This happens a lot… A founder books a call with me, excited to build their first sales team or make their first sales hire. We talk through their needs, their stage, their current revenue. Then they hit me with it: “We need someone who can scale us to £10M ARR.”

The problem? They’re sitting at £500K.

I love the ambition, you want to building something big and you want to hire people who can grow with you, people who won’t need replacing in 18 months.

But the hiring for tomorrow’s problems is one of the fastest ways to fail today.

The experience trap

When you hire someone who’s been there and done that at the scale you aspire to reach, you’re making a costly assumption. You’re assuming that what worked at their previous company with its established brand, mature product, proven playbook, and probably significant funding, will work for you right now.

It won’t.

The person who scaled a sales team from £5M to £50M at a well-funded Series B company is playing a completely different game to what you need at early stage. They’re managing, not doing. They’re optimising established processes, not figuring out your ICP from scratch. They’re probably not even picking up the phone anymore.

What you need is someone who can:

• Get in the trenches and make 50+ calls a day
• Handle the entire sales cycle themselves
• Give you honest feedback when your messaging isn’t landing
• Iterate quickly when something isn’t working
• Deal with the reality that your product probably isn’t perfect yet

That’s not the profile of someone who’s been running a 20-person sales org. That’s someone who’s been doing it, recently, at your stage.

The cost of over-hiring

I had a founder reach out to me last year. They’d hired a Head of Sales with incredible experience, they were a VP at a unicorn, scaled teams, the whole package. Six months in, the founder was pulling their hair out. The hire had spent the entire time building frameworks, creating dashboards, and talking about what they will do when they had a team in place.

Zero revenue generated.

They’d paid top-tier salary for someone who was playing a role that didn’t exist yet. The company needed someone selling, and they’d hired someone who needed a team to manage.

When you over-hire, you waste salary obviously, but you also waste time. And that’s the one resource you absolutely cannot get back at early stage. While your expensive hire is building their perfect tech stack and interview process, your competitors are closing deals with scrappy, hungry salespeople aligned to their stage.

What a right stage candidate looks like

I tell founders all the time to match the hire to their current reality, not your vision deck. This is what I mean by that:

Pre-product market fit (£0-£500K ARR):

You need doers. People who’ve sold in ambiguous environments. Your first sales hire should probably have 2-5 years of experience, ideally at another early-stage company. They’ve felt the pain of changing messaging weekly. They’re comfortable when things aren’t perfect. They can probably help with marketing, customer success, and product feedback because they have to.

Early traction (£500K-£2M ARR):

Now you can think about someone who’s seen scale, but only just. Someone who’s helped take a company from where you are to £5M, not £50M. They know what comes next because they’ve lived it once, but they’re still comfortable rolling their sleeves up. They can start building process while still carrying a bag.

Scaling (£2M+):

This is when you can start thinking about that experienced Head of Sales or VP. You’ve got proven product-market fit, a repeatable playbook, and the revenue to support a proper sales org. Now that experience becomes valuable because there’s something concrete to scale.

When you hire for your current stage, coaching becomes possible.

You can help people develop because they’re solving problems you understand. When you hire too senior, you can’t coach them because they’re supposed to be coaching you. And if they’re not performing you’re stuck, because you don’t know if it’s them or if it’s that your stage doesn’t match their skills.

The real framework for hiring right

Stop thinking about job titles. Start thinking about what needs to happen in the next 6-12 months. Literally write it down:

• How many deals do we need to close?
• What’s our average deal size?
• How long is our sales cycle?
• Do we even know our ICP yet?
• Who’s going to make the calls/send the emails/run the demos?

If your honest answers involve a lot of uncertainty, you need someone who thrives in uncertainty. That’s rarely the person with “VP Sales” on their LinkedIn.

I always ask founders this: “Would you rather have someone who’s helped scale to £50M but hasn’t personally closed a deal in three years, or someone who closed £800K last year at a company similar to yours?”

Nine times out of ten, you want the latter. They know what good looks like at your stage because they’re actually doing it right now.

The One-to-one test

Here’s a quick test for whether you’ve hired right for your stage: Can you have a meaningful one-to-one with them about their deals?

If you’ve hired too senior, these conversations become awkward. They’re talking strategy and team structure. You’re trying to figure out why your demo conversion rate is 12%. You’re speaking different languages.

When you hire for today, one-to-ones become powerful coaching sessions. You can listen to calls together using your conversational intelligence tools. You can see they’re talking 80% of the time and help them flip that. You can spot patterns in lost deals and iterate together.

That collaborative environment where you’re both giving feedback both ways is what builds a coaching culture. I’ve done 360 reviews with salespeople where they tell me what I should stop doing, what I should do more of. That stuff helps both of us develop and grow together. But it only works when you’re operating at a similar altitude.

When things go wrong

The mistake I see most often is confusing high activity with high performance.

If you’ve hired someone who’s used to having a team, they might stay busy building things, creating process, looking productive. But if they’re not in the weeds selling, you’re not getting what you need, or what you should be paying for.

Another red flag to loo for is if they keep talking about when you have more resources or once you’ve built out the team. If your reality is that you need revenue now, not infrastructure, you’ve probably hired wrong.

The impact of getting this right is massive

When you hire people who fit your current stage, everything moves faster.

Your new hire ramps quickly because they’ve literally done this before at this scale. They can give you honest feedback on your product and messaging because they’re using it every day. They build credibility with prospects because they’re confident in the ambiguity. The companies that win are the ones that match their talent to their reality, not their ambition. Build your sales team for today. Tomorrow will sort itself out if you’re still here.

Author: Matthew Codd

I’m Matthew, I have 15 years of commercial leadership experience, helping VC-backed B2B technology companies scale revenue and transition from founder-led sales.  

I use my experience to help early-stage start-ups with GTM expertise, sales best practice, and hiring insights.  

I co-founded Cosmic Partners in 2022. We are SaaS sales recruitment specialists for VC backed B2B tech companies.