INSIDE Inside Sales – Ep 122: Introducing The 0 To 5 Million Podcast

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Have you ever wanted to become a full-time entrepreneur? What about a successful business owner?

In this podcast-within-a-podcast episode of INSIDE Inside Sales, Darryl shines the light on The Zero to Five Million Podcast, hosted by two sales & marketing experts, Shawn Finder, Sales GM at Autoklose, and Ollie Whitfield, Product Marketing Manager at Autoklose. This seasoned duo welcomes successful business founders to their show to help you decide where to invest, how to pick the best channels, scaling your business, and may even prompt you to revisit your career path. You know that learning is earning, so subscribe now to expand your knowledge and hear first-hand experiences from people who have made it.


''Comin' from HubSpot, I'm a big believer in #ContentMarketing...And it can be a huge driver of any business. And I think it scales well because an investment today has a long-term return.'' ~ @pc4media #podcast #entrepreneurs Click To Tweet







Host: Darryl PraillVanillaSoft

Guest: Shawn Finder and Ollie Whitfield, Autoklose – a VanillaSoft brand


Introducing The 0 To 5 Million Podcast – Where Successful Business Owners Share Their Stories

– And we are back, folks. It’s another week of the INSIDE Inside Sales Show. I am, I’m excited. You know why I’m excited? I’ll tell you why I’m excited, and glad you asked. Thanks for asking. I get to do something a little different this week. I’m not gonna be talking to you this week. Instead, I want to introduce you to a brand new podcast that we’re pushin’ out here at VanillaSoft. Now, why am I doin’ this? You can just go subscribe to it yourself, which, by the way, you should do. “Darryl, I tune in to listen to you and your guests. “I don’t want to hear this new different podcast.” That’s great. Let me explain why I’m doin’ this. All right, the podcast is called “The 0 to 5 Million Podcast.” And it’s featuring two co-hosts, my good friend, Shawn Finder, who was co-founder of Autoklose. He’s with VanillaSoft as our General Manager for all Autoklose development, sales, all that kinda stuff. And Ollie Whitfield. Ollie Whitfield you would know, everybody knows Ollie. He’s just in there. He has a regular rant on our, “The Drive” that happens every Friday at three P.M. Eastern, where we recap the weekly news in sales that week. He’s the Product Marketing Manager for Autoklose. Before he joined us, he’s worked with so many people, Vendor Neutral, JBarrows, the list goes on the people he knows and who love him. So the two of ’em are gettin’ together and they’re doin’ a podcast focus on leaders, entrepreneurs, all right. So what does that have to do with you listening to the INSIDE Inside Sales Show? Well, I’ll tell you why. A couple things. First off, we’ve talked before over and over and over again that learning is earning. So you need to expand your, just your knowledge so you can apply that. You’ll be a better salesperson. You will relate better to your customers if you understand their story, right? We’ve had this conversation. You can’t just do feature dumps and value props. You’ve gotta connect with them relationally. So you need to know the world they live in. That’s the first part. Second part, many young salespeople are mistaken to think that sales is the engine that drives the machine, which you get in an echo chamber of other sales reps and you all say the same thing. And you’re like, yeah! And what anybody from any department, especially marketing, says to you, no, no, no, we help, too, you’re like BS, without us, you’re nothing. And you’re puffin’ your chest and you’re doin’ your thing. And that’s bogus. So the question comes down to, how do I better understand the economic buyer, the internal champion, which is often your senior leadership, often the CEO. How do I understand what they’re living with? How do I include that in my outreach, in my approach, in my conversations? How do I better understand the challenges they’re facing to grow revenue? ‘Cause that’s what I’m tasked to do and I’m growin’ revenue, right? And you start to understand, when you listen to these entrepreneurs, that often, sales is not the first or the second or the third place they invest. But they’re gonna go through, as we talk to Shawn and Ollie, and they’re gonna share their story, and they’re gonna tell you where they invested and why. Or they’re gonna tell you how, instead of going sales, maybe they went channels, through resellers, for example, agencies, professional services organizations, and why that strategy made more sense to them. Along the way, you’re gonna have a better understanding of how companies scale. You’re gonna be able to connect one-on-one. You’re gonna be able to then say, hey, maybe that’s where I wanna go in my career. Maybe I don’t wanna be a direct sales rep. Maybe I wanna be a channel manager. Hey, that’s interesting. I’m still kinda selling, but it’s more relational, a little bit of marketing, a little bit of promotion. And maybe that’s appealing to me. You see, for you to be a rock star sales rep, you need to understand the whole story. You can’t just spend all of your time focusing on how to have better openers, better killer subject lines, better mindset, better discovery processes, better storytelling. You need to understand how the process works, how companies scale. You need to understand what it’s like to be an entrepreneur. ‘Cause who knows? Maybe that’ll be you. In this first episode I’m about to share with you, you get to listen to, you’re gonna listen to Peter Caputo. I’m sorry, I say that every time, Caputa. Sorry, Peter. Peter was one of the early, early, early employees at HubSpot, and he basically drove and grew their whole channel strategy. It’s amazing. He’s now the CEO at Databox, a very cool product. And he’s gonna walk through how he went from HubSpot to Databox. And one of the things that stuck out at me when I listened to this episode was literally how he’s on top of the world with HubSpot. And after nine years, he goes to Databox, and he’s back to an extremely small company. And he, himself, as CEO, is selling the product. He’s the only salesperson when he gets there. That’s right, the only salesperson. Can you imagine havin’ that brand awareness, that cache, that infrastructure, that access to budget and capital, and suddenly, even though you have the CEO title, you’re back to selling. See, that’s the thing. Sales skills span you in your whole career. And no matter how high up in the organization you get, you never stop selling. So the skills you’re developing now will lead you to much success if you apply the lessons learned as you progress. Peter, fantastic example. I want you to listen to the “Zero to Five Million Podcast.” I want you to give Shawn and Ollie a shout-out with their thoughts, your feedback, your suggestions. And then I want you to go subscribe. In the meantime, enjoy this. My name is Darryl Praill, and this, my friends, is INSIDE Inside Sales. Have a listen.

– Welcome to the “Zero to $5 Million Podcast.” I’m Shawn Finder, and I’m with my co-host, Ollie Whitfield. This show is brought to you by Autoklose and VanillaSoft Company. Ollie, why don’t you introduce today’s guest? And we are so special, this is very special, because it’s actually our first guest on our new podcast. And talk about what we’re gonna be talking about today, Ollie.

– Folks, I can’t actually begin to tell you how cool this is gonna be. I’ve not actually met this guest in person yet, so this is the first time that we’re talking, but he has taught me so much. It’s not even funny how much his Twitter feed and his LinkedIn feed, his company blog, has taught me about generally how to grow a SAAS company. It’s ridiculous at this point. So what more do I need to say introducing Peter Caputa? Why don’t you introduce yourself, Peter?

– Yeah, so I’ve been doin’ online marketing, and building and selling software since the late ’90s. I built my first e-commerce site, ended up having my own start-up for awhile. Really struggled to get that off of the ground. We basically bootstrapped it for awhile until I ended up meeting the founders of HubSpot, I should say Mark Roberge, who was the first VP of Sales. And meetin’ the founders, and they pitched me on the vision. And I ended up joining HubSpot as a really early employee in the, I think I was the 14th employee or somethin’ like that. Ended up stayin’ there for nine years, built out a big portion of their sales and marketing funnel around working with marketing agencies. And for those that don’t know, HubSpot was started as a marketing software company. And so I ended up rising through the ranks there to, ultimately, to VP of Sales. And then after nine years, kind of, HubSpot was a really mature company, it was a public company by that point. I was lookin’ for a new challenge, lookin’ to be entrepreneurial again. I ended up joining Databox as a CEO. Databox helps companies pool all of their performance data into one spot, so from tools like Google Analytics, and HubSpot or Facebook ads, or QuickBooks or your SQL server or whatever. So we’ll pool all that data, allow people to set goals against it, track it, build dashboards, we call ’em databoards, and ultimately improve their performance by paying closer attention and havin’ more a data-driven culture. So that’s what I’ve been doin’ for the last four years now. And we’ve grown the company, I guess I can CR this, since this is relevant to the title of the podcast, we’ve grown the company to just shy of $4 million. We’re like 3.9-somethin’ million dollars.

– Close.

– Not quite at that 5 million mark. I can assure I’ve built $100 million child at HubSpot and was there from the beginning of that, started that. And then was at HubSpot, I did the math the other day, when I joined HubSpot, the month after, we were doing 25,000 in MRR. So you can do the math on that. I was pretty early at HubSpot, so.

– So we’re gonna have you back when you crack the 5 million.

– And hopefully speak to the zero to five journey twice here.

– Cool, all right. So the first thing that I wanted to ask you, Peter, is when you jumped into Databox, I can imagine the first day you’re getting used to a lot of things and just lookin’ around the office floor, wondering what the next move is, when and how things work, getting a grip on that. Where did you start off when you’re thinkin’ how are we gonna grow this? Where did you start? What were your first plays and your first moves?

– Yeah, so like one minute of background on Databox. They had raised a bunch of capital before. It’s actually the founders of Databox are from Slovenia. They flew over here with no plan, no apartment, no funding. They started building code, writing code. They ended up getting into, long story short, they ended up getting into Techstars, incubating the product. They got $500,000 deals they closed with Fortune 500 companies, mostly around here in Boston, to do mobile analytics. So pulling data out of systems and letting executives track it on their mobile phone. Back then, that was like the hotness. I don’t know if you remember back then, but everybody thought mobile was gonna take over the world and eliminate the need for desktop. So the value prop worked. Unfortunately, they started growing out the go-to market team and it didn’t work. And so when I joined a few years later in 2017, there was like just a handful of customers paying a very small amount per month. They’d just pivoted to more of a self-service model where anybody could sign up for the free version of the product and start using it. And so they had, I think we had a few thousand MRR, similar to when I joined HubSpot. There was no one on the go-to market side. It was just the only people left in the company. They slimmed it down after they had that first kind of shot and didn’t quite work. They slimmed it down to just a very small engineering team. It was 12 people. There was one support person/QA person, and 11 engineers and product people. And so to answer your question, the first thing that I did was got on the phone and started talkin’ to prospects. I had done some due diligence on both the product and the company, and the investors and all of that. And so I had already started introducing Databox, the software, to a few of my close contacts at marketing agencies, and had them start checking it out. And what I discovered pretty quickly, or actually before I joined, was a lot of marketing agencies were doing very manual reporting. They were literally pullin’ data from different systems into spreadsheets. They were takin’ screen grabs, puttin’ them into a slide deck. And that’s what they’d send over to the client every month. So it was clearly a very manual process. And so I started pitching agencies on automating that process. And I think in the first month, I closed maybe 10, 15 of those deals. We weren’t charging a whole lot then. But I would get them onboard. And so then that created an issue of like, all right, now I gotta figure out how to onboard these people. So I did that for awhile. At the same time, I opened up two positions, one for marketing and one for customer onboarding or customer success. And so I hired two very junior people. I continued to do the selling. I proofed every blog post that we published. I was coaching the new person that did onboarding, ’cause she had done it a little bit in a previous job but not a whole lot, certainly not in the context of marketing software and analytics. And so it was just the three of us for a little while. I got lucky, and one of my senior guys from HubSpot was lookin’ for somethin’ new, and he ended up joining me as our first salesperson. And so in the first year, we invested pretty heavily in sales here in the U.S. That worked out really well. He got us to a few-hundred customers. Along the way, a guy that I knew from an agency was lookin’ for a new marketing job. I’ve always respected him, John Bonini. He’s still with the company as our Director of Marketing. And so he came onboard to expand the Marketing team out. We really focused in on content marketing very heavily, and still do. It’s really the main driver of our marketing, main activity with the take-in. At this point, four years later, we are 55 people. A little more than half of that are engineers. About 1/3 of that is Customer Support, so a big portion of Customer Support, and the rest is Sales and Marketing. Or I should say more than, yeah, 1/3 of the total is Customer Support. So we have a big Customer Support team, a small Sales team of three people, a Marketing team of five people now. Plus we rely on a lot of freelance writers for our content marketing.

– That’s interesting, ’cause a lot of the stuff that we did over at Autoklose was, well, when I first started my first business at Exchanges, we focused so much on sales right at the beginning. And we tried to get the sales before we’d build the product. And what I did with my second one was, I told myself let’s continue to build a product and the sales will come.

– Got it.

– So we kept double downing on the product and features, and more features and more features, and as we continued to expand our product market. But one thing we didn’t do is, as you mentioned, and I can totally agree with, is the CSM role. That is such an important role, that what we had was, early on, it was actually me doing the demos, closin’ the deals, doing the customer success, doing the support. And I had eight people beside me doing it. But we actually also do that customer success. But when we actually got the customer success and implemented, like you said, like a 14-day trial or a freemium model, where they can go in and almost white-glove them throughout that experience, it really took our business to the next level with growth, because we were bootstrapped as well. So it’s very interesting how you guys went one way. We went a very similar way, but kinda more doubled down on the product more than the sales, because we just felt like if we can’t continue to grow our product, especially we had already competitors in the market, that we’re gonna fall behind the competitors. So we had to continue to double down on the product but let the sales come in. So it’s an interesting way-

– That makes sense. I don’t know that our investment in product would be that different. Because, before I joined, they invested about a million dollars in the product.

– That’s-

– So there was really a product there, or I should say, the kernel of a product, the most important part of the product. We’ve drastically improved the feature set, and the UI and the UX, and all of that. But the hard part of our product is that we have to, we literally build and manage 70 integrations.

– Yeah.

– So a lot. We had 10 core integrations when I joined, and we built off of that, basically.

– And we were-

– And more than 50% of our headcount has always been in end product, so.

– Yeah.

– So I think we’re pretty heavily invested in product. There were a lot of iterations with refining the features and adding some smaller features along the way in that first year or two, to kinda get to the point where we could sell to a broader part of the market. But at the beginning, I had my customer onboarding person only working with marketing agencies. And the majority of our time was actually, in the beginning, working with HubSpot partners, helping them automate their reporting. So we were very focused in the beginning on who we were selling to. That said, more than 50% of our sales are still touchless, meaning we don’t have a sales call with them.

– That’s good.

– Back then in the first year was even higher. So we’ve always had a lot of sales that didn’t require a lotta onboarding, because we’ve invested a decent amount in the UI and the UX, the onboarding processing and app.

– So a lot of your customers come on through some kind of organic or maybe SEO as a channel, somethin’ like that.

– Yeah.

– And I’ve seen a lot of the content that you have on the website. You’re talking quite a lot about the integrations you have. And, of course, as you said, there’s a lot of them. So that’s a lot of content that you’ve got. Is that fair to say, that’s the winner? That’s where a lot of people-

– Yeah, I think the big opportunity-

– The agencies in China live in that world there. They’re always trying to consume that. So you’re just on the pulse with it.

– Yeah, so obviously comin’ from HubSpot, I’m a big believer in content marketing, so I’ll work there, and of course, with many of our customers. And it can be a huge driver of any business. And I think it scales well, because an investment today has a return, a long-term return, not just a short-term return. But what I really loved about Databox was that we could, our content marketing could be so broad. We can write about Google Analytics one day and then QuickBooks the next, or website analytics and accounting the next. And so that gives us a massive no-limit potential market that we can address. Obviously, we can’t do it all at once. And we’ve really been very focused on marketing and kind of one integration at a time. So like, we’ll create a lotta content around Google Analytics, or then we’ll create a lotta content about Facebook ads, and go from there. So, but yeah, big believer; content’s a major driver. We get about 4,500 sign-ups for the free product every month. It’s all comin’ from content. We don’t spend a dime on ads. We have an affiliate program but we don’t invest much into it, so it doesn’t really produce a lot. So, yeah, content is really the driver, and we’re publishing eight new articles every week that are educational in nature, like something informative that’s designed-

– Eight, that’s a lot.

– It is, yeah.

– That’s a machine.

– Yeah.

– So Peter, I do have a question. When did you guys invest, I guess, ’cause you guys are so content-driven, when did you guys invest in, I guess, your first SEO employer, someone to help you guys with the SEO? ‘Cause I know one of the biggest mistakes we made was not investing in SEO early enough in the process.

– I feel like we’ve gradually improved there, even as late as like this month.

– Okay.

– But like HubSpot, that’s all we sold for the first few years, is the SEO tools and the idea of blogging. And so I know enough to be dangerous there and, but just this past quarter, so four years in, we went back and we updated all our product pages. They’re much longer. Everyone has a video. We have images that show off how to use the product, multiple calls to action. FAQ’s, like value prop story before and after, like these product pages are our gold standard. And they popped, they went from like second, third page for high volume, high intent keywords to first page literally like two days after we relaunched ’em. So we’re still improving. We actually plan to launch, and every piece of content we do now it goes through a process of keyword research, accumulative research. We have a plan for the quarter and all that. So we’ve always been doing some element of SEO. I’d say that we’re still refining. I think as of late, we have a pretty good process, but I still think it could be a bit better, more regimented.

– Yep. Okay, so the next question we wanted to ask you was, how do you guys make your self-service users stickier customers? So I know that’s something we talked about was the freemium and the self-serve. Talk to us a little about that for the audience.

– Yeah, we’re in an interesting situation that it’s actually a bit of a complex sale, not in the traditional sense of like an enterprise sale where you gotta get six different people to buy in, although we often have to get multiple people to buy in, but more in the sense of that the product is actually a custom tool. And by being a tool that can be used in a custom way for every user, it’s difficult for us to actually, one, figure out what they want and get them to explain it, and two, then figure out how to do it. And so unlike other software, even like a HubSpot CRM where it might be some slight variation in how to use it, your sales team might be structured slightly different, you’re all gonna use deals, you’re all gonna use contacts.

– Yeah.

– You’re all gonna use company accounts. That’s different for us. Somebody might come to us and say, I’m using PIPE and Google Analytics, and Semrush. Next day, somebody’s gonna say I gotta integrate my custom SQL database with my product usage information. And I wanna correlate that to my information in Intercom. So there’s all these use cases, really difficult. So the approach that we’ve taken is just building a big support team. It’s actually the first team I’d say we scaled. This year, we’ll scale more of our sales team.

– Cool.

– But the support team is the first team I’d say we scaled. A guy, another guy actually had joined me from HubSpot that I only worked a little bit with there, but he joined a few years ago as our Director of Customer Success. And his first thing was like, we gotta do a knowledge base. And I’m like, what do you need a knowledge base for? I’m like, why can’t you just answer the questions, right? Or how could you even start building a knowledge base? But he was right. We built the knowledge base and that worked out really well. That actually laid the groundwork for us to do chat efficiently, so that was the next thing we did. I pushed back on him, too. I’m like, we have trouble keepin’ up with email tickets. When we add chat, how are we gonna possibly keep up with the staff that we have? And we, I’ll correct you a little bit. We’re not fully bootstrapped, ’cause we raised money before. But for the last two-and-a-half years, we’ve been cashflow breakeven and managing to that.

– I hear you.

– So we went with, we started doing chat. And I said, all right, we’ll start with the people who might buy. So we started with the website. And so we got a little with John, and he’s like, all right, well, can we expand it after that? I’m like, wait two weeks. And so like three days later, he expanded it without telling me. And then we started doin’ chat across the whole customer base. And that’s been huge, because when somebody decides like, hey, I’m gonna go build this dashboard in Databox, and they can’t figure it out, it might be another week-and-a-half before they get back to it if they can’t figure it out then.

– Yep.

– So by offering that chat and that immediate support, and our response rate’s in the low single-digit minutes, not seconds where we’d like it to be. But we respond within a few minutes, and we can help them then, they’re much more likely to move forward. I actually don’t have great data on this, probably surprisingly, but we also use our support team to then identify sales opportunities that our sales team then works. And the close rate on those is really high.

– Yep.

– And we’re able to, out of the 4,500 people that sign up for a free product and the roughly 1,000 people that sign up for a trial every month of our paid version, we can identify through chat the 100 out of the 150 who are likely to buy, and so that our sales team can focus in on those 100 people.

– All right, so Peter, you just discussed about 100 different moving piece of the puzzle there. There’s a lot of stuff going on. Too fast.

– Where and how on earth do you even start with planning the prioritization of all of that? I mean, you’ve got a lotta things going on there. How do you juggle all of it and put it into a piece of paper with an order to it?

– Yeah, every quarter, we probably write about 15,000 words in narrative form to do that. But I’ll back up. I’d start with saying that we’re very good users of project management, especially our product team and especially our support team. So that support connection and product connection is tighter than I’ve ever seen in a SAAS company. And we have processes for not only capturing bugs and issues, of course, but capturing enhancement requests as well as capturing things that confuse users, counting the number of times that happens and then solving that in the product org. And we prioritize that in real time. We don’t wait months or quarters to do that. That all happens, at a minimum, on a weekly basis, and some situations, on a daily basis. Then, of course, the marketing team uses it for our content. So like, oh, yeah, we’re publishing not just eight new pieces of content. We’re publishing generally like 12 pieces of content each week. Eight pieces of content are crowdsourced, and so you can imagine the amount, and some of it’s video. Some of it’s long-form, all of it’s long-form, but some of it’s like 5,000 per page, pillar pages. So we’re doing everything in project management. So long story short, first thing is tight project management. Second thing would be tight processes, like we have somebody who is tellin’ me our processes for support document is now 200 pages long. I think we’re outgrowing our Google Doc. We need to find a better solution. But we’re very tight on processes. And then, third, every team sets goals in two ways, what they’re gonna do that quarter and what result we expect from that. And so every quarter, each director, I have a Director for Marketing, Sales, Customer Support, our Product and Engineering team, as well as our Integrations team is a separate team that builds and manages our integrations. And so each one of them write a long-form report about what are our goals, numeric, if we can, and certainly in Marketing, Sales and Supports in numeric. And then what are our ongoing activities that we will continue, and roughly how much of those will we do. So we write how many blog posts we’re gonna publish. We write how many integrations we’re gonna build, how many metrics we’re gonna add to our integrations, et cetera. And then, lastly, any new initiatives. So for example, for this quarter on the marketing side, we’re hiring a Market Research Analyst so then we can do market research reports for a variety of reasons. And so that initiative is written up in detail and exactly how we’re gonna go about doing that. And we have an interview process and those things.

– Well, that’s definitely how you hold people accountable when you put all that. But listen, this has been amazing. I just want to kind of wrap things up here, because I know, Peter, probably the three of us can talk for hours, but this is a podcast. So we’ll wrap things up here. One last question I have for you. You’ve provided a wealth of knowledge. How do you, A, self-educate yourself? Do you read books? Do you listen to podcasts? How do you grow your self-intellect?

– Yeah, my wife laughs at me ’cause I probably buy like four or five books a month. And then I read like to chapter two before I get antsy. And I’m like, all right, I don’t need to read this. I know most of this stuff. I just need to go back to execution. And so, as an entrepreneur, I’m always struggling, like, do I sit down and sketch out a plan? Or do I sit here and read this book? And so I try to balance that, because books do give me a really good framework for communicating things. I tend to read books that reinforce stuff I either have learned or have done before, or even read about online before, but they do give really good frameworks, ’cause somebody smart sat down and thought about that topic for awhile. So I do read a lotta books. My favorite lately is “How To Be a Capitalist Without Capital” by Nathan Latka. And then I’ve been reading “7 Powers” and then “Machine, Platform, Crowd” by Andrew McAfee. And those are three books that I’ve been kind of skimming and reading for a little while now. And then I love podcasts. I take the dogs for a walk, or if I’m goin’ shopping or whatever, I’ll try to just put my earbuds in and listen to podcasts. So I also love Nathan Latka’s podcast on SAAS. I listen to a bunch of podcasts that are actually recorded for marketing agency owners. Helps me kinda stay abreast of what marketing agencies are thinking, and continue to learn there so that we can help marketing agencies, which is our core market. So that’s what I’m up to.

– And I guess lastly, where can people find you?

– I’m pretty active on Twitter. My Twitter handle is pc4media, as Ollie mentioned. I publish, I do a lotta sub-tweeting there after conversations or after planning where I’ll try to distill some thoughts down into small characters or threads. And then I’m on LinkedIn as well, Peter Caputa. I don’t log into LinkedIn as much ’cause I find that it’s really easy to get caught up in there talking to people, and spend a lotta time, so.

– Perfect. Well, thank you so much, Peter, for joining us. It’s been an absolute blast, incredible talk with you. Also thank you, everybody, for listening today. If you enjoyed the show today, don’t forget to give us a five-star review wherever you’re listening, and subscribe so you don’t miss our next show. Once again, Peter, thank you so much.

– You’re welcome, pleasure.