EXTRA EXTRA

A newsletter about early sales from The Extra Group

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I have a friend who works in sales enablement at one of the hottest growth-stage startups around.

As a sales enablement leader, his job is, essentially, to teach sellers how to sell. What messages to use, how each product and feature works, and how to sell well.

He, and every other enablement lead out there, get the same question over and over from the c-suite: “Why aren’t more people hitting their quotas?!”

Because in every sales org, you’ve got top performers who close deal after deal every quarter. They smash quota reliably. But they’re the minority.

Even at these hot startups, at least 75% of sellers are just getting by. They're not hitting their numbers.

So what is going on? What separates the sellers that win from the rest of the crowd? And what can us early-stage folks learn from that?

My friend’s answer is weirdly simple:

Too many sellers just don’t try hard enough to be excellent at selling.

This is the consistent lament from every single one of my colleagues in revenue and enablement.

It really is that simple.

The sellers who crush are relentless in ways that most sellers aren’t:

• They consistently watch playbacks of their calls with their sales leader, hungry to improve.
• They hold themselves accountable for implementing that feedback. Each call is an opportunity to get better.
• They truly engage with the sales trainings that the enablement team creates for them, instead of going through the motions.
• Even if they’ve got a healthy flow of inbound deals coming in from marketing, they still make time to personally outbound each week. Again, insatiable for more pipeline.

This is what separates them from the majority of sellers. The majority of sellers are satisfied with good enough.

For those good-enough sellers at a growth-stage startup? I get it! Get your paycheck and slam that laptop shut!

But early-stage founders should be operating with the same hunger as a star growth-stage seller. Because you’re not here starting a company to have just-okay traction.

Just-okay traction for the product that you’ve painstakingly ideated, developed, and raised funds for? You want more than that.

Now, as my friends in enablement have repeatedly said, it does require a lot of effort to become excellent at selling. To transcend “fine” revenue numbers and reach a state of real escape velocity.

Running great sales processes – even for sellers who have been in it for years – really isn’t the standard. The convos I’ve been having with enablement leaders lately have made it super clear – if you want great numbers, it takes a great deal of learning and iterating. Week over week, call after call.

The good news is that becoming great at selling is absolutely learnable. I’ve seen it happen many times, and I’ve seen the changes that happen to pipeline and revenue accordingly.

I have two upcoming workshops that will give you tons of actionable tips to sharpen your sales skills:

If you can’t attend, feel free to sign up anyway, as you’ll get a recording link within twenty-four hours.

Once you learn these skills, it’s critical that you keep yourself accountable for deploying them. You also need to make sure every other part of your GTM motion is strong too (getting great at sales calls only does so much if you’re struggling to book any).

If you’d like support there, you can sign up for my upcoming Revenue Intensive. It’s a three-week bootcamp, starting October 26th, that gives you everything to build a more robust revenue process and reach PMF faster, and it comes with three months of support to implement it. I won't be running another one until Spring 2027. I'd love to see you there.

This is Extra Extra, a newsletter about the tactics and mindsets that drive early sales. I’m Caroline Fay, an exited social impact founder who’s spent my career launching and selling new products. I help non-traditional tech founders build sustainable, recurring revenue.

Caroline Fay

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