Marketing Your SaaS System in Today’s Economy – with Greg Head

Greg Head and Matt Wolach discuss how sales and marketing need to work together

Episode Transcript:

Welcome to Saas-Story in The Making. The podcast that features the people who made the software world what it is today and the leaders who are shaping the future of technology. Here’s your host, Matt Wolach.

Matt Wolach: Thank you. Welcome to SaaS-Story in the Making. This is Matt, your host, and I am really excited today to be joined by Greg Head. Greg, welcome.

Greg Head: Hi, Matt. Great to be here.

Matt: Thank you. A little bit about Greg. Greg is the founder and CEO of Selling Point. That’s a firm that helps companies successfully grow from startup to scale up. In his past, he’s also been the former CMO of Infusion Soft, which is now key, and that he was really instrumental in their heyday. He was the one who really helped launch them and helped them become superpower. So he took them from 15 million to 100 million, and it was really impressive. I knew him back then. And they were doing some great stuff. Co-founder of SalesLogix, as well. Many of you have probably heard of that one. That was the first mid market CRM and he was part of the team that took it public in 1999. So that’s big deal for sure. And a lot of people know about Greg’s list as well. Greg Head is the creator, founder and an operator of Greg’s List, and that’s a curated and thorough list of software companies for some specific US markets. So Greg, thank you so much for joining.

Greg: Yeah, happy to be here. And it’s fun, Matt. I don’t know when we first met. Maybe it was 2008 or so? Where we in the early stages of WebPT. I know that’s when we first met but was that 2008 or 2009? I don’t remember. It’s alright, because apparently, I’m a little older than you guys, than you are.

Matt: Yeah. But we’re all, we’re all enjoying the years though, so it doesn’t matter. But yes, so for everybody out there, Greg and I have known each other for quite a while. Really, really helpful and instrumental in helping us design in our marketing program, helping a split WebPT, which many people know WebPT went on to become very, very successful, fortunately. But Greg was part of the early team helping it happen and help grow. So he’s somebody I’ve looked up to for a very long time and really happy to have him on the program. But, Greg, tell me about what you’re doing now with Scaling Point.

Greg: Yeah, Scaling Point is my company I’ve got a small team and it’s a marketing strategy consulting and workshop firm. So all those lessons I’ve learned about the deeper side of the growth game, there’s always the tactical side and that changes by the year and all that. But the things that haven’t changed in the growth game and for all types of businesses are right under all the same principles that are under marketing strategy. That when you time to business strategy and product and line them all up, it makes all the tactics work. So I work with early stage founders, typically with their businesses between one and 10 million, sometimes a little bit less, not very often, a little bit more, that are going from the turn from startup that early run out onto the field and experiment and sell something and all that. And scale, which is a totally different sport. You know, $5 million to $10 million companies involved. It’s just a different sport. And you’ve been through that, yourself, you know, it’s just a totally different game and the early day. So making that turn is where everybody gets stuck and there’s something around there the product market fit before scale, and all of that that’s kind of related. But the tactical, I call it the myth of more, just doing more, you know, raising money, adding more salespeople, emailing harder, is not going to get you to be the big company that you want to be.

So I do work with the crazy founders that say, you know, there’s 10 of us, someday this will be huge and we’ll change the way things work. And again, you and I both have been part of those and you know, that’s possible and that’s how you do it. But the sport changes along the way. So I’m there for the early stage Gary, when it’s really hard and tricky.

Matt: Yeah, that’s great. And that’s something that I’m sure is certainly needed. Because usually at early stages, the team is limited in their breadth of skill set. They haven’t specialized quite yet. So how do you keep up with those changes? I mean, you’ve been a part of the marketing world and led a lot of innovation. How do you keep up with all that?

Greg: Well, there are the changes in tactics. And we’re just now in the middle, you know, in April of 2020, in the middle of the COVID 19 crisis, and we see tactics changing by the week. How we’re reaching people and habits changing and so forth. Over the years and the phases of the tactics have changed a lot. What hasn’t changed is the fundamentals of the strategy. Who you serve? What you ,you know… The category game of what is your thing and how do you play that? Those things are attached to human brains of buyers and markets and founders and all of that then I didn’t invent those laws of nature, you know, the strategic foundations, but it’s exactly what I used to help WebPT. When the guy said we need a new website and we went through the process and got all the way down to the bottom and came back up and made the right decisions to help it grow. And, you know, I’m happy to have contributed to your team at WebPT and everybody else and also to the Infusion Soft team. I didn’t do it personally. I was one of many people that helped in a major growth spurt over there.

Matt: Certainly some good teams but I know that your efforts and input was huge in those efforts, in both of those companies so that is very awesome. One thing that’s also awesome is Greg’s list. In fact, I was talking with a friend in Australia last week and he’s in the SaaS game as well. And you know, it’s funny he said, hey, I saw this company or this thing Greg’s list. Have you ever heard that? I’m like, well, as it happens to be one of my old guys from way back. How did you get the idea? Yeah, it’s something that people know about worldwide, which is very cool. And how did you get the idea for Greg’s list?

Greg: Well, you know, like anything. It came out of necessity. When I left Infusion Soft, four years ago, 2016, I just started helping, you know, founders who I knew including Brad Jannenga, one of the founders WebPT, his next venture and then he said, go help that guy. So I spent time at the whiteboards, you know, and long lunches and coffees of meetings with all the software founders that I knew in Phoenix and then elsewhere. Everybody had the same problem, we’ve gotten a software but not enough customers revenue and growth, which is the modern software problem. And so, you know, it’s harder to make software in the 90s than it was to find markets. Now it’s the complete opposite. But I just started helping everybody. I discovered there’s a lot more going on in Phoenix in the software market app. I’ve been there almost 20 years already and helped grow two companies from founding early to 100 million in revenue. And so I just put myself in the middle of it, helped founders as much as I could and just ran around town and quickly got to about 100 companies on my little Evernote list. And so people were following me around, can you show me that list? Can we can you connect me that guy? And who do you know, right, and all that stuff that I’m doing. And finally I said, you know, I think I’d just make a list of everybody and people can find each other. I was introducing founders to themselves across town, and, you know, so I just published the list and it started like, literally on my way website, my spreadsheet turned in HTML, I posted a list. Now there’s 543 active real software companies on Greg’s list, Phoenix, which was way bigger than anybody thought. So that was part of the magic trick.

Matt: No kidding. Just in Phoenix?

Greg: Just in Phoenix. And these are real companies. These aren’t just like some bought or automated thing or download. You go anywhere else, you’re not going to see the, you’re just going to see that 10%, the funded ones like WebPT. The big ones that everybody knows, you don’t see 90% of the software companies in most towns. And so I published the list and, you know, revealed it and so and now everybody can access. It was just a pet project I did as a volunteer thing. Added about 10 companies every month took away the ones that died. And, you know, put my name on it because people said if Greg knows, it’s a real company. And it was built so these people could get the resources. The founders there’s no funding, there’s no talent. You can’t do it here in Phoenix. It’s not really a software town. And I heard this from everybody. I was like, who started [Hmm], I don’t have that experience. And the talent and the investors were saying, where is everybody? So it’s about getting resources to the crazy people doing the hard job of growing these companies, and they’re the people doing it. So it is about the entrepreneurs and the, you know, the crazy ones who create the next wave, because that’s where all this stuff comes from. There’s always a crazy person at the beginning of anything that exists now, and they didn’t die in between, yeah, and making a big.

Matt: Well, that’s awesome. I know. It’s a cool thing to hear that it’s, you know, world renowned is very awesome. So kudos on that.

Greg: Yeah, I appreciate that. And we’re still curating and I have some help now with my team and some sponsors, and we’re in Dallas and Salt Lake City and Chicago and we’re expanding to more cities. So it’s a useful resource that’s, you know, finding its way. And it’s not global domination and everything, you know, within that crowd, it’s just really useful and become a popular resource. It’s really become one of the bricks in the wall of the tech ecosystem in Phoenix. And nobody else was going to do. I said, I’ll do it. And there it is.

Matt: Well, that’s awesome. And I want to ask you, because I know you’re well versed in many areas, but really your focus is in marketing and your expertise, and I focus on sales myself. So how do you see an ideal sales and marketing relationship?

Greg: Well, there’s something on the tactical front line of B2B SaaS software companies and how do they play the tension between and the roles between sales and marketing, which, you know, that’s always a little bit of a challenge or a lot of one. But I tend to go deeper on the other side, I’d say they’re both trying to save solve the same problem, especially when you talk about all kinds of companies, not just B2B SaaS software companies. Because you could take it all the way to sales, a sale, from I don’t know about you to I’m buying your product with just marketing, which tends to be more consumer products. Or you could do all of that with a just a salesperson, no website, no emails, no air cover, you know, that kind of thing. So, that process, it’s two sides of the same coin. And it always work best when sales and marketing leaders are trying to solve the same overall problem, because there’s a lot of overlap in between. In particular B2B SaaS software sales, marketing is who gets the leads and sales is who closes them, but there’s more synergy than that. And marketing doesn’t stop when you’re talking to a salesperson. One way to distinguish it is, marketing is what you say the same to everybody and sales is the custom conversation that depends on who you’re talking to, and what industry they’re in and so forth. So it always works best when sales and marketing have the bigger goal and you’re not just dividing to either side of the net, saying you get leads and you close deals and go. Right, and compete each other. You gotta work together on that. So that’s how I’ve always approached it.

Matt: That’s great. I love that philosophy as well of keeping sales and marketing in sync and keeping them together. But what can founders do to kind of foster that? Well, one is for the founders to understand the sales and marketing game. Because a lot of founders are technical and they say I guess I need marketing to get me some leads and I guess I need sales to get to flow those leads. And it’s a little more, there’s a deeper game going on there that they need to be students of. And so generally speaking, the simple thing of give me some sales, give me some leads, give me some closers and run and then they compete with each other tends to run into problems. So there’s a little more nuance. If you divide the goals completely separately, yes, they’re all aligned in the funnel math. But if you don’t create some overlap in their goals, where they actually have to kind of help each other be successful, it’s generally not going to work very well or for very long.

Matt: Yeah, I love what you’re saying, people being aligned on a single higher goal, seems to work well. I’ve seen that happen. I’ve seen that work well so I would totally agree.

Greg: Yeah, marketing people tend not to understand the sales game so well. And the salespeople really have no idea about the marketing machine. So if you can keep them, there’s a lot of naiveté and all that kind of stuff. So there’s a lot of education that has to happen and alignment. Because there’s a lot going on in between, especially at a long sales cycle, enterprise software companies, between when somebody first finds out about you, and when they first buy and get on boarded, and so forth. So there’s a lot of steps, it’s really complicated so there’s has to be a lot of alignment to see what’s going on. That’s actually one of the reasons that I… You know, I say I do marketing, but I’ve done just as much sales and product and everything else, and run software businesses. But the marketing side of it touches all of those and is the least well understood. So, generally speaking, in the game. So I like to deal with bigger levels of marketing, which for smaller companies, the marketing strategy is the business strategy. You go after what you are, and so forth, it’s not any different. And how you make decisions about those is the biggest lever on your marketing.

One example is, when Heidi and Brad were starting the WebPT company, physical therapy software. Right, that was the vision, she was a physical therapist, still is. But you remember Chiropractic and massage and OTs and hospitals and we could sell to everybody. And the first strategic, like, technically you could, but the first strategic decision like way down business decision equals marketing decision is. No, we’re just for the little guy PTs. And yeah, and so now they’re expanding but like 10 years later, once you guys have become the Salesforce of PT, but the biggest marketing decisions or the strategy decisions that guide the company.

Matt: Yeah, absolutely. I want to ask you, you’ve worked with hundreds startups and their founders. What do you look for in a software company and its leaders? Which traits and characteristics are important, do you think?

Greg: Well, they have to be between 23 and 33. [Ha ha ha] So, yeah, they come in all types, shapes and sizes. And again, of course, they’re all passionate, energetic, problem solving, because they see a problem in the world and so forth. The biggest challenge these days for software founders is they’re under estimating two things and it’s related to the product market fit and scale stories that they just never been through. So they don’t you know, they just kind of underestimate the game. The first is they underestimate what it takes to make somebody just so blown away by your product or service or the experience. That they want to tell people they won’t stop paying when there’s a depression, a crisis and so forth, it’s just totally underestimated. Everybody is saying, well, everybody has software, it’s easy to create a software business. There’s a problem in the world, their software, they’re totally like a magnitude, 10 times they’re under estimating what it takes to make something go in the world that product market fit.

And the second thing is, they underestimate what it takes to scale from one level to the next, from one segment of a market to an expanded segment, from one region to another region, whether that’s local or state or global, one channel to another channel. It’s just totally underestimated by founders these days, because you think it’s just an open field. And I fall into this myself, like, look at that it’s a big open field, and we all run in, and it’s harder than we imagined. Always was, but there’s a lot more competition now and there’s so much more noise now. And it’s expanding. So I’d say underestimating how they can serve a larger population, which makes them naive about creating, being awesome for a small group, so they could serve really well, faster. So that’s my spiel.

Matt: Yeah, I think that’s why he’s focused on who you can take care of, whether it’s you own your local market, whether you own a certain niche, just make sure that you focus and refine everything out in that niche before you think about taking it bigger and going outside of that. That’s what I try to preach.

Greg: Yeah, and it’s counter-intuitive for talented, ambitious people that are entrepreneurs that are urgent, but they only learn it by beating their head against the wall a few times. That’s how I learned it. But like another way to say, Matt, is that these a players who are starting these companies and it’s not really, these aren’t really lazy people who don’t know their stuff. It’s not the thing. It’s there’s like chefs who could make any kind of food, right. But there’s no restaurant, there’s any kind of food that you want today, a restaurant is just one kind of food in one place for one audience. And the restaurant companies that scale nationally and globally, are known for one thing on the menu, and they got started with like a little narrow crowd. I mean, it’s almost without exception. So everybody starts off kind of in a generalist direction but scale requires specialization. And actually specializations a superpower of marketing, and you can’t scale unless you get people to line up for what you do. So that’s it.

Matt: That’s fantastic. Well, I want to ask you because you’ve worked with a bunch of people, we’ve figured out that they need to get that specialization to focus on their niche. Now once they’ve got that, what tips would you give regulators on how to scale globally?

Greg: Well, in the software industry, it’s interesting because the Greg’s list is about local regions, but software companies do… There’s no local software company, we’re just restaurant stop for restaurants in Phoenix or PTs in Phoenix or whatever. They’re all national and most business type software, outside of healthcare and maybe financial services are pretty global. Infusion Soft always had 25% of its customers overseas, without any investment or interest because it was available everywhere. So the trick is once you actually have a specialty and you’re just killing it for them, you’re going to get pulled globally because PTs in the UK are actually a lot like. They probably called something different but PTs… And we just used this WebPT example, physical therapists. What do they call them over there, Matt?

Matt: Physiotherapist.

Greg: Yeah, physios. Yeah, they’re about the same persona have about the same problems, there’s something a little different. And so when you really stoke the fires for in a specialty, it’ll spread across regions just fine. So there’s the plumbing that goes with doing global business, the hours and currencies and regulations and so forth. But the bigger thing is to get so specialized and so red hot that your beacon can travel that far. And this goes the same for local companies that are trying to scale nationally as it g oes for global. 20 years ago, global was, oh, I have to speak French, there’s regulator, [Yeah] and we have to hire people there, it’s different laws. And like all that, we end up saying, you know, ship your brochures over there, and all that stuff. Now that stuff kind of doesn’t exist. It’s more about having as common specialty. Because if you scale, you can’t be a different thing globally than you are here. Coca Cola is the same thing in Kenya as it is in the US. A little bit different spin on it, but fundamentally, it’s the same thing. So you actually have to be really sure about what your focus is because it’s got to be the same thing everywhere.

Matt: Yeah, that’s great. Well, this is awesome. I really appreciate you laying all this out for us. I think this is really helpful. There’s a lot of great pieces of information, a lot of good nuggets here. And I want to make sure that our listeners can find you if they need to learn more. So how can people get in touch with you, Greg?

Greg: Well, easiest is LinkedIn. I talked to founders so all the time, over 1000 a year, and I’ve worked in some businesses deeply, but I offer free advisory sessions and mentoring, talking to a lot of people right now about their business. And on scaling So you can, there is more information about the workshops we’re doing and what the process is, and there’s useful insights there. And of course, if you want to find out what’s happening in the software industry in Dallas and Phoenix and Salt Lake and Chicago, you can go to

Matt: That’s perfect. And for every out there, I will put all that in the show notes as well so you can get there. But this has been great. So Greg, thank you so much. I appreciate you coming on. It’s great to chat with you again and catch up. And I hope everything continues well for you.

Greg: Thanks, man. Happy to help.

Matt: All right, appreciate it. Well, thank you everybody. That’s it for the show. I will see you next time. Thank you, take care.

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