Dean Mathews, OnTheClock

From Side Project to $5M+ ARR as a Self-Funded SaaS

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Episode Summary

Dean Mathews ran his self-funded SaaS as a side project for over a decade - spending just 20 hours a week on it while consulting full-time. By the time he went all in, OnTheClock had already crossed $1M in annual recurring revenue.

In this episode, Dean reveals how he validated his product idea without talking to a single customer, why paid advertising completely failed for OnTheClock despite repeated attempts, and how making the product ridiculously easy to use became the ultimate growth engine for a business now generating over $5M ARR with 18,000 customers and zero outside funding.

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, browsing through small business and accounting forums. He noticed a pattern: people were constantly complaining about not being able to find a reliable, easy-to-use time tracking system for their companies.

Dean, who was working as a software consultant at the time, had a lightbulb moment. He thought, "I can build that for them." He spent the next few months building the first version of OnTheClock and launched it in June 2004 while still maintaining his consulting work.

For the next decade, OnTheClock remained Dean's passion project. He dedicated about 20 hours a week to it, squeezing in time between client projects to improve the product and learn about marketing. He never talked directly to prospective customers to validate the idea - instead he relied on forum research, competitor analysis, and simple logic: small businesses with hourly employees have to track time.

Despite the limited attention, the self-funded SaaS grew steadily through SEO and word-of-mouth referrals. By 2015, OnTheClock had hit a major milestone - $1 million in annual recurring revenue. The following year, Dean took the plunge. He handed off his consulting clients and brought his brother Mark on board to develop a mobile app.

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 after seeing toxic management dynamics at consulting clients.

Along the way, Dean faced other hurdles. Paid advertising failed repeatedly - even with an outside agency and significant budget, clicks never translated to signups. He had to learn how to be an effective leader and build a culture he could be proud of.

Today, OnTheClock serves about 18,000 customers. The company generates well beyond $5M in annual recurring revenue as a fully self-funded SaaS with a team of 22 people and zero outside funding.

Topics: Bootstrapping|Content & Inbound Marketing

Key Insight

Dean Mathews grew OnTheClock from a kitchen-table side project to over $5M ARR and 18,000 customers as a self-funded SaaS by relying entirely on SEO and word of mouth - spending just 20 hours a week for the first decade and never using paid advertising successfully.

Key Ideas

OnTheClock reached $1M ARR in 2015 after 10 years as a part-time side project with no outside funding
SEO and word of mouth drove all growth - paid ads failed repeatedly despite hiring an agency and significant spend
Dean validated the idea through forum research and competitor analysis without ever talking to prospective customers
Making the product easy to use became the primary differentiator - customer reviews overwhelmingly cited "easy" as the top word
The team grew from a solo founder to 22 employees after Dean went full-time in 2015-2016

Key Lessons

🚀 Self-funded SaaS can scale with patience and SEO: Dean grew OnTheClock to $1M ARR as a part-time side project over 10 years, relying entirely on organic search and word of mouth rather than paid acquisition or outside funding.
🎯 Validate through forums and competitors, not just customer interviews: Dean never spoke to prospective customers before building OnTheClock. He found demand signals in accounting forums, confirmed competitors existed, and applied logic that hourly employees need time tracking.
🛠️ Make ease of use your self-funded SaaS differentiator: OnTheClock's word cloud of thousands of customer reviews showed "easy" as the dominant word. Dean's consulting background helped him obsess over eliminating clicks, simplifying navigation, and keeping core features visible.
📉 Paid ads may never work at low price points: OnTheClock tried PPC independently and with an agency, spending significant budget both times. Clicks never converted to signups, and the team could not determine why despite extensive investigation.
💰 Lead with pain points, not features, in your marketing: Dean's homepage strategy highlights the specific frustrations visitors are already feeling - bad payroll runs, hours of manual calculations - so they immediately connect the product to their problem.
🤝 Build a hiring culture that overcomes founder reluctance: Dean avoided hiring after seeing toxic dynamics at consulting clients, then designed a "passion for people" value system with low turnover and a support team that doubles as a career incubator.
🧠 Use heat maps and session recordings to find UX friction: OnTheClock discovered users rage-clicking to find the employee list buried under a Configure menu. Moving it to the top level eliminated one click and improved the experience.

Watch the Episode

Chapters

00:00Introduction

02:53Dean's backstory as a longtime listener

04:25What OnTheClock does: time tracking for SMBs

06:07Business size: $5-10M ARR, 18,000 customers, 22 team

08:15Origin story: finding the idea in forums in 2003

09:28Validating without talking to customers

10:47Getting the first 10 paying customers

13:13Free plan and early pricing strategy

14:14Why OnTheClock stayed a passion project for 10 years

16:13Reaching $1M ARR and going full-time

19:57Overcoming reluctance to hire employees

22:08How SEO drove growth from $1M to $5M+ ARR

25:04Making the product easy to use as a differentiator

29:44The Purple Cow concept and word of mouth

33:06Using heat maps and Hotjar for UX improvements

38:17Surviving Google algorithm updates

39:41Why paid advertising repeatedly failed

43:53Building team culture and values

47:30Lightning round

51:05Wrap up

Episode Q&A

How did Dean Mathews validate the idea for OnTheClock without talking to customers?

Dean browsed small business and accounting forums where people complained about unreliable time tracking, surveyed existing competitors to confirm market demand, and applied simple logic that hourly employees need time tracking. He never conducted a single customer interview before building the product.

How did OnTheClock grow to $1M ARR as a self-funded SaaS on just 20 hours a week?

Dean spent roughly 20 hours per week for over 10 years improving the product, learning SEO, and responding to customer needs while maintaining his consulting business full-time. Steady SEO traffic and word-of-mouth referrals compounded over the decade to reach $1M ARR by 2015.

Why did paid advertising fail for OnTheClock despite multiple attempts?

Dean tried PPC on his own, hired an outside agency with a significant budget, and tried again independently - each time clicks never translated to signups. The team spent days investigating and suspected click fraud, but could never identify the root cause.

What self-funded SaaS growth strategy did OnTheClock use instead of paid ads?

OnTheClock relied on three channels: organic SEO, word-of-mouth referrals, and App Store Optimization (ASO). Dean focused on producing helpful content and educating customers rather than gaming search algorithms, which protected the site from Google algorithm updates.

How did Dean Mathews make OnTheClock a "purple cow" in a crowded market?

Dean focused obsessively on making the product easy to use - his consulting background gave him strong UX instincts. When OnTheClock ran thousands of customer reviews through a word cloud generator, "easy" appeared as the most common word, confirming that simplicity was their core differentiator.

What tools did OnTheClock use to improve product usability?

Dean used heat mapping tools to identify where users clicked most and Hotjar screen recordings to watch user behavior. One key insight: employees were clicking under a Configure menu to find the employee list, so they moved it to the top level - eliminating one click and improving the experience.

How did Dean Mathews overcome his reluctance to hire at OnTheClock?

After seeing adversarial management cultures at consulting clients, Dean was initially against hiring. He eventually committed to a "passion for people" value system, built a family-like culture with low turnover, and started viewing the support team as an incubator for promoting from within.

How did OnTheClock's self-funded SaaS approach change after Dean went full-time?

Dean handed off all consulting clients in 2015-2016, brought his brother Mark on board to build a mobile app, and hired their first support person Samantha (now customer success manager). The team grew from 2 to 22, and revenue scaled from $1M to over $5M ARR.

What marketing approach does OnTheClock use on its homepage to convert visitors?

Instead of leading with features and benefits, Dean leads with customer pain points - like bad payroll runs and hours spent manually calculating time cards. The goal is for visitors to immediately see their struggle reflected on the page, then reach an "aha moment" quickly when they try the product and see automatic time card calculations.

Book Recommendations

Scaling People: Tactics for Management and Company Building

by Claire Hughes Johnson

Links

OnTheClock: Website | LinkedIn | X
Dean Mathews: LinkedIn
Omer Khan: LinkedIn | X

Full Transcript

Omer Khan [00:00:09]:
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 talk to Dean Mathews, the founder and CEO of On the Clock and 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.

Omer Khan [00:00:45]:
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 light bulb moment. He thought to himself, you know I can build that for them. Dean spent the next few months building the first version of on the Clock. He launched it in June 2004 while still maintaining his consulting work. For the next decade, on the Clock continued to be Dean's passion project.

Omer Khan [00:01:13]:
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, on the Clock had hit a major milestone, $1 million in annual recurring revenue. 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 on the Clock. Focusing full time on the business accelerated growth, but it also brought new challenges.

Omer Khan [00:01:50]:
Dean had to shift from being a hands on developer to to leading a team, something he was initially reluctant to do. Along the way, Dean faced other hurdles. Paid advertising didn't work for them and he had to learn how to become an effective leader, which was difficult for him early on. But he persevered. Today, on the clock serves about 18,000 customers. The company generates well beyond 5 million 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.

Omer Khan [00:02:21]:
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 on the Clock as a side project for over a decade before going all in How Dean overcame his initial reluctance to hire employees and eventually built a strong team culture. Why Dean believes making your product easy to use can be a key differentiator in a competitive market and how Dean transitioned from a solo founder to a team leader and the lessons he's learned along the way.

Omer Khan [00:02:53]:
So I hope you enjoy it. Dean, welcome to the show.

Dean Mathews [00:02:58]:
Thank you, Omer, for having me. Now, I wanted to say I've been a longtime listener. I actually looked at my podcast just a couple of weeks ago 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 was the first episode that I listened to you. It was episode 119, so. And I also want to say congrats. I looked today and I saw you had 400 episodes. That's a big deal. So congrats.

Omer Khan [00:03:25]:
Thank you. Awesome. So you've been around for a while and I think 2016 was about the time that you went like, that's when you shifted. Right. Went all into the business just a

Dean Mathews [00:03:37]:
little before that, like the 15ish 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 on the clock and in our trajectory. So thank you for that.

Omer Khan [00:03:58]:
Awesome. You made my day. Thank you.

Dean Mathews [00:04:00]:
No, you're very welcome.

Omer Khan [00:04:01]:
Do you have a favorite quote, something that inspires or motivates you that you can share with us?

Dean Mathews [00:04:06]:
I do, I do. I was actually looking the other night for the source of this. I couldn't find it. But it's if you want to go fast, go alone. If you want to 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.

Omer Khan [00:04:25]:
Yeah, 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 the journey you've taken. So tell us about on the clock. What does the product do, who's it for, and what's the main problem you're helping to solve?

Dean Mathews [00:04:43]:
So ontheclock is 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. 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 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 time cards that could be sent over to your payroll provider so your employees can get paid.

Dean Mathews [00:05:22]:
We do have some additional features. Like I mentioned, the geo GPS and geo Fencing. 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 allotments and improvements for the employees as well. Quite a few options there. We do automatic overtime calculations as well. So that's a really great feature for. Especially if somebody's doing it manually. You know, that's a lot of work and a lot of errors as well. So.

Omer Khan [00:05:53]:
So typically, like, how big are the. Your. How big is your average customer?

Dean Mathews [00:05:59]:
Sure. We service SMBs, mostly the S's. It's in that below 20, 25 range is really our sweet spot.

Omer Khan [00:06:07]:
25 employees or less.

Dean Mathews [00:06:10]:
But that's. We definitely have accounts that have hundreds and even some accounts that have. I think the highest count is right around three to 4,000 employees.

Omer Khan [00:06:18]:
And give us a sense of the size of the business. Where are you in terms of revenue, number of customers, size of team, that stuff?

Dean Mathews [00:06:24]:
Sure. So we are. We're 22 team members right now. So 22 of us run on the clock. Revenue is. We don't disclose the exact number, but it's between 5 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. Great.

Omer Khan [00:06:44]:
And the business is bootstrapped. You've never raised money, correct?

Dean Mathews [00:06:48]:
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 myself.

Omer Khan [00:07:06]:
So I think you launched the product on the clock. I think it was like 2004, but it. It sort of came, 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?

Dean Mathews [00:07:29]:
Correct. Yeah, right. In that 1516 era, it got to the point to where it was. At that point it was profitable. 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 write various software for customers, custom software. And right about that time, it was just like, you know, if we're going to do something with this, now's the time. And I rehomed all my customers.

Dean Mathews [00:08:04]:
There was a couple other small businesses that I was working with that I went ahead and moved Those off and really put 99% of my effort into on the clock.

Omer Khan [00:08:15]:
Great. Okay, so first of all, let's go back to 2003, 2004. Where did the idea for this product come from?

Dean Mathews [00:08:27]:
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 and accounting forums. You remember those? They're still around actually a lot, but. And I was noticing this 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 can build that for them.

Dean Mathews [00:09:02]:
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 first version out. So that would have been. We actually just celebrated our 20th anniversary here just last month. So that would have been right around June of 2004.

Omer Khan [00:09:28]:
Okay. So most developers, if they get excited about an idea, they often jump to building the product and defer talking to customers later. How did you approach this? Did you do the same?

Dean Mathews [00:09:51]:
Pretty much the same thing. I did validate though. I surveyed competition to see what the competition was out there or potential competition because 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's 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 also just using logic. Right. So small businesses that have hourly employees have to track time.

Dean Mathews [00:10:27]:
So it, those three elements really went into it. And even back then, you know, I said it was, it is a, it was a passion project. It was almost like if it didn't work, it wasn't the end of the world. I wasn't going to dump millions of dollars into was my time, which, you know, is valuable, but it would have only been my time.

Omer Khan [00:10:47]:
Okay, so a few months, you got the product built. How long did it take you to find the first customer?

Dean Mathews [00:10:55]:
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 funny, funny story, feral hair is they signed up with us within the first month. They are still with us. So they do hair replacement. I believe they're down in Florida, and they're still with us, so they've been paying us for 20 years. It's pretty awesome.

Omer Khan [00:11:26]:
Wow. You said we had to do some ppc. Was there a we, or was it just you at that point?

Dean Mathews [00:11:35]:
There was an I've morphed into the we scenario because there is a we. There's been a we now for a lot of years. So it was I.

Omer Khan [00:11:44]:
All right. And then. So first customer in the first month. What about the first 10?

Dean Mathews [00:11:49]:
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. Signups are different than somebody adopting or converting over to a paying customer. That would have happened roughly within the first, probably two months. We had the first 10.

Omer Khan [00:12:14]:
And where were these people coming from? Was this a little ppc?

Dean Mathews [00:12:19]:
So we did PPC for about a month, and then SEO started kicking in. So they started just doing Google searches or whatever search engine they used back then.

Omer Khan [00:12:30]:
Yeah, 2004, when SEO was a little bit different to today.

Dean Mathews [00:12:37]:
Yes, very different. It was a lot simpler back then.

Omer Khan [00:12:40]:
Yeah. Okay, great. So you've got some SEO traffic, some organic search traffic. You're getting these signups and getting to that first 10. Didn't take that long.

Dean Mathews [00:12:54]:
Yeah, two, three months maybe at most.

Omer Khan [00:12:56]:
So for many founders, that's a great sign that basically strangers are coming along and they are signing up. And you were charging people. Right. This wasn't like a free plan or something like that. People are actually coming in and paying.

Dean Mathews [00:13:13]:
We did have a 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 that as your business grows, you use this for, you know, a year or two, and when you hit that third employee, then you start paying. So but those first 10 customers, I would have called the paying customers.

Omer Khan [00:13:36]:
So again, so I think that's a great sign, right? I mean, for many founders, you can take them much longer to get those first 10 customers. So great signal. It almost feels like, okay, you've validated the idea, found problem solution, fit, got the first 10 customers that we all talk about. Great. Let's. Let's just focus on this business. Double down. But that's where it just continued to be, as you said, a passion project for many years. You were still doing the consulting work, and you started building other products as well.

Omer Khan [00:14:14]:
So just tell me what was going through your head at the time and

Dean Mathews [00:14:17]:
why

Omer Khan [00:14:19]:
you sort of left it as this passion project for a while.

Dean Mathews [00:14:22]:
So yeah, 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 really, you know, so on the clock was probably the second or third product that I had built. The one right before that was a check drafting solution, like a payment solution. It involves. It's not electronic. It was a little more old school where you end up with a paper check draft.

Dean Mathews [00:14:58]:
That was one that is actually still in existence today and still actually somewhat profitable. I don't run it anymore. I built a database, kind of a glorified Excel database type product where customers could go ahead and create these database tables with different field types, maybe phone number name, that type of stuff, and they might use it for like a contact list or something like that. That didn't go too far. So I ended up shutting that one down for after a year, a couple of years.

Dean Mathews [00:15:36]:
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 I expected at some point to just charge for it. 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 just kind of faded off.

Omer Khan [00:16:13]:
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 ARR. So a pretty long time. We're talking about a decade to get to that first million. But even at that point it was still a passion project. You were still doing consulting and other stuff.

Dean Mathews [00:16:43]:
Right.

Omer Khan [00:16:43]:
So you're seeing this business grow, but you know, it's. It, you know, it almost sounds like you were reluctant to kind of jump in with both feet on this, on this business.

Dean Mathews [00:16:53]:
Yeah, I don't know if it was reluctance so much. You know, I tend to have my, my hands in three or four or five different things at a time. So it was really just. I saw that it was one of. One of the. My projects that I had, but I saw that it started to really accelerate. Right. The, the growth. And it was probably the. Not probably it was the, the. What would you say? I put my most attention on that particular project. So that obviously that's probably why it grew. Right.

Dean Mathews [00:17:30]:
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. 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.

Dean Mathews [00:17:55]:
That's why I focused on that at that point.

Omer Khan [00:17:56]:
Yeah, and I think especially once you get to the point where you. You've hit a million in ARR with small businesses. We're talking about a good number of customers who are going to need help with onboarding, who are going to need help with support. There might be bugs. There's, 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. Was there a we at that point or was it still just you?

Dean Mathews [00:18:35]:
So right around 15, my brother Mark, who was also a. Who is also a software developer and entrepreneur, he was looking to build apps. And we didn't have an app at the time on the clock. Didn't have an app at the time. And so at that point, I had really started to pivot towards going all in on it. And he wanted to build apps and he was kind of looking to go all in on something too. So I said, well, why don't you come on board?

Dean Mathews [00:19:03]:
We can both focus on this and you can build the app and I'll continue just focusing on the website. And so he came in and he actually did the same thing I did. He had a consulting company as well. So 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 brought on Samantha. She's still with us today, so she's awesome. She's now moved up to customer success manager. So that's a really cool thing to see.

Dean Mathews [00:19:41]:
And from there we just, as we scaled, as we grew, we just kept scaling, we hired, brought on more people and really continued to build out the product. And that's where we're sitting on now, with 22 people and about 18,000 customers.

Omer Khan [00:19:57]:
When you and I were talking earlier, you said that you didn't really want to hire people. It just seemed like you just had A whole bunch of negative 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.

Dean Mathews [00:20:23]:
Sure, absolutely. So I'm a people person. You know, it's. So it's not anything against people in general, but in the consulting world, 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 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 like hourly employees.

Dean Mathews [00:20:56]:
And I was, I was like, you know, I don't want that. You know, I don't. It. I do. Not all work environments were like that, but all of, 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 going to do my absolute best to not have that environment. So I am a people person. People first. I love to see people move up into the right in any dimension that they're looking to move in that direction.

Dean Mathews [00:21:30]:
It always happened, but really just had to adjust my, hence the quote earlier, really had to adjust my biggest business philosophy on bringing on a team and made that decision. And so far we've been really good. We have an extremely low turnover rate at on the clock 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 like I said with Samantha earlier, she started in product support and, and now she's moved up to customer success.

Dean Mathews [00:22:04]:
So we've had a few of those instances over the years and that's really awesome to see.

Omer Khan [00:22:08]:
Great. So one of the things I want to clarify is this journey to the first million in ARR. 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 yes, it took 10 years to get to the first million, but it almost sounded like you weren't really doing that much, like people coming in, signing up and kind of becoming customers and stuff like that.

Omer Khan [00:22:47]:
Was it a difficult thing or did you just get lucky and the thing started just growing on its own without huge amount of effort?

Dean Mathews [00:22:59]:
No, I did put a lot of effort into it, but it wasn't full time and it was only me for that first 10 or so years, 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 the clock. And that was continuing to build out the product. Right.

Dean Mathews [00:23:28]:
So talking to customers, listening to their needs and learning SEO, learning marketing and just learning every other part about running a SaaS company that you have to learn and really just continue to build it. So yeah, it wasn't a hands off by any means. Uh, but it, it wasn't a full time either. So you might call it like a halftime. So that was probably. But I'm, I also work really fast. Right. So it, it's, you know, even though, though it was only 20 hours, you know, it was still, you know, be.

Dean Mathews [00:24:06]:
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.

Omer Khan [00:24:19]:
How easy or hard was it to sell the product? I mean, we talked about the first 10 weren't, first 10 customers weren't that hard. But 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 you know, make that decision for people to choose you an easier one.

Dean Mathews [00:25:04]:
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 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 and then bringing that into marketing and really just showing them that, you know, they have, if they're doing a search for online time tracking or whatever it is.

Dean Mathews [00:25:40]:
So as soon as they hit the homepage, the idea is for them to say, oh yeah, that is something I'm struggling with and if I try this product, that struggle should be alleviated. And then they would try. Right. It was a free trial, typical SaaS type product, at least 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 seeing time cards calculated. That was a no brainer for them. Right.

Dean Mathews [00:26:19]:
So they're like, yeah, 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 had 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. So as soon as they kind of got to that aha moment they, it sold itself basically.

Omer Khan [00:26:43]:
I think it's interesting that you point out 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 is not even mentioned anywhere. Why did you do that? Why was that important to you to. You know, it almost feels like

Dean Mathews [00:27:24]:
there

Omer Khan [00:27:24]:
was some level of education going on there or was it about. Again, just take us through the thought process in terms of why you took that approach.

Dean Mathews [00:27:35]:
Yeah, so it's for sure bringing the pain points to the surface. So generally you may be able to affirm this as well. If you are searching the web for, for something or the app store or talking to a friend or whatever, whatever it is in particular like a product, a software product, you probably hit an event in your day or your life where you're like, you know, I've had too many, in our case, say time cards. I had had too many bad payroll runs. You know, I'm. This is a pain point. Right.

Dean Mathews [00:28:14]:
My employees are getting underpaid, overpaid. So I'm going to search for an automated solution or I'm spending too much time doing this. Right. We calculated it's several minutes per employee per pay period. So you could spend hours a week calculating time cards. 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 or potential customer that this product solves your problem. So if you make that direct connection, that's really important.

Dean Mathews [00:28:48]:
The other thing that's really important too is letting them, letting them know like what your product is. 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 is, app store and, and I was finding so many non project management softwares, it was just amazing.

Dean Mathews [00:29:16]:
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 were 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. So that's the other element, along with the pain points that I would definitely have people look at.

Omer Khan [00:29:44]:
You also told me earlier that word of mouth has been a decent driver of leads and new business, most of it coming from SEO. But word of mouth is also important. And you also mentioned this idea of like the purple cow. Right. That Seth Godin talks about. So 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 try and understand, like how you went about trying to be a purple cow with your product.

Dean Mathews [00:30:26]:
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 that. And I will probably butcher this, but the concept will get out.

Dean Mathews [00:30:44]:
The concept is that if you're driving up and down a road by a farm every day of your life, there's cows, you stop, you don't notice them anymore as you're driving by every day, and then we 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.

Omer Khan [00:31:14]:
And I would, I would just add to that, that in the, in the context of, you know, SAS startup, it's really about how do you make your product outstanding? How do you make it unique? And that is often a very difficult question to answer. So how did you do that? Was it about focusing on unique aspects of the product or features? Or was it about, we're going to, we're going to just have outstanding, you know, customer service or whatever. What was the first thing you picked to.

Omer Khan [00:31:52]:
To kind of become remarkable in this, in this market?

Dean Mathews [00:31:56]:
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. I could take somebody's idea and make it as easy as possible. So that was one of the founding principles that we built into on the clock, was it has to be easy. Right. So, and we actually, funny thing, we did a.

Dean Mathews [00:32:31]:
We took all of our customer reviews, thousands of them, and we put them in a word cloud generator and right in the middle was easy because everybody was saying easy. So I thought that was really cool. But really just making it easy so when you get in there, you just know what to do. It's self directing to the best of your ability. You don't have things hidden underneath menus and behind tabs and such, at least the main features. So for us it was making it easy. That was, that's really our probably biggest purple cow.

Omer Khan [00:33:06]:
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 the product easier to use?

Dean Mathews [00:33:23]:
I think it really goes back to my consulting background. You know, I, I'm a problem solver by just 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, but 99% of the people won't need that checkbox, so why are we putting it right there?

Dean Mathews [00:34:04]:
Or what if we moved it over here where the 1% do need it or button clicks, a fight over one button click. And if you do that 100 times, you've gotten rid of 100 button clicks. Right. So it's things like that and it's just intuition really, just placement of things, elements on a form or on the app, you know, making your navigation like on your website or your app. The top level, top level items, like the main things that people want to do.

Dean Mathews [00:34:49]:
I've seen so many products where one of the main things I want to do is bury two or three menus deep. And it's like really, I mean, think about it for a minute.

Omer Khan [00:34:58]:
Yeah, okay. So it was mainly just about your experience of designing software and just constantly looking at how to make the product easier to use.

Dean Mathews [00:35:14]:
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 them. So I think all that just builds into that intuition.

Omer Khan [00:35:23]:
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 xyz?

Dean Mathews [00:35:37]:
Yeah, I mean Talking to customers definitely helps. One classic example, we used some analytics tools, heat mapping tools in our website, and we started noticing this one really big red spot. People were clicking there a lot, and it turns out that they were clicking on their employee list. We have a concept of an employee list in our system. We're employee time tracking. But this was early on. We had the employee list underneath a configure menu, right? So you had to click configure and then click employees.

Dean Mathews [00:36:16]:
And 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. 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 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.

Dean Mathews [00:36:47]:
It's hard to do that at scale, but you can definitely sit there and watch, you know, a few dozen videos and get a mental image as to where, you know, if they're sitting there and there's a pain point. And a lot of those tools will actually tell you where they are detecting pain points. One of them I thought was very interesting. They call it rage clicking. So if you click, click, click. So you don't want that, right? So if you see that, you want to figure out what's going on and fix it.

Dean Mathews [00:37:12]:
So the tools help a lot. And a lot of it's just like, you know, said, just using your product and, you know, using it as a customer would use it, not as a developer would use it.

Omer Khan [00:37:20]:
We talked about getting to the first million in ARR and SEO being the biggest driver. And then coupled with word of mouth today you said you were doing between 5 and 10 million in ARR. And is it still SEO and word of mouth driving growth?

Dean Mathews [00:37:42]:
Yeah, it really is. I mean, we definitely have some partner relationships with some of the payroll providers. And so when you have a partnership and if you're in their marketplace, you will get customers from there. But the reality is that SEO and word of mouth are still are too big. App Store ASO as well as well, those are really starting to rise up. But those are really our three different or three drivers of new signups in business.

Omer Khan [00:38:17]:
Is your business, like, sensitive to Google changes? Like, you know, we hear about people doing SEO, Google rolls out Panda or whatever the, you know, the update is, and suddenly next day, you know, traffic has disappeared overnight. Have you seen those kinds of fluctuations. And do you worry that having just such a dependence on SEO kind of gives it like a single point of potential failure?

Dean Mathews [00:38:58]:
Yeah. So the whole reason that Google, Bing, whomever released these updates is because one of the reasons at least, is because people have learned to game the system. Right. 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 to my knowledge, and we monitor it pretty well, we have never been dinged by any Google updates.

Dean Mathews [00:39:36]:
I think simply because we just focus on producing good content for people.

Omer Khan [00:39:41]:
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 a handful before SEO kicked in. What's been your experience since then with using paid ads?

Dean Mathews [00:39:56]:
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'd served their customers really well and the customers vouched for them. And that agency came in and, you know, there were several people involved and a bit of setup time, but.

Dean Mathews [00:40:35]:
And we spent a pretty good chunk of money. And I'm not kidding, you almost got nothing back. It was amazing. To the point to where we kind of went into research mode and we're trying to figure out is this fraud, not fraud from the agency, but click fraud or something like that. And it just failed really bad. I don't think it was the agency's fault, but we just kind of left that one be. And then we went out on our own a little bit too.

Dean Mathews [00:41:08]:
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, I'm sorry, I'm getting them mixed up. And we tried to do it on our own, a smaller scale, and again, same result. So, you know, it just didn't work for us. I think if we threw enough money at it, it would, but for our price point, it doesn't make sense.

Omer Khan [00:41:32]:
Got it. So was the problem that you weren't getting enough leads or it was too expensive to get the leads or kind

Dean Mathews [00:41:43]:
of a bit of both. So what was happening is we could see the, you know, 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 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. Was, it was, we had to, had to chalk.

Dean Mathews [00:42:18]:
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. It's not, not Google or the agencies. It's, it's something else and we're not even sure what drives it. It's always money that drives something. Right. But we're not sure exactly what's driving that. Competitors. I, we don't know.

Omer Khan [00:42:40]:
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 results page and for some reason organic traffic going there is clicking the link and you're getting healthy lead there. But for some reason the other links on the page which happen to be paid, don't seem to convert for you.

Dean Mathews [00:43:01]:
And we know our keywords, we know what marketing text to put in there. 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. Like, yeah, they click but they don't do anything, they don't sign up. So it's, it's, it's the strangest thing. We literally spent days trying to figure it out.

Omer Khan [00:43:27]:
Yeah. 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

Dean Mathews [00:43:33]:
did you try it for?

Omer Khan [00:43:33]:
And it was like, yeah, a few months or something. But you 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, so fascinating.

Dean Mathews [00:43:49]:
Yeah, yeah, it's. And I've heard the story before from other people as well.

Omer Khan [00:43:53]:
Okay. So when we started out, we said, you know, you ran the business or built this product and you were reluctant to hire people. And today you have got a team of what, 22 odd people working on the business. How has your perspective changed about hiring people, team building, being a leader?

Dean Mathews [00:44:18]:
Yeah, so it's really, from business perspective, it's really flipped. Right. So you need that Team to go far, right. So I'm in a position now to where, yeah, I don't code anymore. It's been four or five years since I've written code. But I have a team of developers now and they're amazing. You know, they get 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's.

Dean Mathews [00:44:59]:
It wouldn't even be close. So, you know, there's a synergistic effect with bringing the people on. And I really like surrounding myself with people that are smarter than me at their craft. So, you know, marketing, you know, we want somebody there smarter than myself or leadership team at the craft, customer success, development heads, cto, you know, those, those are people that we're putting into place strategically 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?

Dean Mathews [00:45:41]:
So always escalating people and, and looking to just better their careers, better their, better their home life to whatever extent we can. And culture's a big thing for me. So back probably just a little bit after we really started building our team, I had set our values and it took about six months because your values are, you don't so much come up with them, you have them, it's just a matter of getting them out on paper. And the first one is passion for people. So it's really just building those people up.

Dean Mathews [00:46:25]:
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 feeling good about it. So you put those values together and that really builds our culture at work. So we have, like I said, people describe our, our office like a family like atmosphere where, you know, we get along. We have 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.

Dean Mathews [00:46:57]:
And it was also Ken's birthday. One of my star software developers. So he got to choose. So he or we have the lunch. So that's. That lunch isn't really part of the culture, but it's just something we do because we want to sit and eat together. But you know, building 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.

Omer Khan [00:47:30]:
Yeah, that's a. That's a complete 180, isn't it, from where you started?

Dean Mathews [00:47:33]:
Oh, 100%, yes.

Omer Khan [00:47:35]:
Okay, we should wrap up. Let's get on to 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?

Dean Mathews [00:47:46]:
So the best advice that I've received and I probably would give is that have a vision for whatever it is 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.

Omer Khan [00:47:58]:
What book would you recommend to our audience and why?

Dean Mathews [00:48:01]:
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. She was the COO of Stripe and she really gives like a playbook of how Stripe grew and scaled over the last ten 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.

Omer Khan [00:48:30]:
What's one attribute or characteristic in your mind of a successful founder?

Dean Mathews [00:48:34]:
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, it won't happen. So, you know, think about it like all the time. Create a vision in your head and that will drive you.

Omer Khan [00:48:54]:
So far, what's your favorite personal productivity tool or habit?

Dean Mathews [00:48:58]:
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 kind of an older one, but, you know, it really helps me to not have 10,000 emails unread and missing things. 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.

Omer Khan [00:49:20]:
What's a new or crazy business idea you'd love to pursue if you had the time?

Dean Mathews [00:49:24]:
Yeah. So project management at work. Now, we do a lot of projects and we've tried several tools. 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 want to 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 of the other ones and found all the flaws. So we think we could build one.

Omer Khan [00:49:51]:
What's an interesting or fun fact about you that most people don't know?

Dean Mathews [00:49:54]:
Yeah, so it probably depends on who you ask. But I am fairly outgoing person. I'll walk up and talk to anybody. But I really have an introverted side too. So a lot of people might think I'm extroverted or leaning towards that way. But I definitely like that alone time as well.

Omer Khan [00:50:15]:
And finally, what's one of your most important passions outside of your work?

Dean Mathews [00:50:18]:
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 and. And they're still around, so that's fun. So we get to still hang out with them. So really that would be the same. Pretty much building people up.

Omer Khan [00:50:37]:
Awesome. So, Dean, thank you so much for joining me and sharing your story of building the business. If people want to check out on the clock, they can go to ontheclock.com and if folks want to get in touch with you, what's the best way for them to do that?

Dean Mathews [00:50:51]:
So for me, probably LinkedIn, if you just search for my name, Dean Mathews 1T. That is the best way for anybody in the public to get ahold of me.

Omer Khan [00:51:00]:
Great. We'll put a link to your LinkedIn profile in the show notes.

Dean Mathews [00:51:04]:
Great.

Omer Khan [00:51:04]:
Awesome.

Dean Mathews [00:51:05]:
Great.

Omer Khan [00:51:05]:
It's been great to chat. Thanks again for making the time and I wish you and the team the best of success.

Dean Mathews [00:51:12]:
Thank you, Omer. It's been a pleasure. Thank you for having me on.

Omer Khan [00:51:15]:
My pleasure. All the best. Cheers.

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