Successfully Moving Upmarket

Part 2: Guidebook 2014 -2020

(Kevin, Me, Pete and Jeff circa 2015 at our 1 Zoe Street address in San Francisco)

I spend most of my time with founders, CEOs, investors and sales leaders that either want to progress from founder-led sales, or want to move upmarket into the enterprise or both!

The best founders want to move upmarket for good reason. Typically they have built a strong product-led growth business targeted at smaller businesses, but see application at scale in larger companies.

But it’s not always the way. Sometimes they sell to larger companies but have not made themselves core to their customer’s business, or their application is pointed in a direction that provides less value than if it pointed a few degrees elsewhere.

In my last 3 firms, I operationalised this move successfully, but all were very different scenarios, and I want to break down some of the key facets that made those moves upmarket possible.

This is the 2nd of a 3-part series and looks at how we successfully grew Guidebook from $2m to $15m ARR by adapting our go-to-market approach and processes.

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Guidebook (2014 - 2020)

Guidebook was and still is a mobile app platform that enables non-technical people to build and deploy a mobile app for an event of almost any kind, for example: a large conference like a trade show, a medium-sized conference like a sales kick-off, a small series of events such as University open-days, or even one-off private events like weddings.

When I turned up at Guidebook, founders Jeff, Kevin and Pete had built what looked like a well-oiled machine in their home territory of the US.

I fell in love with the product, the culture and frankly the founders. They were (and still are) super cool guys, who have a first-principles mentality that I deeply connected with.

However, once I got in and looked under the hood I observed some immediate big challenges that we’d have to overcome: