DEAR STAGE 2: Developers love our product and adoption is spreading on its own, but my board is pushing for contracts, commitment, and enterprise revenue. I'm terrified that the second I bolt on a traditional sales team, I'll smother the bottoms-up motion that's working. Where do I start? ~ PLG v. SLG
DEAR PLG v. SLG: Before we dig in, let’s acknowledge the reality that you have the hardest thing solved: real demand. Plenty of founders would trade places with you in a heartbeat.
I caught up with Prem Iyer last week, who has deep experience building enterprise motions inside PLG businesses. We talked about what happens when strong bottom-up adoption starts creating pressure to turn that usage into larger contracts, deeper commitments, and enterprise revenue. Here are a few ideas from our conversation:
Reframe what “not a customer” means
No contract does not mean you are starting from zero. In fact, Prem described the opposite based on his recent experience at Cursor. “We have 50,000 customers and ~70% of the Fortune 500. And the ones that are not customers? They might have 80 developers paying for and using it on their own. They’re just not on an enterprise agreement with us yet.” His language for those accounts is worth noting: “I always call them underpenetrated, not zero LTV.” On the enterprise side, the job is conversion. You’re turning usage you already have into a signed commitment.
Timing matters
The reason to move now with a sales-led motion is that your organic lead is on borrowed time. Prem was direct about the dynamic he saw at Cursor: developers picked Cursor and “just did it, whether their CIO or anybody signed off or not.” But once competitors show up, “they’re going to come and try to take that from us. Now we’re moving to SLG so that we can get enterprise commitment”. My takeaway? Every month a company runs on individual self-funded seats is a month you’re susceptible to a competitor. Enterprise contracts allow you to convert user love into locked-in agreements.
Your first sales hire is not any old salesperson
This is where PLG companies often go wrong. They hire a polished enterprise rep who knows how to manage a deal process, and then wonder why it’s not working. What you need is someone who can create a process where there is none. Prem described the candidates he looked for as “glass eaters.” His description: “These are true hunters. They’re not farming accounts. They’re not waiting for a PO. We have to go build it, go into the account, talk to 20 personas, and build the whole thing ground up.” You have to screen for the person who lights up at the idea of multi-threading and working an account bottoms-up and tops-down in parallel until they find a path in.
Bring the CFO in early, and lead with ROI
The magic of PLG is that your ROI case already exists within your user base and usage patterns. Prem shared a story about walking into a Fortune 150 account where he got less than a minute with the CFO. His whole pitch: “If I had a way to show you we could save 30% on your software development economics and add 40% to productive time for the team, would you have that conversation?” He said, ‘we’d have to’. If you are a true PLG product, you have the usage data and can tell a story. Find it, make it defensible, and lead with it!
Making the leap from PLG to SLG is about taking what’s working and wrapping a commercial layer around it. Keep the self-serve on-ramp exactly as it is (don’t mess with a top of funnel that’s working), and layer a small team of genuine hunters whose only job is to turn “everybody here already uses this” into a signed, multi-year yes.
We’ll leave you with one question: do you actually know which of your logos are most underpenetrated right now? If you can’t answer that right now, that’s where you start. You need to have the data infrastructure in place to fuel the sales-led motion.
Until next week!