14 Minutes of SaaS

14 Minutes of SaaS

E18 – Russ Heddleston, Co-Founder & CEO of DocSend – Mobile First is Overrated – 1 of 3

Russ Huddleston CEO Co-founder Docsend Part 1 - 14 Minutes of SaaS

E18 – Russ Heddleston, Co-Founder & CEO of DocSend – Mobile First is Overrated – 1 of 3

Part 1 of a 3 episode interview with Russ Heddleston, CEO and co-Founder of DocSend – a content management and tracking solution that helps teams find and share business critical documents easily and securely in real-time. Russ talks about his career which he kickstarted by interning for a string of superstar software companies. He discusses the pros and cons of starting a company with friends, controversially says that mobile-first strategies can be very over-rated in the context of B2B SaaS, and touches on how people interact with content, attention spans, and even a little bit of deep learning. “It turns out that the majority of views are on desktop, which intuitively makes sense to me but that’s the thing with data – like your intuition might be wrong. So you better check it out …. the thing is you can’t ignore mobile because some of those reads that happen outside of working hours might be some of the most important ones even though they’re a minority of them.”

TRANSCRIPT
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Russ Heddleston – Co-founder & CEO, DocSend

Russ Heddleston (excerpt)

I think it’s important to not have like that hero streak where you try to do everything. I think it also helps that this is my second startup. I think if you’ve been through it once before, it helps you pace yourself a little bit better because everything is critical and you do have to move really fast. You also have to continue to live your life.”

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.

0:42 This episode is part 1 of a 3 part mini-series with Russ Huddleston, CEO and Co-founder of DocSend, a content management and tracking system – recorded in Collision New Orleans. Russ talks about his career which he kickstarted by interning for a string of superstar software companies. He discusses the pros and cons of starting a company with friends, says mobile-first strategies can be overrated and touches on how people interact with content, their attention spans, and brings in even a little bit of deep learning.

1:20 How are you doing Russ?

Russ Heddelston

Great, thanks for having me on Stephen.

Stephen Cummins

Brilliant. Could tell us a little bit about yourself and your life history?

Russ Heddelston

I’ll try to describe it in a concise manner. My family was in the military – so I was an army brat growing up. Lived in Berlin for 5 years, lived in Denver, grew up mostly in South Dakota. I had the very good fortune to go to Stanford for undergrad and grad in computer science. And, I had no idea what I was getting into coming from South Dakota. I certainly wasn’t prepared for it. That’s basically how I got into tech. Spent some time building robots. Decided software was a little bit better suited to me … much faster paced. After leaving Stanford I worked at a company called Graystripe and ended up being their director of engineering and it was a wonderful ride for a few years. They ended up selling the business to ValueClick – that was like my first taste of like, you know, like a startup just kinda doing it from the beginning. I also interned at Trulia as their first intern back in 2006 … back in the day. There were 5 people there and then interned at Microsoft. I left Graystripe and went back to Harvard business school. A lot of people who were in HBS with me had a consulting background or a business background. But for me it was entirely new information. I hadn’t taken any business classes before. And it was really fascinating to see – probably the only business classes I’d taken before was doing this thing called the Mayfield program at Stanford – which is … for anyone in Stanford they should definitely apply to this. It’s an amazing 9 month work study / entrepreneurship program. HBS – a great experience.

I started a company called Pursuit – on the one hand it failed, on the other hand it succeeded because we were acquired by Facebook. Raised a seed round, the funding, got 50 customers, ran for a year. Decided it wasn’t gonna work exactly like we thought. And then, you know, we were very, very lucky to have the option at Facebook.

Stephen Cummins

Why would you describe Perceived as partially failed … in what sense?

Russ Heddelston

Well, if you say, ‘oh … my startup was acquired’ – that can mean so many different things. I’m trying to be honest in that we didn’t accomplish our original goal which was, you know, building something of sustainable, lasting value. And we did a lot of really good work at Facebook that had nothing to do with Pursuit. They had a theory at the time of what they wanna do with it. They change their mind. And then I ended up being the product manager for the Pages team, which is really fun and really cool. That’s why I say it was kind of a failure. And that’s, you know, acquisitions are a really great outcome if you’re in that type of spot – certainly great life experience. I just tried to distinguish it from other types of acquisitions.

Stephen Cummins

 

And I think you wrote about being a product manager in Facebook … I believe it was an important experience for you.

Russ Heddelston

It was a really wonderful and important experience. Yeah, I ended up writing a Quora post the ended up going viral. It still gets viewed a ton because I got so many questions from people like ‘What does a product manager do?’ or like ‘What does the product manager at Facebook do?’ or ‘I want to be a product manager’ … and I’m like ‘okay I’m just gonna write this up in a in a blog post.’ Because it’s more like a theory of what the product manager does … which is really filling in for a lot of gaps. I’ve been fortunate to, you know, be a software engineer. Yeah, I’ve worked a lot of other functions. I’ve started a company. You’re kinda used to being a Jack of all trades. And a good product manager doesn’t involve themselves if they don’t need to be involved. And they’ll jump in and help the team – not dissimilar from being a CEO in some ways …. You want the team to be successful, you want the product to launch. You want us to deliver on the value that you set out to deliver. And so Facebook has just a really good framework for how they enable people to do that which is why I wrote that up.

Stephen Cummins

You’ve created this amazing platform DocSend – which allows sales people to find the best content and attracts the content. It’s a really good content management system. But one thing that stood out to me is that DocSend connects the sales & marketing by attributing content usage to revenue. It’s a very cool value proposition – but you were also telling me before this that it’s a very horizontal play. And it’s a very flexible platform. Tell us about DocSend ….

Russ Heddelston

Sure. So I also interned at Dropbox in 2011 and so, some of the concepts for DocSend come from my time there. I’d be more familiar with the content management world. And I was surprised after leaving Facebook that people were still sending attachments, like in the B2B setting  …like the PDF was created in 1983. And it’s still the state of the Art. Send the PDF out as an attachment. That way it’s more secure. Like I think we can probably do better than that. But there were a lot of other solutions you could use to send the link. And so the question was why aren’t people using those things – like what’s missing? What’s wrong? What can we do? And so when we created DocSend, we decided that it’s gotta be easier to send a DocSend link than an attachment. Like it can’t be any additional effort – and then we have to provide you as the sender enough value that you’re gonna change your behaviour. And, you know, like one of the things if you’re in B2C  – you can’t go and talk to there are too many of them. Like if you’re in enterprise software, you can make people use your software – it doesn’t have to be very useable software. But if you’re trying to create something where people change that behaviour on their own, it’s gotta be easy to use and very intuitive. So that was the very first part of DocSend and … why we built it. I think there’s also a larger trend of data is making everyone more intelligent and more efficient … and one of the things we very quickly realized with DocSend is that if you send the link and not an attachment, you’re able to track information that is very valuable to certain people and can actually help make everyone a lot better at their jobs. And so, you know, with that in mind … after we launched DocSend, we saw there are a few different use cases for it. So ….
* Sales and marketing teams for instance, a great use case.
* But also for like financial firms DocSend is a great use case because it’s easy to use, it’s very secure, you can watermark things, you can have white lists … but under the hood it’s very similar technology in that you’re trying to visualise this content in, you know, a browsing experience. And then maybe let people download or not depending on what you’d like to enable, so it’s horizontal in that sense.
But works better from a growth perspective. If we don’t make people do the guesswork of why is this useful to them? So when we come into a sales and marketing team, we have verticalised positioning for what we do – so we’ll go to a marketer, and say, ‘hey right now you have no idea what content your sales team is sending, you have no control over that’ – like DocSend will show you what they’re using what they’re not using keeping everything up to date. And you don’t have to guess at what’s going to be the most impactful for the business. The data will tell you.

That’s a little bit different than what we tell an investment banker, or a little bit different to what we tell a salesperson because like if you’re a salesperson, you really wonder what’s going on behind the closed doors at those meetings I’m not invited to. You just get a yes or no back at the end of it and the content is actually a wonderful Trojan horse to like collect some of this information about what’s going on there.

And so, yeah, that’s definitely gonna be a theme for us. And from a marketing perspective is a great way to spread awareness about what we do and also add a lot of value to the community.
The stat about there’s no best day to send content was interesting because there’s always this folklorish pieces of advice we’ve heard like, ‘oh, you always got to send your e-mail on Tuesday at 3pm and so forth. There are other technology providers that will do e-mail tracking and stuff and we don’t do any of that – we really just stick with the content and …what is interesting is independent of when you send someone an e-mail … like when people choose to consume that content – like you know sit, down and, actually take a read through it .. like ‘I saw your e-mail, okay there was some deck in there I was supposed to look at it as a follow up’ – like when they consume that it happens like pretty evenly throughout the week – which is just kinda interesting and if nothing else, we can just dispel the notion that depending on when you send it, you might really dictate if they’re gonna read it or not. So you can move on and worry about something else.

Stephen Cummins

And it’s kind of self-defeating because if everybody’s saying the best time to post on Linkedin is between this hour and that hour on this day – then if everyone’s doing the same thing, it actually inverts.

Russ Heddelston

Yeah – that’s right – it’s kind of like waze-ish thing where if everyone’s taking that route, it’s not the best route and the thing that. The thing that we can do that’s unique is because we’re tracking how long someone’s looking at each page, we’re actually really in the weeds understanding when knowledge transfer is happening – and like that kinda happens throughout the week the only other thing. The other I thought that was interesting about that is that people look at content a lot less on weekends – makes sense hopefully they’re out enjoying life and stuff – when they do look at it it’s always on their mobile phone. And actually people do look at content a lot outside of work hours, but it’s always on, the mobile phone which I thought, was, just like good to know as well that sometimes that’s when information transfer happens – when they’re on the go.

Stephen Cummins

Following on from about I did read somewhere that you said that mobile is important but it’s overrated.

Russ Heddelston

It was another surprising thing where people were saying that mobile’s everything – like it was at Facebook .. mobile was everything. And so, yeah, we really had to have a mobile-first strategy. Like that was the right thing to do and whenever we would make designs for stuff, we would always design it for mobile first. And so, you know, one can say, well maybe that’s true for B2B content as well. Maybe everyone is only consuming this content on their mobile phone all the time …. and in a data free world it’s hard to know – is that true or is that not true? That has big implications for the people who are creating that content like … font size, how much should go on each page, you’re trying to make it, you know, on a phone readable. It turns out that the majority of views are on desktop, which intuitively makes sense to me but that’s the thing with data – like your intuition might be wrong. So you better check it out.

And so most people are looking at things from their desktop computer. And the thing is you can’t ignore mobile because some of those reads that happen outside of working hours might be some of the most important ones even though they’re a minority of them. So again, it just kinda paints fuller picture that is helpful for everyone.

Stephen Cummins

Like most of the successful founders that but I interviewed, you’re really  into what you’re doing and the adrenaline is there – I can feel it. How do you keep work life balance when you’re managing a company that’s growing like DocSend.

Russ Heddelston

Well … it’s certainly a challenge. I think it’s important to not have like that… that hero streak where you try to do everything – it’s useful to have good co-founders. My 2 co-founders have been coworkers and friends for many, many years – over a decade, and they know each other quite well too. Whenever people asked me for advice about starting a company and they’re like ‘oh I need to find a technical founder’ .. I say like ‘well it’s kind of like getting married, it’s something, you should definitely put a lot of consideration into’. And having good co-founders is a good way to maintain work life balance later on – because it’s not all on you and they can help even out some of the areas that are weaker. I tend to over delegate things -that’s just my personality and so …I do delegate whenever possible and I don’t want to do it all myself. It helps contribute to work life balance you know. I just got engaged a few weeks ago.

Stephen Cummins

Congratulations! Wow!

Russ Heddelston

Well thank you! Finding time to make sure the rest of life continues to move forward … and then I think it also helps that this is my second startup. I think it helps when you’ve been through it once before – it helps you pace yourself a little bit better, because everything is critical and you do have to move really fast. You also have to continue to live your life.

Stephen Cummins

13:18 In part 2, Russ makes some very interesting and counterintuitive observations around fundraising pitch decks and answers the question of whether voice interfaces could kill DocSend!

13:37  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