Interview with DocSend Founder and CEO, Russ Heddleston

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Russ HeddlestonInterviewee: Russ Heddleston is the CEO at DocSend. Prior to DocSend, Russ was a Product Manager at Facebook, where he arrived via the acquisition of his startup

Russ has also held roles at Dropbox, Greystripe, and Trulia. He received a BS in Computer Engineering and an MS in Computer Science from Stanford University, and an MBA from Harvard Business School.

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Jorge: How did the DocSend team meet and what were you doing before this venture?

Russ: Dave, Tony, and I started DocSend in 2013. We all studied computer science at Stanford; Tony and Dave were freshman year roommates, and Dave and I were also roommates for a year.

After Stanford, we worked on the engineering team at Greystripe together. Immediately before DocSend, Dave and Tony were at ValueClick (who had acquired Greystripe) and I was at Facebook.


Jorge: What was the inspiration behind building DocSend and who is your ideal customer?

Russ: Our inspiration came from a few places. Facebook has an internal product I used while I worked there called Pixelcloud that is similar to DocSend. It shows who looks at designs you create. DocSend applies this to documents.

We believe that analytics are powerful and change communication. Tony and I have also worked in the document space so we understand its importance (I was at Dropbox and Tony was at a startup that was acquired by Box). The ideal customer is anyone who communicates with documents as part of their job and wants to communicate more effectively.

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Jorge: What does DocSend do really well and how can sales and marketing organizations best leverage it?

Russ: DocSend allows you to take the guess work out of sales and marketing. Sales teams get to know who to follow up with, what content is working, and when to engage. Marketers know if the content they create is actually effective. For both salespeople and marketers, baking DocSend into their workflow changes the game for how effective they can be.

Jorge: There are a few offerings in the massive document-sharing space like Clearslide, Fileboard, CycleIO, for example. Do you see these as competitors? or Does it even matter because the market is so huge?

Russ: In some sense, they are competitors as they offer a similar value proposition. DocSend prides itself on being the easiest to use and most powerful of the offerings for documents analytics and control. We also believe that more effective, actionable document communication is a broad need that extends beyond just sales and marketing.

We’ve seen use cases that we didn’t expect from the start: recruiting, M&A, and internal training to name a few. We’ve seen a number of customers come over to us from the services you mentioned already. The market is huge, though, so I don’t think there will be just one winner.


Jorge: What 3rd party integrations are you expecting to support?

Russ: We’re planning to integrate with third party CRM systems like Salesforce as well as email clients like Gmail and Outlook. This will make using DocSend in the context of a workflow much easier.

Integrating with Box and Dropbox is also on the list, although it hasn’t been requested as much by our users.


Jorge: What 3 tips would you give an early stage startup when trying to launch a B2B product?

Russ: I’d say the first and most basic one is to make sure your product solves a problem people can relate to. Without that, it doesn’t matter what you’re launching. Second, I’d recommend doing some really deep user research prior to launch. Develop as strong an intuition as you can about what your ideal user looks like now as well as six or twelve months from now.

Interview people who fit that profile and work to understand their needs. This will inform your roadmap and make product planning much easier. As soon as you launch and start letting in swathes of users this compass will make it much easier to execute your go-to-market strategy. Lastly, I’d of course make sure your product is technically sound – downtime is unacceptable in B2B.


Jorge: What are the most challenging aspects of being a startup founder?

Russ: Even once you’ve convinced yourself you’re working on a problem worth solving, it’s a long road to making that vision a reality. Being successful takes a lot more time, effort, and patience than is visible from the outside. We’ve been working on DocSend for over a year, and it’s still just the beginning.


Jorge: What tips can you give founders about how to effectively raise a seed round?

Russ: I have a lot of tips for this question. Make sure you invest in your pitch like you do in your product. Many founders assume their product speaks for itself, yet it almost never does.

Also, when you do raise money make sure to do it efficiently. Many founders let it drag out for months, which is dangerously distracting. Funding is a means to an end, so be sure to keep your focus on building a great product.


Jorge: Anything else that you’d like share about DocSend, or your team?

Russ: We’re excited to continue building a useful platform and send us feedback anytime at!