The Detective 0:01
Imagine you're the CEO of keep a SaaS company dedicated to providing automated marketing solutions to small businesses.
Clate Mask 0:09
We had a lot of people whose passion was to help that struggling business owner We exist to make our customers successful, meaning that they're growing sales there saving time with our automation
Customer 1 0:20
just make it better for me.
Customer 2 0:22
I wish I had started keep years ago, I would say before key my work life felt very friendly.
The Detective 0:30
Keeks business model is centred around a subscription service that offers a suite of tools for managing sales, marketing and customer relationship. When you're
Clate Mask 0:37
serving small businesses. There's a lot of passion around serving that underserved solopreneur that needs our solution.
The Detective 0:44
you're navigating a world of dynamic markets, customer preferences and rapidly evolving technology. What happens when you try to expand your reach by making your product more accessible to a broader range of businesses only to discover that not every business is ready for what you have to offer.
Clate Mask 1:02
Despite the increase in sales and the increase in morale and enthusiasm, excitement about democratising automation for small businesses, there's something arrived here that needs to be addressed.
The Detective 1:12
What would you do when you realise your ambition to cater to solopreneurs? is causing increased customer churn? Putting your business growth at risk? How would you handle the hard truth that your product might not be suitable for certain types of customers?
Clate Mask 1:28
That's where you start to get indicators of okay, this is taking way too much time and the customer is not able or willing to bring the commitment and they're part of it. This is a problem.
The Detective 1:39
And when you pivot your strategy, focusing on a different customer segment, how do you manage the internal upheaval that comes with such a significant change? This is the story of clay mask, CEO of keep. This is the churn.
Ben Kaplan 2:02
Claim take me back to a little bit in past history where you're a successful marketing automation company, you've got a software product and most people who do that want to grow. And the way that you grow is you remove friction points, you deliver more value, you open up new markets. So at the time, you think that's a great idea, let's remove friction, let's open up markets, let's grow take us through that decision making first what you were pursuing, and then maybe some unintended consequences. We wanted to
Clate Mask 2:34
open up the market and get to more small businesses. And as you know, about 90% of small businesses are solopreneurs. And so our product, which is a marketing automation solution for serious businesses, we wanted to be able to get that to solopreneurs, we wanted to take friction out of the process. So at the time, we required customers to buy an implementation package to get started with us. And that was where we stood at the time where we had a market opportunity that we felt like could be opened up with less friction in the sales process, and an opportunity to bring on more small businesses that are smaller and kind of a solopreneur.
Ben Kaplan 3:14
With this kind of implementation package. What that essentially means for a person is there's an upfront cost to get set up because marketing automation systems are complex, there's a lot of setup involved. And that does do a couple things. It puts a bit of friction in the process. Because you know, I can't just start in a monthly payment. I've got to do that. And it puts some other things you have to do up front to for implementation. You got to have some meetings, you got to have some other things to sort of get going. So you're like Okay, let's get some more people. Let's remove this hurdle. Sounds good. Let's democratise a little bit. This for solo printers sounds like a good thing. And what did you see when you first did this? And in many ways, sounds like a no brainer. Let's just open up the market. If we're not going up market to mid size or enterprise, let's go down market and open up to more customers.
Clate Mask 3:57
Yep, exactly. What we saw was we took away that required implementation package. And we created a light package for smaller businesses. And we brought in more customers and the sales cycle sped up, you know, the number of days in the sales cycle sped up,
Ben Kaplan 4:14
the sales teams happy it's at this point, yeah, one call closes. You
Clate Mask 4:17
know, everybody's excited because people are coming through faster. And everybody's excited about, you know, more more recurring revenue that's coming in. So did what you wanted it to do. Yes. And it definitely took friction out of the process. And it brought in more customers and more of these more smaller businesses more solopreneurs.
Ben Kaplan 4:36
Okay, great. So you're like Check, check, check. All goals are going well, what was the feeling in the company at this point? I mean, sales is probably thrilled where everyone's thrilled or was it also like bring a lot more customers, there's more overhead, there's more customer service, there's more support? What was the feeling or was everyone on board, you know, on the ship that is moving forward as you hoped?
Clate Mask 4:54
Yeah. People were excited and not just the obvious reasons of more sales probably The more powerful thing that was creating excitement was you use the word democratisation of our automation software for small businesses. So you know, it feels really good when you're able to get your product to more customers. And in particular, when you're serving small businesses, there's a lot of, especially in our company, there's a lot of passion around serving that, you know that that underserved solopreneur that needs that needs our solution, kind of
Ben Kaplan 5:25
like the underdog, that could be the next Airbnb, but he's like, or she is working from their garage now, and we could help them and maybe they are the next great success story. And we could play a role in
Clate Mask 5:35
that. Yes, and there's a lot in our company, there's a lot of pride and enthusiasm about serving small businesses. And so the fact that we're able to serve more, and frankly, the strugglers, a lot of them are in their first year of business, and they're solopreneurs. And, and so there's a bleeding heart component of you, man, you just want to serve these people, and you, they need help. And so it was exciting to be able to get your product to more of these customers. So it wasn't just a sales enthusiasm. It was across customer success and product, and indeed, across the company that we're getting our product to more customers with less friction,
Ben Kaplan 6:11
which aligns with it sounds like I don't know your company values or mission and purpose. But it sounds like it's aligned with that, if part of this is is to empower more entrepreneurs and small businesses to realise their business goals and realise their entrepreneurial dreams. The sounds good from that lens. Yes, exactly. And so all of those metrics are are going well going up. How far were you in after you made this decision that there might be unintended consequences? Or some other impact? When did you start seeing that,
Clate Mask 6:42
first of all, the whole risk was, will these customers be successful with the product. And so we knew that churn was likely to go up, some small teams do great with our software, when it's one person, and they're trying to implement marketing automation. And they've never thought through their sales process very well, they don't have a customer journey that is followed, they don't have a strategy for how they bring customers into their business. And that's a lot of work to help that solopreneur actually put all of that together. And so it wasn't an issue of smaller teams, it was an issue of solopreneurs. And the question was, how would solopreneurs do putting marketing automation in place, and we knew that was a risk. And that's what we started to see, we started to see the struggle that solopreneurs have in putting automation software in place, because not because of the automation software. But because of the immaturity of their business processes, the things they don't know yet, there's just, there's just so much that you learn in the first couple of years of business. And when you're first getting started, you don't know a lot of times you don't even have your products yet you don't have not only do you not have a process, but you might not even know for sure what your product or services, you're still, you're still trying to get some kind of product market fit going. And if you are a solopreneur, where you're doing, where you're wearing all kinds of different hats, it takes a while before you're able to get clear on who your customers are, what you serve them how you do it, and how automation can help you in that process.
Ben Kaplan 8:20
And by definition, if I use the word automation, in this case, we're talking about marketing automation. Automation is usually very helpful in any type of business. I mean, from the industrial age, right? When you have a process that is defined, and you have to do it manually, the opposite of automation, you bring in automation, and it can speed up whatever you're doing, whether that's delivering marketing, emails, making Model T cars, whatever it is, but you usually have a defined process first, but now you're going down market, there might be companies at various stages of figuring out not only their process manually, but like what is the business, they're in the product market fit what their ideal customer is. And so there's suddenly a lot more variables. So what did you start to see, when you start to get more concerned about this? I mean, was it purely churn numbers and you get a report? I don't know what you get claimed as SC Do you just get like a report each month and you see it or each week? Or how are you set up? Do you have people who track this and they knock on your door and say, Hey, we got to talk like what is your mechanism for recognising it's a problem? Or do you get customer service anecdotes from the team and you get stories? And how did you start to become aware on your CEO plate? What was going on? You get
Clate Mask 9:22
churn data, but that's lagging. What we started to see was indicators of usage and customer commitment. So those indicators can be as simple as not showing up on a call with your implementation coach. It can be more telling, like not logging into the software. It can be more telling, like not sending out any emails, you know, so and when you get when you get right down to it. What we learned was these new businesses they struggle because they don't know what to say in their email so we can serve them have templates, we can serve them up prebuilt automations. But if they're asking themselves, Who am I talking to in my audience? And what am I saying? And I don't even have a list yet. I mean, you can see why a marketing automation is a challenge for a brand new business that hasn't figured out some of those questions, let alone create an actual process. Because we work with a lot of customers who don't have their processes worked out, and that's fine, we can work with them. But when they haven't even answered basic questions about who is my customer, and what am I selling? And what's my message to them, you know, what's my value proposition and compelling reason to buy, and you've got to actually coach a brand new business through that well, that's, that's where you start to get indicators of, okay, this is taking way too much time on our part, and the customer is not able or willing to bring the commitment, and they're part of it. This is a problem.
Ben Kaplan 10:53
I want to mention one thing that you mentioned there in passing, that I think is important for anyone who looks at data, you actually talked about lagging indicators. And then you actually referenced a number of leading indicators and lagging and I always describe it as the leading indicators are things that give you the closest you know, if we were going to drive from I don't know, Austin to Houston, we want to get to Houston. We know if we got there successfully, but we went see some road signs on the way Did we make the right turn? Did we stop for a rest stop? Did we get back on the right highway, we can see some indicators. So in your scenario, you're starting to see things I mean, the problem is if people are missing meetings, they're not sending out emails, they're not doing these things, they're probably not getting a good result from the marketing automation software, because they haven't done enough to get a good result, then, you know, that lagging indicator? Do they get to Houston or not, they're probably not going to get to Houston, if they're not gonna get the Houston they're probably going to cancel. Yeah, you
Clate Mask 11:43
see, the leading indicators are customer behaviours. And those customer behaviours can be in the product, they can be outside of the product interactions with teams, and it starts anecdotally. But then you start to put together patterns and you start to see, you know, sets of data that begin to, you know, either confirm or call into question the direction that you're taking. Okay, so
Ben Kaplan 12:05
you're starting to see these and how many months in are you to the process where it starts to be more of a concern, you make the change? How long does time goes by
Clate Mask 12:13
within a couple of months, you start to get some concern within four or five months, the data starts to corroborate those concerns. And so you know, within six months, you've got a pretty good sense of Okay. Despite the increase in sales and the increase in morale and enthusiasm, excitement about democratising automation for small businesses, there's something awry here that needs to be addressed.
The Detective 12:39
Clay made a bold decision to democratise their product, aiming to empower the underserved solopreneur market. The initial response was electrifying. Sales rocketed, and morale hit an all time high as the company served more businesses than ever. However, beneath the surface, something was amiss. Within months, red flags were raised. The newcomers these solopreneurs was struggling to utilise the sophisticated automation tools effectively. Despite the apparent triumph, the mission started to waver in a race against the clock, and armed with key insights, Clank began devising a strategy to tackle this unexpected challenge.
Ben Kaplan 13:29
Okay, so six months in, you realise this needs to be addressed, it needs your attention. What do you start to do at that point? Are you at that point, considering I need to reverse this decision? Like right away? Are you thinking we just need I don't know a different way to screen customers. Maybe it's not with the service package? Something else? Oh, we need more better training, we need more videos or other stuff just to get people or help them. As you start looking for a solution. What do you do at that point?
Clate Mask 13:55
You go through all of those things you look at, you know, what do we need to do in the product? What do we need to do in our training process, our onboarding process? What do we need to do in customer selection and filtering, and you go through all of those things. And that's why it's not quick to change a decision. Because if you just change the decision, then you wouldn't innovate, you wouldn't actually improve. And you have to go through a process of of improvement and innovation. And that's the reason why it's tricky to go through a decision like this. Because it's not like there's just a perfect answer here, where you say, oh, let's just go back and do exactly what we're doing before. That's the easy answer a lot of times, but it's not the answer that's going to make the business better. It's not going to be better for customers. It's not going to create future growth potential. You know, we made that let's remember, we made that decision for a reason we wanted to open up the market more, we wanted to be able to get our product into more customers hands. And so you have to look at all of the ramifications of that decision, and then figure out well, where can we improve and get better that might either cause us to be more effective if we reverse the decision one ad, or more effective in changing course, not in one ad, but you know, adjusting the decision in a less extreme way or in a more creative way.
Ben Kaplan 15:12
Could you live with the turn? Could you say, hey, sales are up? You knew there was going to be some churn? Could you just say, you know, it's okay, we can live with it? Or let's reduce it a bit, it's gonna be up, or could you not? What did it mean for the business to have that higher churn rate?
Clate Mask 15:28
I think that's the most important question. Because the answer depends on really where you are in the scale of your business. You can live with churn, when the business is smaller, you get to escape a certain scale, and you have to have the churn in a better place. Otherwise, you can't outrun it. So let me just do some simple math for people to help them see what I'm talking about. If you've got 100 customers, and you have 3%, monthly churn, that means you got to find three new customers the next month, just to make up what you lost no big deal, we you know, we can do that no problem. And let's, by the way, let's say your customer acquisition cost is 1000 bucks. So we're going to invest $3,000, find three new customers to make up for those three that we lost. And if we're at that stage of our business, that's no big deal, because we're probably looking for 1020 30 customers next month, no problem. Three is not that big a deal. Now, let's say you're at 1000 customers, well, now you got to find 30 customers, and you got to have $30,000 in sales and marketing investment to acquire those customers at $1,000. CAC, again, probably not that big a deal, because you're probably growing at that point, by, you know, maybe 50 7500 customers a month 30 customers just to break even, it's not that big a deal, you probably got investors and capital behind you. So you can go invest that customer acquisition costs on those 30 customers. Now let's take it to 10,000 customers, well, now you got to find 300 Customers starts to get a little trickier, you get to 100,000 customers, and now you're talking about 3000 customers to find next month to make up for the customers you're losing this month, you got to $3 million to invest, you know, so you start to see how when people say you can't outrun the churn at scale, that's what we're talking about, you get to a scale. So if keep we're a small business that had 100 customers, 1000 customers to 10,000 customer, it's not as big a deal. How many customers does this keep have now we've got about 25,000 businesses. And so the more customers you have, now, the more customers do, you have to acquire just to replace the ones you lost. So what happens for Sass companies in their decision making the right decision, it depends on your scale, because when you're smaller, you can do lots of different things, your experiments or you know, you, you can kind of work your way through those in a much quicker, more fluid way, the more scale you have, the more you've got to bring down the churn. Otherwise, you're spending a lot of your investment just to try to break even on the customers that you're losing.
Unknown Speaker 17:56
If you enjoy this show,
Ben Kaplan 17:58
you'll love top cmo with me, Ben Kaplan, there's never been a better chance of opportunity to do that.
Speaker 4 18:06
I would definitely encourage marketers to be engaged in the product development process, because you're banking
Speaker 5 18:11
your brand's great moments, but it's the great brands that create movements. And that's the spirit
Ben Kaplan 18:16
of justice. Of course, this is the podcast where we go around the globe to interview marketing leaders from the world's biggest brands, fastest growing companies and most disruptive startups available wherever you get your podcasts. Clay, you got about about a year after the initial decision to kind of remove some of those implementation packages or the upfront costs. The writing was on the wall, you had to maybe undo some things that were kind of ambitions that you had or think about the problem differently. And so at that point, did you do the 180? Or did you do the more tweaks? Or did you do the 180 mean, undo the decision with a twist and try to maybe go back but do it better than before?
Clate Mask 18:58
Yeah, it's a 180 with a twist. But it all starts with what you let me tell you what we what we've done. And what's playing out now. Well, we can get to what's playing out. But here was the decision, the decision was our customers need to put some skin in the game with some services, we basically said we're coming at this from a customer success, brand promise delivery standpoint. And we don't want to bring on customers that we can't deliver our brand promise for and our brand promises gross sales and save time with with automation from key. So if we can't deliver that brand promise, then we don't want to bring on that customer. So what we said was, well, to deliver the brand promise, we need to bring some services to the mix. And the twist was that we began to focus more on customers who make an annual commitment versus month to month. And so whereas we had services before it was still very much month to month. So we changed things a little bit adjusted the package, but we lead now with annual commitment and we're really converted In the company to be an annual commitment company. What that does is it weeds out the businesses that aren't serious yet that don't have the problem that we solve and, and that's the real thing that we had to get to. And this is why it's not just a decision you make to change your delivery of your product and service, it's really a concerted and aligned effort and agreement around the company that says, Let's get really clear on who we serve, and who wins with keep, and who we don't serve. And as much as we would like to and want to and try to, it's too much of an unnatural act to take a piece of automation software like keep, and try to take it to a customer who's perfectly capable of keeping everything straight in their outlook and spreadsheets. Was
Ben Kaplan 20:47
everyone on board? No? No, we're top lieutenants in each division, you got sales, you got marketing, you got product, you got customer success, maybe you have engineering, what did you have to do? Did you get to a consensus? Do you just have to make a decision regardless of a consensus and say, boxtops? Here, I got to make a tough decision. What was the feeling in the company at that point?
Clate Mask 21:09
Yeah, it's a great question. The reason I respond with, you know, so emphatically is that this is the hard stuff of leadership. I mean, if we could all go look at a, you know, a perfect data set that shows beautifully, exactly what you know what we should do, that's easy, but the reality is, that's not that's not life in SAS, you know, you're trying to make the best decision you can based on the data, but more importantly, you have people's emotions, you've got people's jobs and their careers and their passion. You know, we had a lot of people whose passion was to help that struggling business owner, that struggling small business that doesn't have things figured out at all yet. And I got a lot of that passion, I want to help them too. So no, we had people who left the company as we made this decision, because they're like, No, that's not what I want to do. I want to go democratise automation for all small businesses. That's why I wake up in the morning and get excited about what I do every day. And what I'm saying is, well, what we need to do is be excited about, about creating amazing automation, for serious businesses that want to grow sales and save time. And if they, if they're not, if they're not, to the point where they've got enough success going, that they're kind of scrambling to keep it all together, then they're not our customer, if they're if their issue is, you know, they're trying to make a decision about their first product. That's just not a customer that we're going to win with, as much as we'd love to help them. And as much as you want. If you're an engineer, and you want to convince yourself that the solution that we have is going to help them make the decision about their product, that's a product for a different company than keep, so you're gonna need to go to that company,
Ben Kaplan 22:47
I'm putting myself in the mind of your VP of sales, whoever he or she may be, are they like, our numbers are up, we're driving sales? Did you have to talk them down? And they're gonna say, but maybe you're gonna judge me based on my numbers, and all my numbers are going to be down? And do you have to reassure them? Like what happens to the sales? Because like, we've been killing it, we've been bringing in people in the year like, Yeah, but we got to slow that down. Yeah,
Clate Mask 23:05
it's so fun. You know, there's, there's a rush, there's an energy, there's an excitement to it. And now all of a sudden, oh, we can only bring him in if this and if that and they need to commit this. And boy, you know, the velocity has slowed down. It's not as fun and yeah, that's a, you know, that's not just one conversation I've had with my VP of sales, we've had many conversations. And to her credit, she recognises that what matters is our customers success. And that's the key thing that everybody has to align to, when you get right down to it. You asked it, you know, how do you do it was it? Well, everybody has to come down to the fact that we exist to make our customers successful not to make a sale, not to feel good about a feature that we've created that we think is going to democratise automation for these small businesses, we exist to make our customers successful, meaning that they're growing sales, they're saving time with our automation. And so that's what you've got to get everybody aligned to our brand promise was probably the most significant thing, the significant lever that we use to help people to pull on that and help people understand this is why we do what we do. And that's hard. Because like I said, you have people who, when you really press on it, you realise, oh, that's not why you're here. You're here for a different reason. And then you have to have hard conversations with people about well, do you want to be here with this new direction we're going or do you not want to be here? And some people chose not to be here?
Ben Kaplan 24:30
And did you do a formal branding project and realign your values? And do that formally? Or was it more that didn't really need to happen? And it was just a realignment, just what you're focused on in your monthly numbers and everything else? Or did you actually try to rewrite the mission statement or things like that?
Clate Mask 24:45
Yeah, it's a really great question. Ours was more nuanced. So we didn't have to rewrite our purpose and our values and our mission, you know, we have a long term mission to 2030. And so the the entrenched purpose to liberate and empower are entrepreneurs to strengthen families community economies, that that didn't change our long term mission to simplify growth for a million small businesses worldwide by 2030. That didn't change now how we'll do that. So a little bit different. And our seven values that didn't change, but our strategy plan for the three years that changed. And that's where people became a little bit undone and said, Well wait, hold on, I'm not sure that that aligns with the work I want to do. And so we had pretty significant change in our product org, in particular, because many of those people were on a different path to create something free and light and ubiquitous for millions. And that's a noble purpose. It's a noble desire. It's not the reality of what small businesses who need automation are actually looking for right now in our product. Could that be the case in three 510 years? Sure. But we've got a three year plan that needs to connect up to that, and some people didn't want to be on board for that three years? Well, and I
Ben Kaplan 26:01
think one of the challenges of being a CEO and one, particularly at the scale keep his at is that there may be a lot of things you want to do. But that doesn't mean you can do everything. Right now, there may be a sequence to things, there may be a thing that we aspire to do this, but we've got to accomplish these things first, to sort of like earn the ability to do it. And like anything else, a good idea with even good execution times wrong, actually may not work. And so you're constantly juggling a long time horizon, a medium time horizon and a short time horizon, and things may be good in one horizon and terrible. In another time horizon.
Clate Mask 26:42
Yeah, that's a perfect way to illuminate the point I was making about our purpose, values and mission are intact, because those are long term where, you know, we're not changing. Do I believe that our automation solution will get better and better and be more applicable to more and more small businesses over time, of course. But I also know what we need to do over the next three years to connect up to that long term vision. And so most of our people got that and they were aligned with that. But there's some who said, Well, I don't want to do that I want to be able to work on these projects I really care about right now. Oh, sorry, we're not taking freemium to the world in an aggressive way right now, because that doesn't match up with what we need to do in order to get ourselves to where we want to be. And so those are the kinds of rubber meets the road decisions that individuals have to make when you make a strategic decision like the one we did. Because it's not just as simple as well, let's just put services back in play, or let's just, you know, no, there's there's a bigger strategic question about the market that we serve. And the customers who are successful with this, and our commitment to that customer success and the delivery of our brand promise and a an uncomfortable realisation that we needed that we came to, and that we needed to just call out, which is oh, well, for these brand new small businesses. They're not ready for our software,
Ben Kaplan 28:09
in terms of other big milestones in the company's history. And we can go all the way back to the founding story. But previously, the company's called Keep now it used to be called Infusion Soft and you had a following and a loyal customer base from that. That was a big decision, probably to change that name. And I don't know, what was the key thinking there. What were the other big milestones in the company from how you found it on were there? This was a big moment. What were the other big moments that define the trajectory of keep formerly Infusionsoft?
Clate Mask 28:35
Yeah, oh, gosh, that's probably another podcast. Another episode, but I would say, you know, obviously, there was a, an appetite to go down market from where we were with Infusionsoft. And it's a similar conversation to what we just talked about with the services. But you know, and so we brought in a lot of leaders for, you know, different people. And there was a strong push for that. And I took a back seat for a period of time. And it took me a while to realise that wasn't, that wasn't a good approach. We needed to not not do that. So we changed our product approach. But we were still kind of pointed downstream, as evidenced by this whole conversation we had. So that's really kind of a meta theme of different decisions we've had to make over time. And it was why I mentioned the point about, you know, night beers and this CEO and what I needed to learn it wasn't
Ben Kaplan 29:26
just that you had made a decision a year prior to remove some friction points, your trajectory, even the fact that you had sounds like change your name was your desire to head more downstream. It was something that was in other decisions that leading up to that that you had to go against that tide, which was the direction the company was headed.
Clate Mask 29:47
That's exactly right. There have been several decisions we made prior few years that were all under the umbrella of a down market push. And so when we made the decision, you know, several months back that we're going And to not do that it was a major adjustment and what it's done and I guess this sort of transitions to well, what does it look like now what it's done is it's brought back the energy and the fire and the focus that created the marketing automation success that we had with Infusionsoft. But now it's being done in a paradigm, a product and a paradigm that's more intuitive, a little more user friendly, you know, just just the things you do to know if you stop and think about it. If you've got a marketing automation solution you want to take downstream, you've got to make it easier and more intuitive. Well, now what we're doing is we're saying we're taking that easier and more intuitive. But we're refocusing on the segment of the market where we win and that I believe, is the right combination, and is as already helping us see that those are the customers we win with. That's where we want to be in the market, we want to be in that Salesforce is in the enterprise and hub spots in the mid market and keep is the one for small business.
The Detective 30:59
Clay Mask and his dynamic team turned adversity into advantage. They bravely faced the issue of customer churn, devising innovative strategies to promote growth, keep grow emerged as the solution, opening up to a broader range of clientele. That focus shifted to improving usability, putting user needs at the centre of their software's evolution. But that wasn't all. Keep reintroduced the service package element, offering an even more customizable and comprehensive solution for businesses of all sizes, embracing customer feedback as a cornerstone, they enhanced their support system to world class levels, ensuring each customer felt valued and their voice heard. But what does the future hold for keep?
Ben Kaplan 31:54
As you think about the future, what's going to define success? What are the key things now the key decisions, key execution, things that you have to do that are going to determine what your next three year plan looks like, as you refocus?
Clate Mask 32:09
Yeah, with small businesses in sales and marketing automation. It's always about the amount of time and effort that people need to invest in order to get returns. So you know, I love what's happening with AI, we, you know, we jumped on that a year ago, because we wanted to make it easier for customers to create content. That was a
Ben Kaplan 32:28
big friction point, if you don't know what to write, and I don't know what to say. But here comes around Chad GPT, there's generative AI, there's ways to speed that up, and maybe remove that friction point.
Clate Mask 32:39
That's right. So we've built that into the product, you know, we did an integration with open AI before Chet GPT had really hit the scene. But But creating that that generative content, you know that that agenda of AI to create content is a big movement, and there's going to be a lot that I think will make its way into sales and marketing automation. And I think that's going to be a great thing for small businesses, it already has been for our customers and partners who use it. And I think we're, you know, we're just getting started there. So that's really exciting. I think it fits under the broader theme of simplifying the path, you know, you heard our mission is to simplify growth. For small businesses, it's about making it easier and faster for them to get the benefits of automation. But we're also clear that we're not taking that to solopreneurs. Now, there's some solopreneurs, kind of the top 10% of them that have a pretty, pretty serious business, they just have chosen to be solopreneurs. And they can get a lot out of our solution. But it's the it's the 90% of the 90 90% of small businesses are solopreneurs, and about 90% of those in the very early stages of their business, and they're figuring a lot of stuff out and they can get MailChimp or something else to go help them kind of get started with that stuff, we are very clear that we are serious automation for serious businesses. And we want to be that and maintain that position. And frankly, that was the position that Infusionsoft had in the small business market. And that's the position that keep will have
Ben Kaplan 34:03
interesting that the times are matching this idea of a lot of us, we all went through the pandemic and you had people using business software like zoom personally and people discovering that, oh, maybe simple and easy to use isn't just a consumer thing. That would be good in the business thing. It sounds like your direction matches the moment in that regard. And if you're gonna go back, would you change anything you've done during this big decision? And would you just I don't know, would you just go back and just not make that decision? Or do you feel you had to go through it? Would you have approached the solution any differently? Would he have sped things up? If just 2020 hindsight as CEO would have done anything differently over this journey?
Clate Mask 34:40
You know, there's always things that you wish you didn't have to go through or but here's the way I looked at it. You made the comment about the simplification. The consumerization of IT, you know, is kind of the broad term that people use. I don't think we could have taken what we built with Infusionsoft and and simplified it and created what we're doing with Keith, without going through what we went through. I'm grateful to those leaders we brought in, you know, many of them were friend to it. And although they had a different approach of what the product should be, they helped us to create a simpler paradigm. And I just don't think we would have figured that out without going through that experience. And so, you know, you could say, well, gosh, there's a whole bundle of decisions we made about going down market that didn't pan out for us in the numbers and the growth of the business over that period of time. But what they did do is they taught us a bunch of things, they taught us a lot of things of what not to do, and they helped us create a paradigm and a user experience for our software. That's dramatically easier than what it was when we had Infusionsoft. And, you know, I've learned a tonne through the process, our people have learned a tonne through the process. So I have gratitude for what we went through. And I have humility, that you've got to go through some of those hard things, and they're challenging, and you don't really want them but they're, it's just, you know, it's part of the process. So, no, I don't necessarily say, oh, we should have done this, we shouldn't have that. I don't know that all those things are helping us become who we're becoming. And I'm really excited about who keep is and what our future is and the opportunity, we have to help small businesses grow with sales and marketing automation.
Ben Kaplan 36:24
How have you changed as a CEO from the early days of Infusionsoft over this journey? And what is your advice for other CEOs, software's or service companies? Maybe not going through some similar journey that you've been on? How have you changed? And what is your advice for others?
Clate Mask 36:41
Well, this is definitely another episode. But I'll give you the short version, I was much more sales oriented early on. And partnership oriented and business development kind of started to, you know, evolve, I think I've become more product oriented and more customer success oriented, and also a little more financial oriented. I think that in the early stages, I was probably a little more missionary on a cause, you know, just on a mission. And, and that's super important. And I haven't lost that. But I think I've balanced it better with the financial imperatives of the business. And, and the reason why so many businesses go up market is because that's really the only way you can make those financial imperatives work. At a certain point, I was stubborn and not wanting to do that. And so I would tell you that I am a I'm a far more grateful and humble CEO than I was many years ago. And I think I've also come to a place of just recognising that that all progress starts with taking responsibility. And I think there were times where I wasn't taking responsibility at the level that I needed to gratitude, humility, responsibility, those are things I've learned, and I, you know, hopefully, an observer would say, yes, this version of clay mask is quite different from that 110 years ago,
Ben Kaplan 38:04
if you're going to do this for a long time, and you're going to build business for a long time. You've got to embrace the growth, embrace the journey, embrace the change, and to get more than you have as a business, you have to become more than you are. And it sounds like you've been on that path. In many ways, the path of the company parallels the growth of the people who are driving.
Clate Mask 38:24
Yeah, very true. I say that a similar thing all the time. I'm actually in the process of doing a pretty significant revised edition of my book, and I talk a little bit about this, there's just a growth that's required. And if you don't have that appetite, you're probably going to move from company to company relatively quickly. Because to do the same thing for a long period of time, you have to be really committed to a level of personal growth and development and improvement. So you know, I put a lot of investment into coaching and breeding and development and just try to get better and better.
The Detective 38:56
we've navigated the twists and tonnes of keeps journey under the stewardship of CEO and co founder kite mask,
Clate Mask 39:04
there was a major adjustment if you've got a marketing automation solution you want to take downstream, you've got to make it easier and more intuitive. Well, now what we're doing is we're refocusing on the segment of the market where we when
The Detective 39:16
the company face significant challenges whilst expanding, grappling with customer churn and an increased demand for support.
Clate Mask 39:23
Let's get really clear on who we serve who wins with keep and who we don't serve.
The Detective 39:30
That solution, focusing on customers ready for an annual commitment. This tough but crucial decision ensured keep sustainability
Clate Mask 39:38
well what we need to do is be excited about creating amazing automation for serious businesses that want to grow sales and save time. If they're not to the point where they've got enough success going that they're scrambling to keep it all together, then they're not our customer.
The Detective 39:52
Even when strategic shifts stirred internal changes. maaske stood firm, keeping the company's core mission and value Use insight masks experience underscore the importance of adaptability in leadership and learning from past decisions.
Clate Mask 40:07
I'm a far more grateful and humble CEO than I was many years ago. And I think I've also come to a place of recognising that all progress starts with taking responsibility.
The Detective 40:20
His evolution as a CEO is a testament to this belief, paving the way for sustainable growth in the SAS world. And with that, it's case closed
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