Introducing The 0 To 5 Million Podcast

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This is a podcast episode titled, Introducing The 0 To 5 Million Podcast. The summary for this episode is: <p>Have you ever wanted to become a full-time</p><p>entrepreneur? </p><p>In this podcast-within-a-podcast episode of INSIDE Inside Sales, Darryl shines</p><p>the light on The Zero to Five Million Podcast, hosted by two sales &amp;</p><p>marketing experts, Shawn Finder, Sales GM at Autoklose, and Ollie Whitfield,</p><p>Product Marketing Manager at Autoklose. This seasoned duo welcome successful</p><p>business founders together and will help you decide where to invest, how to pick</p><p>the best channels, scaling your business, and ultimately prompt you to revisit</p><p>your career path. You know that learning is earning, so subscribe now to expand</p><p>your knowledge and hear first-hand experiences from people who have made it. </p><p><br></p>

Darryl Praill: We are back, folks. It's another week of the Inside Inside Sales Show. I am excited. You know why I'm excited? I'll tell you why I'm excited. I'm glad you asked. Thanks for asking. I get to do something a little different this week. I'm not going to be talking to you this week. Instead, I want to introduce you to a brand new podcast that we're pushing out here at VanillaSoft. Now, why am I doing 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 listen to a different podcast. That's great. Let me explain why I'm doing this. All right, the podcast is called the 0 to 5 Million Podcast. 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 kind of stuff, and Ollie Whitfield. Ollie Whitfield, you would know. Everybody knows Ollie, he's just in there. He has a regular rant on The Drive that happens every Friday at 3: 00 PM Eastern where we recap that 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. At Vendor Neutral with J. Barrows, like the list goes on, the people he knows and who love him. So the two of them are getting together and they're doing 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 of things. First off, we've talked before over and over and over again that learning is earning. So you need to expand 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 got to 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 an echo chamber of other sales reps and you all say the same thing and you're like, yeah. And when 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 puffing your chest and you're doing your thing. 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 are 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? Because that's what I'm tasked to do, and I'm growing revenue, right? 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 going to go through, as they talk to Shawn and Ollie, and they're going to share their story and they're going to tell you where they invested and why. Or they're going to 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 going to have a better understanding of how companies scale. You're going to be able to connect one- on- one. You're going to be able to then say," Hey, maybe that's where I want to go in my career. Maybe I don't want to be a direct sales rep, maybe I want to be a channel manager. Hey, that's interesting. It's still kind of selling, but it's more relational, a little bit of marketing, a little bit of promotion. 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, because 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 going to 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 of Databox, a very cool product, and he's going to walk through how he went from HubSpot to Databox. 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. Imagine having 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. 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 0 to 5 Million Podcast, I want you to give Shawn and Ollie a shout out with your thoughts, your feedback, your suggestions, and then I want you to go subscribe. In the meantime, enjoy this. My name is Daryl Praill and this, my friends, is Inside Inside Sales. Have a listen.

Shawn Finder: Welcome to the 0 to$ 5 Million Podcast. I'm Shawn Finder, and I'm with my cohost, Ollie Whitfield. This show is brought to you by Autoklose and VanillaSoft company. Ollie, why don't you introduce today's guest? This is very special because it's actually our first guest on our new podcast. Talk about what we're going to be talking about today, Ollie.

Ollie Whitfield: Folks, I can't actually begin to tell you how cool this is going to be. I've not actually met this guest in person yet, so this is the first time that we're talking, but he's 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?

Peter Caputa: Yeah, so I've been doing online marketing and building and selling software since the late nineties when I built my first e- commerce site. Ended up having my own startup for a while, really struggled to get that off the ground. We basically bootstrapped it for a while until I ended up meeting the founders of HubSpot, and, I should say, Mark Roberge, who was the first VP of sales. Ended up meeting the founders and they pitched me on their vision and I ended up joining HubSpot as a really early employee. I think I was the 14th employee or something like that. I ended up staying there for nine years, built out a big portion of their sales and marketing funnel around working with marketing agencies. For those that don't know, HubSpot started as a marketing software company. So I ended up rising through the ranks there to ultimately to VP of sales. Then after nine years, HubSpot was really mature company. It was a public company by that point. I was looking for a new challenge, looking to be entrepreneurial again, and ended up joining Databox as CEO. Databox helps companies pull all of their performance data into one spot, so from tools like Google Analytics, or HubSpot, or Facebook Ads, or QuickBooks, or your SQL server, or whatever. So we'll pull all that data, allow people to set goals against it, track it, build databoards, or build dashboards, we call them databoards, and ultimately improve their performance by paying closer attention and having more of a data- driven culture. So that's what I've been doing for the last four years now. We've grown the company, I guess I can share 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 something million dollars.

Ollie Whitfield: Close.

Peter Caputa: Not quite at that 5 million mark. I can show you I've built$ 100 million 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, a month after we were doing 25, 000 in MRR. So you can do the math on that. It was pretty early at HubSpot.

Ollie Whitfield: So we're going to have you back when you crack the five million.

Peter Caputa: So I can hopefully speak to the zero to five journey twice here.

Ollie Whitfield: 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 looking 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 thinking how are we going to grow this? Where did you start? What were your first plays and your first moves?

Peter Caputa: 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 writing code. Long story short, they ended up getting into Techstars, incubating the product. They got five$ 100, 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 going to take over the world and eliminate the need for desktops, so the value prop worked. Unfortunately, they started growing out the go- to market team and it didn't work. So when I joined 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 I think we had a few thousand MRR, similar to like when I joined HubSpot. There was no one on the go- to market side. The only people left in the company, they slimmed it down after they had that first kind of shot and it 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. So to answer your question, the first thing that I did was got on the phone and started talking 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. What I discovered pretty quickly, actually, before I joined was a lot of marketing agencies were doing very manual reporting. They were literally pulling data from different systems and the spreadsheets, they were taking screen grabs, putting 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. So I started pitching agencies on automating that process. 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 on board. So then that created an issue of like, all right, now I've got to figure out how to onboard these people. So I did that for a while. At the same time, I opened up two positions, one for marketing and one for customer onboarding or customer success. So I hired two very junior people. I continued to do the selling. I approved every blog post that we published. I was coaching the new person that did onboarding, because 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. So it was just the three of us for a little while. I got lucky and one of my senior guys from HubSpot was looking for something new and he ended up joining me as our first salesperson. So in the first year, we invested pretty heavily in sales here in the US. 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 looking for a new marketing job, I'd always respected him, John Bonini, he's still with the company as our director of marketing. So he came on board 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. At this point, 4 years later, we are 55 people. A little more than half of that are engineers, about a third of that is customer support, so a big portion is customer support, and the rest is sales and marketing. I should say a third 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.

Shawn Finder: That's interesting, because a lot of that 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 built the product. What I did with my second one was I told myself let's continue to build the product and the sales will come.

Peter Caputa: Got it.

Shawn Finder: So we kept double- downing on the product and features and more features and more features as we continued to expand our product. But one thing we didn't do is, as you mentioned, and I, and I 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, closing the deals, doing the customer success, doing the support. I had inaudible 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 kind of 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 when there was already competitors in the market, that we're going to fall behind our competitors. So we had to continue to double- down on the product, but let the sales come. It's an interesting way.

Peter Caputa: It 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. There was really a product there. 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've literally built and managed 70 integrations. You know, a lot. We had 10 core integrations when I joined and we built off of that, basically. crosstalk. More than 50% of our head counts has always been in product, 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 kind of 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. Back then, in the first year, it was even higher. So we've always had a lot of sales that didn't require a lot of onboarding because we've invested a decent amount in the UI and UX in onboarding process and app.

Ollie Whitfield: So a lot of your customers come on through some kind of organic or maybe SEO as a channel or something like that.

Peter Caputa: Yep.

Ollie Whitfield: 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 there's a lot of content that you've got. Is that fair to say, that's the winner, because that's where a lot of people crosstalk.

Peter Caputa: Yeah, I think like the big opportunity-

Ollie Whitfield: crosstalk live in that world, they're always trying to consume that. So you're just on the pulse with it.

Peter Caputa: Yeah. So obviously, coming from HubSpot, I'm a big believer in content marketing. I saw it work there and, of course, with many of our customers and it can be a huge driver of any business. I think it scales well because an investment today has a long- term return, not just a short- term return. But what I really loved about Databox was that 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. 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 we'll create a lot of content around Google Analytics, or then we'll create a lot of contact about Facebook Ads and then go from there. But yeah, big believer content is a major driver. We get about 4, 500 signups for the free product every month. It's all coming 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.

Ollie Whitfield: Hey, that's a lot.

Peter Caputa: It is, yeah.

Ollie Whitfield: That's a machine.

Peter Caputa: Yeah.

Shawn Finder: So Peter, I do have a question. When did you guys invest? I guess, because you guys are so content driven, when did you guys invest in your first SEO employer, someone that helped you guys with the SEO? Because I know one of the biggest mistakes we made was not investing in SEO early enough in the process.

Peter Caputa: I feel like we've gradually improved there, even as late as like this month.

Shawn Finder: Okay.

Peter Caputa: HubSpot, that's all we sold for the first few years is crosstalk tools and the idea of blogging, so I know enough to be dangerous there. But just this past quarter, so four years in, we went back and we updated all our product pages, they're now much longer. Everyone has a video. We have images that show off how to use the product, multiple calls to action, FAQ's, value prop story, before and after. These product pages are our gold standard and they pop. They went from like second, third page for high volume, high intent keywords to first page literally like two days after we relaunched them. So we're still improving. We actually planned to launch and every piece of content we do now, it goes through a process of keyword 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.

Shawn Finder: Yep. Okay, so the next question we wanted to ask you was how do you guys make yourself service users like stick your customers? So I know that's something we talked about was the freemium, the self- serve. Talk to us about a little bit about that for the audience.

Peter Caputa: Yeah, we're in an interesting situation. It's actually a bit of a complex sale. Not in the traditional sense of like an enterprise sale where you've got to 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. 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. Unlike other software, even like a HubSpot CRM, where there might be some slight variation in how you use it, your sales team might be structured slightly different, you're all going to use deals, you're all going to use contacts, you're all going to use company accounts. That's different for us. Somebody might come to us and say I'm using Pipe and Google Analytics and SEMrush, and the next day somebody is going to say, oh, I've got to integrate my custom SQL database with my product usage information, and I want to correlate that to my information intercom. So like there's all these use cases. It's 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've scaled. This year, we'll scale more of our sales team, but the support team is the first team I'd say we've scaled you. A guy, another guy who 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. His first thing was like,"We've got to do a knowledge base." 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. He 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 keeping up with email tickets, when we add chat, how are we going to possibly keep up with inaudible? I'll correct you a little bit, we're not fully butched out, because we raised money before, but for the last two and a half years, we've been cashflow break even in managing.

Shawn Finder: Amazing.

Peter Caputa: So we started doing chat and I said, all right, we'll start with the people who might buy, and so we started with the website. 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." So like three days later he expanded it without telling me and then we started doing chat across the whole customer base. That's been huge because when somebody decides like, hey, I'm going to 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. By offering that chat and that immediate support, and our response rate is 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. Actually, we 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. The close rate on those is really high. We're able to, out of the 4, 500 people that sign up for a free product and the roughly thousand 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.

Shawn Finder: Got it.

Ollie Whitfield: So, Peter, you just discussed about 100 different moving pieces of the puzzle there. There's a lot of stuff going on.

Peter Caputa: Is it too fast?

Ollie Whitfield: Where and how on earth do you even start with planning the prioritization of all of that? I mean, you've got a lot of things going on there, how do you juggle all of it and put it into a piece of paper with an order to it?

Peter Caputa: 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 like that support connection and product connection is tighter than I've ever seen in a SaaS company. We have processes for not only capturing like 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. 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 in some situations on a daily basis. Of course, the marketing team uses it for our content. So 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. So you can imagine the amount. 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 page pillar pages. So we're doing everything inaudible. So long story short, first thing is like tight project management. Second thing would be tight processes. Like we have, somebody was telling 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. Then third, every team sets goals in two ways, what they're going to do that quarter and what result we expect from that. 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 support, it's 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 going to publish, we write how many integrations we're going to build, how many metrics we're going to 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 that 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 going to go about doing that. We have an interview process and crosstalk.

Shawn Finder: 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 just you've provided a wealth of knowledge. How do you, A, self- educate yourself? Do you read books, do you listen to podcasts, like how do you grow your self- intellect?

Peter Caputa: Yeah. My wife laughs at me because I probably buy like four or five books a month and then I read like to chapter two before I get antsy. 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. 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? 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 like read about online before, but they do give really good frameworks because somebody smart sat down and thought about that topic for a while. So I do read a lot of books. My favorite lately is How to be a Capitalist Without Capital by Nathan Latka. Then I've been reading Seven Powers and then Machine Platform Crowd by Andrew McAfee. Those are three books that I've been kind of skimming and reading for a little while now. Then I love podcasts. I take the dogs for a walk or if I'm going going 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. It helps me kind of 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.

Shawn Finder: Then I guess, lastly, where can people find you?

Peter Caputa: I'm pretty active on Twitter. My Twitter handle is pc4media. As Ollie mentioned, I do a lot of sub- tweeting there after conversations or after planning, where I'll try to distill some thoughts down into small character threads. Then I'm on LinkedIn as well, Peter Caputa. I don't log into LinkedIn as much because I find that it's really easy to get caught up in there talking to people and spend a lot of time.

Shawn Finder: 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.

Peter Caputa: You're welcome. Pleasure.


Have you ever wanted to become a full-time


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 welcome successful

business founders together and will help you decide where to invest, how to pick

the best channels, scaling your business, and ultimately 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.

Subscribe to the INSIDE Inside Sales Podcast!

Today's Guests

Guest Thumbnail

Ollie Whitfield

|Product Marketing Manager, Autoklose
Guest Thumbnail

Shawn Finder

|Sales GM, Autoklose