[00:29:52] So I think all that just builds into that intuition.

[00:29:55] Omer: Did you do anything to, to measure this or get feedback from customers? Like how did you, how did you check the box that say, yeah, we made it easier to use over the last month because we did X, Y, Z?

[00:30:09] Dean: Yeah, I mean, talking to customers definitely helps.

[00:30:11] One classic example, we used some, some analytics tools heat mapping tools in our tool, in our, in our website. And we started noticing this this one really big red spot, you know, heat people were clicking there a lot and it turns out that it, they were clicking on their employee list. You know, we have a concept of an employee list in our system.

[00:30:32] We're employee time tracking, but, or this was early on, we had the employee list. Underneath a configure menu, right? So you had to click configure and then click employees. And you know, I looked at it and I'm like, well, that's two clicks. So we moved the employee to the top level and we eliminated one click.

[00:30:54] And all of a sudden the heat map went there, right? I mean, that's naturally what would happen. So that's one form of, you know, using a tool to do that, a heat mapping tool. You know, the other things we do currently we're using some tools like Hotjar, you know, screen recordings just to watch user behavior.

[00:31:11] It's hard to do that at scale, but you can definitely sit there and watch, you know, a few dozen videos and can get a mental image as to where, you know, if they're sitting there and, and there's a pain point. And a lot of those tools will actually tell you. Where they are detecting pain points. One of 'em I, I thought was very interesting.

[00:31:28] They call it rage clicking. So if you're click, click, click so you don't want that, right? So if you see that, you wanna figure out what's going on and fix it. So the tools help a lot and a lot of it's just like, you know, said, just use using your product and, you know, use it as a customer would use it, not as a developer would use it.

[00:31:42] Omer: We talked about getting to the first million in ARR and SEO being the biggest driver, and then, you know, a couple with word of mouth. Today you are, you, you said you were doing between five and 10 million in ARR.

[00:32:00] Is it still SEO and word of mouth driving growth?

[00:32:04] Dean: Yeah, you know, it, it really is. I mean, we definitely have partner relationships with some of the payroll providers. And so when you have a partnership and, and if you're in their marketplace, you will get customers from there. But the reality is, is that SEO and word of mouth are, are, are, are still our two two big app store a SO as well.

[00:32:25] As well, you know, those, those are really starting to rise up. But those are really our three different, or three, three drivers of, of new signups and, and business.

[00:32:35] Omer: Is, is your bus business like sensitive to Google changes. Like, you know, we, we hear about people doing SEO, Google rolls out, Pando, whatever the, you know, the update is and suddenly next day, you know, traffic has disappeared overnight.

[00:32:55] What, what, what's I. Have you seen those kinds of fluctuations and, and, you know, do you, do you worry that, you know, having just such a dependence on, on SEO kind of gives it like a single point of, you know, potential failure?

[00:33:12] Dean: Yeah, so I think so the whole reason that Google being whomever released these updates is because one of the reasons at least is because people have learned to kind of game the system, right.

[00:33:24] You know, you hear about the black hats, the gray hats. You know, we never tried to really game the system. We just really tried to put out good content and educate our customers. So whether it's blogs or marketing pages so the, we, I, to my knowledge, and we monitor it pretty well, we have never been dinged by any Google updates.

[00:33:44] I think simply because we just focus on producing good content for people. I.

[00:33:48] Omer: You, you mentioned PPC at the beginning, like the first month you said, Hey, you know, did that for a month, got my first customer, or, or a handful before SEO kicked in. What's been your experience since then with using paid ads?

[00:34:03] Dean: We've, we've struggled. So we we, we experimented a little bit on our own probably four or five years ago. You know, not being experts by any means, but the tools are relatively easy to use. And that failed pretty, pretty bad. And then we decided a few years ago to hire a firm, a firm that actually we knew some of their customers and that they served their customers really well, and the customers vouched for them.

[00:34:29] And that, that that agency came in and, you know, there were several people involved and a bit of setup time. But and we spent a pretty good chunk of money. And I, I am not kidding, you almost got. Nothing back. It was, it was amazing to the point to where we kind of went into research mode and we're trying to figure out is, is this fraud?

[00:34:50] Not fraud from the agency, but click, click fraud, you know, or something like that. And it just, it just failed really bad. I don't think it was the agency's fault, but we, we just kind of left that one b. And then we went out on our own a little bit too. Again this was probably a few years before that one or two years before that, and really just said, okay, no, it was actually after that.

[00:35:12] I'm sorry, I'm getting it mixed up. And we tried to do it on our own, a smaller scale, and again, same result. So, you know, we, it just didn't work for us. I think if we threw enough money at it, it would, but for our, for our price point, it doesn't make sense.

[00:35:27] Omer: Got it. So was it, you weren't. Was the problem that you weren't getting enough leads or it was too expensive to get the leads, or kind of a bit of both?

[00:35:40] Dean: So, so what was happening is we, we could see the, you know, in in Google's portal we could see that the clicks happening but the clicks weren't translating to leads or signups for us. That's, that's what we, what we were seeing. So it, it really, it was very difficult. We spent, we had several really smart people that worked with us looking at this, and we could not make heads or tails out of it.

[00:36:05] It was, it was, we had to, had to chalk. And I've actually talked to a few people since then over the last year or two that have indicated that there are, there is, there is some fraud going on out there. Is that not Google or the agencies? It's. It's something else and we're not even sure what drives it.

[00:36:22] It's always money that drives something. Right. But we're not sure exactly what's driving that, I don't, competitors I, we don't know.

[00:36:28] Omer: Yeah, it's kind of interesting because. On, on the one, I mean, it's the SERP, right? So you've got, you've got the resource page and for some reason, organic traffic going there is clicking the link and you're getting healthy lead there.

[00:36:42] But for some reason, the other links on the page, which happen to be paid don't seem to, to convert for you.

[00:36:49] Dean: And, and we know our keywords, we know our, we know what marketing text to put in there. You know, we've been doing it with SEO, the SERP for years. But you do the same thing in paid. And it's like the quality of lead is almost zero.

[00:37:02] Like the, you know, they, they click but they don't do anything. They don't sign up. So it's, it's, it's the strangest thing. I, we, it literally spent. Days trying to figure it out.

[00:37:13] Omer: Yeah. You, you know, often I talk to founders who will say, you know, we tried paid ads and it didn't work. And it was like, well, how long did you try it for?

[00:37:20] And it was like, yeah, a few months or something. But you've tried repeatedly. This wasn't just like a one-off thing that we tried for a month and it didn't work. And you've tried with your own team and external and Yeah. It's kind of fascinating.

[00:37:35] Dean: Yeah. Yeah. It's, and I've heard this story before from other people as well.

[00:37:39] Omer: Okay. So when we started out, we said, you know, you, you ran the business or, or build this product and you were reluctant to hire people. And today you have got you know, a team of what, 22 odd people working on the business. How, how has your perspective changed about hiring people, team building, being a leader?

[00:38:03] Dean: Yeah, so it's, it's really from business perspective, it's really flipped, right? So you need that team to go far, right? So I am in a, in a position now to where I, I don't code anymore. It's been four or five years since I've written code. But, i, I have a team of developers now and they're amazing.

[00:38:25] You know, they, they get us so much done. You know, to have the key people in place is how you go go far, right? So if it was still me just trying to do this, we would not be anywhere where we're at today. It, it, it, it wouldn't even be close. So, you know, there's a synergistic effect with bringing the people on and.

[00:38:47] I really like surrounding myself with people that are smarter than me at their craft. So, you know, marketing you know, we, we want somebody there smarter than, than myself or, or leadership team at the craft. Customer success development heads CTO you know, those, those are people that we're putting into place strategically.

[00:39:09] That are really just going to escalate it. And I just really love watching them, you know, do their work and it's, and then building their teams up too, right? So always escalating people and, and looking to just better their careers, better, their, better their home life to whatever extent we can. And, and culture's a big thing for me.

[00:39:31] So back probably just a little bit after we really started building our team. I had set our values and it, it took about six months. 'cause you know, your values are, you, you don't so much come up with them, you have them, right. It's just a matter of getting them out on paper. And the, the first one is passion for people.

[00:39:52] So it's really just building those people up. And, and one of the other ones is that your work should be meaningful, right? You should go home at the end of the day. Knowing you made a difference and, and feeling good about it. So you, you put those values together and that really builds our culture at work.

[00:40:09] So, you know, we have a, like I said, people describe our, our office, like a family-like atmosphere where, you know, we could, along, we, we have a, a, a little cliche, but we have a Thursday lunch every today we had our Thursday lunch and we order food today. We had barbecue. It was great. And it was also Ken's birthday, one of my star software developers, so he got to choose.

[00:40:32] So he or we, we have the lunch. So that's, that, that lunch isn't really part of the culture, but it's just something we do because we wanna sit and eat together. But, you know, building the, the value, you know, setting the values, building the culture embodying the culture, watching people grow. That is, is helping people grow as well is really a passion of mine, and I go home at the end of the day feeling really, really good about that.

[00:40:56] Omer: Yeah, that's a, that's a complete 180, isn't it, from where you started?

[00:40:59] Dean: Oh, a hundred percent, yes.

[00:41:01] Omer: Okay. 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 received?

[00:41:10] Dean: So, the best advice that I've received, and I probably would give is that have a vision for whatever it's you're trying to do, like literally form it in your head and then once you have that vision, just go after it and don't stop.

[00:41:23] Omer: What book would you recommend to our audience and why?

[00:41:26] Dean: So a more recent book I just read I actually had a book club at work with Nicole on this is Scaling People and it's Claire Hughes.

[00:41:35] She was the CEO/COO of Stripe. And she, she really gives like a playbook of how Stripe grew and scaled over the the last 10 years or so. So that was really awesome. So you get to kind of see inside the company it was entertaining and also very informative.

[00:41:51] Omer: What's one attribute or characteristic in your mind of a successful founder?

[00:41:56] Dean: Sure. It probably goes back to the first question, and that's vision. So if you can't see what you're trying to build and articulate that. Especially if you have a team, like if you can't articulate to your team what you're trying to do you will, it won't happen. So, you know, think about it like all the time.

[00:42:11] Create a vision in your head and, and that will drive you so far.

[00:42:14] Omer: What's your favorite personal productivity tool or habit?

[00:42:18] Dean: Sure. So there's probably four or five favorites, but one of them that I use every day is inbox zero. So it's, it's kinda an older one, but, you know, it really helps me to not have 10,000 emails unread and missing things.

[00:42:31] And it really helps me to make sure that every email gets answered or at least read. So that's really one of my big ones.

[00:42:38] Omer: What's a new or crazy business idea you'd love to pursue if you had the time?

[00:42:42] Dean: Yeah, so project management. At work now we do a lot of projects and we've tried several tools.

[00:42:48] Like I mentioned earlier, I was searching for project management and finding all these tools that weren't project management. But we have actually had some kind of semi joking conversations that. Do you wanna go out and build a project management software because we know how to build it now because we've seen, we've literally used all the, all of the other ones and and found all the flaws, so we think we could build one.

[00:43:07] Omer: What's an interesting or fun fact about you that most people don't know?

[00:43:10] Dean: Yeah, so it probably depends on who you ask, but I am fairly outgoing person. You know, I'll walk up and talk to anybody, but I'm, I really have an introverted side too, so, you know, a lot of people might think I'm extroverted or.

[00:43:23] Leaning towards that way. But I, you know, I definitely like that alone time as well.

[00:43:29] Omer: And finally, what's one of your most important passions outside of your work?

[00:43:33] Dean: Yeah, so it's probably the same as work. It's really just building up family, friends, helping them out. I have three kids love watching them grow.

[00:43:41] And they're still around, so that's, that's fun. So we get to still hang out with them. So really that, that, that would be, its same, pretty much building people up.

[00:43:49] Omer: Awesome. So Dean, thank, thank you so much for joining me and sharing your story of building the business. If people wanna check out OnTheClock, they can go to OnTheClock.com.

[00:43:59] And if folks wanna get in touch with you, what's the best way for them to do that?

[00:44:03] Dean: So for me, probably LinkedIn if you just search for my name, Dean Mathews one T. That is the best way for anybody in the public to get ahold of me.

[00:44:11] Omer: Great. We'll put a link to your LinkedIn profile in the show notes.

[00:44:14] Dean: Great.

[00:44:14] Omer: Awesome. Great. It's been great to chat. Thanks again for making the time and I wish you and the team the best of success.

[00:44:21] Dean: Thank you, Omer. It's been a pleasure. Thank you for the for having me on.

[00:44:24] Omer: My pleasure. All the best. Cheers.

Book Recommendation

The Show Notes