DEV Community: Pete Ryan

Selling Trello to the Enterprise: What I Learned Turning a Product People Loved Into Enterprise Revenue

Pete Ryan — Tue, 03 Nov 2026 13:32:51 +0000

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

Atlassian press release, "Atlassian to acquire Trello" (Jan 9, 2017), via SEC Form 6-K exhibit: https://www.sec.gov/Archives/edgar/data/1650372/000165037217000002/a992atlassianpressrelease1.htm
Atlassian Form 6-K (Jan 9, 2017), deal terms: https://www.sec.gov/Archives/edgar/data/1650372/000165037217000002/a6ktrello010917.htm
TechCrunch, "Atlassian acquires Trello for $425M" (Jan 9, 2017): https://techcrunch.com/2017/01/09/atlassian-acquires-trello/

Originally published at heypeteryan.com.

How We Landed LinkedIn Sales Solutions' First 100 Logos

Pete Ryan — Tue, 03 Nov 2026 13:31:15 +0000

If you build developer tools, the core lesson here will feel familiar: put your product where people already work, and sell first to the teams already using you. Here's how we learned that when I started LinkedIn Sales Solutions.

Pete Ryan joined LinkedIn in 2009 as one of its first sales hires, went from AE to Head of SMB Sales, and started LinkedIn Sales Solutions, an experiment to test whether people would pay to use LinkedIn for sales. Its first product put LinkedIn profiles inside Salesforce. He landed its first 100 logos between 2009 and 2013 by selling to sales teams that were already using LinkedIn heavily, starting with Eloqua.

In 2009 I left Oracle, where I'd been an AE selling databases, and joined LinkedIn as one of its first sales hires. Over the next four years I went from AE to Head of SMB Sales. I started LinkedIn Sales Solutions, ran SMB sales for it as Head of SMB Sales, and landed its first 100 logos.

Most people know LinkedIn's sales product today as Sales Navigator, which relaunched as a standalone product in July 2014. This is the story of what came before that, and the lessons I still use.

It started as an experiment

I ended up at LinkedIn because my former Oracle colleague James Volpentest went there first, and I thought it was a really interesting company. The sales team was six or seven people, all hired at about the same time. LinkedIn had a few tens of millions of members back then. It passed 50 million in October 2009.

Sales Solutions started because we were seeing early demand for a sales product. Salespeople were already on LinkedIn, researching prospects and looking for a way in. So we ran an experiment with one question: is there a market for people using LinkedIn for sales?

Framing it as an experiment was the right call, and it's the first lesson I'd pass on. If you're launching a new product inside a company that already has a winner, don't ask for a big budget on day one. Follow the demand you're already seeing, and ask for permission to test one clear question.

Version one: LinkedIn inside Salesforce

The first version of the product was basically LinkedIn inside Salesforce. Reps lived in their CRM all day. Every time they wanted to look someone up, they toggled to another tab, searched LinkedIn, and toggled back.

We cut out the toggle. A rep could stay in Salesforce and see the LinkedIn profile tied to a contact, an opportunity, or an account, right where they were already working.

The lesson: put your product where your buyer already works. We didn't ask reps to adopt a new tool. We made the tool they already used better.

Sell to the teams already using you

Our first buyers were mostly mid-market tech companies. The person who signed was usually the CRO or VP of Sales, and sometimes the VP of Marketing.

The original pitch was a design-partner pitch. We were looking for companies that wanted to join the mission of building a tool for sales, give us honest feedback, and help shape the product.

Our first Sales Solutions deal was with Eloqua, the marketing automation company Oracle later acquired. Eloqua's sales team was already using LinkedIn very heavily. We didn't have to convince them LinkedIn mattered for selling. They were living it every day and wanted more.

That turned out to be the most important lesson of the whole run.

What didn't work: lots of outbound to heads of sales whose teams weren't using LinkedIn much yet. We were asking them to buy into a behavior change and a product at the same time. Those conversations went nowhere.

What worked best: customers whose sales teams were already bought into LinkedIn and wanted to supercharge what they were already seeing. The reps had the habit. The leader just had to make it official and give them better tools.

If you take one thing from this essay, take this: find the warm demand first. Look for the teams whose people already use your product, or something close to it, on their own. Selling to them is about scaling something that's already working, not changing minds. Cold outbound to people who haven't felt the value yet is the hardest sale there is, especially for a brand-new product.

Focusing on warm demand is also what made the motion repeatable. Once it was, the pitch changed. We stopped asking people to help us build something and started showing them what teams like theirs were already getting out of it.

Why sales was the bigger prize

In my view, LinkedIn's three biggest revenue lines were, and still are, Talent Solutions (recruiting), Marketing Solutions (ads), and Sales Solutions, in that order.

The public numbers back that up for the years I was there. In LinkedIn's last annual report as a public company, for 2015, Talent Solutions brought in about $1.9 billion, Marketing Solutions $581 million, and Premium Subscriptions, which included Sales Solutions, $532 million. Microsoft no longer breaks LinkedIn's revenue out by line. It reports one number, $19.8 billion for fiscal 2026.

Here's what always struck me: the market for selling software is bigger than the market for hiring software. Gartner puts CRM sales software at $25.7 billion in 2024. Global Market Insights puts talent acquisition software at $10.8 billion for the same year. These come from different firms with different definitions, so treat it as a rough comparison. Even so, sales software comes out more than twice as big.

That's why I believe LinkedIn had a chance to build something really special on the go-to-market side.

The DNA problem: why a sales InMail isn't a recruiting InMail

So why didn't sales become LinkedIn's biggest business? My take is that it may not have been in LinkedIn's DNA. LinkedIn was a consumer internet company, not a B2B software company.

There was also a real tension at the heart of the product. As I understood Reid Hoffman's thinking, you never want to disrupt the ecosystem. The network only works if members trust it.

A recruiting InMail fits that rule. A recruiter reaches out with a job, and a lot of people are happy to hear about one. Both sides win. A sales InMail is different. The buyer may not be looking for anything in that category, so the same message can feel like a nuisance.

The lesson for anyone selling into a platform or community: the buyer's success can't come at the expense of the people on the other side. If your growth makes the network worse, you're spending trust you can't easily earn back.

The network is the moat, and what I still use

Of all the companies I've worked at, LinkedIn really had something special. It laid the golden goose egg because it had the network, and to this day no one has been able to displace it. Features can be copied. A network of professionals who keep their own profiles up to date can't.

After LinkedIn, I led enterprise sales at Trello, which was acquired by Atlassian. I founded Gogohire and co-founded HiFive, where I was CEO until it was acquired by HeyLois in November 2025. Today I work on Growth at Supabase.

LinkedIn and Supabase are, in a lot of ways, both product-led companies. You build a groundswell of people who actively use the product. Then you go over the top and sell top-down: consolidate all that usage and bring everything under one roof. That can be a challenge, but it's also an amazing opportunity. It's the same lesson Eloqua taught me: the best deals start with people who are already using you.

If you're launching something new, here's the short version:

Follow the demand you're already seeing, and frame it as an experiment.
Put the product where your buyer already works.
Sell first to the teams already using you. Skip cold outbound to people who haven't felt the value.
Size the market honestly, and know which slice you're going after.
Protect the ecosystem your growth depends on.

Pete Ryan works on Growth at Supabase. He's a two-time VC-backed founder (HiFive, Gogohire), led enterprise sales at Trello, and started LinkedIn Sales Solutions as one of LinkedIn's first sales hires, running SMB sales for it as Head of SMB Sales. He's based in Austin, Texas. More at heypeteryan.com.

Sources

LinkedIn, "Empowering Social Sellers with LinkedIn's New Sales Navigator" (July 31, 2014): https://www.linkedin.com/business/sales/blog/modern-selling/the-social-selling-era-starts-now
TechCrunch, "LinkedIn Launches A Standalone Sales Navigator" (July 31, 2014): https://techcrunch.com/2014/07/31/linkedin-sales-navigator/
LinkedIn blog, "LinkedIn: 50 million professionals worldwide" (Oct 14, 2009): https://www.linkedin.com/blog/member/archive/linkedin-50-million-professionals-worldwide
Oracle, "Oracle Buys Eloqua" (Dec 20, 2012): https://www.oracle.com/corporate/pressrelease/oracle-buys-eloqua-122012.html
LinkedIn Corporation 10-K, FY2015, revenue by product: https://www.sec.gov/Archives/edgar/data/1271024/000127102416000035/R24.htm
LinkedIn 2015 annual report and shareholder letter: https://www.annualreports.com/HostedData/AnnualReportArchive/l/NYSE_LNKD_2015.PDF
Microsoft 10-K, FY2026, revenue by product and service: https://www.sec.gov/Archives/edgar/data/789019/000119312526323660/R110.htm
Gartner, "Market Share Analysis: CRM Sales, Worldwide, 2024": https://www.gartner.com/en/documents/6791434
Global Market Insights, "Talent Acquisition Software Market Size & Share 2025-2034": https://www.gminsights.com/industry-analysis/talent-acquisition-software-market

Originally published at heypeteryan.com.