14 Minutes of SaaS

14 Minutes of SaaS

E19 – Russ Heddleston, Co-Founder & CEO of DocSend – Deconstructing Content Consumption – 2 of 3

Russ Huddleston CEO Co-founder Docsend Part 2 - 14 Minutes of SaaS

E19 – Russ Heddleston, Co-Founder & CEO of DocSend – Deconstructing Content Consumption – 2 of 3

This is part 2 of a 3 part mini series with Russ Heddleston, CEO and C0-founder of Docsend (founded 2013, raised $10M). Russ chats about some counter-intuitive observations around fund raising pitch decks, the consumerisation of enterprise apps and whether the rise of voice interfaces could kill Docsend. “Buzzfeed has been very successful. They create these little tiny little snippets that are easy to intake. You should think about your content, the same way. It should accomplish a specific purpose. If you need to build the giant white paper thing, fine –make sure you track it. But like don’t put too much content there because people don’t have a lot of time.”

TRANSCRIPT

Russ Heddleston – Co-founder & CEO, DocSend (excerpt)

“But then we looked at decks that were successful raising money and those that weren’t. And the decks that failed to raise money were actually looked at longer on average than the success decks – and within the failure decks the product pages are actually looked at way longer. Buzzfeed has been very successful. They create these little tiny snippets that are easy to intake. You should think about your content in the same way – it should accomplish a specific purpose. If you need to build the giant white paper thing, fine … make sure you track it. But don’t put too much content there because people don’t have a lot of time.”

Stephen Cummins

Welcome to 14 minutes of SaaS, the show where you can listen to the stories and opinions of founders of the world’s most remarkable SaaS ScaleUps.

0:51 This is part 2 of a 3 part mini-series with Russ Huddleston, CEO and Co-founder of DocSend. Russ chats about some counter-intuitive observations around fundraising pitch decks, the consumerization of enterprise apps … and whether the rise of voice interfaces could actually kill DocSend.

1:19 Founding with two friends. I think that’s an ideal thing. It’s a wonderful thing – was there ever a sense that the start or maybe when you’re going through rough times that, you know, it could put friendship at risk as well? Because it’s such a big deal to be with each other and working hard together so long. Is there ever a consideration there? Do you think all friends can start companies together?

Russ Heddelston

Definitely not! Some people are great co-workers, some are great friends. They’re definitely not the same thing. They’re not the same thing. And some people can be both. And yeah, you’re definitely putting your friendship at risk if you decide to work with somebody. Yeah our VP of Strategy is also someone we went to Stanford with – and I remember when we were deciding to work together or not, we kinda like sat down and kind of made the rules where it’s like .. we really want to work out and we really like you, but just remember you can be fired and this might, you know, end badly. And so just think if you really want to put that at risk, but if it goes well, like this could be great. You know, and so I think you do have to acknowledge that that’s a possibility. Happy to say nothing like that has happened. We’ve also worked together before as well. And so we’ve already been through it and I’ve already kind of figured out each other’s working styles which goes a long way towards making sure you have like a continued healthy like work relationship and… and friendship outside of work. Although we work enough at this point that, you know, we like when we see each other enough – so that we hand out with other people when we’re outside the office.

Stephen Cummins

Which would be totally normal. An article which you co-wrote in the Harvard Business Review mentions that you examined 34M interactions between customers and content on your platform. That’s a lot of data focused on a very defined area. So do you have a strategy to deploy some… some deep learning to your platform at some point in time?

Russ Heddelston

Yeah, you know, we always joke about AI. And our CTO, Tony says like, Oh, do you mean a little bit of math? … yeah!’ We apply a little bit of math in a lot of places. I took an AI courses at Stanford. One of the intern projects we had – a Stanford intern – used a neural net to basically take in a whole bunch of factors – because we know what’s in the content, we know the words and everything in the content – so we basically score things based in a predictive way on how engaging we think those pieces of content are going to be. And it was actually like a fun proof of concept. And that’s definitely something we’re gonna do a lot more of in the future, using the data to help make people more efficient, to be smarter, to save them time.

It’s crazy to think about going forward – AI will apply in a lot of places and there’s going to be a spectrum of like people tend to over use like deep learning or ML or like …. some things are definitely more complicated and others … sometimes just a little bit of math will actually go a long way in getting done what you want to get done. And in saving people time. You don’t necessarily need to over engineer it. But yeah, you’re right in pointing out that there are a lot of areas in what DocSend does where we can leverage the data we have to help people be better at their job.

Stephen Cummins

Very cool. In that same article, you mentioned an interesting stat that the average viewing time is two minutes and 27 seconds for content. Do you think that’s going to shrink dramatically over the next five or six years?

Russ Heddelston

Yeah people’s attention span is definitely changed. I would say yeah … let’s just say people’s attention spans have changed … ever since the invention of the internet. I usually tell marketers when they asking for advice on content that Buzzfeed, who’s also a customer like, Buzzfeed has been very successful. They create these little tiny little snippets that are easy to intake. You should think about your content, the same way. It should accomplish a specific purpose. If you need to build the giant white paper thing, fine –make sure you track it. But like don’t put too much content there because people don’t have a lot of time. Oddly enough most ICO white papers are sent out as DocSend links as well – which is kind of a fun fact, but the two and a half minutes … I think it’s actually a really long amount of time. There’s a lot of information transfer that can happen in two and a half minutes. I was shocked I thought it was gonna be like 30 seconds or something.

Stephen Cummins

Me too. I had the pleasure of meeting and introducing to the SaaS Monster stage yesterday Monica Adractas from Workplace in Facebook – and she mentioned that currently humans have an attention span of eight seconds, which is one second less than a fish. And she says that we’re not far away from dipping below three seconds.

Russ Heddelston

Yeah … I’ve heard of that narrative as well. Yeah, yeah. One thing that I thought was interesting. We did this research on fundraising decks a few years ago – and the research is still valid – that actually hasn’t changed at all. But we had asked everyone for permission obviously. But then we looked at decks that were successful raising money and those that weren’t – and the decks that failed to raise money were actually looked at longer on average then success decks, and within the failure decks the product pages were actually looked at way longer. And so I was… I was kinda looking through some of these things, I found myself looking at them longer too because I didn’t understand what they were trying to communicate to him. So sometimes more is not, you know, like more time spent is like not a good sign. If you ever heard a good narrative, it seems obvious to you – it flows well. It seems obvious to you… you don’t have to over focus on it.

6:43 If a part of it doesn’t make sense, you’re asking a lot of questions around it … that’s not necessarily good for the story teller because there you’re not getting to the end and they’re not communicating efficiently what they want to.

Stephen Cummins

Absolutely. So how busy we’ve been here …. have you had a chance to see the wonderful city of New Orleans.

Russ Heddelston

NOLA! Yeah, I went jogging around on Sunday and on Monday and I was like running around to get to know the city – beautiful spot. So yeah, it’s my first time here. It’s been wonderful to see.

Stephen Cummins

You have amazing reviews on G2 crowd. Do you follow that, where you are in the quadrant for sales enablement and stuff like that.

Russ Heddelston

7:23 Yeah. Yeah. I mean we’ve always got these words and G2 Crowd is actually a really good business and they’ve done a very good job of like kind of disrupting that particular space. And that’s actually great for us because they, you know, some of the other like more entrenched players … let’s just say ….  it’s a little bit harder to get the voice of the people and to like really discern what the truth of the matter is. And so, you know, DocSend really shines in a place like G2 Crowd because we have really emphasised and spent a lotta time on usability, ease of adoption, like really removing barriers to using the software which is why we have almost 6,000 companies that pay us now. And, and so that’s great to see – like we haven’t had to do anything. We just have enough customers and they’re all typically forward leaning companies – they’re all on G2 crowd. And they review us – and then give us great reviews and then that creates a feedback loop – and that’s also why G2 Crowd has a great business.

Stephen Cummins

Oh, they’ve an amazing business. It’s the third one for Godard Abel and I think it’ll be bigger than the previous 2 put together.

Russ Heddelston

I think so too, yeah. People have talked about the consumerization of enterprise for a long time … and everyone’s like ‘why isn’t that here yet?’ And I think G2 Crowd is actually doing a lot to further that because you can browse vendors faster, getting a more accurate answer … and to the extent you want to prioritize easy to use software. Or software that’s adopted well or software that just delivers on the value proposition as promised … G2 Crowd can help you discover those things.

Stephen Cummins

I agree. I use it all the time. When I look at Captura, I think of us just a place to see what’s out there and I know it’s a good marketing tool. And when you look at the Gartners and the Forresters of this world …Gartner is a very strong business but, you know, they… they are really too slow. And it’s basically a magic quadrant because humans decide where things go, whereas G2 is data driven and, you know, data driven crowdsourced reviews in G2 Crowd. So it’s great to see you’re doing so well there. Phenomenally well.

Russ Heddelston

Thank you.

Stephen Cummins

So one of the things that’s happening today. And I believe it’ll be even more impactful than maybe it’s predicted … is that voice is becoming a huge area of focus voice interfaces. Do you see a day coming maybe five, six, seven years down the line where there will be less documents, less reading and there will be more hearing … and if that paradigm shift did happen, would you have a plan with your platform …. how you might work with that?…

Russ Heddelston

We might be left in the dust. Well. I remember hearing a conversation while I interned at Facebook or at Microsoft where someone else was telling me about how Gates and Balmer were taking about in the early nineties about when office would die, because they could see the internet coming, you know … kind of the localized wiziwig editor was like maybe an outdated concept with the notion of the internet here….. And we still have powerpoint, and there’s all these startups saying ‘we’re going to kill powerpoint’. And it’s like I don’t think anyone’s ever going to kill powerpoint. I think what usually happens is just the number of things in use expands but very few things die ..  if they are that entrenched as I think you’re always gonna have synchronous versus asynchronous and I’m a huge believer in the power of voice and voices interface.

I actually figured out, I had hearing loss about a year and a half ago in one ear … and I got a hearing aid … and it’s awesome for listening to podcast through or for taking calls on. Like voice is really powerful – especially the notion of being able to do that through a hearing aid. But I do think perhaps as your point about attention span goes down, the importance of content and being able to consume it on your own time in a really busy world will actually probably increase in importance as well. You know, asking for a face to face meeting – like who has time for that anymore. Can you just send me the cliff notes – I’ll read it in two minutes and 27 seconds and get all the value would have gotten out of a 30 minute meeting. You know, so I think that there’s a drive for efficiency as well. The voice interfaces I think will definitely play a role in the whole thing. But I think they’ll probably be kind have a parallel track to what DocSend doing.

Stephen Cummins

And speaking of tech trends … Is there a tech trend outside of what you’re doing directly with DocSend that really excites you at the moment?

Russ Heddelston

Yeah. There are a lot of them. I used to be an adviser for StartX for number of years and you know .. I’m fortunate to invest in a few startups and just try to be helpful whenever I can. And one of the trends that I’ve been seeing among startups has been like really pushing people to do is some businesses really have great defensible moats built really out of the gate. And sometimes if you’re able to pool data together, you’re able to leverage that to just do smart things that were never possible before. So, you know, a startup I was talking with is gonna have like a biolab on a chip and so they want to help biology researchers move faster. Everyone’s kind of doing this on their own or labs now. And if you have this on a chip, well 1 …. it’s faster, cheaper, smaller. That’s really good. But 2 you actually can see everything that they’re doing if you can centralize all that data. Maybe the big idea is not just a better faster, cheaper thing. It’s that we can use the combined intelligence of every single biology Lab in the world to make everyone move faster. And like that’s the sort of thing where sometimes it’s just a little step away… and for entrepreneurs be like, ‘oh, that’s actually the really big idea here.’ We need to make that the goal – this other thing is just a mechanism to get there. And so whenever there’s businesses created like that, they’re really big businesses … and I think that there are a lot of them still needs to be created and there’s just more opportunities for them everyday.

Stephen Cummins

13:27 In the final part of our 3-part mini-series with Russ, he reflects on San Francisco as a startup city, discusses whether it’s better to go after small or big customers initially in the B2B SaaS world …and gives some advice on personal financial stability before an entrepreneur jumps into a startup.

13:53  You’ve been listening to 14 minutes of SaaS. Thank you to Ketsu for music provided under a creative commons license. This episode was brought to you by me, Stephen Cummins. If you enjoy the podcast, please don’t forget to share it with your network, subscribe to the series and give the show a rating.

14 Minutes of SaaS