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How To Make the Most of Your Company’s Data, Including Making it Available to All Employees

Host Jon Penland, 

Tune in to learn how Peter Caputa IV, CEO of a business analytics company and marketing/sales expert, approaches data in a professional setting. This includes the importance of proper data collection and usage, as well as why you should make it accessible to all employees. Peter and Jon also discuss the power of partnering with marketing agencies as SaaS resellers.


1 hour 10 minutes



Episode Summary

In this episode of the Reverse Engineered podcast, you’ll meet Peter Caputa IV, CEO at Databox. Peter previously worked as VP Sales at HubSpot and has maintained a successful career in growing businesses and agencies. 

Many companies do not take full advantage of the data at their disposal. Peter explains the main data issues companies face: an overwhelming amount of data sources, improper data collection, and lack of data analysis training. 

With a career’s worth of experience working with agencies, Peter also delves into how to bring on marketing agencies as resellers and the reasons to do so.

Key Insights:

  • Picking the vital metrics is the most important step. Data is critical for understanding your clients’ needs and satisfaction with the services provided by your company. “The bigger challenge is most people just aren’t using data. And it doesn’t have to be that hard. I think that the predominant use case for data is to justify decisions. And I think that’s okay,” Peter claims.
  • Software is eating the world. We are surrounded by software, especially now, during the pandemic. “Restaurants are being disintermediated from their customers because nobody can go to them anymore. But we got things like GrubHub, Toast, and a bunch of other systems that take the order and take a cut or charge. In the case of Toast, they’re charging for the software. But, every industry, not only B2C and B2B, is going to go through a reckoning where they have to think about how to leverage software to go to market more efficiently.” Is software really eating the world or is it making everything more straightforward?
  • Content, SEO, inbound marketing: advertising without interrupting people. “Instead of interrupting people with sales, marketing messages, and advertising that they don’t want, do things that attract and pull them to you,” explains Peter. “A big part of that is creating content that can be found in search engines. It could be shared on social media by other people, even paid ads. At this point, I think it is pretty inbound because it’s so targeted and personalized to the experience, and you can ignore it if you don’t want to pay attention to it.”

Today’s Guest: Peter Caputa IV, CEO at Databox

Prior to joining Databox in 2017, Peter was VP Sales at HubSpot where he built their agency program to $100M+. Peter has helped over 100 businesses, and over 100 agencies and media companies grow by implementing sales and marketing excellence.

Episode Highlights

Databox – Pulling All Your Data and Performance into One Spot

“At Databox, we basically help companies pull all their performance data into one spot so that they can monitor their performance, report on it, make sure that goals are hit, and things like that. We plug into a bunch of different software companies, software tools, like Google Analytics, HubSpot, MailChimp, Google Ads, LinkedIn Ads, Facebook Ads, et cetera, to help people have a consolidated view of how they’re doing.”

Not All Data Is Good Data

“Not all data is good data… I think that it’s rare I see a business that’s too analytical, especially in the SMB market. I think that, as companies get bigger, they end up hiring analysts, and they might go down rabbit holes. The bigger problem is that most companies don’t use data at all.”

Be Proactive, Not Just Reactive

“I’m a big believer in tasking customer support with both being reactive and proactive. And most companies, I think, separate those responsibilities. But there are always ways to task your customer support team with being reactive. […] I like to think of customer support as almost like demand generation for both my sales and my services teams. […] I always talk about being proactive and not just reactive. The other term I use is being responsive versus being prescriptive.”

Software Still Has a Lot of Eating to Do

“Marc Andreessen says, ‘Software is eating the world.’ I think that we’re in inning 1 of that. Software still has a lot of eating to do. But I do think it’ll happen. The way that we [software companies] go to market is very software-enabled. And it wasn’t that way 20 years ago, for sure.”

“If I want to hire somebody to fix my house, I go to Yelp’s list. If I want to buy groceries, I go to Instacart or directly to the website of Amazon.”

Does Unforgettable Mean Successful?

“When we started [HubSpot], the focus was on inbound marketing. And it basically meant that instead of interrupting people with sales, marketing messages, and advertising that they don’t want, do things that attract them and pull them to you.

At the time, nobody was selling inbound marketing services. Agencies were selling the opposite. They wanted to sell you the billboard and the magazine ad and help you with your trade show set up and all this other stuff that was expensive and interruptive. And when we said, ‘Hey, that stuff doesn’t work anymore,’ they’re like, ‘Of course it works.’ […] All that stuff works if you do it well. But we came out with this message, and it was not forgettable because it pissed people off.”

“I’d highly recommend a certification program because most agencies I mentioned earlier are very small. And so they rely on MarTech companies to train their team members. And if you have a certification, it makes it real for them to say, ‘All right, go get your HubSpot certification, and go get your Drift certification, and go get your Databox certification.’ And you can literally tell a new employee to go and do that in their first month, without a lot of effort on the agency’s part.”


[00:00:04] Jon Penland: Hey everyone. My name is Jon Penland, and this podcast is brought to you by Kinsta, a premium managed hosting provider. In today’s episode, we’re talking to Peter Caputa IV, CEO of Databox. Pete, welcome to Reverse Engineered.

[00:00:18] Peter Caputa IV: Thanks, Jon. It’s a pleasure to be here. Looking forward to the conversation.

[00:00:22] Jon Penland: Yeah, I really appreciate you taking some time out of your day to chat with us. So to start us off, can you introduce yourself to our listeners?

[00:00:28] Peter Caputa IV: Sure. You got my name right. So that’s good, Pete, and go by Pete here. But yeah, I run a company called Databox. I joined the company about four years ago, as CEO. Before that, I spent nine years at HubSpot marketing software, now a CRM software plus marketing and software. Build out the, and before that, I ran a small marketing agency that specializes in helping people with online promotion of events.

[00:00:57] So I’ve been doing marketing for the better part of 20 years here, online marketing for the department, 20 years, building websites, things like that. And then got into sales there at HubSpot and now, running a company, a software company. At Databox we basically help companies pull all their performance data into one spot so that they can then monitor their performance, report on it, make sure that goals are hit, and things like that.

[00:01:24] So we plug into a bunch of different software company, software tools, like Google Analytics and HubSpot and MailChimp and Google ads and LinkedIn as Facebook ads, et cetera, et cetera, and help people have a consolidated view of how they’re doing.

[00:01:37] Jon Penland: Okay. Awesome. So you’ve already told us a little bit about who Databox is and how it plugs into a whole bunch of different outside systems to pull data in. So what is the problem that Databox is trying to solve?

[00:01:51] Peter Caputa IV: Yeah, so the problem is so there’s a really simple problem we solve. And then there’s the harder problem that I still think we’re trying to help people solve. But the simple problem is that when you start doing marketing and when you have a sales team and the customer service team. And you might have a product that you’re tracking the performance of, if you’re a software company or you’re selling online and you’re going to have a shopping cart, et cetera, et cetera.

[00:02:20] And of course you’ve got your website and all of that. And so when you start to do all those different marketing activities and sales activities, et cetera, it’s really hard to have a consolidated view of how things are going. Most marketers alone are using 12 different tools to do stuff, to just run their own monthly marketing activities.

[00:02:45] And so where we come in is helping them pull that together where. Most of them were spending a lot of time trying to get a handle on that. And then the problem is really acute at marketing agencies where they will have say 10, 20, we have some agencies have a 100 clients.

[00:03:03] And imagine trying to like, look at data from 12 different tools across 100 clients, you’re talking hundreds of different logins and logouts and screens and all of that. And so where we really come in is just helping agencies automate that time. There’s a lot of agencies they’ll spend a day or two just pulling reports together to show their clients how their work’s performing.

[00:03:22] And so we can automate the hard parts or the time-consuming parts of that.

[00:03:29] Jon Penland: Yeah. What’s interesting, you actually hit on two different things there. And I didn’t realize that there was a dual focus there for Databoxes. You talked about bringing data into a consolidated view, so you can see all of that data in a single place. But the other piece you talked about is the automation aspect where, you know, as somebody who works in operations for my company, I can tell you, I would have to count.

[00:03:50] We have a lot of log-ins, right? There are just so many systems that we’re using and trying to keep track of all of that is a significant operational challenge. So that it really isn’t a piece that I thought about that Databox really helps with that kind of operational overhead in the risk of sharing all those log-ins potentially.

[00:04:07] Peter Caputa IV: Yeah. Yeah. We rarely get into that, the risk part was an interesting point. Yeah. You don’t want to be sharing log-ins to all these different systems. We do have a very sophisticated permissions system. So we have some agencies that don’t want to share their financial performance with all of their team members.

[00:04:26] In which case they can still connect the QuickBooks or Xero account and have just a dashboard just for them or maybe their CFO or their outsourced accountant. So there is, we do, we have put a lot of thought into managing that risk. But yeah, but I’d say the biggest thing is people come to us and say, “Hey, I’m spending hours and hours every month, trying to get a handle on this. How do we automate that?”

[00:04:45] The bigger problem we’re trying to ultimately solve is to help people more efficiently manage and improve performance. If you don’t have a centralized place, it’s really hard to get a handle on that. If you don’t have one place to set goals for different members or different teams across your company, it’s really hard to get a handle on how you’re performing at any given time.

[00:05:04] And it’s really hard to analyze if you’re in all in and out of all of these different interfaces. And so analyzing more regularly tracking performance and getting, even getting alerts sent when performance is off. That’s where we’re spending more of our development time is really helping companies figure that out.

[00:05:21] Jon Penland: Yeah, that’s a really interesting distinction. I’m glad you pointed that out because what I’m hearing is that you’re not just pulling the data into a single place, but then you’re helping companies make decisions and move forward based on that data. So it’s not just about, “Let’s make this data accessible.”

[00:05:42] It’s “Let’s make good decisions with this data.”

[00:05:43] Peter Caputa IV: Yeah. It’s playing a football game, a coach in a football game. I don’t know what sports you play, or bask, baseball, any game without a scoreboard. If you don’t have a scoreboard and you got to ask all your players how things are going, you’re not going to get a feel for how to make the next call, right, in the game.

[00:06:00] So similarly with your business, if you have to go to 10 different people and they have to go into three, three different tools each and in order to get a feel for how performance going, there’s no way that you as an individual or executive can really figure out what’s the next play. What’s the next move, who should you hire next.

[00:06:14] What project or initiative should you greenlight next, what things should you invest more in, that’s working already, what things should you shut down. If they’re not working all that stuff.

[00:06:22] Jon Penland: Yeah. So is there a wrong way for a business to use data and their decision-making and management or is all data good data?

[00:06:29] Peter Caputa IV: Not all data is good data, right? Bad data and bad decisions out. It’s rare that I see a business that’s too analytical, especially in the SMB market. I think as companies get bigger, they end up hiring analysts and they might go down rabbit holes but I think the bigger problem is most companies don’t use data at all.

[00:06:58] Really they’re seeing, they’re observing more and what happens in meetings and the financial statement, maybe they have a leaderboard for the sales team. They’re not thinking about every step of their marketing process, they’re certainly not breaking up their sales process and trying to think how do they optimize different parts of the sales process.

[00:07:19] So I think that the bigger challenge is most people just aren’t using data. And it doesn’t have to be that hard. I think the most important step is actually picking the metrics that are important, both in terms of what you want to achieve as, as well as what work you’re going to be doing.

[00:07:36] And then setting goals around it and holding people accountable to that. It doesn’t have to be that sophisticated. You don’t have to analyze it six ways from Sunday to figure out what to do usually.

[00:07:45] Jon Penland: Yeah. It strikes me that it’s probably common for small businesses who haven’t done a lot of, haven’t used a lot of data in their decision making in the past for them to use data to back up decisions they’ve already made, as opposed to starting from the other direction, saying “Let’s look at the data and see what that tells us.”

[00:08:08] Or do you see it, as somebody who has a number of customers who are looking at data for the first time, are you seeing that sort of a mentality shift from does this data from our thinking as opposed to let’s start with the data and go from there?

[00:08:20] Peter Caputa IV: Yeah, I think in most small businesses, first of all, there’s not a lot of data, right?

[00:08:26] Maybe you have two salespeople or something like that. And you’re, let’s stick with websites and marketing. Maybe you’re producing a handful of pieces of content every month and sending out an email newsletter.

[00:08:35] So I think yes, people use data to justify their decisions. In fact, that is the main reason to do reporting, right? It’s like you made a bunch of decisions or whether you’re the one doing the work or you’ve delegated it, but you want to know, did that work or not, was that investment that I made in time or money worth it.

[00:08:54] And so I think, yes, the predominant use case for data is to justify decisions. And I think that’s okay. I think the more important thing to use data for is like once you know something working, you should do more of that. And so it’s really about in most businesses, you’re not trying 10 different new things every quarter.

[00:09:15] You’re going to try two or three new things and you’re going to keep doing 10 things that you already know to figure it out. And so it’s really a matter of like how much more do I invest in which of those 10 things. And I think that’s the part that most companies miss, right? It’s, “Yep, that’s working, let’s try something new.”

[00:09:30] Instead of saying, “Hey, that’s working. Can we do, can we have, can we get three times the results out of that, if we double down on it or…?”

[00:09:37] Jon Penland: Yeah. So let’s say that I’m the typical small business owner, CEO, not really using data the way that I should. What’s the first step? How do I get started moving in that direction?

[00:09:48] Peter Caputa IV: I think, first of all, you got to have the right tools and place. And I don’t know how small you’re talking here, but we still like the most part, our most popular integration is Google Analytics. And the sad thing is like the majority of those people still don’t even set goals for goal tracking.

[00:10:04] They’re not tracking to see did someone fill out a form on their website. And so I think starting really simple there, right? You might start with SEO, if you’re already doing some content marketing or at least optimize your website, maybe you start with SEO. Maybe you’re spending money on ads, but you’ve set it and forget it instead of thinking about different creative ways that you could get people to your website and convert.

[00:10:28] So it really depends on which initiatives they’re doing and starting from that, right? The first thing that we do when somebody signs up for our product is we’re asking them, “Hey, we noticed you connected this data source, Google Analytics, here are 10 things we could help you measure with Google Analytics. Which of these would you like us to help you with?”

[00:10:52] And so I think it really starts with what they’re doing now, what tools are they using now.

[00:10:56] Jon Penland: Okay. So taking a step then back from this really small company that’s really just getting started to a larger company that has some data. Based on some things I’ve seen you write, I think you’re a big believer in the idea that data should be visible, that there should be a degree of transparency across the company around that data.

[00:11:16] Am I right in making that statement that you don’t think data should be siloed to a small group of decision-makers?

[00:11:21] Peter Caputa IV: Oh, yeah, absolutely. I feel like that ship sailed 10 years ago and it’s a great question. And most companies don’t operate this way still, but I guess the people that I hang out with in software as a service companies and marketing agencies have all embraced that approach of sharing almost all of the performance data with all of the team members.

[00:11:41] In fact, many of the agencies I know, and the way we operate, we share our financial results at the end of the month with everyone. In fact, we train our team members on how to understand our financial performance, so that when they’re making decisions or when, when they’re proposing ideas or raising issues that need to be addressed, they’re informed by the strategic goals of the company, financial goals of the company. And yeah, absolutely big believer in that. And so I think one of the things that Databox helps with is pulling that data into one spot and then delivering it.

[00:12:18] And we’ve built a bunch of tools so that people can basically monitor that data anywhere. So there’s you can put it up on a TV in your office, home office, if you want, you can put it on your mobile device and access all your data on mobile. Of course, you can access it through a browser on your desktop or laptop.

[00:12:35] But then we also have things we have ways of integrating with Slack so we can send updates to Slack, or you can call data from Slack, query data from Slack, as well as through email scorecards and snapshots of dashboards that sent an email on a periodic basis. So we’re all about getting the data in front of everyone.

[00:12:53] I think that’s what empowers organizations to improve from the bottom up. I think business is just too complex today for… just take marketing’s too complex today for one or two people to really understand and optimize. So you really need to empower your people to…

[00:13:12] Jon Penland: Yeah. Something that you touched on in that answer that I think can be missed, is the need to educate around that data. Because I think it’s possible that single pieces of data absent context around what that data means can be misleading and can create confusion or wrong assumptions or whatever.

[00:13:38] And so I appreciate that you made the point there around the need to educate around, if you’re sharing financials. Well, that’s great, but we need to explain how to understand. Yeah. Cause especially with the financials, it can cause a cause concern as much as it can educate. Yeah, agreed, yeah we’re a software as a service company and so there’s a very standard way of analyzing a software as a service company around different activities, different things that customers do where they’re buying, it’s upgrading, downgrading, canceling, reactivating, all that stuff.

[00:14:14] Peter Caputa IV: And we actually review those numbers with our entire team every quarter. Those, they can access those inside our own Databox account. And then we have training for new members just to learn those things. So that when they’re looking at that and there they can connect the work they’re doing to the results of the business.

[00:14:36] And it really motivates, I think, people. For example, we have this, when someone signs up for our product, we have a team that will reach out and say, “Can I build a dashboard for you?” Our tools are easy to use. Most people figure it out on their own, but we do that just because people don’t know what they don’t know.

[00:14:54] So we’ll do that. And, and that correlates directly to the number of deals that we create for our sales team, which correlates then very consistently to the number of closes and number of new customers. And we can continue to correlate it to other numbers as well. And we put our new people doing that activity.

[00:15:15] And so having them do that activity, but explained to them that connection between the deals, the new customers are then the revenue and our growth, then they can see, “All right, the work I’m doing is helping to basically cover my paycheck every month.”

[00:13:58] Jon Penland: That’s really interesting. So something that a lot of companies do and it’s something that we do at Kinsta is to try and tie individual efforts into the company effort using goal-setting systems, whether it’s OKRs or whatever. And so it’s interesting to hear you talk about, really, if I’m understanding correctly using data for the same type of purpose where it’s like, “How can I correlate what I’m doing from a data-driven perspective? How can I correlate it back to the overall company results?”

[00:16:00] So it’s maybe, I guess if you have key metrics identified that these are the needles we’re really trying to move and somebody can then tie their own efforts directly back to moving those needles. It really is accomplishing the same type of objective as being able to associate individual effort to company goals.

[00:16:21] Peter Caputa IV: Yeah. Yeah. I love, we love the OKR system. We use a modified version of it. I won’t get into the why, but yeah. OKR is, I think for people that don’t know, key results and objectives could be to grow website traffic just to keep it real simple. Key result could be the number of sessions that you’re getting at the end of the quarter.

[00:16:43] And in most OKR systems, you’re looking at that on a quarterly basis, setting a quarterly goal, and then checking in on a weekly basis in order to make sure that you’re on target. And the whole team knows that key result is important and so they’re focused on that even on a daily basis to say, “Hey, is what I’m doing actually contributing to that key result?”

[00:17:01] So yeah, big fan of that. One of the things OKR I think fall short in, in few practical ways when it comes to operating an empowered company where everybody’s empowered to improve performance. And one of those I think is connecting what we call the outputs or output metrics to the outcomes.

[00:17:22] And so key results are, you could probably say key results could be either one, but I think it’s really important to say, “Hey, we’re going to get that, we’re going to target the key result of a certain amount of monthly sessions at the end, by the end of the quarter in order to grow our website traffic.

[00:17:37] But in order to do that, the way we’re going to do that is we’re going to write X number of blog posts.” Let’s just say it’s a hundred. And so that team should be measuring how many blog posts if they have gotten out the door on a weekly basis in order to make sure that they’re hitting that hundred target.

[00:17:52] And obviously you want to have some data, ideally that says a hundred is going to get you to the outcome goal, right? But we’re very keen on connecting those outputs to that outcome. Because if your marketing team is tasked with growing traffic, it’s not going to happen through organic, especially through organic marketing. It’s not going to happen on a linear basis.

[00:18:09] And so they need to be motivated on a daily basis to produce the work that will ultimately produce the result.

[00:18:16] Jon Penland: One of the things that I like about the concept you’re talking about here of using data to connect individual performance, to company performance, there are roles that are not a great fit or those that are difficult to fit into the OKR framework. So where you have a role where the work really shows up on your desk and you need to do it?

[00:18:40] So I’m thinking of things like customer support development, these types of things, where you’re assigned a task, you complete the task you move on to the next. These roles can be really difficult to tie into an OKR system because these people are not necessarily working on long-reaching projects or those sorts of things that they have control over.

[00:18:59] But what they do have control over, if you’re a support engineer there’s some degree of control over is your ratings that you’re getting back from your customers.

[00:19:07] Peter Caputa IV: Yeah. Or just the number of bucks or yeah, the downtime, whatever it is. Yeah, exactly. Certain roles are easier, right? Sales is really easy. You can say, all right, you got a certain number of calls, a certain number of deals, a certain number of deals closed. I think marketing is relatively easy because everything is measurable, especially digital marketing.

[00:19:29] Customer support… what I’m a big believer in is tasking customer support with both being reactive and proactive. And most companies, I think, separate those responsibilities, but there’s always ways I think to find, even if it’s simple ways to task your customer support team with being reactive. It could be simple as once they solve the question that they’re asked by the customer, then proposing something else that’s related to that, that they could also be doing in your product or with your service or whatever. And then putting a number behind that. One of the things that we do is for customers that are not quite set up as well as we would like them to be, our customer support team is responsible for getting them on calls with somebody in account management, in order to further their onboarding process.

[00:20:21] And we track that. And so I think I, I like to think of customer support as almost like demand generation, both for my sales and my services teams.

[00:20:31] In many of those services we’re doing for free are not trying to make money on the services per se, because we’re a software company. But I’ve, I always talk about being proactive and not just reactive. The other thing, the other term I use is being responsive versus being prescriptive.

[00:20:50] And I think in many companies, cause you’re helping your clients or your customers with the same thing over and over again, you have experience that your, most of your customers don’t have. And so instead of just saying, “Hey, yeah, I can help you with that.” It’s “Hey, I can help you with that for sure, but I’d also recommend this because 9 out of 10 companies that I work with, like you, also do these other things and this should correlate to success in this area of business. Is that something you’d be interested in learning about?” Those things, I think help organizations thinking about how to put numbers to customer support.

[00:21:26] Jon Penland: Now I really love that. Something we place an extremely high priority on the quality of service, quality of support. One of the questions you wrestle with is how do you quantify good customer support outside of just what rating did the customer give you and how many tickets did you close?

[00:21:46] And I love these ideas of, being proactive as opposed to just reactive. Did you just close the ticket or did you take the opportunity to educate the customer? And now figuring out how to attach data to those points. That’s… probably a whole other challenge.

[00:21:58] Peter Caputa IV: You need some kind of activity that they then do pitching, you know, in a nice way. I think that’s important. The other thing, since we’re on the topic of customer success, we look at first response time and resolution time as two things. We’re a software company. So our customers typically pay us either monthly or annually, and since we’re a software company similar to you, right? I imagine you can measure usage. So we’re looking to see, are we moving customers into a usage level that correlates ultimately to retention, right?

[00:22:35] Retention is a very lagging indicator. But if we can see that short-term activities that we can cause a customer to do that will correlate to retention, like a big win for that, you know, the customer support team. And then of upgrades.

[00:22:48] Jon Penland: One of the tricky things with some of the metrics site, first response time jumps out to me is that it’s important to couch a metric like that. In a way that it doesn’t lead to unintended consequences. Right? Cause if the support they’re going to be measured on first response time, they might jump in, you know, really, really fast going to get right back to you. Then it’s before they’re back. Right. So you got to figure out how to stacks these things against themselves.

[00:23:17] Peter Caputa IV: Whenever we set goals, we try to set a pair of goals, where we’re setting both a quantity goal as well as a quality goal. And so the quantity goal might be the number of tickets that you’re resolving or responding to, or number of chats in our case that you’re responding to, the quality metric might be the response time and the satisfaction score.

[00:23:38] And so, like, I think if you just look at one metric, yes. Companies can over-optimize on that. In fact, we rely on chat to book sales calls because people are in our app and that’s when they have questions. And so that leads to a sales call. And so my sales leader is always on top of measuring response time in chat and bringing it up every week to say, “Hey, this dropped a little.”

[00:24:00] And so, you know, therefore it causes the support team to say, “Hey, we’ve got to put that just as prominently as the number of deals we’ve created because it’s important that we keep that response time high.” So I think, it’s a matter of balancing quality and quantity. 

[00:24:16] Jon Penland: Absolutely. All right. I’m going to shift the conversation in a little bit of a different direction. So I’ve a couple of times where you refer to yourself as a challenger. In fact, I’ll read from an article you wrote a couple of years back that I read. It says: “I’m motivated by proving other people wrong more than almost anything.” I’m just curious where this mentality came from. And, and how do you think it’s helped you over time?

[00:24:45] Peter Caputa IV: I think it started from my Italian stubbornness from my heritage. Like my great-great-grandfather came over, and I didn’t know him, but my grandfather, a rule-abiding guy, never broke the law that I know of, but was always challenging systems and people. My father was the same way.

[00:25:12] I think I kind of inherited – always raised to ask questions and challenge things. And, then a little bit of a chip on my shoulder just to, you know, prove myself which I think came from my dad, setting a high bar and having high expectations for me. So that’s where it comes from.

[00:25:36] I’ve had success in my career challenging people. The biggest one so far would be at HubSpot where I was hired as a direct sales rep and started working with marketing agencies to get them to resell the software. And, initially, I was told, not to do it, and they kind of just did it for a little while and made sure it didn’t cause any problems, but after a while, I started pitching a program that we should build and was told no a bunch of times. In fact, the first time HubSpot made the Inc 500, Brian Halligan wrote an article that’s in the magazine and the article is all about how I was really stubborn and made this happen and how it was a model now for HubSpot to innovate and that they were looking for people that were willing to take something on in the nights and weekends.

[00:26:29] And so it’s lore now, I guess at HubSpot that Brian Halligan, the CEO didn’t want to do it. And I did it anyway and it worked out to be nearly 50% of their revenue and a market cap now close to $20 billion. I can’t remember exactly, but it’s up there.

[00:26:48] So that’s, that’s kind of the first thing. I’m constantly thinking in question form, about different ways to do things. And I think innovation, comes from the combination of two things that people didn’t think about before. I think where there’s a combination of business models or a combination of marketing practices or leveraging a marketing practice in a sales funnel. I like to think about different ways that ultimately result in either faster growth or more efficient processes.

[00:27:26] Jon Penland: Yeah. So actually the quote that I read was from an article where you talking about this idea of the marketing agencies how that was an effective way kind of putting some stubbornness to good use, I guess. And the idea of working with marketing agencies, sticking with that concept that seems to Reared its head a couple of times in your career. Like that’s, that seems to be what you were doing before you were at HubSpot. That seems to be a key part of what happened at HubSpot. And then I noticed a large part of who you’re working with today. So I’m actually, I’m curious, when did you pinpoint marketing agencies as a powerful way of going to market? 

[00:28:13] Peter Caputa IV: Before I joined HubSpot, we had built a SaaS company basically that helped people promote events. But we were in our early twenties, SaaS wasn’t a word back then. This was really no model for scaling those we just didn’t know what we were doing.

[00:28:40] We kind of made a living for a few years, but didn’t really scale a business. And so I ended up selling websites and doing email marketing because I was networking with all these local businesses and they had no idea how to do that stuff. Meanwhile, we’re building a SaaS company. We were building websites and sending email, like we had actually built an email server and everything.

[00:29:01] All that stuff was like second nature. Uh, so I ended up selling a lot of marketing services, did some SEO for people back then, which was really easy back then. That’s how I got into the value of that stuff. And still today, I think your business owner doesn’t understand digital marketing very well.

[00:29:21] So there’s still this huge opportunity. Based on the data that we had at HubSpot, and I’m not sharing anything that’s private, but a good portion of marketing gets done by marketing agents. It gets outsourced to marketing and it is probably 40 to 50% of the work or maybe even more. So if you want to sell marketing software you should think about how marketing agencies involved.

[00:29:49] That was really obvious to me in 2007/8 when I started the program. It was not obvious to others there. Most marketing agencies were not doing digital marketing very well, which is the reason why HubSpot did so well so quickly. And most SaaS companies thought at that time in 2000, 10 years ago, it was around 2008, 2009 thought, okay, SaaS is a more efficient go-to-market model. We don’t need re-sellers, we don’t need service providers. We’re building simple tools that people use by logging in. Nobody thought it was a good idea, except for me. I think the lived experience of selling and delivering marketing services helped me feel so confident with that, but also just working with a handful of forward-thinking agencies back then, I validated it and realized that like, all right, there’s really something here.

[00:30:46] They don’t know what to do. We don’t know what services to sell. Nobody’s out there setting a standard. We had an opportunity at HubSpot to tell these agencies, sell these services in this way. And we could create air cover where it’s like, all right, we’re going to be going to market. We have lots of millions of dollars in the bank. So we’re going to spread the word about this concept, which HubSpot called inbound marketing calls. And so that a path for agencies to follow and a market for them to capitalize on.

[00:31:18] Jon Penland: Seems like there was a really strong, I dunno, convergence of factors all at the same time, there where you had this background in marketing and you went to work for a marketing company, that for whatever reason didn’t feel at the time that working with marketing agencies was the best fit. And that’s where you came from.

[00:31:36] And you happen to have the stubbornness we’ve talked about, right. Or the challenger mentality. We should use that word. Challenger is nicer than stubborn. So you were a challenger and you stepped in there and were like “No, we, we really need to do this.”

[00:31:48] And I think, it’s kind of a unique convergence of factors there to make that work. I’m curious…

[00:31:55] Peter Caputa IV: Sure. Yeah. There’s, you know, 20 more factors that made it work, I think more luck than smart.

[00:32:00] Jon Penland: Yeah, of course. Right. The question I wanted to get to is: do you think it’s something about marketing agencies that makes them uniquely powerful as effective partners for SaaS, or do you think it’s just the idea of selling through partners that’s powerful?

[00:32:16] Peter Caputa IV: No, there’s a uniqueness about agencies that makes them unique for selling marketing technology, versus any other reseller out there. In fact, the only parallel that seen is accountants and accounting software, which obviously is very boring. The reason is that marketing agencies and accountants provide ongoing services to their clients.

[00:32:38] Like, I don’t know how often if ever you’ve changed your accountant, but I never have. And I don’t plan to. Things have to get really bad. Marketing agencies rotate through clients faster, but generally, if you’re happy with the marketing agency, you aren’t going anywhere for a few years.

[00:32:54] You might augment them with another marketing agency does something different, but, but for the most part, you’re sticking with them. So I think the fact that they’re already offering ongoing services was a perfect connection to SaaS companies that were trying to sell ongoing software subscriptions.

[00:33:12] And so what we did – one of the unique things that made me the right guy to start that was also my sales background. I had just learned how to sell. I went through an intensive program with a sales coach and learned how to sell. And I realized that marketing agencies aren’t good at selling.

[00:33:26] And so not only do we teach them what services to sell, we taught them exactly how to sell them. What questions to ask, ask how to position value, the steps to go through in the sales process to ensure they’re not wasting their time with prospects and aren’t gonna move forward. Quantifying the upside for the prospect.

[00:33:40] Closing the prospect, we taught them all of that stuff. We gave them what most people would pay 20 grand for a sales training course for free. That uniqueness of the agency. It also helps, and this isn’t true with accountants, but it also helps that marketing agencies often are pretty good at marketing themselves, and a lot of times they’re also are awful at it, but because they just don’t do it very well, but very frequently, marketing agencies are pretty good marketers. So partnering with a company that’s good at marketing, one of them is great, but partnering with thousands of them partnering them gives you some extreme advantages when it comes to search engine optimization. One of the reasons that HubSpot has done so well with their own content marketing is because they have thousands of companies talking about the same stuff, linking to them as the source.

[00:34:31] Jon Penland: Yeah. That’s interesting. And one of the things that you mentioned early on there in that answer is that when you started working with agencies, it was important for you to train them in how will they go to market? How do they sell the services? That brings to mind the question, what are the keys for a wants to work with agencies?

[00:34:54] Like how do they do that? Well, you can’t just say, “Hey, we have agency partners now” and then offer a program. Right?

[00:35:03] Peter Caputa IV: Yeah. It’s a lot harder now because – I’m sure you’ve seen the infographic from Scott Brinker, whereas it’s like he’s squeezed like 5,000 logos on a slide where it shows all the different marketing technology companies out there. I’m sure you guys are on it. So there’s just so much marketing technology out there.

[00:35:20] And most marketing agencies are very small. In fact, like 50% of them are less than 10 employees. And they don’t make payroll unless everybody’s billable at least 60, 70%, which is low. It’s really hard to get mindshare, it’s hard to get attention let alone mindshare, from agencies. At HubSpot, we had good timing, with Databox we figured out some, some angles to get their attention.

[00:35:46] But I think if you’re approaching that agency, just to get to them to resell your technology, it’s not going to work well. You need to find a way that they either use that technology to make themselves more efficient or you’re helping them get to a market that they couldn’t get to otherwise. Or you’re cutting them in of course, or…

[00:36:10] And this is how I usually recommend small MarTech companies start is you’re going to pick a small number of marketing agencies and work pretty tightly with them to go to market. Meaning you’re going to help them go to market as much as they help you go to market by working with them to make them look good and look like a good option for someone that wants to implement your technology and you’re sending them referrals. That’s really common in reseller programs to the enterprise. Like I advise on Drift and, if you can see my sweatshirt here, but Drift is another marketing software company for chat website, chat, conversational marketing, and a bunch of other stuff.

[00:36:46] They’re largely selling to the enterprise. And so they’re sending business to their top partners, which engages those people to gain mindshare with those partners. So I think that’s important no matter who you’re selling to these days, if you want to get agencies committed to you, you gotta bring them something.

[00:37:05] Jon Penland: Right. Yeah. I mean, it sounds like basically, you’re saying if you’re going to effectively launch an agency program, it can’t be about, you know, you have a particularly different pricing structure for them or whatever. You really have to tell them and demonstrate how you’re going to put money in their pocket.

[00:37:25] Right? Like they’ve got to come away and say, this is going to put money in my pocket either by saving me massive amounts of time or by actually pulling customers in the door. That has to be a really, really strong value proposition. 

[00:37:35] Peter Caputa IV: Yup, exactly. The other thing, it can’t just be, “Hey, my tool is really cool and it does this really amazing thing for your clients. You should sell it.” That’s not going to work most likely because there are already 4 other, 10 other, 50 other options like that. You did say like, pricing is important.

[00:37:58] I think it can be a wedge for getting an agency program started. We offer significant discounts as agencies use us for more clients. They can make money on the software. It’s not a lot. I actually did a poll on Twitter. I got like maybe 60 responses, and 20% of them make more than 10% on commissions or from reselling technology way, which I was more than I thought. It wasn’t a scientific poll but 50 responses is pretty good. So yeah there are different ways to go about it. The other thing that’s really important is that enablement, and we haven’t done this at Databox, it’s on the list of things to do, we need to hire someone to do this if that’s ok to say, is partner enabling. You can’t expect them to come in and figure everything out on their own. Most likely you’re going to get delegated to someone. And so the easier you make it for them to go learn your product, learn the services they can earn on top of it, learn how to present it or position it to clients or prospects, the better it is.

[00:39:13] And I’d highly recommend a certification program because most agencies, as I mentioned earlier are very small. They rely on MarTech companies to train their team members. So if you have a certification, it makes it real for them to say, all right, go get your HubSpot certification and go get your Drift certification and go get your Databox certification. You can literally tell a new employee to go do that in their first month, without a whole lot of effort on the agency’s part.

[00:39:44] Jon Penland: Yeah. Yeah. Interesting. One of the things you touched on a little while back was this idea that one of the things that made agencies such a particularly valuable partner at HubSpot was that they provided so much visibility. And there was a quote that I read, as I was preparing, which was about not being forgettable.

[00:40:05] And it made me think of this quote, which is something you wrote, which was that if you can accept the fact that not every company will be your customer, anytime soon, you’ll recognize that the riskiest thing a new business can do is to be forgettable. I wanted to start by asking the question. What do you mean when you say don’t be forgettable? What do you mean by that, what does forgettable mean? 

[00:40:29] Peter Caputa IV: I don’t think I could take credit for that thought. I don’t think anyone put it together that way. But I’m not the first one to say something like this. HubSpot’s a good example. When we started, you know I didn’t start the company but I was there earlier, so when we started the company, the focus was on inbound marketing which meant something else actually to note, to a very small group of people back then.

[00:40:53] Uh, so it was really an uncoined phrase. And so we coined this phrase, inbound marketing, I give credit to Brian and Dharmesh for that. And it basically meant instead of interrupting people with sales and marketing messaging and advertising they don’t want it, do things that attract them and pull you to pull them to you. Part of that is creating content that can be found in the search engines. It could be shared on social by other people, even paid ads at this point, I think is pretty inbound because it’s so targeted and personalized to the experience that you can ignore it if you don’t want to pay attention to it.

[00:41:29] Educating the customer through content and all that is a piece of it. But at the time, nobody was selling inbound marketing services. In fact, agencies were selling the opposite. They wanted to sell you the billboard, the magazine ad, and help you with your trade show set up and all this other stuff that was expensive but made them a good amount of money and interruptive. And so when said, “Hey, that stuff doesn’t work anymore.” They’re like, “BS that doesn’t work anymore. It still works, of course it works.” And you’re like “Prove it” and they’re like, “Ahh” because there isn’t a mathematical way of proving it. Of course ,all that stuff works if you do it well. But, we came out with this message and it was not forgettable because it pissed people off.

[00:42:20] I think Salesforce was a good one before that, in that they have a symbol with software in the middle and the X through it, like no software, because they were selling software as a service and they were the first ones to do that. And they were selling to these big companies that spent literally millions of dollars on implementing SAP or Oracle or whatever. And they were saying, stop doing that and pay us a few grand a month instead, so that pissed off a lot of people and was not forgettable. Right. Those are two good examples. There aren’t a lot of good examples of companies doing that – I don’t feel like we do that very well. We tried to but it kind of fell flat. 

[00:42:58] Jon Penland: Next question is, you know, I think doing things that are not forgettable, you can do that at different levels of scale. Do you have examples of ways that you’re trying to do that at Databox? You know, maybe you’re not creating a new category and you’re not creating SaaS and distinguishing from software prior, or creating inbound marketing as a new concept, you’re not creating an entire new industry. But are there ways you try not to be forgettable at Databox?

[00:43:32] Peter Caputa IV: Every software company wants to build a category. I don’t know that it’s advisable. It feels like it’s a long process. Like people ignored us and scorned us for years. And our CEO would, would listen to our demos and say, “Why aren’t you giving them the inbound pitch?” and I’d say “It’s because they just told me how much they love their radio advertising and direct mail.”

[00:43:55] So it doesn’t work right away. It takes a commitment. And so for us, we think that most reporting meetings are a waste of time. Most info can be digested almost ambiently not even, you know, periodically. Our thing is like, you don’t need reporting meetings.

[00:44:20] You don’t need analysts to sit there and analyze your business. You just need to democratize access to performance data so that everybody has it, and just their own performance, but others, and make sure everything’s working the system’s working to grow your business.

[00:44:34] So that’s our thing. We do a lot of stuff around crowdsourcing content that really kind of sets us apart. Not only allowed us to grow our organic reach and our customer base, but allows us to highlight the perspectives and opinions of other people. Sometimes we’ll write an article with two opposing opinions in it, or three or four.

[00:44:55] A lot of our content, and in the four years we’ve been doing that, we’ve quoted more than a thousand unique people. So that’s an interesting way to go about doing it, kind of like what you’re doing in this podcast. I think it’s a matter of innovating, not just your category of trying to create your own market or category, but being clever and innovative in the way that you’re marketing, the way that you’re selling.

[00:45:18] We’re very generous with our sales process. We have a free product, and then we offer a free trial on top of that. If you want it, we’ll build you dashboards for free. We will jump on calls and not try to sell you, but help you get set up on that. We’ll extend your trial if you need more time to evaluate it, like we’re very generous. You can start monthly if you’re not quite sure there are all kinds of things that we’re doing. We offer a discount if you pay annually and it’s a very public and transparent thing. So like there’s a lot of different ways I think you can go about doing business in a unique way that’s also beneficial for your customers, your prospects, and you know challenge things that way.

[00:46:01] Jon Penland: That’s interesting. Most companies are not creating a new industry, you know, Kinsta’s not creating a new industry. There are still ways to approach your business in… I guess the idea is don’t pull anything off the shelf, you know, whatever, whatever you’re approaching…

[00:46:17] Peter Caputa IV: Yeah. Like there’s value in pulling things off the shelf, but yeah. Maybe tweak it a little.

[00:46:20] Jon Penland: Exactly. If you’re pulling it, you’re going to do content marketing. You’re going to have a blog, but don’t have a blog that looks like everybody else’s, right? Like, find a way to make it unique, find a way to make it different, find a way to make it something that folks they’re going to remember. Interesting. So you’ve been in the SaaS space for a number of years. We’ve talked about that, you said marketing agency, but then you kind of pivoted and said it really kind of turned into a SaaS over time. And then you were with HubSpot.

[00:46:46] Peter Caputa IV: Well, it was in SaaS we always wanted to build a tool to help people promote events. It started with me planning, ski trips with Yahoo invites. If you remember Yahoo invites and then realized right, this software sucks. We could build something way better. And so that’s how it started, but because we didn’t know how to scale as a SaaS company, we ended up selling things that weren’t necessarily in line with that. We really pivoted into a marketing agency because it helped us pay the bills.

[00:47:10] Jon Penland: Okay. Oh, so you actually went the other direction. So, you started as a SaaS company and ended up turning it into an agency because you needed to pay the bills. That’s interesting.

[00:47:20] Peter Caputa IV: And that, you know, and then I joined HubSpot because I was tired of paycheck to paycheck.

[00:47:42] Jon Penland: Right. Yeah. I hear ya. So you’ve been in SaaS, I don’t know what that means, like 15 years, maybe something in that range?

[00:47:27] Peter Caputa IV: I, yeah, I’ve been 20 years, I guess. Technically. Like I said, it wasn’t called SaaS back then.

[00:47:34] Jon Penland: Yeah, right, exactly. Right. I’m curious. Are there any things, anything that you ran into frequently 10, 15, 20 years ago that you don’t run into anymore? Any objections you used to get frequently 10-20 years ago that you don’t just don’t get anymore?

[00:47:49] Peter Caputa IV: Yeah. Back then we used to get, “Wait a minute, you own all my data. You have access to all my data like that one.” Right? You don’t get that anymore. And we do have access to people’s data, of course, but we have controls in place and we track everything and we limit who has access and when and all that.

[00:48:09] So all that stuff’s covered under laws these days. That was one. But I think the bigger thing, and I think this is going to happen to every industry but Marc Andreessen says “Software is eating the world.” I think we’re in inning one of that, like there’s still has a lot of eating to do. But I do think it’ll happen. And I think SaaS companies… Obviously, we are software companies, but I think the way that we go to market is very software enabled. It wasn’t that way 20 years ago, for sure. And it wasn’t that way 10 years ago. So 10 years ago when we said “Hey, let’s scale HubSpot,” we said, “Okay, let’s hire 30 salespeople. Pay them 110 grand a year and put them on a quota and fire them in three months if they don’t make it.” That was state of the art, and still is. Honestly for most companies, that’s how they operate. Today, the first thing a software should do is think about what’s a piece of value you can give away for free to anyone?

[00:49:19] Right? No questions asked, like go to our website, sign up and get this thing for free. That’s a game-changer for the efficiency of the marketing and sales funnel. And then, how can we start? Like in our case, I’m giving away services for free, because I know that if I invest, you know, say a hundred dollars just to keep it round, I’ll get back around a few thousand dollars 10% of the time. I’ll make that bet any day. I think what’s really changed is the efficiency of going to market. Like I said a few minutes ago, I think that will affect every industry and we’re seeing it, right? Restaurants are being disintermediated from their customers because nobody can go to them anymore, but we got things like GrubHub and Toast and a bunch of other systems that take the order and take a cut, or charge, in the case of Toast, they’re charging for the software. But, every industry, literally not, you know, B2C and B2B, is going to go through a reckoning where they have about how do we leverage software to go to market more efficiently – software and marketing.

[00:50:34] So I think we’ll see a shift of like 10 years ago, the job to be was in sales. You can make a lot of money in sales. I don’t think that will be true in 10 years. I don’t think you’ll be able to make a lot of money in sales in 10 years. In fact, I think you’ll have to own things to make a lot of money years in 10 years, but, but I think in the process, marketers will do much better along the way and engineers. 

[00:50:54] Jon Penland: Right, right. So interesting. So fundamentally, basically the idea is that 10, 20 years ago, SaaS just really wasn’t a thing. And, what has really happened over the last 10 or 20 years, is SaaS has become established as an industry, as a concept. And we’re moving into an era where it’s not just a concept, but it really permeates every industry. Every interaction that we have with the world around permeated in some way by software.  

[00:51:23] Peter Caputa IV: Literally everything.If I want to hire somebody to fix something in my house, I go to Yelp Brandy’s list. Right. If I want to buy groceries, I go to Instacart or directly to the website of the… or Amazon.

[00:51:39] Jon Penland: Right. You’ve been in this SaaS space now, particularly in the startup SaaS space with HubSpot, with Databox, and you mentioned Drift, I know you advise a couple of different companies. What is it about the software start-up space you interested in? That keeps you coming back and staying in this space?

[00:51:58] Peter Caputa IV: It’s the pace of growth. HubSpot’s a public company and they grew, they just hit a billion dollars in annual revenue. They did that in 13 years. That’s not the fastest but for a B2B company, that’s pretty darn fast. You know, at Databox, they raised money. We raised some money. They raised money before I came and we raised a small amount when I joined. But for the last two years, we’ve been cash flow break-even and growing 40% year after year so the growth is amazing. Right? We literally just hired 15 people this year so far. I think that makes it fun that every day, practically, I’m doing something new, every quarter, our team’s doing something new. You know, we’re changing or improving processes, I’ve created new roles. We’ll be creating another new role next month at the company. So that pace of growth, obviously that’s fun and challenging, I feel like if you’re not growing your SaaS company, you’re really missing the markets. I think it’s kind of the easiest thing type of company to grow. You gotta get a lot of things right. And all needs to be rowing in the same direction, but once you get there, growth happens.

[00:53:20] So that excites me. From a financial perspective, it was a smart move for me to go to HubSpot, of course, and I think is there still another good 10, 20 years of this kind of growth where companies are gonna grow so fast and the multiples would be so big. So from a financial perspective, it’s a smart space to be in.

[00:43:54] Jon Penland: Yeah it’s interesting you mentioned the pace of change. I feel like that is a bit of a double-edged sword. If you love to have a different job every six months, SaaS is fantastic. Right. You know, I can say that about our company. I’ve had the same title for almost three years now.

[00:54:18] Peter Caputa IV: But that’s the COO right? I don’t know where you go from there. There’s only one other option. 

[00:54:20] Jon Penland: I’ve had that title for three years now, but I can easily pencil out at least four different jobs I’ve had in that time. Like at different job descriptions that I’ve had in the last three years. And I’m really going through another transition right now. So even within the same title, as the company grows and the needs of the company change you know, you have a new job every six months.

[00:54:48] Peter Caputa IV: Yeah. And most of the time it’s the job you should have been doing about six months ago, right? Yeah. You know, same here. Like I like when I joined, there was very little revenue. We had a handful of customers. So I spent the first just closing deals.

[00:55:02] I hired a junior marketer. I ended up at nighttime editing his content, trained our first customer success person who is now our Chief of Staff. That is the beauty of a fast-growth company, is that there are amazing career opportunities for people.

[00:55:26] Um, we actually have a global team and so some of the people that I’m hiring have 20 years of work experience. One guy managed five bank branches, and I have him starting helping our users and chat. I think, you know, there are compelling reasons to join a fast-growth SaaS company, no matter where you’re at in your career because it’s going to grow fast, you’re going to learn a lot and you’re going to have opportunities to move up of roles and responsibilities, as well as compensation.

[00:55:56] Jon Penland: Yeah, yeah, absolutely. You know, I’ve been with Kinston now for four years or so, a little over four years, and it was a similar journey to your own where I joined the company when it was a company of about 15 people. And so I can echo that recommendation that, if you’re in the job market, if you can embrace the idea of a changing role of just leaning into opportunities where you within the company, that it’s a fantastic space to find your way into. You mentioned distributed, remote. Is DataBox a distributed company? Do you guys have folks all over the world?

[00:56:33] Peter Caputa IV: We are, we have some coworking spaces where groups of people are. It just kind of happened that way. The founders are from Slovenia and so, we have a co-working space there. But, yeah, I’m in Massachusetts. My Director of Sales lives about two hours from me in Massachusetts. It makes no sense for us to drive to see each other. The Director of Marketing is in Connecticut and my Chief of Staff in Philadelphia. We’re all over here. We’ve started recruiting from different countries as well in order to get kind of time zone coverage and things like that. So I’d say we’re a little bit of a mix. Right now, the coworking spaces are closed because, cause there’s COVID and stuff, but we’re a bit mixed. From a management perspective, we operate as if we were remote and processes and systems in place for communication and planning. All in the cloud for us so that… and then we try to get together in Slovenia. So far it’s been like once a year, we’re going to try to make it twice a year, and then COVID hit. Hopefully we can do that next year.

[00:57:54] Jon Penland: I just don’t know anything about how HubSpot is set up. Is HubSpot distributed or are they working out of offices?

[00:57:58] Peter Caputa IV: They’ve moved that way. Yeah. So, for a while, we were all in the office. I actually used to commute two hours, one way to get there. I did that for a lot of years until I could afford to move closer. It’s hard to live in Boston unless you want to live in a box. That was a big part of the culture.

[00:58:24] One of my best friends and the guy I actually worked with when we started our first start-up and worked with him at a company before that. He let out all the opening of all of the HubSpot offices. And so HubSpot got to the point where there was, I don’t know, I’m guessing there are 10 offices. Somewhere, so they still have the offices.

[00:58:40] But they realized that it was hard to fill certain positions over time when you’re drawing from a limited pool. And so a few years ago, I believe, and this is all my observations, no inside information here, but a few years ago, I believe they started being more flexible with work location and hiring people remotely more the role then anything. And then with COVID, I think they went to that whole, it’s a remote-first culture and really make making it possible for you to work just as effectively at home. I think they have a stipend or budget to set up your office. I think they’ve embraced it.

[00:59:30] Jon  Penland: Did you come to Databox with remote experience? 

[00:59:31] Peter Caputa IV: No. Well, the last year at HubSpot, I basically quit my role and Brian asked me to stay. And so I said, “Okay, what do want me to do?” And he’s like, “How about this?” I’m like, “No” and I said, “How about I write for the blog?” So the last year I wrote for the blog and I worked mostly from home. I went in one day a week. I wasn’t managing a team at that point or anything. So, no it was pretty new. In fact, when I joined Databox a bunch of people were in Boston, including one of the founders. And so I would go in, three, four days a week and work from home the other day.

[1:00:04] Somebody moved to Connecticut, somebody moved to the other side of Massachusetts, somebody moved to Philadelphia, like, we’re getting rid of space. And, the founder moved actually back to Slovenia. So we’ve embraced it. It was well before COVID, I’ve been working from home for almost three years now. 

[1:00:21] Jon Penland: Okay. All right. So as somebody then who, it sounds like you really jumped into a management role for a somewhat distributed company without really a whole lot of…

[1:00:36] Peter Caputa IV: Yeah. Well, we were on two continents, so it’s pretty distributed.

[1:00:37] Jon Penland: Yeah. Yeah. So did you find anything uniquely challenging about it? I moved into management for remote companies after having worked remotely for a few years.

[1:00:48] Peter Caputa IV: Gotcha. Yeah, no. So I was managing for a while. I had several hundred people in my organization at HubSpot. And, you know, worked on the executive team, so worked closely with leaders of the other departments. So, my management experience was pretty strong. It was a great way to get an MBA basically through learning how to run a business. And so no, I didn’t have any big issues. I would say that, you know, we were early. The company didn’t have a go-to-market function. The product was pivoted away from enterprise more towards SMB and self-service. So there was a lot of change to drive, and it was a small team.

[1:01:25] Like we didn’t really need much management overhead. We could basically have a few conversations say, all right let’s go. Over time, we’ve gotten much better about using internal wikis for process documentation, for announcements, using Asana or project management tool for planning out initiatives, projects, and some recurring tasks, even like writing a blog post. You don’t write a blog post without putting a brief into Asana and the 20 associated tasks with it.

[1:01:54] So we’re good there. Then, of course, we use Databox to track the performance of everything and we have a free training course that I’ll mention here ’cause we talked about it a lot at the beginning called Predictable Performance. So we practice our own methodology, critical methodology in terms of picking our quarterly initiatives, setting our output and outcome goals, or OKR or another language, and of course, tracking that on a basis and holding accountable to results and all that. So not a lot of challenges. Although we’ve had to along, as we’ve grown, we’ve grown when I joined four years ago, it was 12 people and we just crossed 60 people. There are different challenges at different levels there.

[1:02:41] Jon Penland: Yeah. It’s Interesting you mentioned that Databox uses the software. I really love it when SaaS companies can find a way to use their own product. Just a side note, I think there’s so much value. The beautiful thing about what we offer is that not only does our business use it, but tons of our individual team members use it as well.

[1:03:10] Peter Caputa IV: That’s cool. 

[00:56:18] Jon  Penland: I’m using the product myself. We have tons of beta users and internal users, which is just tremendously valuable.

[01:03:21] Peter Caputa IV: Yep. Yeah. I was actually having a conversation on LinkedIn with one of the guys who used to report to me at HubSpot. He was talking about how HubSpot had that unique thing where somebody would come in and they’d read a blog post, they download an ebook, they’d get an email, they’d book a sales call, and then they’d get on the call and say, “what do you guys do at HubSpot? What does HubSpot do?” And I’m like, “Well, can you tell me how you found us?” And they say “Yeah, I read a blog post and then I downloaded an ebook.” And then they’re like, “Oh, that’s what’s what HubSpot does!” It’s the easiest way to sell someone if you can demonstrate it too.

[01:03:59] Jon Penland: All right. So I’m ready to move this conversation towards a conclusion and heading in that direction I’ve got two wrap-up questions for you. So first off, do you have a go-to resource you would want to recommend to our listeners? So for example, a newsletter or a blog you follow, or a particular business leader you find inspiring, or maybe a practice you’ve adopted, is there a resource you’d really say your listeners should check this out?

[01:04:22] Peter Caputa IV: If you’re a software company and you’re not listening to Nathan Latka that I think you’re missing out. I’m a sales guy and pretty aggressive in a nice way might be a lie in terms of how aggressive he is but you will learn a lot from listening to his podcast. So that’s a big one. I love following David Cancel and of course my old boss, Brian Halligan. I think those guys are really sharp. Not just at marketing and also just building and running organizations. I learned a lot from both of them while we were both at HubSpot and then David at Drift. So, those guys are the three I follow quite closely. They probably don’t like the fact that I’m stalking them on Twitter these days.

[01:05:19] Jon Penland: That was going to be my question. Is Twitter the best place to find these guys? What’s the best way to track them down?

[01:05:22] Peter Caputa IV: It used to be. They’re all a little quieter than they used to be because they’re running large organizations. But when they share something, I know that them all, I know that it required a lot of thinking. So when they share something it’s usually thoughtful. I like following them. Brian is an excellent commun- like marketing communicator. One of the things I learned from him is just the value of repeating your message. He used to make us repeat it and it would kill me cause I hated just sounding repetitive. But he was right. you know, there are not too many marketers in the world that don’t know what inbound marketing is.

[1:06:12] Jon Penland: This isn’t in a marketing context, but something I’ve said internally is, you know, as managers, we know we’ve repeated a message enough when people find it annoying and start making fun of it. When you reached the point where, where people are getting a little bit annoyed and starting to playfully you know, poke fun at it.

[01:06:35] Peter Caputa IV: I only get that from my US team members. I think that’s a uniquely American thing. But actually, it’s true. I’ve seen that. Right. And I used to do that all the time at HubSpot, but most of my teams in Slovenia and Serbia, they’re such genuine, like thoughtful people. They start repeating it and they start, that’s when I know. I don’t know if it’s a cultural thing or maybe there’s hit right. But, make fun of your boss.

[01:07:18] Jon Penland: Right, right. So yeah, the thing internally are OKRs are something we do work with and I’m always the one who talks about OKR and after about six months, folks started to make fun of me as the OKR guy and I’m like, we finally reached the necessary saturation.

[01:07:39] Peter Caputa IV: I feel like, OKR is like, it takes years to get good at that. Like, you know, you do the process but then you’re going to miss half of them for a while. Or feel compelled to scrap something mid – but you should have your team watch our Predictable Performance Methodology Training. Again, it’s free. It’s a video course, and it will reinforce a lot of the OKR stuff. Then it won’t just be you, they might even pull out some new tech terminology that you, that you don’t use yet.

[01:08:07] Jon Penland: So this is the Predictable Performance course, did I get that right? Predictable Performance. All right. So this may be the answer to my last but my last question for you is where can our listeners go to connect with you to learn more about Databox? 

[01:08:20] Peter Caputa IV: Go to and sign up for the free product. It’s free forever, you know, with a certain level of usage. I’ve been told it’s pretty generous. We of lots of free users that use this on an ongoing basis. The limits are high. So it’s an easy way to at least check us out and about what consolidated performance monitoring can do for you.

[01:08:48] Jon Penland: Well, Pete, thank you so much for appearing on Reverse Engineered. All Well, that’s it for today’s podcast, you can access the episode and Show notes at If you enjoyed this episode, don’t forget to subscribe to Reverse Engineered and leave us a review on Apple Podcasts or the platform you’re listening on right now. See you next time.

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