The Exchanges

Q So let's, let's jump into Docsend now. So what year did you make the decision to leave Facebook and start Docsend?

A Uh, we started Docsend in 2013. So it's, you know, over three and a half years ago now that we started the company. And the very first version of it was something that came from an insight I had while I interned at Dropbox while I was in business school in, uh, and that is that sending attachments is just really not a great way to go. Uh, just brings up a lot of problems. So we wanted to come up with a system that worked well for businesses to send, uh, documents as links and not attachments. And there are a few properties that we really wanted that were just missing from all the other systems out there. Around security and tracking and being able to update things and just insight and what, what is happening when I send, uh, content, uh, or documents out to people. And so, uh, the first version of docs and was, was just that that's just what we wanted. Very simple, easy to use system, sign up, get going, uh, just hit the ground running. And we launched that at tech crunch disrupt in 2014.

AI assessment note: “we started Docsend in 2013.”

Q Is that, is that same no matter, no matter the size?

A It, it varies. No, it varies between If there's screen sharing, if there's Salesforce involved in there, I think it comes out to around like 70 or 80 dollars a user a month. So let's just say roughly a thousand dollars a user a year. Uh, we, uh, for our outbound only target teams of 30 and above. Uh, so that'd be about 30,000 dollars a year, uh, an annual contract value for that. We found that like selling to a team at 10 is the same amount of time as selling to a team at 30. And if you have outbound, it's expensive. And so, you know, it needs to make sense. If you get up into the hundreds of salespeople, the, um, time it takes to get that deal closed goes up significantly. So when you ask like what's your average annual contract value, like any outbound company, the answer is it depends on who we're targeting and we can target various size. It's interesting because Dropbox has had a similar experience where they've gone way up market and they've closed some of those big logos and then they've pulled back looking at how long those take, uh, and just kind of the cost benefit there.

AI assessment note: “It, it varies. No, it varies between If there's screen sharing”

Q Happy about that, or do you regret it?

A Oh, no, super happy about that. August Capital led the A round. Howard Hartman Baum is on our board. He's fantastic. Uh, Jeff Clavier from SoftTech led our seed round, and he's on our board, and he's also fantastic. Um, I think it's a team sport. Uh, I have a lot of admiration for the companies that bootstrap it and get it there. Uh, I think for us having access to those networks and having access to that help has been really helpful for us. Um, even just having board meetings, uh, every couple of months is just great to check in every once in a while, look back, get an outside perspective and make sure you're on track. Um, so I've been very happy with the, the investors that we've, we've picked a partner with.

AI assessment note: “Oh, no, super happy about that.”

Q I appreciate being transparent there and saying kind of you shopped it. A lot of people say never, you know, you never want to sell your company. What, what kind of made you guys decide to go through that? If that was truly an intentional process.

A It was, we looked at our own numbers and the theory that we had, we had a hypothesis we wanted to test it. You know, we got, you know, 40 companies signed up for the service, a few thousand users, and then the numbers just weren't looking like we wanted them to. Absolutely. So we would look at how many people were being referred. And we figured out that they were going out of band, like those hires were happening. And then we were like, why? And then we kind of dug into psychology of what we're doing and without it being a separate podcast, basically decided that some of our assumptions were incorrect in our product and that to change those assumptions would be a huge process. And we were just kind of out at that point. We'd been doing it a little over a year, raised about 500 K and Facebook's one of our first customers. So while we went and talked to them, we talked to LinkedIn about, you know, just like joining them. Yeah. And you're right. We totally decided to sell the company. Uh, and to shop it around. Um, so that, that just made the most sense for us.

AI assessment note: “decided that some of our assumptions were incorrect in our product”

Q What is the rest though? Quantify that five percent monthly, 10% monthly.

A I don't know off the top of my head. What's high mean? What's high mean? Well, those numbers are certainly high that you gave me. Um, and the thing that matters there is the net promoter score that we get and people are really happy with it. They're like, Oh, I love Docsend, but, but yeah, of course I'm not going to pay for it anymore. I don't, I don't really need it now, but I might use it again later this year. And so for me, that's, oh, that's great. It's a nice product. They like it, but it's, it's not a great business characteristic. I think like, what is it? One, one percent monthly is kind of a general target for companies to aim for. If it's much above that, then that's pretty worrying.

AI assessment note: “I don't know off the top of my head.”

Q Don't say, don't say anything, but on average, all those 2800 paying companies, how many seats per company would you say on average?

A Well, no, it's bucketed between ones that are just a few. We don't really care a lot about them. And then amongst the 10 or above, I get really excited when it's like a team of 50 or more salespeople, because that's, that's a really interesting sale to get done. There's a sales ops person involved. There's a content marketing person involved. The sales and the marketing teams need to work together effectively. The complexity of that sale really goes up. So the teams of 50 or more that we get locked into Docsend and actually buy into the value prop, that for me is really exciting because it, it feels like a whole different product and different sale and different company than what we launched in 2013 and the economics are way better.

AI assessment note: “Well, no, it's bucketed between ones that are just a few.”