47 Insights / Podcast  / Ep. 18: How Checkfront Started Marketing with Jason Morehouse
Jason Morehouse, Checkfront

Ep. 18: How Checkfront Started Marketing with Jason Morehouse

SaaS Marketing Insights Episode 18: Jason Morehouse, Checkfront

In 2010 Jason Morehouse and his fellow Co-Founder Grant Jurgeneit started moonlighting on an idea for an online booking system. They had no money to spend on marketing so they concentrated on understanding customers’ needs. If he could go back and do it all again, what would Jason do differently?

Editor: breandanmcghee@gmail.com

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Episode 18 Transcript

Paul: Hello, and welcome to SaaS Marketing Insights, the show where we ask SaaS founders, CEOs, marketers and investors about the lessons they’ve learned in their quest to grow their companies.

My name is Paul Stephenson, and I’m founder and CEO of SAS marketing agency 47 insights. On today’s show, I have an interview with Jason Morehouse, Co-founder and CEO of Checkfront. Hope you enjoy it.

Hi, i’m with Jason Morehouse, from Checkfront and today, this is the first part of a two part conversation with both Jason, who’s co founder and CEO and Angela, who is your marketing manager, Angela is on holiday at the moment so we’re going to film her later and then stitch it together.

Jason: Do the magic.

Paul: So if anybody doesn’t know anything about Checkfront, what’s your kind of elevator pitch? What do you tell them?

Jason:  Well they should know. Yeah, so we’re an online booking system for tours, activities is kind of where we spend most of our time. So whale watching in the inner harbour, bungee jumping, city tours, that’s really how we started was those small local tours. So we really run… effectively run their business in the background. So we process all the bookings, their payments, analytics, integrate into all their marketing software, accounting software. So we’re really the backend system for those tour activity… kind of experience based businesses.

Paul: And when you say for them, you mean, you know, these businesses are? global, worldwide?

Jason: Yeah. So we’re in 120 odd countries of active. I mean, primarily the US, Canada, Australia, New Zealand, UK, those are the biggest markets for us, but we’ve got them in Dubai and Portugal, Italy, Iceland.

Paul: Fantastic. So take me back to you know, how you guys got started, how Checkfront got started, what was the? The journey? Where did it come from?

Jason: Yeah, so I mean, I’ve been… most of my experiences is in ecommerce effectively. Before that, my co founder kind of had a enterprise sales background and we wanted to do something but we really found the need from the consumer side of it. We had two small families, each of us… and we were frustrated when we would go to book, whatever it was a ski trip or some small activity and we were constantly filling out email forms or literally having to mail checks. So we knew that there was a need, especially in the small business side, because the was large enterprise software at that point, it was lots of on premise. So the old, clunky software. So we we built out a small prototype, we found one customer that we knew, and built out a little prototype forum, we were still working day jobs. There was some interest and traction there and kind of left it on, we left it for free, might have had a lead a week…

Paul: So how long did that go on… that gestation period.

Jason: That was far too long. So it was probably a year and again, it was moonlit. Then the product was poor… it was not great. There was no support there. The support box was my inbox. There was no documentation but people would come in, they would use it and then really the accelerator was when we started to build some integrations into it.

Paul: So when did you… just for the sake of accuaracy… when did you guys get started?

Jason: So 2010. It was still moonlit really, 2011, 2012 was when we started charging for it so we could make some money off of it. You know, added a staff member or two. It was a lot of education early on.

Paul: Wow, so you just scratched your own itch, created this thing, just to see if it would fly and it just slowly gathered momentum?

Jason: That’s right

Paul: On its own accord or…? How did anybody… did you do any marketing start off with?

Jason: No marketing, per se? I mean… I guess you could consider it Growth Hacking. That’s kind of a goofy term but there was no budget, there was no money because nobody’s paying us. So it was a lot of early link building, building those integrations, which ended up really accelerating the company. The WordPress one was a big one. So that was one we deployed, 30 lines of code and then went to bed and in the morning, my inbox was full of really angry customers who didn’t know how to use the plugin. But there was a market there, validated. At that point we did kind of rethink it and say, all right, there’s something here. Obviously, we have to make it better and fix it and probably bring some people to support it and build it out. And then really took that approach for another couple of years, just… both on both the sides of our go to market, our marketing and really the product.

Paul: So at what point did you guys leave your day jobs? At what point did this… did you go all in? Like this is serious now.

Jason: Yeah, so it was a bit of progression. So at that point, I was contracting. So I kept cutting back the contracts so that I cover the mortgage. And then at one point… it was still a big stretch for probably about a year to get to a point where there was enough revenue to cover the basic essentials. 2012 was really the year I think, where we started to see a business and unlike probably what you might see today with a great company vision and this lofty business plan. This was a very organic process where we knew there was opportunity. It wasn’t… it didn’t end up where we were initially kind of thinking about… it was much bigger. But through, you know, those three, four years, we started to see that there was an emerging market right. So there was an early business case for it, but it just wasn’t ready so it was literally waiting for a couple of years.

Paul: Wow. So you were slightly ahead of the game?

Jason: Probably a couple years ahead, because there was a lot of education still around cloud, right. And so small businesses, were still installing their software using Microsoft Office system, CD ROMs and whatnot, which really kind of ages the company a bit… and myself. But that changed over time, as we know and SaaS is not novelty anymore.

Paul: So tell me a bit more about those… just because I’m intrigued. Those early growth hacking tactics that you employed. This was before growth hacking was even a term.

Jason: We invented it.

Paul: Haha.

Jason: I mean, there was… we struggled to kind of find our identity. In the early days, we were effectively kind of a booking system for everything. Our use cases were fairly close to where we are now. But in the early days, our marketing was very just ‘Hey, if you have a service that you need to sell, and we’re we’re option for you’. Which even today, it’s an eclectic group of customers, there’s still, you know, a wide range of verticals that use us and ones that we don’t necessarily focus on from a marketing lens. So it took that year of customers coming in and putting pricing on and increasing the pricing and figuring out who are the ones that would actually pay and stick around. So starting at $9, you know, going from that actually helped us build the business.

Paul: Yeah, separate the wheat from the chaff, you know, the serious people from…

Jason: We didn’t want to build a passive product. And so the ones that were angry to pay $9 a month, bless their hearts, there’s lots of services for them. But we figured that we couldn’t build a sustainable business on $9 a month for people using it for, you know, a dog walking service or something.

Paul: That’s the interesting thing about, you know, what you said about WordPress, people still think WordPress is being this, like, free for all where, you know, people don’t want to instal or use a plugin, unless it’s free or use a service unless it’s free. And you actually broke that mould, you actually created something that was a paid for SaaS service that had a WordPress plugin, as a way of going viral, if you like or a way of, you know, getting the message out there. But then you found a segment within that that would actually pay and, you know, even to this day, when you look at… you know, the typical WordPress user the impression people get is, ‘these guys won’t pay for anything’.

Jason: Yeah. Yeah, I mean, the… and again, our early target was the SMBs. But the fact that we… the value add, which is we’re going to run your business for you like convincing me to pay $100 a month or $200 a month, versus maybe some of the free stuff you’ll get is not overly difficult. You can get a booking system and WordPress that cost you nothing but they tap out really quickly.

Paul: And you welcome people to use that and try it…

Jason: Yeah, it is… you know, if it works for you. You probably don’t need us.

So yeah, there was a, it was a real progression and learning experience for us to understand all of the components of the business, I mean, the product… we’ve been very product focused throughout and have been lucky enough to have a lot of solid organic growth that we’ve been able to generate, whether it’s a partner channel, or an early referral programme, we always had great organic traffic through search engines, there was not a lot of competition, whereas now there’s a tonne. And after we built our WordPress integration, there was no… we were the only booking system in there paid. There was 15, probably by the end of the year.

Paul: Right okay. That’s… that must have been frustrating for you to keep up with that. But you know, it’s like anything, people see a market opportunity and jump in and you know, some people hang around, some people are in and out. The WordPress, plugin directories is full of corpses, there are alot of dead buckets in there, people who’ve tried different things.

So it started off as the two of you rumbling along for a couple years. And then… so who was your first hire? And what role is it first hire?

Jason: Support So we… going way back… I worked in a technical support team answering like Windows 95.

Paul: You poor sole.

Jason: But I’ve seen how much support really changes the product. So we didn’t have all the answers as to what we were building effectively. And we needed that early feedback from our customers, prospects, whatever… angry people that didn’t like the platform. As to why and why. Because in our space, it’s, it’s complicated, because unlike a shopping cart like Shopify, you’re selling t shirts, you’re selling coffee mugs that are kind of the same whereas we’ll have a rafting operator that runs a business one way and the next one is completely different. So we had to figure out and get the input segment of the customers we didn’t want to build for. And then really…

Paul: Build in a lot of flexibility as well.

Jason: We did Yeah, yeah. I mean, it bites us sometimes. But… so the support team was four or five people before we ever had a second developer.

Paul: Wow.

Jason:  So we wanted all that, that feedback, good and bad.

Paul: So at what point did you get to the stage where you thought, we need to hire a marketer, we need some full time marketing help?

Jason: Early on, but again, we carried on, we do as best effort for probably far too long, I think we got complacent with the generous organic traffic that we were getting, and it was enough to continue to build the product out. So probably a year or two earlier, we should really have put some more effort into it. So we actually brought on a marketing manager 20… i’m going to mess up the dates… in 2015, I think. And her experiences is really in kind of funnel management analysts all that so that that worked out well, she ended up actually moving into product. So she’s our Director of Product now. Angela came in and picked up from there and also was, you know… we were just like here…

Paul:  Thank goodness… someone, haha.

Jason: Yeah I was… I remember she was rather stressed out for those first few months, but there was a lot. And again, we knew there was opportunity there. And we really wanted somebody to kind of own it and take that momentum and continue to build on it. The the big thing for us was brand awareness that was early on, because we were seeing smaller, fractionally smaller competitors highlighted in press and industry news as these emerging companies, while we were in some cases, you know, 100 times bigger than them and we were never mentioned. Because again, we were relient on a very organic… which is fine. it really got us to where we were. But when Angela came in, it was really about defining the brand. You know, the usual kind of things like paid marketing, and an optimising all the leads that were coming in. Marketing automation, all those things didn’t exist. We didn’t have any marketing software, it was Google Analytics, and like MailChimp, or something which we we set out like one newsletter every 24 months… It was good.

Paul:  There’s some companies still doing that.

Jason: Yeah. Then… and so Angela, basically built up the team along with Mark who heads up the kind of ‘go to market’. And, you know, I think it’s five, six people now, which is, drastically bigger than it must be for

Paul: Great. So as a business, you know, you started off with booking… you’ve grown in the last 10 years enormously. So how many folks are you now?

Jason: Staff or customers?

Paul: Both ish?

Jason: Full time… it’s sort of 65 people, with a couple more starting this week?

Paul: Wow. I think I met someone in the elevator that was starting.

Jason: Yeah. On two floors now. Customers… Yeah: 4300, 4400. So it’s been good. It’s been a nice steady pace right. So we were maybe 40 people this time last year. I guess that’s a bit but It’s not crazy. We just hit those different inflexion points and things change.

Paul: And so, you know, from growing this business from scratch, wearing a developer hat, a support hat, the marketing hat? Sounds like you probably worn all hats…

You know, you’ve obviously had to grow your CEO role. And you know, what you do? A lot. So, you know, you’re not from a marketing’s perspective, you’ve got Angela, Mark, and a whole team. Now responsible for that, but kind of looking back from your high position now.

What would you have done differently? If you could have… especially in terms of marketing, I mean, there’s probably a lot of things that you change, right. But particularly with regard to marketing.

Jason: Yeah, I can… I could write a book. I mean, sales and marketing should have come online earlier.

It’s difficult when you’re a bootstrap business, right? Because you have a finite amount of capital, usally none to a little and we just continued to see growth without it. Right? Which really should be an indicator that that’s where you start to tumble down. And, you know, I think that was probably in hindsight, we could have gone a bit earlier, sales didn’t come online, you know… till probably a bit later, and we’ve gone up market. So those SMEs are still a huge part of our business, but so are the kind of bigger and multi-location high-volume businesses, and that’s kind of where sales focuses for the most part. Marketing… we should have just scaled it earlier. In SaaS, it’s really easy to measure, for the most part, right, versus, you know, versus other traditional companies. And when it relates to marketing, so, you know, when something’s working, you can change it really quickly.

And if we could have acquired a small amount of capital to start to just test out and then just double down on the things that are, are kind of working.

Paul: And so… thinking of the various different marketing leavers. You know, content marketing, organic, paid, social, you know, the whole range of different things. Would you have done anything differently? Would you have gone harder on something or softer?

Jason: Yeah, I think… I think paid acquisition, especially then it was actually really cheap.

Paul: Haha, you’re kicking yourself that you didn’t do it when it was cheap.

Jason: It’s costing us, you know, 6x as much now for that. So… and again, it’s very easily measured, to put some capital into that. We always have an all those channels, social paid social, you know, PPC, content marketing has been best effort. But we did when we were early on in, we were doing PPC, and we were seeing results. But we never pushed it. We never pushed it and put somebody in to kind of own it. Like early on. And so I think that was probably a misstep, amongst many.

Paul:  Well, it’s, it’s been fantastic talking to you. I don’t know how long we’ve spoken for. But I’m conscious of your time, because you’re a very busy man. And we’re going to do another bit with Angela, so she can bring us up to date with the other half of the storey I guess, dealing with, running a marketing department in a in a SaaS business that’s, that’s really growing now.

Jason: Well yeah, with Angela, it’s building a marketing department, right. She came at an interesting time where there, there was traction, there was revenue, and the team might have been 25 or something. So there was an emerging business there with a you know, very minimal kind of footprint when it came to marketing and it was her responsibility to learn a lot I think, and move in from kind of doing the day to day to to building a team, which is actually the hardest part. And it’s hard to step away at least in my experience to, to going from from doing those things day to day because they are gratifying… you’re accomplishing things.

Paul: Yeah, you feel like you’ve achieved something.

Jason: Yeah. Versus you know, you sometimes have a whole week where you think what did I achieve, because all you’re doing is you know, kind of working with your team. So I look forward to that segment.

Paul:  Jason, thank you very much for your time. Really appreciate it.

Jason: Yeah.

Paul: I hope you enjoyed my conversation with Jason. For more info on the Checkfront, please visit www.Checkfront.com. For more info about this show and to get our links to iTunes, Google Play SoundCloud, Stitcher and YouTube, check out www.47insights.com. And if you have any sass marketing insights that you’d like to share on the show, please get in touch. Until next time.

Transcribed by https://otter.ai


Founder & CEO

Paul is Founder & CEO of 47 Insights. He has been helping software and publishing subscription companies with growth strategies since 1995.

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