The SaaS Podcast

From Struggling Bootstrapper to $10M+ SaaS CEO – with Ryan Fyfe [294]

From Struggling Bootstrapper to $10M+ SaaS CEO

Ryan Fyfe is the co-founder and COO of Workpuls, an employee monitoring, and time tracking software. Previously, he founded Humanity, an employee scheduling software product.

In 2010, Ryan set out to build better employee scheduling software.

Early in his career, he had worked in the service industry and experienced the pains of scheduling shifts both as an employee and manager. He believed there was an opportunity to build an easier solution. He targeted the lower end of the market and quickly built a basic scheduling solution.

He didn't do customer interviews or much market research.

Instead, he trusted his gut that based on his experience, there was a need for his solution. But getting early customers was disheartening. He went from being excited about how his product was going to help hundreds or maybe even thousands of small businesses to struggling to get even 10 customers.

People seemed interested in his product but always seemed to have an excuse for why they couldn't or weren't ready to pay for it.

And things got worse when Ryan realized that it wasn't working out with his co-founder and decided to buy him out. Suddenly he became a solo founder of a product that he believed in, but one that was clearly struggling to get traction. And now Ryan had to do everything from product, marketing, and sales on his own.

But after a lot of persistence and hard work, he figured out how to sell his product.

He went from having a struggling product that nobody wanted to bootstrap it to $100K ARR. And then after raising VC funding, he went on to grow the business to over $12M ARR, 150 employees, and 40,000 customers (including companies such as Nike, CNN, and Lyft).

In this interview, you'll learn exactly how he did that, what mistakes he made along the way, the lessons he learned, and what he's doing differently with his latest startup.

I hope you enjoy it.

Transcript

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[00:00:00] Omer Khan: Welcome to another episode of The SaaS Podcast. I'm your host Omer Khan. And this is the 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 in this interview, I talked to Ryan Fyfe, the co-founder and COO of Workpuls, an employee monitoring and time tracking software.

[00:00:35] In 2010 Ryan set out to build better employees scheduling software. Early in his career he'd worked in the service industry and experienced the pains of scheduling shifts, both as an employee and manager. He believed there was an opportunity to build an easier solution. He targeted the lower end of the market and quickly built a basic scheduling app. He didn't do any customer interviews or much market research. Instead, he trusted his gut that based on his experience, there was a need for this solution. But getting early customers was disheartening. He went from being excited about how his product was going to help hundreds, or maybe even thousands of small businesses to struggling to get even 10 customers.

[00:01:22] People seemed interested in his product, but always seem to have an excuse for why they couldn't or weren't ready to pay for it. And things got worse when Ryan realized that it wasn't working out with his co-founder and decided to buy him out. Suddenly he became a solo founder of a product that he believed in, but one that was clearly struggling to get traction.

[00:01:47] And now Ryan had to do everything from product marketing and sales on his. But after a lot of persistence and hard work, he eventually figured out how to sell his product. He went from having a struggling product that nobody wanted to bootstrapping it to a hundred K in annual recurring revenue. And then after raising VC funding, he went on to grow to over $12 million in ARR, 150 employees and 40,000 customers, including companies such as Nike, CNN, and Lyft. In this interview, you'll learn exactly how he did that, what mistakes he made along the way, the lessons he learned and what he's doing differently with his latest startup. So I hope you enjoy it.

[00:02:35] Ryan welcome to the show.

[00:02:37] Ryan Fyfe: Thank you so much for having me.

[00:02:39] Omer Khan: So you have a quote, something that inspires or motivates you, or just gets you out of bed everyday that you can share with us?

[00:02:44] Ryan Fyfe: Yeah I do. I used to be a big quote guy and used to have them all around early offices. Everyone works home. So I guess that's not as applicable, but I was looking around or thinking through one now.

[00:02:54] And I do have a quote on my wall. Actually, it's a poster, a metal poster of Harvey Specter from the show Suits if you're familiar and the quote is when you are backed against the wall and break the goddamn thing down. So for me, that's about never giving up. I'm always looking for a solution and not, you know, getting excuses with problems, so awesome.

[00:03:12] Omer Khan: Love it. All right. So we're going to start the story talking about your previous company, Humanity, which you just sold late part of last year. And then we'll, we'll get into what you're doing right now. Why don't you start by just telling us about Humanity? Like what does the product do? Who's it for? What's the main problem that it's helping to solve?

[00:03:35] Ryan Fyfe: Yeah, great just kind of quick comment as it was originally called shift planning in the early days. And that's really the core of what Humanity still does today is around employee scheduling. But if you hear me intermixed, humanity, or shift planning, that's why.

[00:03:50] So my, my background is ever since I was very young, I was working through all sorts of part-time hourly jobs. And so I worked at, you know, retail and then a lot at the end food and beverage, for example, I built the front end back of the house, and that was where kind of the initial seed for the idea came from, was in the restaurant industry.

[00:04:09] There's a lot of shift change. It's all scheduled work. A lot of part-time staff we used to have to phone in to find out when our schedules were. We used to have to, sometimes if we wanted to change a shift, for example. I was an athlete in school and so if I had a track meets or something that would coincide with a prescheduled shift, I would actually have to go into the restaurant, you know, run through the staff list of calling people.

[00:04:31] Oftentimes you would even have to incentivize them by paying them a little bit out of your own pocket, so they would take your shifts so you could keep your job. So very inefficient and that's where the idea of, you know, something that was scheduling suited. It was mobile. It involved, you know, the managers to set the schedule, communicate that easily out to employees, but then also included employees in the process, making it easy for them to set their availability, swap shifts amongst one another et cetera. So that's kind of where things were, were born. And that was around 2010 2000.

[00:05:03] Omer Khan: Right. So what was, what was going on around that time? Like, was it just, you were working in places that weren't using any technology or was there still like, not that many solutions around at the time?

[00:05:19] Ryan Fyfe: Yeah, it's really interesting to think back as even SaaS in 2009, like this is just at the time when kind of smartphone adoption is becoming like mainstream businesses are starting to think about the cloud, but there really wasn't anyone doing that actively.

[00:05:35] And so one of the things that. You know, I first did was kind of go out and look at, okay, who's on the market. Who's doing this now. What are they doing? Well, what aren't they doing well? But the bigger question was like, why, why can't I walk down the street? Or in every single business that I've worked in why are none of them using a tool like this now? And so there was a number of legacy competitors that had done well, but they had a very complex product. And it required, you know, a very like sales and onboarding intense motion. And so that really cornered them into going after bigger chains, for example, like franchises or larger buses.

[00:06:11] And so when I was working at, you know, individual like kind of mom and pop SMBs or retail stores that are like individually managed, things like that, those solutions were just kind of priced out of the market or just too complex to be adopted. So that was, that was kind of a driving point behind really focusing on a lower end. Almost like very small business solution at the beginning to make it super easy to use and, and allow for things like self onboarding.

[00:06:36] Omer Khan: Okay, so, so you you've got the idea. It's come from a personal experience you had previously, how did you get started?

[00:06:44] Ryan Fyfe: So immediately I'm kind of out of high school, I was competing as an athlete. And then that's when I was working through these different jobs kind of part-time jobs. And I started learning about internet marketing. And so that was kind of my initial let's call it foray into, to working online, doing kind of, you know, search engine marketing and things like that. And I did well with that.

[00:07:06] And then it kind of stemmed naturally into product development. And I had a number of product ideas that I had, I was building kind of on the side. And when I initially started thinking about this. Humanity was the first time that I thought kind of away from things like social networking and all the sexy stuff that, you know, my friends would want to use.

[00:07:26] And it was the first time that I thought, okay, there's a real business problem here. People are going to pay money for this. I could see a path to, you know, 10, a hundred customers know that there would be revenues kind of immediately from that. And that was kind of when I got hooked.

[00:07:40] Omer Khan: And what kind of validation did you do? Did you do any market research? Did you start going into restaurants and talking to people like how did you figure out whether there was enough demand and people were willing to pay for.

[00:07:55] Ryan Fyfe: I'm a big believer in trusting your gut. And so I guess I felt the pain on both sides of the house, like kind of as a manager and individual employee, having worked through the place as I did to sort of know the validation was there.

[00:08:07] And I remember walking, like I remember he was so excited about this. Like when I, when I stopped. Building it all out. And like, in my mind, and just walking down the street, you know, you go through a strip mall or like past that past the commercial center and you're like, yep. This business, could you shift planning?

[00:08:23] So could this one, so could, this was one this one, it was just like a blank canvas at the time. And what was I wrong though? Is one of the kind of early mistakes was assuming that just because every business could use the tool that they use. And so there was probably, I would say two to three months of kind of in-person pilots that we tried to run with with different stores.

[00:08:45] That was very demoralizing. They, they, they say they would pick it up. We would come back a week later and you know, they hadn't gotten started yet, or it was time to, to ask them for their credit card, but they wouldn't pay because they needed one more feature. One more feature, one more time. And so that was kind of a frustrating part in the early years then that just kind of pushed the company just to kind of ignore really that, and really just go online early, kind of that lean startup model, just release early, get early adopters in and then build things out that way. And that's when we really hit our stride and had a ton of success.

[00:09:19] Omer Khan: How did you build the product? Was it, did you do that yourself? Do you have a co-founder?

[00:09:25] Ryan Fyfe: I did. Yeah. So I built the product myself. I was kind of developer number one, sales person, number one, all of those, all of that stuff to get it online.

[00:09:33] I did have an early partner as well in the company, but that didn't work out. And so I ended up kind of putting the project on hold. We came to an agreement after a few months for me to buy him out. And that's what allows me to continue going kind of on my own stuff.

[00:09:45] Omer Khan: So what, what, what, what did that first version of the product actually do.

[00:09:49] Ryan Fyfe: First version of the product was super crude, as you can imagine, but I think we did hit a lot of things, right? So the first version of the product, you can kind of imagine it, like, you know, an Excel sheet where you can enter in your staff times. But the beauty of it was that the program had the knowledge of kind of what was behind the cell. So rather than just, you know, numbers that could print out and knew how to do things like send shift reminders to staff eventually allow staff to, to swap their shifts amongst one, another, et cetera. So it was really scheduling focus to start and still was and is, but we also did build out things like a time clock a learning module, a lot of, kind of broader workforce management stuff around the schedule.

[00:10:30] Omer Khan: Okay. So the story so far sounds pretty similar to many other stories that I've heard, you know, you have a founder come up with an idea. They're super excited about it. They get a product built and there's this, there's this kind of just excitement, right? Like you sort of described like walking through the mall and like, yeah, they could use it, they could use it.

[00:10:55] Right. And you're kind of building this, this excitement and this, this kind of vision or this future in your mind. And then you get the product in front of people and it's like crickets either. They don't seem to care about replying to you, or they tell you the product is great, but they don't use it. They have excuses like it needs to do X, Y, Z before we, and it sounds like you went through exactly that, but at that point, many people would sort of just keep doing that and feel like they're hitting the wall and eventually just.

[00:11:27] You know, like that's kind of like the public gets burst, right. It's just like, maybe I was just excited about it, but it's not, there's not a real business opportunity here. So what, what kept you going when you were going through that period when you just felt demoralized and not seeming to get that breakthrough?

[00:11:45] Ryan Fyfe: Yeah. I guess as a founder, you're probably a little bit stubborn and opinionated on where you see a product or market or different things going, and that's what gets you started and hopefully keeps you. But I think you also have to really balance that out with, you know, what the market is telling you.

[00:12:01] And so that was kind of one of the early lessons that I learned is really building that feed loop into the business and kind of into myself as well as kind of like an individual, especially as a first-time founder, like you're your own product, you're trying to push yourself. As the company's growing the same way that your, your company is as it's scaling.

[00:12:19] The actual ironic or I guess ironic, but the, the connection to sort of the change in strategy was really tied to the initial partner that I had in the business. The way that we had thought was best to divide the, the business up and our responsibilities, as you know, Ryan was the product and engineering guy and he was going to be the sales marketing go to market guy.

[00:12:40] And so it was really the two of us kind of bumping heads around that as we just weren't getting the traction that we were looking for. We didn't have a mature product, like you mentioned, and I think when you try to shop a product into a store, most of those people aren't going to be are passionate, early adopters, which you really need to grab a hold, see the vision and help provide you, like help get that feedback loop moving.

[00:13:04] And so it was after we parted ways that I was able to, you know, just quickly launch online the, the first version of the product I actually launched free before I started monetizing, it was able to get a lot of kind of press and traction and early adopters that way. And actually, our first paying customer ended up becoming an investor in the business, which was, which is always a super cool story.

[00:13:23] Omer Khan: Interesting. Yeah. And because I think when people are at that stage, there's, there's like so many unknowns, right. In terms of, is, is it, is it my product? Am I, am I really missing some cool function functionality here? Or are people just telling me that because it'll it's, they can get rid of me by telling me, you know, the product doesn't do this, or am I focusing on the wrong market or is my message not quite right here.

[00:13:52] And that's why they're not paying attention, but it sounds like from what you just said, it, there was definitely some, some things missing in the product. And so how did you figure out what that was because it's easy to come up with like a list of things that you could go and build for the next three years.

[00:14:10] Right. So how did you figure out like this, these are the things that if I get in there, I feel confident I can close some sales.

[00:14:18] Ryan Fyfe: Yeah. So I think you're right. It's easy to, especially if I think for founders it's super easy yeah. To, you know, be a dreamer. You're a product guy, you have a million ideas, some things that your customers are asking for.

[00:14:30] Hopefully a lot of things that they're not, and that's kind of like the vision of. The product and the company are going. I think how you get there though is kind of a, a balance between staying true to your roadmap, but also being very flexible to what the market is telling you. And keep in mind that, you know, when I started this 2009 and then kind of really getting steam in 2010, This was the wild.

[00:14:53] There really wasn't the tool stack or the infrastructure that you'd like founders have today when they're starting something, you know, customer support, software, product, feedback, software, product analytics, revenue, analytics, like all of these, all this tool stack that we have now to just kind of move super quick on our core business, didn't exist back then.

[00:15:13] So. It to be a lot more intentional or collecting that and building those systems up. Whereas now I think, you know, implementing tools, inner calm, or whatever it is can help you keep a very close and tight feedback loop so that you can start making those decisions very early on based on kind of what the market is telling you, whether that's through kind of proactively running AB tests or things that are a little bit more reactionary based on customer feedback, customer requests, those types of things.

[00:15:42] Omer Khan: And, and in the early days, how were you getting that feedback? Was that mostly by, by talking to prospects or, or did you have enough going on online to, to be able to sort of track behavior.

[00:15:59] Ryan Fyfe: Yeah, it was a combination of things. We were lucky that we had very active and kind of vocal customers early on.

[00:16:05] And, and we spent a lot of time harvesting that as well. So we actually implemented if you know, forum software and we had our customers all engaged. The moment you signed up for our product and account was created in this customer community for you. And that's where we would share things like product ideas. We would allow them to provide feedback, request things, and vote on other's ideas and things like that.

[00:16:25] So that was something that's an example of something that was very effective at ensuring that we stayed close to them and their ideas. Yeah.

[00:16:33] Omer Khan: Okay. Yeah. So. You've gone from a founding team to a solo founder. So was it just you, or did you have any help in, in, in those early days? It was

[00:16:43] Ryan Fyfe: just me in terms of the very beginning that I was working closely with the designer actually, who still works at the company, he's worked there longer than I have now.

[00:16:52] And as, as have a number of people, which is super cool. And then the first, the first individuals that I went out to hire was a remote 24 7 support team. I really believed in products that, you know, having an amazing customer experience and they acted as kind of part sales, part success and, and support.

[00:17:11] That kind of ties again, back into, you know, it was super easy for our customers to get in touch with us. And so they did, and that made a very fast feedback loop into, you know, where things were going wrong and what were the types of needs that they have. So it started out that way. And then immediately after getting some support on the customer facing side, I put a job ad out to hire my first engineer.

[00:17:32] And then around them, we ended up building a team, you know, pretty quickly afterwards. So I was able to start stepping back from the product development stuff as well.

[00:17:40] Omer Khan: Now you, you bootstrapped this business to get to your first couple of hundred customers.

[00:17:48] Ryan Fyfe: I did. Yup. The initial product, like I mentioned, came online with essentially like a free freemium model.

[00:17:55] And then after a few months of doing that and getting kind of, I think the confidence to stop charging, we implemented a billing plan where customers were paying again, very, very cheap. I think it's easy as a first-time founder to not have a lot of confidence to ask people for money. I'm seeing that again in our current customer or sorry, my, the second business that I'm part of.

[00:18:15] The kind of need to like say yes, excessively discount and those types of things. So went through all of that the first time before we ended up kind of positioning ourselves as the premium player in the market, which was a fantastic move. We wish we had made it sooner, but yes, after we had reached first few hundred paying customers, wasn't it really fundraising.

[00:18:37] I was following tech crunch and a lot of stuff. And probably like in the back of my mind was dreaming about that or like thought it was the right thing to do. But a fantastic investor actually reached out to me after, you know, seeing some product reviews and some press that we had received. And then that's kind of where I got started on a fundraising pass.

[00:18:54] We raised a very small seed round, especially. 2021 terms. And after that had both, you know, fantastic investor and board member that was able to help kind of guide the rest of the journey.

[00:19:07] Omer Khan: So you, you bootstrap the business up to, yeah, I know we talked about this earlier. You, you, it was kind of a ballpark number, but around 10 K MRR was kind of your estimate. Then you raised the, the seed round. Eventually you, you grew this business to doing what, in terms of revenue?

[00:19:28] Ryan Fyfe: Personally. Yeah, I was I saw the business as CEO through to about 10 million in revenue. And then I handed it off to somebody that's kind of come up from within the team, but to be honest, by the time I handed it off, he was already running the company.

[00:19:42] So it was like, what am I doing here? We had the conversation like you don't need me. And I handed things off about two years ago and that was about a year. Prior to us you know, having an incoming offer and selling the business.

[00:19:55] Yeah. Yeah. And I want to, I want to talk about that because there's w we, we, we had a good chat about that previously, and I think there's this good, good lessons there for a lot of people in terms of being more self-aware.

[00:20:07] But before we get into that, so, okay. So in the early days, you're, you're, you're building the product you're having to do. Basically the marketing is well. And so what, what did you do to get these first couple of a hundred customers? What, what kind of marketing was going on? Yeah,

[00:20:26] I think the first 1,000 are the hardest.

[00:20:28] And I think to get those, you, you, as the founder or the founding team need to be scrappy and do a lot of things that are kind of, non-scalable longer term. And so the stuff that I really focused on at the time was a lot of search engine, organic kind of content marketing. And that's I think, I guess always my first recommendation to companies is, you know, building that online presence.

[00:20:50] It's slow to get the ball moving but it just creates this fantastic foundation later on. And then I think one of the things that actually. Came as a result of me just trying to be out link-building is a lot of the sites that I was trying to build links on at the time were these SaaS review sites.

[00:21:08] And they were just like SaaS business application review sites. And at that time they were just starting themselves. And so they were, you know, they didn't charge me. They maybe had hundreds of listings, not tens of thousands. And they were happy to feature new products that were in new categories. And so that kind of came almost by chance that I was able to get a lot of coverage on a lot of those sites.

[00:21:28] So people that were researching for, I think it's the, the, the number one way people are researching for this stuff now is, you know, through Google search, but also really relying a lot on reviews. Like we all do when they combined. Back then, that was still very early days, you know, dead app G2 crowd, all the cat hair, all these sites were just still quite in their emphasi as well.

[00:21:47] And so that was kind of part of what moved the needle.

[00:21:51] Omer Khan: Do you think those are still a good place to kind of focus on if, if you're you're in the early stages of trying to get traction?

[00:21:58] Ryan Fyfe: You have to, you have to play the game. I, I hate the game personally. I think it's just kind of such a misleading process where you've got.

[00:22:06] You know, these review sites that are kind of putting their hands in both cookie jars, not fully transparent about what's going on, we're paying them. So we rank et cetera, et cetera. I should be careful what I'm saying, but I absolutely do think it is right. If you know, the top like Google is doing this intentionally the, in the top listing page, you'll see kind of for every core product category, they're going to rotate in two or three of their top 10 spots for the top review sites.

[00:22:30] It's almost like two rankings that are happening. One for the organic products themselves. And then the other one is for the ranking sites. And so, you know, three of the top 10 are for, you know, XYZ review website. And you also want to make sure that you're well reviewed on that second site as well. So you definitely have to play in both in both ponds.

[00:22:49] Omer Khan: All right. So, so in terms of SEO, like what, what exactly were you doing there? Was it just like figuring out here's a bunch of keywords that. I'm good at target. And then just making sure that you're optimized, you know, you did the on page optimization for that. Were you doing a bunch of content to create more sort of top of the funnel, you know, blog posts or articles for people? Like what, what, what was the approach that you took?

[00:23:15] Ryan Fyfe: Yeah. So the approach that I took them is very different than what we're taking now or what I could recommend. Now, back then, it was still kind of the wild west where, and I'd actually just come out of, like I mentioned, doing internet marketing prior to this, which was really just SEO, really optimizing for specific words, and then being able to market products or sell ad space after that.

[00:23:35] So I was well-suited for this, I guess, during the early days. And so we were doing kind of some stuff now that would be considered like black hat, like link insertion, link buying, building link wheels, all of that type of stuff that you wouldn't want to do today. And over time, you know, we cleaned and removed all of that.

[00:23:51] But then there was a lot of other stuff that I guess at the time, I didn't really know what it was called, but it was kind of, you know, early PR. So by reaching out to different sites and trying to go for coverage and different things like that. To content and thought leadership. So I was publishing a lot of content myself.

[00:24:07] Every time we would release a new product or we had a new product idea, or we talked kind of about where we thought the employee scheduling space was going and those types of things. And so all of that content itself created just a huge trove of, of keyword dense content that did very well. So.

[00:24:27] Omer Khan: Okay. Great. So you mentioned earlier that, I mean, this stuff does take time to kick in, but focusing on getting started with some type of SEO for most businesses is probably a smart thing to do. Sooner the better.

[00:24:43] Ryan Fyfe: Absolutely. It can be kind of demoralizing, especially when you're starting off. And there's some, you know, entrenched or even just like one or two year old competitors that have had that time to already start their thing going.

[00:24:54] But I think, you know, the, the worst thing you can do is delay. And so what we do is we set, for example, some goals. Now it's just like, well, if we get one new review per week or per month or whatever, that that's that cadence. We know that at least we're not falling behind and that over time we can see those things kind of compounding and they'll, they'll accelerate as the business does as well.

[00:25:14] So it's just setting targets and staying at it. If not, you're never going to catch up and you'll just be constantly falling further behind.

[00:25:20] Omer Khan: So from the point where you started doing the SEO, like roughly, how long did it take before it became your primary driver of new leads?

[00:25:33] Ryan Fyfe: Again, because of the, like, because this was 10 years ago, it was very fast.

[00:25:38] Two to three months, we were ranking quite well. And then we're able to continue to grow and sort of maintain that lead as well as extend outs on a lot of the initial terms that we had. So our best terms were things like employee scheduling, software, online employee scheduling software, you know, very core to the product.

[00:25:55] But then over time, we were also able to rank for lateral products and workforce management, you know, an increasing number of long tail terms and things. That today, that's just not the reality. And so I think it's imperative that you start, but you can't be relying on organic. Within a few months you might be, you know, looking at a year plus before you're going to start kind of seeing those investments payoff.

[00:26:20] Omer Khan: Yeah. Yeah. And I think one of the mistakes I've seen people make is that they start doing SEO and then sort of get some results and then sort of just leave it and move onto something else. I did that.

[00:26:34] Ryan Fyfe: Yeah. Well, I think I thought what I thought you were going to say though, and I've see this way too often with, with other companies that I've been networked with is they almost put it off way too late and they think they need to stay in quote unquote stealth mode and, you know, just have a simple landing page up and they're going to do everything through their pilot group and then go big after that. I'm like, well, why I can't think of many, you know, there's very few use cases where remaining in stealth is a good thing.

[00:27:00] And so the faster that you get that website, that brand, that content and those wheels moving just always, always better. So,

[00:27:08] Omer Khan: yeah. Okay. So you kind of signed to slowly grow there, online funnel to, to attract leads. You'll be focusing on the product and, and listening to the market and, and trying to improve that.

[00:27:24] I'm kind of curious about once you switched from a completely free product and you, you, you added a paid plan. How well or poorly did that do when you, when you got started with that?

[00:27:36] Ryan Fyfe: In one incredibly well, and again, it was one of those things that I had to kind of keep learning at humanity and I'm not doing that again.

[00:27:44] The second time is I was always sort of on the cautious edge. You know, are we charging too much? Do we always need to be like, I always thought we needed to be the most cost effective solution on the markets, all of those types of things, which just kind of came, I think from a lack of confidence or experience and really, and in some cases as well, a lack of understanding of like, what were the most profitable deals and segments that we were in. And it was actually the person that's still running the business today that, that ended up growing up that really introduced me to what is now kind of embarrassing, but the idea of really, really segmenting the business. So, you know, we always segmented leads to go after.

[00:28:26] With our sales team, potentially bigger deals are the ones that were more engaged. So when we really say, when we did the same thing to our customer base in our revenues, it was just eyeopening to think that potentially the majority of our customers were driving a small minority of our revenues, but eating up exponentially more resources and those types of things.

[00:28:47] And so once we, once I was able to see the data, we had the confidence to do a number of things. You know, we just started treating our customers different. We immediately raise pricing again to become one of the most expensive on the market. And we also introduced a price minimum so that we kind of weeded out the very small businesses, you know, three people at a, at a mom and pop shop versus 10 to 20 or multi location or more enterprise, which is where we ended off.

[00:29:13] And I wish I had made those decisions faster and had the confidence to do then.

[00:29:17] Omer Khan: Yeah. Like at what point did you do that? Like, was that in the end of the first year or five years later? Like when did you start doing that?

[00:29:26] Ryan Fyfe: It's five years to later. It was, yeah, it was, it was pretty late stage. I didn't have the finance background.

[00:29:32] I'd sort of over time, started to get a little bit disconnected from even some of our core metrics and things like that as different people started coming in and yeah. Having someone with a finance background and, you know, very analytical sort of cleaned all of that back up, brought a lot of this stuff to light again, so we could see and then start making some of those decisions.

[00:29:50] So it was, I would say, yeah, mid flight, you know, year five or six of the company.

[00:29:55] Omer Khan: So what I'm hearing is you, you basically went through and you said, okay, let's look at all the customers we have let's figure out. How we can put them into different buckets of types of customers. And I dunno how you segmented them, but maybe it was based on things like size of company or location or whatever, and then you were trying to figure out, okay, how much revenue are these people generating? What does it cost to acquire these customers? All that sort of stuff.

[00:30:19] Ryan Fyfe: Essentially. Yes. And I didn't implement this, that was Chris. So hats off to Chris for this cause. It's kind of one of the key things that really helped get the business moving become a lot more efficient and then growing faster and it was implemented.

[00:30:33] He implemented a quad systems. We had quads, one through four, a one being small business that will always stay small business to being medium that has the opportunity to grow, et cetera. And so we kind of had this quadrant system about where we were focusing different types of our resources.

[00:30:49] And at the end, we were really focused on moving up markets going after bigger, more sophisticated deals. And so it was a combination of, you know, which quadrants had the opportunity to expand with us as land and expand was very a very strong motion for us. And so that's where we focused a lot of our client success materials on whereas, or resources on.

[00:31:12] Whereas for, you know, small business, that's always going to stay small. We tried to automate and move as much of that to self-service as possible. And then for him, from a new business perspective, it was really going after the enterprise, which was that, that, that highest quad.

[00:31:25] Omer Khan: And your existing customers that were on kind of not necessarily the, what you wanted to invest in the future, did you grandfather them into the pricing that they were paying or did you increase prices for everyone, including existing customers?

[00:31:40] Ryan Fyfe: So as a policy, we always grandfathered everyone historically. And then I know more recently they have started going back over some of the older customer segments and then increasing pricing as well.

[00:31:52] And especially I think best practices, always grandfather. And then best in classes you don't always, and this is again, a lesson I learned is we, we built a significant amount of products after let's say month one, when the product launched, there was an MVP out there. And I think there's a, there's a certain point where you get the product to finished.

[00:32:11] And you're, you're able to compete in your, your market segment with that baseline version of the products. And so, while I believe that you should grandfather and respect your earliest customers, that doesn't mean you have to give them every product and feature that you release after that. So you can do things like implement pro plans, ad-ons the enterprise tier, those types of things. And that's one thing that we're doing early now. At at work pulse, which we didn't have the opportunity to really do at Humanity, which would have introduced a lot more kind of flywheel effects that we could have got from revenue expansion on our existing customer base.

[00:32:46] Omer Khan: So you've mentioned this briefly, when you said that at some point you were kind of stepping away from the, the CEO type role. And, and I think that you, you and I had a good chat about being kind of more self-aware and getting, I guess, be honest with yourself in terms of where the things that and, you know, the work that you do that energizes you the most, or you're most naturally a good fit for. So what, what happened there and what, what was it that you learned from that experience?

[00:33:23] Ryan Fyfe: Yeah, it ties back in almost all the way to kind of the, like the co-founder followed, which is that I think not everyone's a good founder and the partnership that we had at that time, just wasn't working out in terms of expectations, time commitment.

[00:33:37] And so, you know, it's super risky having like a 50 50 divide when those types of things aren't aligned and there's a lot better and no one ways to, you know, split the pie or those types of models now. But then I think the second thing that you're talking about now is that not every founder is a good operator or someone that's good to scale the business and that was me in a nutshell, I didn't have the experience and, you know, maybe even more importantly, I didn't enjoy it and it, and it showed to the business. So, you know, once things became, once I got a little bit too hands-off I tend to disengage. So I like seeing the pieces kind of seeing them directly and being able to move them around.

[00:34:13] But when I'm working through potentially multiple people that kind of naturally disengaged. And then one of the kind of fatal things with the businesses, I was way too late to hire executives. I didn't know what they looked like. Even once we found them or the board of helped me find them, I didn't know how to manage them.

[00:34:31] And so it was just kind of, you know, a few years of sort of disastrous hiring to kind of get in the, the types of people that we needed to be able to take the business from. Kind of something that worked incredibly well as a startup the first few years, or several years worked very well, great product market fit, very fantastic funnel, but operationally and internally things were a little bit of a mess and I was kind of at the center of that.

[00:34:54] Omer Khan: Yeah, I mean, I think that those, those, those a great insights and that I think it is important too. As I mentioned earlier, like for us all to be more self-aware and to sort of figure out what are the things that, that we do best and then advise us the most and then how we can spend more time there.

[00:35:13] And, and you have a you have a, I guess, a technique or a hack that, you know, use to, to keep yourself more grounded and aware of what's going on, right?

[00:35:24] Ryan Fyfe: Yeah. So, I mean, I'm a, I'm a different person the second time around part of that's just being older, a little bit more mature, having gone through a lot of this, and then I'm in a different role, sort of joining I've joined essentially my longtime good friend, his startup.

[00:35:38] And I feel like my role is there to kind of be the operational component that I was missing on my first startup. And then, so that's really what keeps me going every day, kind of alluding back to that question. Like what wakes you up every day? It's like, well, I'm really there for him as well as being able to be able to do some of these things are kind of have a second run.

[00:35:56] But one of the, one of the tricks that I used early on and what I recommend is at the end. Yeah. It's easy to get lost in the day-to-day problem, solving of a, of a startup. There's always something that is urgent and high priority. It needed to be done yesterday. X customer's gonna sign if you, if you finish this feature, those types of things.

[00:36:14] But it's, if you get lost in that pattern for too long, you lose sight I think on what the bigger picture is and how you build something that's really scalable. And so one of the techniques that I've used is do a weekly recap. And you can build a framework around what that looks like. It's kind of like a weekly journal, I guess.

[00:36:31] So ask yourself questions like. Where did you spend your time? And try to divide it into, you know, meaningful buckets and a few schedule stuff that can become easier. But the ad hoc stuff that can often over encroach on things makes it harder. But, so what did you spend your time? Where did you spend time on things that you didn't enjoy?

[00:36:50] What things did you spend time on now in hindsight had potentially poor business return on investment. What did you spend your time on things that you could have delegated. And if you didn't delegate, why not? Do you not have the person, et cetera. And then how much time did you spend on recruiting and mentoring your staff?

[00:37:09] So there's a number of questions you can sort of build into your framework, but then close it off with like, how am I going to spend my time differently for the week ahead and be a bit more intentional with what trying to schedule what those blocks are. So you can kind of stay in tune and then reflect again and continue to iterate on that.

[00:37:24] Omer Khan: Yeah. Those are great questions. And I think it's just, I guess it's just like kind of like journaling and reflecting. Yeah. Well, I would say even just tracking your time can be a really eye-opening experience. I went through this some time back where. You know, I was really reluctant to track my time.

[00:37:43] It's like, ah, what's, you know, it just feels like a whole bunch of, you know, wasted effort tracking what I did for 15 minutes. But someone had me go through this exercise where it was like, okay, think about like, what are the buckets that you should be spending your time. Okay. Really, to be successful in, in, in your role.

[00:38:00] And how much of your time should you be spending in there in terms of, okay, if it's a strategy piece, maybe I should be spending 20% of my time there, if it's, you know, leading or coaching people or I should be spending X percentage of my time there. And then I went through and track that time for a couple of weeks, you know, against those buckets then I realized, the way that I thought I should be spending my time was completely different to the way I was actually spending my time. And that on its own was really eye opening because if I hadn't gone through that, I would have been like, yeah, of course I'm doing all the right things.

[00:38:32] Ryan Fyfe: For sure. Yeah, no, I've had that same experience and I like to, there is no perfect.

[00:38:37] It's kind of an, a constantly evolving thing. So I'm absolutely still doing the same thing. Now. I can always get better at it. So. That's why we're having some sort of a framework, I think, where you're measuring things or reflecting on them on set milestones just kind of helps you continue to calibrate.

[00:38:53] So, because those things will change over time, you know, as a startup in the early days, you know, fixing problems yourself or being hands-on with stuff is where you do spend the most of your time. But over time that becomes more of a recruiting mentoring, doing a lot of different activities. So there, it has to be an evolving framework.

[00:39:10] Omer Khan: Yeah. Yeah, I agree. So let's talk about the acquisition quickly. So like, how did that come about? Like, did you and the board sort of decided, okay, we're going to go out and find a buyer, or what did you guys get approached? How did that happen?

[00:39:25] Ryan Fyfe: Yeah, so just want to proceed in advance. There's some things that I wish I could talk more about, but we're still kind of in in process with, with kind of a closing and an earn-out period.

[00:39:34] So I'll try to share as much as I can, and maybe there'll be a later opportunity to offer that. Being the, the, for the acquisition of the business did come inbound. And over the years we'd had a number of inbound offers. I think my personal appetite was there to exit the company. I had fully stepped back.

[00:39:52] I had essentially no liquidity leading up to it and that's pretty hard spot to be in after investing 10 years of my life, essentially my entire professional career was all of that value is tied up into a single private stock. And so, you know, learning from that diversification and a lot of things I would have done differently along the way, but the reality was that the business was doing well.

[00:40:14] We had a fantastic operator in place and our core investors didn't want to sell. And so that was I was, I was part of that and agreed, you know, longterm, it would hopefully work out for something a lot better. And then COVID hits and kind of changed a lot of stuff very quickly for everyone, including our segments.

[00:40:32] So we went from having you know, well, a hundred percent of our, the employees that we had on the platform are scheduled and, you know, over week or over month, like 50% less a drop in scheduling. And so the inbound offer came at that time and it, it took us, it was heart wrenching, to be honest, because it's like, well, we think the world's going to bounce back, but what's going to happen if the market stays down like this for, for longer, et cetera.

[00:40:59] And so it was kind of the timing of it's where we ultimately came to the right price, the right the right buyer and things like that, to be able to get the deal done.

[00:41:09] Omer Khan: Okay. Well, we'll, we'll leave it there and, and I'll invite you back sometime in the future. And we'll talk more about that experience.

[00:41:16] So let let's let's go onto your current company Workpuls. So you've been involved with work pretty much from the start, but you sort of, you joined as a late co-founder, right?

[00:41:29] Ryan Fyfe: Yeah. I don't like to consider myself a co-founder my good friend. The founder calls me that. So I guess I'll, I'll take it, I'll take it on here. So the reality is that we've known each other for several years. He actually worked for a short time at humanity. And I became kind of a good friend, a mentor to him. And so was involved with the company for the last several years from that perspective as an advisor and as his friend, really more than anything.

[00:41:53] And then again, when COVID hits their business started taking off. Workpuls started taking off incredibly well. And there was kind of an instant need to inject. I think some operational capacity, some go to market capacity, those types of things. So there was a good fit for me to join full time which I did then, and then also have, have joined now and then let a couple of the previous investing rounds to sort of on both sides of the fence at this time as well, which is a fun experience.

[00:42:20] Omer Khan: Cool. So just tell us about Workpuls. So w what is the product do? Who's it for? What's the main problem it solves?

[00:42:28] Ryan Fyfe: Yeah. So Workpuls is a productivity and analytics tool that helps businesses really understand where their time's going. So I guess I kind of said that I was going to segue that from your last comment around understanding where our individual time is going and it can do that.

[00:42:44] It can help an individual analyze, you know, where are they spending their time on the computer during the day. But really our core customers are larger businesses that were sort of thrown into the mix of having no clue how to manage remote staff or figure out productivity and a remote first or a hybrid hybrid world that COVID us has accelerated.

[00:43:04] And so the core problem that we're helping them with is time and attendance, accurate time and attendance. And then being able to sort of peel back, layers around, understanding when our staff most productive. When did they have the best focus times? Which tools are they using? Which routine processes are they completing?

[00:43:22] And then even things like around staff wellness, you know, our staff working too much from home, or are these things going to lead to burnout? How does work from home compared to work at the office and those types of things?

[00:43:34] Omer Khan: Yeah, no. Cause when I, when I first looked at work, Paul, so I was like, You know, the, the whole idea of like employee monitoring. Like for me, it was like, oh,

[00:43:43] Ryan Fyfe: I know it's hard for me still. Yeah, I know. Yeah.

[00:43:49] Omer Khan: And, and I think that I don't know exactly what's going on with people working remotely, but I do read things where they say, well, people aren't actually more productive remotely. They're just working longer hours. And sometimes people are.

[00:44:06] They feel like, you know, because they're not in the office, they need to be spending more time just doing stuff. Right. So I, it'd be interesting to see cause you know, a lot of startups have been doing remote work for some time. And so they've had many years to figure this stuff out and you know, and still figuring, figuring it out.

[00:44:25] Over the last year it's been like it's been thrown on so many companies that never thought they were going to have a remote workforce anytime soon. And so I'm kind of really curious to know how that plays out, both in terms of running a business, but also for like just people's wellbeing and then kind of mental health and stuff like that.

[00:44:48] So I'm glad you talked about some of that, that, that you're trying to tackle that side of it as well. It's not just about, you know, our people sitting in front of a computer doing stuff.

[00:45:00] Ryan Fyfe: For sure. I think like, like any tool, I guess it can be used for good or for bad. And so, you know, part of why I was hesitant to join at the beginning was, you know, I don't personally agree that we should be, you know, quote unquote spying or trying to catch, you know, people cheating on company time, like stealing time, essentially that element of it.

[00:45:18] And so we've implemented a lot of stuff that I'm actually really proud of, you know, being the, the standing behind staff productivity being able to start and stop what our program is doing and kind of control. To find that balance between company awareness, productivity, analytics, all the cool stuff that we can do in the right way while also standing by staff privacy.

[00:45:39] For example, on the other hand, And, you know, look, I think all businesses are kind of, if I sum it up, we're in the business of providing some product or service, we want to be more efficient, build more of them, et cetera. And human capital is the biggest component that we have around that. And so when we're in the office, there is this, I would say it's almost a false sense.

[00:45:59] Look, I've, I've worked in now, a number of different offices that I've coached that I've, I was the founder of where I've been kind of, I'm proud to see like how unproductive or kind of how much abuse on company time or those types of things is happening. Or even, even if it's not kind of intentional abuse, it's just, for me, I always loved open office spaces, just non-stop distractions.

[00:46:18] And now we've just moved those distractions to, you know, an online chat room, like Slack. It's just kind of nonstop all day long notifications coming from everywhere. And so I think that's where. A tool like Workpuls can really help to analyze that and, and help businesses understand for the first time, whether they're in the office or remote, but especially when they're remote, because like you mentioned, most companies had essentially zero experience with that before the pandemic, and then we're essentially forced to think about it overnight. So,

[00:46:49] Omer Khan: Yeah. Yeah, no, I, I, I think hearing you talk about that, so I think that with a product like this, there's going to be reactions like, like the reaction I had when we started like, wait, it kind of monitors people with spies on people and knowing that I think, you know, haven't got to know you and, and kind of your kind of mindset and mentality around this hopefully tools like this, there's an opportunity to turn them into being of, of some value to do some good as well. But yeah, it still makes me nervous.

[00:47:27] Ryan Fyfe: For sure it does. Yep. And I think the businesses or leaders are going to micromanage their people regardless of whether they use our tool or not. And I think the flip side to this narrative is the ability for both, it's because it's not just like monitoring a staff productivity for the aim of like termination, for example, it's it's okay. Can I understand what my best performers are doing and how can I replicate that? How can I continue driving the business forward? And so we see some of our customers that gamify the products that can clearly measure a week over week, what the performance of the team is.

[00:48:04] They can actually tie that back to real world results, whether that's increasing customer satisfaction and more sales, more, whatever it is. And so that's, I think where the positive is, and the individual is part of that conversation. They can see all of their own data, they can help analyze their time.

[00:48:20] They can also help and, and, and better understand how they can use their time effectively to do better at their job, which I think is ultimately, I'd like to think of what we all want is to be able to, you know, do better and add more value. And so there are definitely, yeah. The positives that we can come from the tool. And there's a lot that we're building into the tool to help kind of encourage those types of behaviors.

[00:48:42] Omer Khan: Awesome. And what kind of, what kind of businesses that are using work pulse? Like we talked about segmentation earlier, so w what have you learned so far about the kinds of companies where this, this sort of product generally resonates more or, or is providing more value?

[00:49:00] Ryan Fyfe: Yeah. So the, one of the first things I did was segmentation. I was like, oh no, not going to get fooled by this one again. And so we cannot our revenues and our customer base, same story as, as Humanity. Roughly 70% of our customers by volume where like 10% of our revenues, but we were treating them from a sales and support experience, the same, et cetera.

[00:49:22] So we've done a lot already around that just in the last few months. So we've automated and then moved to self-service entirely that bottom end of the funnel with very minor kind of impacts to the actual like bottom line in terms of things like conversion rates and retention. So that's been, been super fantastic.

[00:49:39] And then where we're focused on is, is upmarket. Our products really scales. Well, it's got a fantastic user experience, the infrastructure and the security and things are very sound, but one of the unique things is that it, while we're a B2B SaaS, we also support our cloud. So our customers can host in the cloud.

[00:49:58] And so, as you can imagine, we're recording a lot of very sensitive data. And so whether. Enterprise or just because of specific verticals, we allow our customers to actually host and then store all their data on premise. So that's, that's a unique part. So really moving up markets and the types of businesses are, I would say a combination of, you know, very large enterprises like we talked about, they're having to think through remote workforce management and productivity management for the first time. And so that's, that's been very well for us. And then there's been some really interesting things that have happened as well. For example, business process, outsourcing call centers and other strong vertical for us.

[00:50:39] And what we're actually seeing is that our tool is being brought into the BPO a number of times by the end clients, because they want to see kind of how their, the resources that they're paying through this, this intermediary are actually performing and, and kind of, you know, compliance around which tools that they're using.

[00:50:56] So there's a compliance element to working remote as well. You have non-government networks you've potentially have personal devices. Those devices are going to be more prone to having viruses on them, data leaks, all of those types of things. So if you're in any sort of a sensitive business or really any business as well, where patient data, client data, customer, case data, those types of things can be leaked.

[00:51:19] There's a lot of focus around that as well. So ensuring that when people are remote, they're still working quote unquote, safely in terms of the type of data and the tools that they're using.

[00:51:29] Omer Khan: Yeah. All right. Cool. Well yeah, I think we should wrap up there and get onto the lightning round. So I've got seven quickfire questions for you. Just try to answer them as quickly as you can. Ready?

[00:51:43] Ryan Fyfe: All right. Let's do it.

[00:51:45] Omer Khan: What's the best piece of business advice you've ever seen?

[00:51:48] Ryan Fyfe: Follow your guts. So whether that means, you know, evaluating people, I generally know in the first minute, whether someone will be a good hire or not. And so it's just worth kind of making that gut decision and not trying to spend time analyze after and convince yourself otherwise.

[00:52:03] What book would you recommend to our audience?

[00:52:05] The last book I read was Greenlights, which is a fun read and recommended. But the book I would recommend the most is sitting on my desk actually to reread for probably the 10th time on my upcoming time off. And it's Atomic Habits by James Clear.

[00:52:18] Omer Khan: Nice, yeah.

[00:52:19] Ryan Fyfe: Just incredible work, actionable framework for, for building good habits and breaking bad ones.

[00:52:25] Omer Khan: What's one attribute or characteristic in your mind of a successful founder?

[00:52:29] Ryan Fyfe: I think never giving up, grits. One of my favorite posters was in my dad's office, growing up it's stuff, a frog that's being eaten by a Pelican and his hands are coming out of the mouth of the Pelican and he's choking the bird so that I can eat them. And then it's the words are never give up. I love that.

[00:52:46] Omer Khan: What's your favorite personal productivity tool or habit?

[00:52:50] Ryan Fyfe: Coming back, I guess, just to Atomic Habits. So in that book, he aligns so many cool methods. I think just making things easy and inevitable to do so, making them visible, making them easy, not trying to overdo things when you're starting and focusing on building the habits that ultimately changes your behavior versus on the end goal itself. So that habits will help you get there.

[00:53:10] Omer Khan: What's a new or crazy business idea. You'd love to pursue if you had the extra time?

[00:53:15] Ryan Fyfe: I'm working on it right now, it's called StrataSix. And so, you know, with offices in different places, I'm working kind of always from home over the last decade, I've spent a lot of time in hotels and Airbnbs.

[00:53:27] And so the idea is really just around my frustration with the lack of consistent service that you get from a distributed network like AirBnB. So trying to combine kind of a guaranteed level of accommodations and things that are really built for remote work first versus that kind of being an afterthought.

[00:53:46] So that's, that's something I'm actively working on in my side time.

[00:53:49] Omer Khan: Why did I have a feeling you were already working on something else as well?

[00:53:52] Ryan Fyfe: Yeah, it's hard to have focus, but it's kind of a part of a diversification and really a pet project more than something else.

[00:53:59] Omer Khan: What's an interesting and fun fact about you that most people don't know?

[00:54:02] Ryan Fyfe: I spend time in New Zealand growing up.

[00:54:05] Omer Khan: Well, you spent time all over the place, right?

[00:54:10] Ryan Fyfe: I'm everywhere.

[00:54:11] Omer Khan: And, and finally, what's one of your most important passions outside your work?

[00:54:13] Ryan Fyfe: Probably exercise trying to stay in shape. I was a competitive middle-distance runner growing up, kind of a fun back there, I guess, as well. And then now I've taken to cycling, so trying to get out as much as I can.

[00:54:26] Omer Khan: Awesome. All right. So if people want to find out about Humanity, then go to humanity.com. Workpuls is at workpuls that's p-u-l-s-dot-com. And if folks want to get in touch with you, what's the best way for them to do that?

[00:54:44] Ryan Fyfe: LinkedIn would be the best.

[00:54:46] Omer Khan: All right. We'll include a link to your LinkedIn profile in the show notes, and people can say hello from there.

[00:54:53] Great. Well, Ryan, thank you so much for joining me and sharing your story. Congratulations on the decade-long journey with humanity and, and exiting that business. And I wish you all the best of luck with Workpuls and Strata Six.

[00:55:10] Ryan Fyfe: I appreciate that on my end. Thank you so much for having me on the show and hope this was helpful for anyone listening and feel free to reach out like Omer mentioned, so thanks again.

[00:55:19] Omer Khan: Awesome. Thanks a lot. Cheers.

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