7 Hard Truths About PLG from Someone Who's Built It Three Times

Enrich members and select guests gathered for an eye-opening conversation with Adam Gross, former CEO of Heroku and a luminary in the product-led growth (PLG) space.

Product-led growth sounds clean on a slide. In practice, it's one of the most organizationally demanding models a company can adopt. Adam has navigated PLG from the inside at Heroku, Dropbox, and Vimeo, and what he shared wasn't a playbook. It was a reckoning. Here are the seven ideas that stuck.

#1 - PLG Is Hard Because It Requires Unprecedented Cross-Org Collaboration

PLG isn't just a go-to-market motion — it's an organizational challenge unlike anything the software industry has faced before. Because iteration and feature releases happen continuously, the old handoff model breaks down entirely. Compare it to the software CD era: a disc shipped, sales grabbed it, and they sold it. Clean. Sequential. Slow.

PLG collapses that sequence. Product, marketing, sales, and customer success must operate in near-constant coordination. Most organizations simply aren't built for that.

To understand where we are now, it helps to see the full arc of go-to-market evolution:

1980s – 90s

Traditional Sales

Relationship-driven, golf courses, enterprise contracts. Slow cycles, high-touch, high-margin.

2000s

The SaaS Revolution

Salesforce rewrites the rules. Cloud delivery, recurring revenue, inbound funnel logic.

2010s

PLG Era

Dropbox, Slack, Zoom. The product becomes the sales motion. Growth through usage.

Now

PLG + AI

OpenAI, Anthropic, Cursor. AI-native products redefine onboarding, activation, and value delivery.

#2 - Alignment Comes from Stories, Not Spreadsheets

Alignment doesn't happen through OKR reviews or all-hands decks. It comes from intentional planning processes designed to create narrative clarity, which only happens when people understand the story they're inside of.

"Your planning process should be as satisfying as watching a great movie with three clear acts."

The goal isn't to align on a roadmap. It's to align on a story with a beginning, a conflict, and a resolution people can see themselves in. That's what drives real organizational coherence.

#3 - Organizational Planning Is a Practice, Not an Event

Most companies treat planning as a calendar milestone - a painful quarterly ritual that produces a deck nobody looks at two weeks later. That's the wrong frame entirely.

Think of it like yoga or exercise. The point isn't any single session. The point is showing up on a regular cadence and the discipline itself is the value. Teams that plan well don't just plan once a quarter. They've built planning into how they think and operate all the time.

#4 - OKRs Don't Drive Alignment. They Manufacture the Illusion of It

OKRs have become the default planning methodology at most startups and scaleups. They're also, according to Adam, fundamentally misaligned with what alignment actually requires.

"OKRs are a thousand pebbles and no actual bigger vision. If your planning output is a spreadsheet, you're doing it wrong."

The problem is structural. OKRs are bottoms-up by design, with each team setting their own objectives, which then get aggregated into a company view. But real alignment requires a top-down starting point. Someone has to decide what matters most before everyone else can organize around it. Without that clarity, you get synchronized busyness, not direction.

#5 - Internal Communication Is an Investment, Not a Cost

Most executives think about communication as a drain on time they could be spending with customers or on strategy. Adam used to think the same way but he doesn't anymore.

Every message, every all-hands, every Slack post is a signal that ripples through the organization. People read into what you say, and what you don't say. Treating internal communication as an investment means treating it with the same craft and intentionality you'd give a customer pitch.

#6 - The Best Operators Remove Metrics, Not Add Them

When most executives inherit a business, their instinct is to instrument everything. More dashboards. More KPIs. More signals. Adam takes the opposite approach.

"One thing I do when I come into companies is remove metrics, not add them. Operational excellence is having the discipline to understand what's important."

Metrics proliferate because they feel like progress. They're not. A metric only earns its place in a dashboard if it tells you something genuinely important, something that changes how you act. Everything else is noise that teaches your team to stop paying attention.

#7 - Your Pricing Page Is the X-Ray of Your Business

When Adam walks into a company as a new CEO or advisor, the first thing he looks at isn't the financials or the roadmap. It's the pricing page.

Not because pricing is the most important thing, but because the pricing page is a compressed representation of everything: how the company understands its own value, how it segments its customers, what journey it's inviting people onto. A clear pricing page signals a company that knows what it's doing. A confusing one signals something broken underneath, usually in how the business thinks about value delivery altogether.

“The pricing page is ‘the map of the journey,’ it communicates your product's value proposition and the customer's path all in one place.”

If your customers can't figure out which plan they belong in, chances are your company doesn't fully know either.