If you work on a product-led dev tool, whole teams at some companies may already rely on you before IT knows. This is how we turned that kind of bottom-up usage at Trello into enterprise deals, and where it can go wrong.

Pete Ryan was Head of Enterprise Sales at Trello in 2016–17, through Atlassian's $425 million acquisition. His team of about ten sold top-down into companies whose employees were already using Trello, found ready accounts with product usage data, and won deals by pairing champions' love for the product with the security, admin controls, and business case IT needed.

When I joined Trello in 2016, there were about 10 million people using it, and that number was growing fast. By the time Atlassian announced the acquisition in January 2017, Trello had more than 19 million registered users. Almost all of that came bottom-up. People found Trello, liked it, and brought their teams.

My job was to turn that love into enterprise revenue. I was Head of Enterprise Sales from 2016 to 2017, and in January 2017 Atlassian announced it was buying Trello for about $425 million. This is what we learned along the way, and the lessons I still use today.

What was Trello's enterprise problem when I joined?

Trello had massive free, bottom-up usage, but no real enterprise motion yet. Enterprise revenue came from a top-down sale into target companies, mostly digital natives, whose people were already using Trello.

In the early days, what we were really selling was SSO. A company already had hundreds or thousands of employees on Trello, and IT wanted them logging in the way they logged in to everything else. That was the wedge.

The team I built grew to about ten people. That's small for a product with 10 million users, which meant we couldn't chase everyone. We had to be very picky about where we spent our time.

How did we find which accounts were ready to buy?

We used product usage data to find them. We looked at active users inside each company, blended with how many boards they were creating and how many Power-Ups, Trello's integrations, they were using.

We ran that analysis in Mode Analytics (mode.com). Active users told us how big the footprint was. Boards and Power-Ups told us how deep it went. A company with lots of boards and lots of integrations wasn't just trying Trello. They had built real work on top of it.

Once an account looked ready, we'd suss out who the champions were: the people driving usage on the ground. We'd reach out to them and usually ask them to fill out a quick survey about how they used Trello.

That survey did two jobs. It told us what the use cases actually were, so we weren't guessing. And it started a relationship with the people who'd later help us make the case inside their company.

Who did we actually sell to: the users or the bosses?

Both. The champions were the users who loved Trello, but the deal was usually signed top-down, by a leader, with IT and security weighing in.

Here's what made Trello unusual. Of any company I've worked at, aside from Supabase, Trello had an amazing brand and amazing product-market fit. Most users loved chatting with us as sellers. That's pretty uncommon. Usually people dodge the sales rep. At Trello, they wanted to tell us how they used the product.

A good example is a large networking company. Their head of digital transformation uncovered that they had a few thousand users on Trello. That's the kind of discovery that changes the conversation. It wasn't "should we try this tool?" It was "a few thousand of our people already chose this tool, so how do we support it properly?"

By then we offered more than SSO: admin controls, answers to the SOC 2 questionnaire, those types of things. We closed a six-figure, multi-year deal.

What did enterprise buyers need that free users didn't?

They needed control and proof. Security and IT teams wanted SSO, granular admin controls, and security documentation like SOC 2, and someone had to justify paying for a tool people were already using for free.

The hardest objection from IT or security was usually that we didn't have granular enough admin controls. When we sold to government, we didn't have FedRAMP at the time. (Trello has FedRAMP now.) Some of those gaps you can't talk your way around. You either have the control they need or you don't, and you have to be honest about it.

The bigger challenge was budget. Most IT and security teams don't want to pay for software or security. From their side, people were already using Trello, so why pay?

So we worked hard to build a business case:

  • The footprint: here's how many users you already have.
  • The use cases: here's how your teams are actually using Trello.
  • The value: we'd try to tie it back to ROI.
  • The voice of the users: quotes from champions sharing their love for Trello.

That last piece mattered more than people expect. When an IT leader reads their own employees saying how much they rely on a tool, the conversation shifts from "do we need this?" to "how do we manage this?"

What changed after Atlassian bought Trello?

The biggest change was distribution. Atlassian had many thousands of customers that Trello didn't have yet, and we were able to sell alongside Atlassian into a ton of them.

When Atlassian announced the deal, it said its products were used by more than 65,000 organizations. Before, we were finding enterprise accounts one usage report at a time. After, we could also walk in alongside a vendor those companies already bought from and trusted.

That's a very different starting point. A lot of the procurement and security groundwork we used to do from scratch was easier when the company already had a relationship with Atlassian.

What would I tell a PLG company starting enterprise sales today?

Go top-down carefully, with strong math, and get every decision maker in the room. Those are the two lessons from Trello I use most in my work on Growth at Supabase.

1. Be very strategic and careful when you go top-down. When you go to IT or security, you can blow the cover of all the people using the product. Someone in IT or security can shut it down really quickly. That's the risk of product-led growth: the usage is real, but it may not be sanctioned. So bring really strong math and a strong business case before you walk in. Show them how many people are using it, what they use it for, and why taking it away would hurt.

2. Do your homework on who the players in the room are, and get as many of them in the room as possible. PLG purchases often have many decision makers: the champions who use the product, the leader who owns the budget, and the IT and security people who can say no. The more people you have involved in the deal, the higher the likelihood it closes. It's sales 101, but it's easy to forget when one enthusiastic champion makes a deal feel done.

Key takeaways

  • Start where the love already is. Sell into companies whose people already use and like your product.
  • Let usage data pick your accounts. Active users show the footprint. Depth, like boards and integrations, shows commitment.
  • Find and talk to the champions first. A quick survey tells you the real use cases and starts the relationship.
  • Know what IT needs, and be honest about gaps. SSO, admin controls, and security documentation are table stakes. Some gaps, like FedRAMP, you can't talk around.
  • Build the business case for the people who don't want to pay. Users, use cases, ROI, and champion quotes.
  • Go top-down carefully. You can expose unsanctioned usage, and IT can shut it down fast.
  • Get everyone in the room. More decision makers involved means a higher chance the deal closes.

I work on Growth at Supabase. I'm a two-time VC-backed founder (HiFive, acquired by HeyLois; Gogohire), I led enterprise sales at Trello, and I started LinkedIn Sales Solutions. More at heypeteryan.com.

Sources

Originally published at heypeteryan.com.