4. When It Comes To Product Strategy, It’s Never Too Early To Test

Product strategy is all about testing. If you think it’s too early to test, it’s not and if you think you’re late to testing, you are way more than late.

A DocuSign client said, not in these exact words, that your signing experience is a little bit of a clown car. It looks like it was built in the late 1990s and maybe you should think about updating it. We agreed and they worked with us. We spent almost two years trying to get it right. Then along the way, HelloSign launches the same product about six months before we do. It was seriously unfortunate because they were able to capitalize on it, while we were building the same product and in the end, we looked like a me-too product.

The idea is that these things are out there and other people have the same ideas. In the end, we got disrupted while we were trying to disrupt ourselves. 

The Take-Away

When you get into the business of taking risks, it requires you to be more disciplined and how you think about roadmaps, how you think about milestones, how you think about deliverables—all those types of things.

It pushes everybody. There is nothing better than an existential crisis to get everybody to start thinking about the risks you’re taking. I don’t mean pushing the engineers and developers, I’m talking about pushing sales and marketing, and getting people to sign up to be a part of a journey versus not letting it sit solely within a product organization.

Finally, you need time to learn. If you’re going to take the risks you have to be disciplined enough to know that even if it trends in the wrong direction to pull the plug.

But give products time because in most cases when you’re doing something that’s net-new, the cohorts, when you watch them, initially will trend down and you need to, whether that’s a freemium product or whether that’s time in market for new things or adoptions, they’re going to trend lower at the beginning.

You need the appropriate amount of time to find the nuggets of when they actually will start to turn upward.

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.