Boring Wins - Stop Trying to Be Interesting

I’ve been obsessed with studying how enterprises actually hold onto accounts. How do they keep them, grow them, and eventually make them impossible to remove?

It is not the sales team and their brilliant Zuora-esque story narratives, nor the suave dinner at a Mediterranean resort island, nor at the elite golf courses. The sales do their job, but retention and switching on the tap to introduce new products are increasing, and customers are buying more and more into it.

What Salesforce Actually Sold

When Salesforce was growing through the 2000s, the pitch was “no software.” The cloud model was new, and that got them in the door. But that’s not why they own so many accounts twenty years later.

What kept them was boring. Quarterly releases that came on schedule. Honest status pages. Support that enterprise IT teams could actually work with. Over time, they became the system that the forecast ran through, the comp plans referenced, the one thing nobody wanted to migrate away from. They stayed dominant because they stopped surprising people in bad ways.

How ServiceNow Grew Without Selling

ServiceNow is an interesting one to study. IT workflow is not a glamorous category. But if you look at how they expanded inside accounts, it had almost nothing to do with sales motion.

IT deployed it. IT had no problems with it. So HR asked to use it. Then legal. Then facilities. Each team adopted it because the previous team never complained about it.

That’s a compounding loop that most GTM teams never build intentionally. The product just worked consistently, and word traveled internally without a sales rep involved. By the time procurement reviewed the expanded contract, the decision had already been made three floors up.

Microsoft’s Boring Cloud Strategy

AWS had a head start in the cloud. By most technical measures, they had the better product in the early years, too. Microsoft didn’t try to out-engineer them.

What Azure offered was familiarity. If you were already running Windows servers, Active Directory, and Office 365, Azure was the path of least resistance. The integrations weren’t exciting. The support spoke the same language as the IT teams buying it. And for large enterprises with complex procurement and risk committees, “least risky” is often a more powerful position than “most capable.” They played a longer game, and it worked.

None of these companies won in the long term by being the most interesting option. They won by becoming the option no one in the account wanted to argue against.

“Nobody Ever Got Fired for Buying IBM.”

In enterprise sales, your champion is constantly defending the decision to buy from you. Every renewal, every expansion, every time something goes slightly wrong. The more predictable your execution, the easier their job is. And the easier their job is, the more they go to bat for you.

Reliability compounds in ways that features don’t. A feature can be copied. A three-year track record of doing what you said you would do is very hard to replicate quickly.

Most teams spend their energy on the new logo. The pitch, the demo, the close. That’s important. But the GTM motion that actually builds a business is what happens in the twelve months after the contract is signed.

How many of your customers, right now, could tell a clear story about why staying with you is an easy decision? Not why you’re great. Why switching is not worth it.