Jon was recently a guest on A Better Product Podcast from InnovateMap. The episode is called What to Do When the Product Doesn’t Sell Itself. With hosts Christian Beck and Anna Eaglin, Jon discusses how Clear Software navigates the complex sale to drive value for our users. Jon shares how we had to shift our vision as we learned that we were targeting the wrong audience and we modified the go-to-market strategy to deliver to the enterprise space.

Podcast Transcript

Christian Beck: Welcome to today’s show. In a complex enterprise sale, there’s a lot of different people who care about different things, and sometimes you have to learn that the hard way.

Anna Eaglin: Today we’re talking with Jon Gilman, CEO of Clear Software, an automation platform that allows businesses to be more operationally efficient. It was born out of the consulting work that Jon was doing where he kept finding a common problem.

Jon Gilman: I worked for Accenture and Deloitte, two very large consulting firms and we would implement ERP systems at Fortune 500 companies. Every single time we did it, it would take two or three years, cost $400 million and, ultimately, at the end, our customers felt like they were worse off than before we showed up.

Christian Beck: ERP?

Anna Eaglin: It’s an enterprise resource planning system that’s designed to improve productivity, increase efficiencies, decrease costs, and streamline processes. I mean, just off the top of my head.

Christian Beck: Oh, yeah, thanks a lot Wikipedia. But I think it’s a bit more complicated than that. An ERP is a monolithic term that can mean a bunch of things.

Jon Gilman: We created Clear as an automation platform to essentially fulfill that original promise they were made when they bought the ERP system in the first place.

Anna Eaglin: One thing Jon shared is his idea for creating Clear Software was an almost virtuous calling, and consulting the businesses run on billable hours, and he essentially built the antithesis of this model.

Jon Gilman: What drove me was this basically empathy for these users and how their jobs were made more complicated by software when they were supposed to be made simpler.

Christian Beck: He was clear, pun intended, there was a market based on his years of industry experience. We had product market fit, which is a huge hurdle to overcome right out of the gate. But it still took them three to four years to create his first MVP, and the result?

Jon Gilman: The first demo I ever gave, the customer bought it on the spot.

Anna Eaglin: Ten the reality set in, selling to an enterprise is going to be a lot more complex than showing one demo and having someone say ye. Although, that would be nice.

Jon Gilman: One of the issues with trying to grow a business is that if you’re not actively building a sales pipeline, it’s not going to grow very quickly.

Christian Beck: Jon was running his consulting business during the day and not actively driving an effective go-to-market strategy.

Jon Gilman: We were foolish to think, “Well, this thing is going to sell itself, all we got to do is just get it in front of eyeballs.” But it turns out that a complex solution sale requires a lot of effort.

Anna Eaglin: In the world of VC and enterprise sales, there are a lot of factors to consider. One, you have the pressure to go revenue quickly while selling to a target with a lot of stakeholders involved in the decision making process. Which pushes the sales cycle out from six months to a year or sometimes even longer.

Christian Beck: Through all of this, Jon learned that he had the wrong audience, the wrong messaging, and when he actually got the software in front of his target, it wasn’t converting. The days of one demo and sold were over. How did he change his go-to-market strategy to yield results?

Anna Eaglin: To hear that, you’ll have to listen in and be sure to hang out with us after the interview as we break down the keys to an effective go-to-market strategy.

Jon Gilman: You definitely have to be more targeted in the enterprise space. So just because we can solve any business process and efficiency doesn’t necessarily mean you go-to-market that way and say, “We can solve any problem for you, just tell me what your problems are.” Generally, a buyer needs to be told what their problem is. What we discovered in looking at our past customers was that we were generally always coming in and automating two business processes, two really core business processes that are a problem everywhere throughout the world. Order to Cash, which is essentially taking in a customer order, fulfilling that order, getting it invoiced and getting it paid and then Procure-to-Pay, which is essentially buying products from vendors, receiving an invoice from that vendor, and getting that invoice paid.

Jon Gilman: Those are two things we do really well, the rinse and repeat processes, but they also happen to be burning dumpster fires at most organizations. We come in with our messaging and say, “We’re an automation platform with a particular focus on Order to Cash and Procure-to-Pay,” doesn’t preclude us from automating other business processes but it is our foot to get in the door. That also allows us to be a little more targeted in terms of who we’re advertising to. We can advertise to a VP of Finance or a VP of Sales or a CFO who has metrics around those two business processes that indicate the general health of a business.

Christian Beck: Now the main focus is order to cash and procure-to-pay, what was it before?

Jon Gilman: Yeah, well, one, it was any company that was running a big ERP package, which is there are 500,000 or 600,000 companies worldwide so that’s not very targeted. Then we essentially say we’re an automation platform that makes people faster at their jobs. Okay, but which people? Which people in my organization are you helping? when you say, “Well, all of them,” we’re like, “Okay, well, I don’t really know where you fit in the software vendor ecosystem.” It’s a little bit of an identity crisis, you can’t boil the ocean and say that we can fix all of your problems. You have to let them figure that out over time, but initially you can come in and say, “Look, you’ve got aged receivables that are out of control, your day’s sales outstanding are high.” These are terms that catch a CFO’s ear and say, “You are right, our day sales outstanding are really high. Okay, but how is automation going to help me drive that down and get my customer’s invoices paid faster?” We get more money in the door and we become a better business.

Christian Beck: Has the overall vision for Clear Software changed as a result of the shift in go-to-market strategy?

Jon Gilman: No, it’s still the same mission, we still have the same mission which is just making people’s lives less miserable and making companies less dependent on consulting firms. But how that’s messaged to the buyer is really important. We’ve discovered that a CFO doesn’t really care if your mission is altruistic, they’re looking at the balance sheet, they’re looking at the P&L and they want to make it better.

Anna Eaglin: You mentioned people don’t want to hear anything too general, they want to be told their pains. Unpack that a little more for me, what do you mean by that?

Jon Gilman: It’s almost like a little bit from the challenger sale. One of the first meetings I ever had with a CFO, we had gone through our presentation and talked about how automation can help all these different business processes and make them a better business. He said, “Yeah, I get it, but I don’t even know where to start.” It’s like the Ten Years After song, I’d love to change the world but I don’t know what to do. He’s like, “I know we’ve got problems throughout the organization, I just don’t know where to start.” At which point we said, “Look, order to cash is probably where you need to start and here’s why.” Because it’s how revenue comes into the business, it’s going to improve your top line, it’s going to improve your bottom line, that’s where you need to start. Once you’re done, you need to move to procure-to-pay and here’s why. You’ve got vendors that are negotiating rates for products that you buy on an annual basis and you have no idea how much of it you buy.

Jon Gilman: We need to fix this process and make you better on the procurement side. Then after that, it’s whatever else needs fixing, let’s fix your call center, let’s fix your assembly line if you have people you want to shop for. But it’s really they need to be steered in that direction because, ultimately, a buyer needs to be educated about how to buy.

Christian Beck: Now that you have those with certain customers, are you starting to layer in the conversations about additional things you can do or are you still just focusing on those two?

Jon Gilman: The primary messaging is around that, that’s the hook. You get the fish on the line, you reel them in and then that ends up being what we implement with our platform initially. But once we’re done, we can essentially go back to our buyer and say, “Look, we implemented Clear in 45 days, here are the results we’ve had with this business process. It’s time to look at these other five or six things within your organization, and here’s the estimated cost savings we can find for you.

Anna Eaglin: You’re going to these companies and you’re telling them, “The software you have is not good. Here’s some more software and this is going to be good.” Do you have any issues when you come in with like, “I have a software solution for your software solution.”

Jon Gilman: We used to in our old go-to-market when we were going through the IT organization because a CIO will tell you, “I need another software vendor like I need a bullet in the head. I don’t need more software, I’ve already got tons of it. I’ve got subscriptions and maintenance fees at the Wazoo.” It’s really hard to navigate through the IT side, however, the business side they don’t really care how many software subscriptions they have, they’re really all about how do I run a better business? They’ve been a lot more receptive to putting software on top of software and that’s essentially the world we live in which is been coined robotic process automation. But it’s really just software that automates software, that can be confusing to an outsider. In fact, one of our early investors took me about seven or eight times to convince them to invest in Clear, but the first time he’s like, “Wait a second, you’re putting software on top of software, that doesn’t make any sense.”

Jon Gilman: I’m like, “Well, it does. let’s actually look at some of these customer case studies and I’ll walk you through it.” Then he went, “Oh, okay, okay, yeah, maybe software on top of software does make sense.”

Christian Beck: Was the term robotic process automation a term commonly used when you started Clear Software? It seems fairly new.

Jon Gilman: No, and what’s interesting is we didn’t even know we were a robotic process automation platform until somebody told us. Another term that didn’t exist when we started Clear was just user experience. I was messing around in 2008 or 2009 when I talk about three or four years to create my MVP, I started around 2009 on Clear, and we got our first customer in 2012. In 2009, nobody knew what user experience was and then the industry finally caught up so that in the 2012, 2013 time period, people were starting to talk about design thinking and UX and it became a known quantity. But the process automation piece was still pretty foreign up until about two or three years ago when companies like UiPath and Blue Prism and Automation Anywhere started getting huge. They’re doing 200, 300 million a year in revenue just through screen automation.

Jon Gilman: That’s when people started to look at it and say, “Okay, now I really see the value of process automation.” We’re merging the two worlds together, so we’re user experience and process automation merged into the same platform.

Christian Beck: I know we’ve talked with people about creating categories but yours is a little bit different because a category emerged on your journey. You said you weren’t familiar with that term, who came up it and was it a prospect or?

Jon Gilman: Yeah, so one of my customers who’s actually a buddy of mine, and that’s how they became a customer, he said… I was giving him a demo and showing him all these different processes that we automated in their SAP system and he goes, “Oh, you’re an automation platform?” I said, “Well, no, no, no, we’re a UX platform and automation is a nice output of that.” But he goes, “No, you really need to be advertising that you’re an automation platform, not a UX platform.” We heard that and then about a month later we had an analyst call with Forrester and they looked at it and they said, “Oh, yeah, you guys are an RPA platform.” We’re like, “What is RPA?” He said, “Robotic process automation.” We’re like googling real-time during the analyst call and we’re like, “Oh, yeah, I guess we are robotic process automation, we just didn’t know it.”

Christian Beck: What’s been the impact of that on your messaging and on general sales overall?

Jon Gilman: Well, given that, that particular topic is hot right now with CFOs who that’s our buyer, we’re using it as much as we can. Because that’s something that they understand now. Gartner and Forrester and all these analysts firms have been pounding RPA down the throats of finance organizations now for two or three years, so they’re familiar with that term. If there’s a way for us to get our message through to our buyer more quickly, then we need to take advantage of that.

Christian Beck: Will you continue to evolve to match the trends in terms of conversations easier or do you think you’ll stay in this space for a while?

Jon Gilman: I think we’ll stay in the space. We’re pioneering a term right now called attended RPA, so because we have user interface that can invoke automation, that’s becoming a hot term. I’m not sure if we coined it or yet another Forrester or Gartner analyst coined it, but it was, again, during one of these calls where I said, “We’re really an attended platform that allows your actual business users on a day to day basis, whether they’re in a call center or in an AR department, they can click a button and invoke a pretty complex automation in one of your ERP systems. But the beauty is they just have to click a button. This idea of attended RPA or a robotic desktop automation is something that we’re pioneering right now. The big three that I already mentioned, Blue Prism, Automation Anywhere, and UiPath, they’re desperately scrambling to try to find a way to build an attended RPA solution that allows all these great automations that they’ve built to be exposed to an actual end user.

Anna Eaglin: Why are you pioneering the term the attended RPA, is it attended RPA?

Jon Gilman: Yeah, attended RPA or a synonym would be robotic desktop automation.

Anna Eaglin: Okay, yeah, so why are you pioneering that? What are you hoping will come from that?

Jon Gilman: I think because it speaks to our two audiences, which are the end user who just wants their daily jobs to be more efficient. If I can automate as much on their desktop as possible, their lives are better. But it’s also something that the finance department or the CFO or our buyer is going to latch on to as well and say, “Okay, I get RPA and this is a flavor of RPA that everybody wins. I get to drive down my operational expense and my users’ jobs are less miserable,” so everybody wins in this scenario.

Anna Eaglin: You’re not creating a category, but you’re creating a subcategory inside of an existing category?

Christian Beck: I want to actually stay on this because I love nitpicking at the most like the smallest pieces. But this is, I think, fascinating because of what Anna just said, the general discourse in products is to create categories but this is it’s almost like creating a subcategory. If I’m hearing your evolution over time, it’s like you didn’t really have a category, just blanket UX or improving the UI. Then RPA comes out and you’re like, “Oh, yeah, we’re RPA.” Then as you’re hearing from people that you’re a new flavor of RPA, so I guess what I want to understand in that evolution, was it accidental or was it all intentional? When you start hearing things like your flavor of RPA, how do you figure out that that’s something you want to double down on?

Jon Gilman: Oh, it’s probably a mix of accidents and being intentional about it. In this specific case that you’re talking about with attended RPA, when we came up with the term, we went around to all the different RPA vendors out there and did our own marketing case study to say, “All right, how many of these guys actually have an attended solution?” We found out none, zero, and it’s the holy grail of process automation and the big three are scrambling and spending 10s of millions of dollars to build out a solution that, guess what, already exists here in Indianapolis.

Christian Beck: Is that worth showing up in your website, in your marketing materials, or sales materials or is it just conversational right now?

Jon Gilman: A little bit, it’s been worked into our website. We’ve updated the homepage to actually use the term robotic process automation instead of process automation because that’s something that people understand and it’s becoming a known quantity. We do a lot of analytics, SEO, and what terms are ranking highly, and that kept coming up. So order to cash kept coming up and robotic process automation, turns out we do RPA for order to cash. We double down on that, so it’s a combination of using tools like Vambora and a lot of great tools out there to figure out what are people searching for on the web? Then looking at heat maps of our own website to figure out what people actually care about. One of the things we actually discovered over the last few months when we overhauled our website and messaging was that people were going to the automation part of our website and they were going to the business process part of the website, order to cash and procure-to-pay.

Jon Gilman: We realized that neither of those things were actually on our homepage, so we reswizzled the homepage to get people to actually go to the homepage in the first place. It was actually our lowest ranking page of all the pages of our website which is usually the inverse. Usually, your homepage is the top ranking page. We watched that and we watched what people were searching on intent and keywords and that sort of thing and updated it accordingly. It’s a very scientific process which I’m glad because it’s taken me a while to realize that sales and marketing is you go into business initially thinking that sales and marketing is more of an art and everything else is science. But everything is science, marketing is science, I’m going to put X dollars into something and I expect to get Y number of leads out of it. It’s all math, so you just got to figure out what the right combinations are.

Christian Beck: What’s the future for Clear in the next year or the next three years? I’m curious with some of those fundamental shifts you started to evolve into over the last three to six months, what does that mean for the next year for Clear Software?

Jon Gilman: It doesn’t change our long-term roadmap at all, we still we just want to get more customers, get more automation out there. I think one of our major long-term missions is to reduce companies’ reliance on consulting firms. One of the interesting things that I stepped back and realized a year or two ago was that when I joined Accenture, there were 30,000 employees there. Now there are 500,000 at Accenture, Deloitte has a few hundred thousand employees, IBM has 400,000 employees. Over the last 10 or 15 years, we’ve seen these consulting firms increase 10x, and it’s exactly because of these kinds of problems that we’re addressing.

Jon Gilman: Interoperability of systems, a lack of automation, and it’s pretty alarming. That’s the fastest growing industry in the world is professional services, and it’s insane to me that it should be that expensive and that something should grow like that. Companies should be able to solve their own problems internally with the right set of tools.

Christian Beck: 30,000 is like an insane number to me, 30,000, and you joined when they’re 30,000 and they’re now at half a million. I guess I always think about product and software and think that’s where all the growth is, but I guess that’s not the case.

Jon Gilman: Well, the growth of software and really point solutions within the software industry has given rise to the consulting firms. 30 years ago, we had generic ERP systems where you ran your entire business on one software platform, then Salesforce comes out, then Workday comes out. And then all these hyper specific solutions come out to address a specific business process within an organization. All of a sudden, you have 45 software applications instead of one. Guess what, none of them talk to each other, so you’ve got IBM and Accenture sitting there like Mr. Burns and the Simpsons going, Excellent, excellent,” because there’s systems integration fees there for them to be had. Every new cloud based technology that addresses one specific business problem makes consulting firm salivate.

Anna Eaglin: What does better product mean to you?

Jon Gilman: Better product needs to address a real need, a real business need. It can’t be a bunch of fluff, it needs to actually have measurable results within, not necessarily business. If you’re a consumer product, it needs to improve something in the consumer’s life that is direct and measurable.

Christian Beck: That was Jon Gilman with Clear Software. You can connect with him on LinkedIn or head on over to

Anna Eaglin: So, Christian, one thing I’d like to talk about from our interview with Jon is that he mentions that when he got started, he started to learn of the person using the product and the pains that the buyer was experiencing were not necessarily the same thing. The product really speaking to the features but the buyer, that wasn’t really resonating with the buyer. What are your thoughts about that? The idea that when you’re selling, it’s not necessarily that you’re speaking to user pains, but you’re actually speaking to buyer pains?

Christian Beck: That’s a common thing that happens in the B2B world. I think what he’s describing is something that’s really common amongst a lot of people who have an idea based on personal experience because they have this pain that they initially inspire them to build a product. They start building their product and see, “Oh, this would immediately help me.” In Jon’s case, it was also sounding helpful to people he was talking to so that all made sense. Once he actually starts to take the product to market and goes to sell it, the actual people who own the buying decisions don’t see the same thing he is. It’s not as much as the old like it’s so well designed it sells itself or it’s not quite that, but it’s a little bit of that.

Christian Beck: I think maybe there’s some idea that people in product have that, “Well, if we knock out these things, it’ll pretty much just sell itself because it’ll be self evident. That might be true to end users but in a lot of cases, especially, in this ERP space, the user is not the buyer. You actually literally have to talk about it differently to them.

Anna Eaglin: In the same vein, though, he was talking about the rise of UX and designing for the user, and I think it’s like educating that buyer is the next evolution, the next product evolution which was that product marketing, speaking to the pain, speaking to the features for the buyer and not necessarily the user. I think the idea that the product will sell itself, I think we see that all the time.

Christian Beck: Yeah, so it just keeps repeating itself. I think when you’re trying to figure out where your space is, you have to step outside your own value when you’re innovating something that you know really well. Because it’s true, you are building something and Jon’s building Clear Software for people that are doing things like he used to be doing. But you have to talk about it a lot differently to the person making that buying decision on behalf of an organization.

Anna Eaglin: Yeah, he also really focused his message quite a bit because he mentions that Clear Software can do lots of things. It’s a very complex piece of software that can optimize so many parts of the business, but he had to say very specifically, it’s not like, “Hey, we can do anything you want.” It’s more of like, “We can really help you with your orders and your sales. It’s that land and expand, so he also had to really focus his message as opposed to just saying, “Hey, this can do anything.”

Christian Beck: Yeah, people can’t always connect those dots, some people might but they can’t always do it. But he has to like… I think he said something of the buyer needs to be told what to buy, like teaching them what they’re doing, right?

Anna Eaglin: Yeah.

Christian Beck: I think about the history of some of the different trends that happen in technology like for you and me we were in UX, “UX” 10 years ago. When I was trying to find jobs in UX, I had to first educate people on what UX even is before they could do it. Then once it gets mature, people start to understand it and you don’t have to actually convince them. I think that’s I thought about UX because that’s what he was initially talking about with the Clear Software value prop. But, eventually, people do start to get that, then you have to move on to the next thing. He mentioned RPA, robotic process automation, he had a bunch of features that you could say could do anything. But then they started leveraging this robotic process automation, but then he said something that was interesting because it was like leveraging robotic process. It wasn’t a category they invented so they did something slightly different based off of that, wasn’t it?

Anna Eaglin: Yeah, it was I think the attended RPA or the robotic processing automation and they said that that’s a category that their buyers will resonate with. But the way that they attended part of it I think is what would resonate even more then. Taking a category they’re already familiar with and saying, “Hey, we do that but we do this in this different way that will really appeal to you or really appeal to the way that you want to do business.”

Christian Beck: He almost had to wait until RPA became big, he didn’t need… We talked about inventing categories before, he didn’t have to invent it, it was only had to wait for it to come out. He was talking a lot about how different theirs is, but he needed RPA to get a critical mass and then say, “We’re not like other RPAs, we’re like attended RPA which is something new.” It almost gave him an opportunity to have a different message in the market.

Anna Eaglin: Yeah, it’s actually a really common research term to actually anchor people to say, “Here’s this thing that you are very familiar with and now I’m going to take you on a journey to this other thing that you didn’t even know you wanted. But in order for me to do that, I first had to ground you in exactly something that you know.

Christian Beck: He seems to do that really well with Clear Software, the journey he’s gone on it seems to have started with, “I can do all these things, it will make your life better.” He goes to market and finds out, “Well, this isn’t resonating with the people buying it, it resonates with the users. I need to change this up.” Goes back to the drawing board and figures out, “What is resonating with people and then how can you differentiate himself with that?” Anchoring against something that they already know. Anna, in finalizing this conversation, it’s looking at the path of Clear Software. What’s sticking out to me is that you can look back on where Jon started and maybe the mistakes that might have been made in going to Market, but the other lens to look at it through is something that’s natural. They started with something that was useful, that actually solved real problems, which I think you have to have.

Anna Eaglin: Yeah, so foundationally you have a product that solves a problem. Building on that then it’s designed in a way that people can use it, it’s delightful, it makes sense, it’s intuitive, so people can actually use it. They can find that value that you initially created it for, but then I think that third level is really then helping people understand how to buy it and how it fits and what are the features and what are the benefits? Because a lot of times, again, going back to what we said earlier, people assume that if something is well designed and easy to use, the inherent benefits and the value will just be very clear to you. It’s like, “It’s not actually the case, you have to go out and tell people, “This is how it can fit in your life, this is how it can be better. Here’s what exactly what it can do for your business.” I think a good example of that in a company that it’s in a more B2C, I guess a B2B context.

Anna Eaglin: I think Airtable does it really well. Airtable is a tool that you can do anything with, oh my gosh, so many different incarnations of Airtable but they’ve really doubled down I think in the last couple of years to say, “here are templates, here’s Airtable universe, here’s what other people have created, here’s a way that you can put this tool to work for you.” They’re so intentional about saying, “Don’t start from scratch, take what we’ve got here and then customize it for yourself. I think that’s one really interesting way to say it. Airtable is a great tool to use. It’s easy, it’s intuitive, it’s delightful but it’s complex. That those directions have really helped people I think understand how it can fit into their lives.

Christian Beck: Yeah, it also reminds me of a tool, Asana, so Asana for project management and all of that like a JIRA competitor. I remember, I don’t know if it’s still like that, but at the bottom of their site, they have all these workflow orientations for Asana. So it’s Asana for, I think, it’s actually Asana for development teams and they cater it there. It’s partly a persona based thing but I think you can still use this approach for buyers. To your point, especially, in large companies, the reasons the buyers need a different message is because the buyers have a different job. If you’re managing a team of somebody who’s going to be using Clear Software, those people that use Clear Software have different goals than the person who manages them, who manages that, or somebody who’s in a different IT budget and just manages software and doesn’t really know.

Christian Beck: You have to educate them, and some of that is just educating them that your team does things like this. I think Jon was able to leverage a lot of his knowledge when he’s reporting back to the buyer that your team is going to like this but it has to be slightly catered to that in a way that makes sense to them. The point is finding the right message, especially, when you have a different buyer than a user is extremely important. But that doesn’t necessarily mean you make that top, a higher priority than making sure the product is valuable to begin with. It’s just maybe the take home for our listeners is that don’t think that just because you have something it’s got an obvious value to your end users that it will just sell itself. You’ve still got to figure out what the right message is to the person that’s in charge of buying it.

Anna Eaglin: Exactly, what he said. Thanks so much for listening to the show this week. If you haven’t yet, be sure to subscribe, rate, and review this podcast. Until then, visit and subscribe to learn how you can take your product to the next level. As always, we’re curious, what does better product mean to you? Hit us up on Twitter at @innovatemap or shoot us an email at

Christian Beck: I’m Christian.

Anna Eaglin: And I’m Anna, and you’ve been listening to Better Product.

Christian Beck: Better Product.