Breaking Into Enterprise: The 2024 Playbook

I’ve been writing about product building and growth every day for the last 1,460 days…

The two most common questions I get are:

“I’ve built product-market fit with SMBs. How do we expand upmarket?”

“I run product at my company, and we’re ready to tackle enterprise deals. What needs to change in our product, team, and motion?”

Here’s how to navigate this transition profitably and at scale (from 15 years of my experience):

𝗧𝗵𝗲 𝗛𝗶𝗱𝗱𝗲𝗻 𝗥𝗲𝗮𝗹𝗶𝘁𝘆 𝗼𝗳 𝗘𝗻𝘁𝗲𝗿𝗽𝗿𝗶𝘀𝗲 𝗦𝘂𝗰𝗰𝗲𝘀𝘀

I’ve had the privilege of helping companies like Scout, Apollo, and Google Hire make this transformation. What you’re about to learn is grounded in real-time experimentation and proven results.

Many companies still believe that hiring an expensive enterprise sales team, abandoning Product-Led Growth, and overhauling security will bring success.

It’s wrong and here’s why:

↳ It’s Not Just About Sales or Marketing
If success were only about sales, any company could simply increase resources and win big, right? But it’s not that simple.

↳ Customer Success as the Epicenter
Enterprise clients are great, but if customer success doesn’t evolve alongside, it will ultimately backfire.

↳ Holistic Changes Are Required
Moving upmarket means transforming the entire ecosystem — sales, marketing, and product must evolve together.

𝗪𝗵𝘆 𝗘𝗻𝘁𝗲𝗿𝗽𝗿𝗶𝘀𝗲 𝗡𝗼𝘄? 𝗧𝗵𝗲 𝗥𝗲𝗮𝗹𝗶𝘁𝘆 𝗧𝗼𝗱𝗮𝘆

Now is the ideal time to target enterprise clients:

↳ Enterprise CIOs are ready to increase their software spend.
↳ Enterprise Net Revenue Retention (NRR) typically exceeds 100%, while SMBs often fall below 90%.
↳ Buyers are increasingly willing to switch from outdated legacy systems to modern, high-quality products.

Here’s what works now…

𝗧𝗵𝗲 𝗠𝗼𝗱𝗲𝗿𝗻 𝗘𝗻𝘁𝗲𝗿𝗽𝗿𝗶𝘀𝗲 𝗠𝗼𝘁𝗶𝗼𝗻

I call this approach Continuous Enterprise Expansion (CEE) — a transformative strategy grounded in a product-first philosophy. It accelerates your entry into the enterprise market while creating a sustainable growth engine that supports ongoing success from day one.

Here’s why it works:

↳ Enable organic growth as user engagement builds momentum for attracting enterprise accounts.

↳ Allow users to explore independently, driving organic growth before sales involvement.

↳ Minimize reliance on traditional sales tactics for efficient acquisition.

↳ Lower overhead enables better resource allocation and higher profit margins.

𝗧𝗵𝗲 𝗣𝗿𝗼𝗼𝗳 𝗜𝘀 𝗜𝗻 𝗧𝗵𝗲 𝗡𝘂𝗺𝗯𝗲𝗿𝘀

↳ Apollo achieved unicorn status by leveraging the CEE model.

↳ Datadog (valued at $42.5B) found that about 50% of its $1M+ ARR customer base started as self-serve users.

So, how do you transition your product for enterprise deals?

How do you master the 7 Layers of Growth to win enterprise deals at scale?

Thanks to our sponsor WorkOS, this deep dive is completely free for all.