Enterprise sales are hard

I'm an engineer, not a sales person. Even as a CTO, I thought that distinction would shield me from any pain as we moved upmarket. I was wrong.

So, you built something great. You gained product market fit with mid-sized companies. You ship features, they use them. All things are balanced.

Except for growth.

See, SMEs don't have a heap of cash, so you're not getting the big hockey stick graphs you were hoping for.

Maybe instead of chasing this small game, you could aim at a different market? Large, slow moving enterprise beasts. Flush with cash and too large to change once they make a decision. One tough sale, sure, but then a long tail of sweet sweet profit. Even better, the software they're currently using is decades old! There's basically no competition.

The buyer, the user, and Magic Mike.

Most people understand the difference between the buyer and the user. A parent buys a toy for their kid. The parent is the buyer, the kid is the user. Enterprise companies don't work like that though.

"I want the toy, the kid wants the toy, but if you want us to buy the toy you're going to have to talk to Mike."

"Who the hell is Mike?"

"Oh Mike? He decides if we're actually going to buy the toy. He'll get quotes for a bunch of other toys that we have no intention of buying, and then use those to negotiate for a cheaper toy. He'll squeeze a little more value out of you. Perhaps we want you to come to our house and show us exactly how to play with the toy. Mike is great. We get him in and everything becomes cheaper. It's magic."

Mike is procurement.

If you've never sold to a company with a procurement team, you're in for a bumpy ride. Their job is to drive down the price of whatever you're selling, and they do it well. Most startups don't even factor procurement teams into their "go upmarket" strategy. With big pockets comes the ability to pay people to exclusively negotiate software purchases. These teams have time, and they have spoken to hundreds or thousands of sales people in their life. This might be a sale you've worked on for a month, but this is just Tuesday for them.

I've said it before, but this is why I think companies like Clickup and Monday are in such a good position. They do everything. They compete with everyone. They have an answer for everything a procurement team throws at them. I don't particularly like their software, but I respect their ability to sell.

Your value prop isn't as strong as you think it is

Startups tend to be overly optimistic about their value proposition. They focus on features, on what makes them unique in the marketplace. And that's great, but for enterprise customers, your distinctive features are just part of the story. They're also looking at things like:

• Someone to sit next to them and show them everything about the software
• Dedicated support with near zero response times
• The Account Executives immortal soul
• Integrations with any tooling they already have
• API access and support for it

All of these factors are part of your value proposition. They all cost money. Money that eats into your margins and complicates your pricing strategy.

The other other thing about procurement teams

You've probably made this connection already, but there's an even bigger issue with procurement teams that startups may not be ready for. They are a dedicated team for procuring software. That means for some enterprise customers, they are able to move significantly faster than SMEs. They're literally paying a person internally to help them switch software!

You think enterprise sales will be a steady paycheck, but there is going to be just as much pressure on churn as there was before. Every other competitor in the market is reaching out to those teams and trying to convince them to switch.

Churn is going to hit way harder than you think too. When an SME churns, it's a great opportunity to learn about their experience and make your product more resilient. When a massive customer churns, it tangibly impacts your runway. Come renewal time, customers hold enormous leverage over you. You may have to drop pricing, or change something on the roadmap in order to retain them.

The culture shift: from product-led to service-led

Here's where things are a little more subtle. Moving upmarket often requires a fundamental shift in how your company operates. You're going from a product-led approach, where your metrics are clear and your feedback loops are tight, to a more service-led model.

Suddenly, your product and engineering teams aren't talking directly to customers anymore. Instead, they're getting feedback filtered through sales and customer success teams. This can create internal friction, especially if your company culture is built around a "move fast and break things" mentality.

Because here's the thing: enterprise customers don't want you to break things. They want stability, reliability, and a product that just works. Every bug, every outage, every little hiccup becomes ammunition for the procurement team when renewal time rolls around.

The part where I mention Founder Mode

I'm no expert, but here's what I think should be top of mind moving up market for founders.

1. Be selective: Not every big company is worth chasing. Some will have such bureaucratic processes that they're simply not worth the effort. It's okay to say no.
2. Stay flexible internally: Just because your customers are becoming more rigid doesn't mean you have to.
3. Prepare for the culture shift: Be aware that moving upmarket will change your company's internal dynamics. Product and engineering teams may need to become more humble.
4. Don't rush it: The luxury startups can't afford is trying to go upmarket too quickly. Take your time, build your processes, and make sure you're ready for the shift.
5. Keep communication channels open: As you grow, make sure your teams are still talking to each other.
6. Founder mode: This has quickly become a meme, but I think it's important. Leaders should try to stay across the entire org. Do some skip meetings, try to improve cohesion. You're going to be adding a lot more people than you may think to your headcount, so account for it.

At the end of the day, selling to enterprise is a challenge, but obviously heaps of companies have seen massive success from it. If you can support it, do it.

And remember, if all else fails, you can always pivot to selling procurement as a service. After all, you'll be an expert by the time you're done.