How Startups Sell More Product Using a Trojan Horse Approach

A step-by-step guide to building a product that’s enterprise-viral

Joe Procopio
7 min readJun 14, 2021


I’m willing to bet that there’s at least one software app that you use regularly for work that got on your radar because someone you know was already using it.

The most obvious culprit is Zoom, which became the de facto means of remote communication during the pandemic lockdown. Even though GoToMeeting and Webex were already the industry standard for company web conferencing and Microsoft’s Teams and Google’s Meet had begun their evolution from personal video chat to business tool, Zoom became as ubiquitous to video meetings as Google was to search.

But there are a host of other apps in that category. Slack and Trello are two of the more high-profile examples of products that invaded the enterprise like a trojan horse: A single person brings a free version to a small team, that team connects to other teams, then suddenly the company is buying 1,000 seats.

There’s a little bit of lightning-in-a-bottle luck to this organic and viral means of infiltrating a large enterprise customer. But there’s also a massive amount of strategy, including in the design of the product itself.

I’ve broken down that strategy into its components, and I’ll use my experience with my own startups and those I advise to give you an idea of how you can help your product sell itself to large and deep-pocketed enterprises.

The viral lure: Doing big things a better way

I knew I had something special with Teaching Startup when two people with the same URL in their email address joined within the same month. The first person from the company signed up for a free trial and ended up converting to a paid membership. Then the second person signed up. Then they also converted.

This small signal, which I wasn’t looking for, opened up all kinds of new ideas for what I could do with the product. I could evolve Teaching Startup from a solution for individuals to a solution for an entire organization.

I was an early adopter of both Slack and Zoom, before those two products became universal. I watched as Slack was…



Joe Procopio

I'm a multi-exit, multi-failure entrepreneur. NLG pioneer. Building & GROWERS. Write at and More at