How CloudApp Grew to 4 Million Users During the Global Pandemic

How CloudApp Grew to 4 Million Users During the Global Pandemic

Interview with CloudApp Scott Smith (CEO) & Joe Martin (CMO)

Show Notes

Companies are doing their best to remain efficient in this remote-working world. They are eager to try any tool that helps to keep their employees productive. CloudApp is one of the tools benefiting from this trend.

In this episode, Roland Siebelink speaks with CEO Scott Smith and CMO Joe Martin. They discuss the growth of their startup and what CloudApp brings to the SaaS market.

Listen to the full podcast to hear Scott and Joe share:

  • How CloudApp can save time and be a useful tool for async workers.
  • Why working for a startup is an attractive option compared to a larger company.
  • The best times to seek advice and suggestions from investors and board members.
  • Why CloudApp doesn’t subscribe to the typical Silicon Valley approach to business.
  • The new meaning behind the acronym ARR and how it’s shaping CloudApp’s approach.


Roland Siebelink: Hello and welcome to the Silicon Valley Momentum Podcast. I'm Roland Seibelink, and I'm so excited because today I have two amazing guests, Scott Smith and Joe Martin of CloudApp. Hello, guys, thank you for joining.

Scott Smith: Thanks for having us. It's great to be here.

Joe Martin: Thanks, Roland.

Roland Siebelink: That's awesome. Let's dive right in. Tell people who are completely new to your company, what is CloudApp and how do you differentiate from the other providers around you?

Scott Smith: Sure. CloudApp is a way of expressing yourself through video images and gifs, instantly with a short shareable link. The idea is, like the phrase goes, images are worth a thousand words. Instead of trying to type up a long email or jump on a quick 15-to-20 minute video call, you can just capture a portion of your screen. It gets uploaded to a cloud and you can share it as a link and somebody can immediately view it and understand what you're talking about. And how we differentiate ourselves from competitors, different companies out there providing similar tools, I think the way that we think about CloudApp is: one, bringing together two, three, four, five different simple tools that you use every day. Screenshots, screenshot annotation, videos, gifs, all in one centralized tool. The second part is the speed. Within every workflow, every tool that people use, usually they're using it as a means to increase productivity, speed up their workflow, simplifying things. Our main and almost entire focus at CloudApp is to enable our customers to do things faster. Every part of the experience of the app, we ideally intend for it to be fast.

Roland Siebelink: Oh, that's amazing. That sounds to me a little bit like the equivalent of emailing in an app like Superhuman that is focused on keeping things fast and moving along quickly. Joe, what's a typical customer you target with this app?

Joe Martin: We have a lot of different people using the product, as you can imagine. Most people take screenshots every day and use video. And so we try and target mostly businesses though, where we see the largest amount of use cases. You have anywhere from a customer support agent who is using video to close the ticket faster and with higher satisfaction rates to the executive who's wanting to skip a meeting to free up their calendar and send a video instead. These things are all really focused on saving time, creating efficiency, cutting out the long emails, cutting out the long interactions when it could have just been a very simple video or a simple screenshot.

Roland Siebelink: That's so awesome. Yeah, go ahead, Scott.

Scott Smith: Yeah, just to add onto that, one of the ways that I've always thought about our product is we want to help and enable builders and help and enable people who support their customers. And that's a big, big, gigantic audience.

Roland Siebelink: Absolutely. Absolutely. And how has the pandemic this year affected you guys? Have you been a net beneficiary?

Scott Smith:Yes. I think it goes both ways. In some ways, we've definitely seen customers who have experienced some downside from the pandemic, whether they're a software company or a physical goods company or an in-person company. On the other hand, a lot of our customers historically have been B2B, knowledge workers who have customers building products. As a result, more of them are working remotely now and more of them are feeling the pain of being disconnected. And one thing that was really interesting is as we looked back at data from March 13th and on what we started to see was instead of people commuting every day from eight to nine or five to six PM, we saw this 20 to 30% increase during that time of day of usage. And then in addition, we saw the number of videos being created increased by over three X.

Roland Siebelink: What have you learned about your users in terms of when they now work from home? You said like the video is often a way to replace the tap on the shoulder. Do you think there's also somewhat more comfort with recording your cell phone video than before?

Scott Smith: I think there's two different things that we find pretty interesting is one: a lot of our customers that use the products will want to create these videos that are short, succinct. They're actually personal and then they include ums and ahs. So there's this raw, true, actual, real video. On the other hand, you have people who now are trying to battle wifi connectivity and internet infrastructure stability. I have three kids in my house run zoom calls in the mornings. In some ways, we're sort of battling for bandwidth. I think one of the main themes and one of the questions that you highlighted in terms of what are we focusing on? One of the ones for the quarter is just improving and increasing stability so that we can make sure that we deliver the expected product for our customers. One of the things that I think was really interesting is I am personally experiencing this and I think we're seeing others who were saying I had four or five, seven, eight video calls back-to-back-to-back-to-back and I have this video fatigue. And I'm trying to find solutions to either eliminate a call or just turn the call into something shorter, quicker, faster. I think that's been a big part of this synchronous and asynchronous work experience. Where people are trying to balance when do I actually need to be in person versus when can I do it? Asynchronously.

Roland Siebelink: Absolutely. And I love that you just honed in on that right away at the beginning of the call, when you said the value proposition, one of them at least is for executives to be able to skip another meeting. Can you tell me a little bit more about who's part of CloudApp? How did they come to your team and how have you divided up in the different functions that you have.

Scott Smith: Sure. I can give you a couple quick examples. For example, we have a developer in Ohio who I found on angel list and he had been building apps for libraries. And when we reached out, he had an incredible background in building these library apps when you would walk in and register. But when we reached out to him, he was looking for a new job and it was interesting because he was one of our first developers who was local within the United States, as opposed to local within California or Utah, where we have offices. We also have one of the things that I think we've seen a lot of is people who have backgrounds in larger companies who had for a long time been considering “I want to move into the suburbs.” I hate the idea of the commute. Maybe I should find a company that supports or is willing to do remote or some sort of async. And so we have an engineer actually up in Seattle who had worked for both Disney and Starbucks for quite a long time. And he wanted to move away from being in person, having those meetings, having to deal with that. And so we have now a team that's basically spread mostly across the US, some folks in Mexico. We have a couple in Europe, a couple in India. And I think what really has helped us become masters of the tools that we use to allow us to communicate succinctly. From an organizational perspective, we use JIRA and Atlassian to ensure that our projects are detailed and prescriptive. We use Zoom when we need to. We use Slack for quick questions. But again,Joe, he's an hour ahead of me. Our developer is three hours ahead of me. You kind of have to figure out the right strategy to communicate and async in the tools is probably the best.

Roland Siebelink: Just a little side thought but, Joe, I saw in your background that you were one of those people moving into CloudApp from a larger company, right? I hear a lot of questions. People asking me, should I do that? What's the benefit? What's the things I have to prepare for if I make that jump? Can you talk a little bit about that for our listeners?

Joe Martin: Yeah, absolutely. I was one of the people that loved the vision and what CloudApp did so much when I was over at Adobe that I decided to join the company. Actually, we started having discussions probably about two years ago now. Prepping for Adobe MAX Conference, I think both are good and bad and there's no perfect job out there. For me, it was knowing that video was kind of peak to explode. I saw Adobe was one of the companies going to video as the norm. It made sense with remote work trends as well that CloudApp would be primed to be able to jump on that as well. Those were the kinds of the things that led me to CloudApp as well as Scott, as a leader and Jason and the rest of the team that was already in place. I knew that marketing had been a secondary focus before I came on. And so I knew that I could kind of bring some things that I knew and could just do those consistently to bring us in line with what we could get from marketing. Overall, it's been a good experience, lots of growing pains, but honestly, similar growing pains that you'd see in a massive company. I shook my tin cup at Adobe just as much as I do with CloudApp. Like, “Hey, I need money for this.” I see it as a startup gives you the speed and the enterprise gives you the resources. Both kinds have benefits. I'm glad to have experienced kind of both.

Roland Siebelink: You had a pretty broad range of investors I saw in your Crunchbase profile. How's that been working out for you if I may ask, to have a nice range of angels but also CEOs executives, as you said, to all be part of your investor lineup.

Scott Smith: I think one thing that we've noticed is that people who are new to investing, for example, one of my first bosses at a company up in New Hampshire called Dine, he is an investor and he would frequently say to me, “Hey, what should I be doing? And how should I work with you? And how should I understand what's going on with the company?”And it helped me realize that I could be doing better in terms of updates. On the other hand, CEOs who have invested in giving us capital, they themselves are busy and they'll say things like, “How can I be helpful and what can I do?” And it's more about me reaching out to them when it comes to our board of investors and some of the executives who have invested. I think having that quarterly board check-in has been incredibly effective for us. To figure out which resources and which investors do we go to. The early investors that we might've had, for example, one of them is named Max. He was a Facebook director and he was heavily focused on product. And I think over time we've continued to keep him and involve folks like him. But we've also added on people like Kyle York, who's more of a go to market focused investor.

Roland Siebelink: Okay. It's not just that they're you know individuals with a different range of interest in helping you, on a concrete level, but also that they come from different backgrounds and they bring a different level of functional expertise, as I understand it.

Scott Smith: Yeah, exactly. I think capital from an investor perspective is often just deployed and they say to you, “You figure it out.” On the other hand, if you invite the right people in, they're going to be much more value-driven and helpful. And I think that's what we've found. It's definitely a balance of not wanting to demand or expect too much time from them in addition to their money. But in many cases, their insights, their ideas, their suggestions. I don't have to go out and bang my head against the wall because they've already solved that problem. And they can tell me here's two ways to try.

Roland Siebelink: That's something I hear a lot from founders and startup executives that you have this urge to try and solve it all by yourself, but that you really need to learn how much advice is really available to you just for the asking.

Scott Smith: Yeah, absolutely. One of our investors, he's on our board, Kyle York. He and I frequently text message and his wife often jokes that maybe we text message a little too much. But I think he's a good example of someone who's been really helpful when it's really needed and then kind of backs off and it can be hard to figure that out. But I think people who are a part of your business and your company, who are willing to put the time in, it feels really great and you feel so supported as opposed to “I don't know what to do.”

Roland Siebelink: Do you feel, just building on that a little bit, that a good investor or somebody who takes on a coaching role in your career, should they be mostly a cheerleader or should they also proactively point out some blind spots? Some areas that they think you're challenged in.

Scott Smith: Personally, I find it much more valuable to get feedback that's corrective and helpful as opposed to just positive. And I think it's mostly because, to Joe's point earlier, he and I both left much larger companies with much larger paychecks and our time is really valuable, whether it's literally from a dollar perspective or from a family perspective. And if the feedback I'm getting is just, “Hey, you're doing really great.” It's not useful at all. It does not make me feel good because I'm already used to the pain of trying to, like Joe mentioned, try to grow the business or trying to hire or try to acquire new customers. I just want to know how do we do it better?

Roland Siebelink: Joe, as somebody slightly newer in CloudApp, how have you observed the culture and experienced the culture in terms of are people giving each other feedback? Are they comfortable with that? How's the CloudApp culture in terms of people holding each other to accounts?

Joe Martin: Yeah, I think that was one of the parts that intrigued me as well it's really helping establish the culture. A lot of the focus before COVID obviously was centralizing some of the office. Growing in Utah with go-to market and bring a little bit of a culture together versus fully remote, which it had mostly been. And I think we've definitely put a focus on some core values and looking for ways to help each other. We have all the managers have one-on-ones with their teams. I encourage skip levels with Scott, or my team, or Jason our COO if they want to meet and talk about their careers or talk about things I'm doing well or not doing well. I think we're a customer-led feedback business. None of us are very shy of giving feedback for good and bad sometimes cause there's a lot to be done and sometimes that feedback can be harder to fit into your already busy schedule. But I think the culture has grown well. It's one of those things that you want to be very strong and then hopefully, it can scale with you as you grow. We're at around 30 to 40 people now. And I think we've scaled to that point well. And then it's doubling to 100 that it gets new challenges. But I still remember me, Jason, Scott, and Cody (Cody's our head of sales), met last summer and we hashed out what we wanted the company to be and wrote it all down and documented it and then shared that with everybody. And we review it in our all hands every couple of weeks, so everyone knows what the goals are and knows what we are as a company. And it feeds into how people are productive.

Roland Siebelink: That's amazing that you did that work together as the gang of four at the top. Were you able to give concrete examples? Is there something that you've been telling your employees that you might share with this audience? That is a good example of where you draw a line where you say, “This is what I expect. This is not what I expect.”

Scott Smith: Sure. I think there's a couple different examples. They're probably pretty pithy and simple. In the office where I sit there's this big board with red letters that says “work hard and be kind to people.” For me, I love the idea of Silicon Valley, but I don't subscribe to the be-a-jerk-and-get-it-done approach that some people like to believe is the model. I prefer to think that we can work just as hard, we can be just as clever, and we can get just as much done without any of that tough-guy approach. I think another simple one is before you ship something, you should check to ensure that it works. When I was working at Facebook, we had interns who would ship code live to production that would completely bring down Facebook for the day. And you're like, “Well, did you have it checked?” “Oh, no, I skipped the process or whatever.” And we had the exact same happen. I think my first week I sent an email to 500,000 people and it was just wrong cause I didn't check. For me, one of the things that's important is that I slow down. I ensure that the process is right. I check my work and then we distribute it because if we don't that first experience or that second experience is the last thing and people lose trust in us.

Roland Siebelink: It's also a little bit moving on from the old move-fast-and-break-things mentality that Facebook used to have. Right?

Scott Smith:Yeah, the new one is move fast and build stable infrastructure.

Roland Siebelink: Yes. A little bit less sexy, of course. Where do you see CloudApp evolve in the longer term? Five to 10 years from now, where do you see yourself? What place do you see yourself occupy? Where are you in the markets and what do we think of as we think of CloudApp at that date?

Scott Smith:Joe, if you have an idea, if you want to jump in there, I'm happy to go right after it.

Joe Martin:Yeah. When we've talked about our end game, it's definitely every company on the planet has integrated CloudApp into their daily workflows and it's so delighted by it that they want to tell everybody. I still remember when I was just joining the team when we were doing a fundraising round and one of our investors had met with the customer and that customer said if we took CloudApp away, there would be a riot!

Roland Siebelink: Oh I love that

Joe Martin:I think we included that in the press release because it was such a good quote from one of our customers. But that's really what we want. We want people to get to value quickly. We want it to replace long meetings. We want it to replace long emails. Those meetings and emails are not going away, but we can make some of them easier to kind of communicate and make it faster. I think that's our end goal, end game that we've been focused on.

Roland Siebelink: Does that mean you know taking that big lofty vision and turning it into really down-to-earth goals that may sometimes not be so sexy? Joe?

Joe Martin:Yeah. That's a perfect segue of what I was thinking of jumping in on. At CloudApp we have our core values that we mentioned earlier. Those are customers first, no egos, collaboration and check before you ship. And those are the qualitative feel good, keep-this-going core values. And then we also have our quantitative, which we broke down into everybody in SaaS loves ARR, which is annual recurring revenue. We broke that into acquisition, retention, and revenue, which is also ARR. Those are our three important goals that we've always focused on.

Roland Siebelink: You're being subversive to the SaaS industry, right? I love it, but sorry for interrupting you.

Joe Martin:No worries. Scott is looking overall at ARR (acquisition retention revenue) and seeing, “Hey, here's our revenue growth. Here's how many weekly active users we have, and here's how many people signed up?” And then me on the marketing side is like, “Okay, I'm looking at ARR. And I'm seeing what ones I can influence,” which is a little bit of each of those three. But my goals for my team, the automation team, the demand gen, and the content team, all funnel up into how we can influence ARR. The same with sales, same with products, they all funnel up into ARR. That makes it into now we have three really important goals. And we create smaller goals that feed it into those bigger goals. That's how we tried to make it digestible internally, but also really impactful.

Roland Siebelink: I wanted to finish with some open questions around what key learnings have you found as startup founders or joining the team afterwards that you would like to impart on other people that may be a little bit earlier in their startup journey that are looking up to you to get to the level where you are and get to a similar journey.

Joe Martin: My first 90 days are pretty crucial as a leader, any division. And I remember just writing down millions of things that could be done. Like, “Oh my gosh, this isn't happening or this isn't happening.” That's just part of being a small company. It doesn't have mature campaigns or teams like an enterprise. And then I went back to my core metrics. It was like, “Okay, I need to look at the data and see what are some things that we can just double down on right now and find that success and just juice those for the next couple of years while we build other programs.” And I saw content SEO, there were some nice foundational pieces for SEO and content. And then I found demand and automation, automation was important to help people onboard correctly and get to the “aha” moment quickly. Those were the two first hires that I brought on for the company. In marketing we've doubled website visits, we've doubled signups from marketing being consistent with things that were already working and proven for the company. And we just doubled down, tripled down and put a real investment into it. That's the thing that I would say. It's really just finding the little pieces. If you're a brand new startup, then figure out what other companies have done and maybe mock them for a while. But if you already have existing data, find what's working and really just double down on those things. And then along the way, you're adding new wrinkles, but you're mostly focusing on those things that have been proven in the beginning.

Roland Siebelink: How can the audience help you guys? What are you looking for? You're looking for hires or you're looking for trial users. What do you need most and how can they help you?

Joe Martin: Yeah, I think we're always looking to hire great talent. There's been some tough times with a lot of companies in tech. And so we're always reaching out when there is a layoff or something else. And seeing if there's someone who might be a fit there. so definitely connect with us on that. Give CloudApp a try. It's a pretty robust free product before you start to hit any type of paywall to go into the pro and team products, like I mentioned before. I loved it so much at a massive company at Adobe that I joined the company. And so there's some pretty quick immediate value and there's a real magic to creating a video, talking to whatever you need to be done, sending that link and having it understood versus typing out an email that took you 45 minutes to write and then you send it. And then they only respond to the last question you asked and the context and tone is missing, so you don't know if someone's upset or

Roland Siebelink: Oh the pain of it.

Joe Martin: So let us solve some of that pain and definitely give us a try.

Roland Siebelink: That's awesome. Scott, anything to add there?

Scott Smith:No, I think, that's perfect.

Roland Siebelink: Okay. Joe, since we have the CMO on the podcast, which is a rarity, what's the best way to get in touch. What's the website and what do you want them to download?

Joe Martin:Our website is And it's a pretty easy signup process. Just enter your email and you can sign up, download the Mac, Windows, or Chrome app, whatever your preference is. And then you're ready to go, ready to take your first screenshot, first video, first annotation on a screenshot or first gif.

Roland Siebelink: And I can say to the listeners also that I've tried this out myself and in comparison with many other tools, it was a breeze to go through and I got productive right away. So I warmly recommend it. Thank you Scott Smith and Joe Martin, CEO and CMO of CloudApp. Thank you for joining this podcast. It was an absolute pleasure. And I am looking forward to seeing you on every single desktop in every single company every single hour of every single working day in less than 10 years time.

Joe Martin:That's right.

Scott Smith: Thank you. Roland.

Joe Martin:Thanks. Roland.

Roland Siebelink talks all things tech startup and bring you interviews with tech cofounders across the world.