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The Biggest Mistake in Founder-Led Sales

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The Biggest Mistake in Founder-Led Sales

How Glengarry Glen Ross & Wolf of Wall Street Can Hurt Product-Market Fit

Sandy Kory
Apr 11, 2023
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The Biggest Mistake in Founder-Led Sales

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I’ve seen many SaaS founders with no sales experience become sales rainmakers. It’s a beautiful thing. It’s also extremely dangerous. It can lead to the biggest mistake I see in founder-led sales.

Of course, the awesomeness that translates into great founder-led sales does not necessarily generalize across all sales.

Are you selling shady real estate to unsuspecting retail investors? The approach evangelized by Alec Baldwin’s character in Glengarry Glen Ross might do the job.

Always be closing GIFs - Find & Share on GIPHY

Selling shady stocks? Leonardo DiCaprio’s character from Wolf of Wall Street seems a good role model.

Wolf Of Wall Street GIF - Wolf Of Wall Street GIFs

OK, you get the point. Sales best practices depend on what's being sold and to whom.

Founders realize this pretty quickly. But since they often have a distorted point of reference from pop culture of what great sales looks like, I think it can make it harder for them to recognize when they have become sales rainmakers.

What’s the big problem with a founder not appreciating their superpowers?

Actually, this can create a very serious problem. If a founder doesn’t think they are particularly good at selling, they assume their first professional sales hire will likely be more productive than them. But if the founder is actually a sales rainmaker, than inevitably their first sales hire will be less productive.

This leads to the most painful mistake I see in founder-led sales:

Not giving yourself enough credit as a sales ninja means you underestimate the challenge of hiring a sales person who can hit quota.

This founder misunderstanding means they often don’t realize that they need to invest much more in marketing and sales enablement to support a sales person who can hit a quota. Worse, the product that’s selling via founder led-sales might not be as good as the founder thinks. In other words, when the founder doesn’t realize their sales prowess, they are likely further away from PMF than they realize.

What to do? Here are some tips:

  • If you are a founder doing most of the sales and you are steadily growing revenue, there’s a good chance you are sales rainmaker.

  • So, when you bring on your first sales hire, expect lead-to-close rates and other sales productivity metrics to go down, not up.

  • Make sure you have efficient channels to bring in leads, as that’s usually the biggest gating factor on efficiency.

  • Understand that if a product has tight PMF, you will not need an amazing sales rep to close deals: the sales function will be order-taking, not rain-making.

  • If you haven’t yet completed your metamorphosis into sales ninja, read this great post on selling.

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The Biggest Mistake in Founder-Led Sales

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The Biggest Mistake in Founder-Led Sales

sandykory.substack.com
Coleman McCormick
Writes Res Extensa
Apr 12·edited Apr 12Liked by Sandy Kory

One of the factors that seems corny to point out — but out in the field is shockingly uncommon — is that salespeople that know the product they're selling *well* can explode quota (if other armaments are in place anyway, like lead volume is sufficient, etc).

Founders and sales-oriented technical people can sell by accident merely by knowing the benefits of their product and showing off all its best attributes effortlessly. I generally like the approach of "know the product, know the strengths and weaknesses (and direct attention accordingly), and tee users up to buy, versus *selling to* them.

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