How do you build your product strategy for success? As the former Product VP at DocuSign, Damon Dean set out to answer this question.

The 4 Tenets of Disruption

Damon describes a meeting between DocuSign and its best paying and first customer, Fidelity.

1. Disruptors can be disrupted

Fidelity presents a version of a friction diagram. They hypothesize that its great that DocuSign built this platform, but this is going to transition to the web and DocuSign will become obsolete and will be a commodity.

At this time, we’re trying to acquire our primary competitor, EchoSign. We botched this. Adobe, however, didn’t and they acquire EchoSign. The strategy behind Adobe’s acquisition of EchoSign is that it is going to be a great feature that will add value to the document cloud.

Is DocuSign really just a feature? We started reflecting on this concept. This was, after all,  our founder, Tom Gonser’s, worst nightmare. Tom would always say his worst nightmare is becoming “Clippy,” the Windows 95 paperclip-designed assistant.

In 2011, we raised a lot of money at DocuSign.  And, we were almost profitable! Until, of course, we realized that our biggest customer was raising red flags, our primary competitor has been acquired, and our founder is afraid we’re becoming “Clippy.” 

While we thought everything was positive, signals were telling us ‘Hey, we have a problem.’ We were in the business of disruption. Could we be disrupted?

2. Be Deliberate

At this time, our founder started doing interviews and making statements such as ‘I think when you’re inventing a new category, it has to be OK to eat your own.” This is a bombastic hypothesis, particularly when trying to make money as a growing SaaS business.

Our product strategy involved embracing this. This is what all those signals were trying to tell us. We needed to add value – but is it around just these features, or is it other things?  Is it OK to ‘eat your own?’ We started to find out.

We created DocuSign Inc.,  a standalone product. It was a free product that allowed the user to do limited versions of what was possible with the core DocuSign. The thought was if somebody’s going to disrupt it, it better be us. We’re going to do it on our terms in a very systematic and thoughtful way.

After years of tracking to see what kind of cannibalization we were doing to our core business, we found that wasn’t an issue. Instead, it morphed into what exists today, the DocuSign app. The DocuSign app is still freemium and generates more than 10 million downloads and more than $10 million annually. And, whatever our competitors tried to do, we were entrenched enough that it did not matter.

Interested in disruption? Be deliberate by having a plan. Know what you’re going to do and know how you’re going to measure it.


About the speaker
Damon Dean Flexport, VP Product Member

Damon Dean is the VP of Product at Flexport - setting the company’s strategy for building innovative solutions for freight forwarding. Prior to joining Flexport, he served as VP of Product at Docusign - holding product leadership roles for nearly a decade. In addition, Damon has held product roles at Sprout Designs, Revcube and the California Healthcare Foundation. Damon is a graduate of UCLA and currently lives in the Bay Area.

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