You’ve decided to expand into the U.S. You have a product that works, customers in Europe, and a revenue target for the new market.
Now you need a salesperson in the U.S., right?
Maybe. But before you start looking for someone, ask yourself what you’re actually hiring them to do.
Are you giving them a sales process that has worked and asking them to execute and improve it? Or are you asking them to figure out the market, find the right customers, develop the messaging, build a process, and deliver revenue, all at the same time?
Those are very different jobs. And if you’re expecting one person to do all of the second one, you’re making an already difficult hire much harder.
Your new hire doesn’t know what you know
As a founder, you carry a lot of knowledge that isn’t written down anywhere.
You know why you built the product. You’ve heard the objections. You understand which problems customers get excited about and which features they don’t care about as much as you thought they would.
You may not even realize how much of that knowledge you use in a sales conversation. You just respond to a question, adjust your explanation, or bring up a customer example because you’ve done it before.
A new salesperson doesn’t have that history. And if they’re also selling into a market where you haven’t yet figured out who buys, why they buy, and how they make decisions, they have a lot of learning to do before they can build a predictable pipeline.
That doesn’t mean a salesperson can’t help you learn. They absolutely can. But if you can’t give them a reasonable starting point, it becomes difficult to tell whether the person is struggling or the approach itself isn’t working.
One deal is encouraging. It isn’t necessarily a process.
Let’s say you’ve closed your first U.S. customer. That’s a great milestone. You should absolutely learn everything you can from it.
How did you find them? What problem were they trying to solve? Who was involved in the decision? What convinced them to move forward?
But also ask yourself what was unique about that deal.
Maybe it came through a personal introduction. Maybe the buyer already knew your category and had a budget. Or maybe there was a particular event that made solving the problem unusually urgent.
That doesn’t make the deal any less valuable. It just means you need to be careful about assuming the same approach will work across the market.
The more often you’ve been able to repeat the important parts of the process, the better equipped you’ll be to bring someone in and say, “Here’s what we’ve learned. Start here, and let’s improve it together.”
What should you have in place before you hire?
You don’t need a perfect playbook. You do need enough information to give a new salesperson direction and a way to evaluate what’s working.
Here’s where I would start.
A clear picture of your target customer
Who are you going after, and why?
That means more than saying “mid-market companies in the U.S.” What kinds of businesses have the problem you solve? Which roles feel that problem? Are there characteristics that make a company more likely to see value or move forward?
Your European customers are a useful starting point, but don’t assume the same profile will translate perfectly to the U.S. Treat it as a hypothesis and pay attention to what you learn from real conversations.
A message that starts a conversation
Your salesperson needs to know how to explain why a prospect should care.
What problem are you solving? What is the impact of that problem? What becomes possible if the customer addresses it?
You should have a few ways to talk about these questions that you’ve actually tested with potential U.S. buyers. The wording can and should evolve, but your new hire shouldn’t have to start with a blank page.
An understanding of the value
If a prospect asks, “What’s this worth to us?” can you help them answer?
You don’t need a complicated ROI calculator for every conversation. But you should understand the main ways your product creates value and what information you need from the customer to make that value concrete.
For example, if your product saves time, how much time could it save? Who spends that time today? What could they do with it instead? Is the impact significant enough for the customer to make this a priority?
A salesperson will have a much easier time building urgency when they can work through those questions with a prospect early in the process.
A documented path from first conversation to customer
Think through the steps a deal has gone through so far.
How did you find the prospect? What did you cover in discovery? What needed to happen before a demo was useful? Who else got involved? What questions came up before the decision?
Write it down in plain English. Include the questions you ask, the objections you hear, and the customer examples that help explain your value.
This doesn’t need to be a 50-page document. It needs to be useful enough that someone new can understand what you’ve done, try it themselves, and tell you where they’re getting stuck.
Expectations that connect activity to the goal
If you want a certain number of customers in the next 12 months, work backward from that goal.
How many opportunities might you need? How many conversations would it take to create those opportunities? How many relevant companies and contacts do you need to reach?
Early on, some of these numbers will be estimates. That’s fine. The point is to make your assumptions visible so you can test and adjust them.
If you expect someone to close five customers, but you haven’t thought about where the pipeline will come from or how long deals tend to take, you’re setting a target without giving them a plan.
What the salesperson should do with the playbook
A playbook is a starting point, not a script that can never change.
Your new hire will bring their own experience. They may ask better questions, find a more effective way to reach prospects, or notice that a different type of customer responds more strongly. That’s exactly what you want.
But now you have something to compare those observations against. You can discuss what’s changing and why, rather than trying a completely new approach every week and hoping something sticks.
And as the founder, you still have a role. Stay close to customer conversations, help with product and market questions, and make time to review what the salesperson is learning. Hiring someone doesn’t mean you can step away from the sales process entirely.
So, when are you ready?
There isn’t a magic number of deals that applies to every company. The right timing depends on your product, your sales cycle, the complexity of the market, and the kind of person you’re hiring.
But before you make the hire, I’d want to be able to answer these questions:
- Can we describe the customer we’re targeting and why?
- Have we had enough conversations to know which problems and messages resonate?
- Can we explain the value in terms a customer cares about?
- Do we understand the main steps from first conversation to a decision?
- Can we give this person realistic expectations and support them as they learn?
If you can’t answer those questions yet, that doesn’t mean you’re behind. It means you have some useful work to do before you add the cost and complexity of a hire.
Spend some more time selling, learning, and documenting what works. Then bring in someone who can build on that foundation.