I tried to sell software to an AI simulator. I wound up crushing my quota and getting promoted! My biggest lesson: you can’t sell to every buyer the same way.
Every day, I’m evaluating founders’ sales skills. The founder is the first salesman for the startup.
If they’re good at it, the company can scale fast. If not, the company will struggle.
But there’s one little problem: I’ve never actually done sales myself. So when Jason Lemkin from SaaStr launched Vaporsell.ai, I had to try it!
Here are three buyers I sold to and what I learned…
John: The Busy Buyer
“Give me your value prop in 30 seconds.”
John is on his way to the airport and doesn’t have much time. He wants me to get straight to the point.
Some might consider John rude. But I live in the NYC area, so I’m used to people being blunt.
I actually sold to John pretty successfully. I just had to keep my responses short and specific.
When a response required more time, I offered to send more detailed information to his email. In the end, I was able to close a large contract.
I actually like buyers like John. Getting to the point makes things easier for both of us.
But John wasn’t my favorite customer. No, that’s Gavin…
Gavin: The Gullible Buyer
“That’s amazing! What else can this software do?”
Gavin is like a breath of fresh air. He’s already really excited about the product.
It would be hard to screw this sale up. Everything I say, Gavin likes.
If you have PMF/market pull, you’ll meet a lot of Gavins. You’ll be the leader in your area and people will be predisposed to buy.
What worked for me here was to not overthink it.
Gavin wants the product. Just give quick and cheery answers to his questions, and soon he’ll be signing on the dotted line.
I wish they were all Gavins! But then where’s the challenge, right?
Speaking of challenge, it’s time we meet Sarah.
Sarah: My Most Hated Buyer
“I don’t buy software from amateurs.”
I was feeling pretty good about my sales skills. Then I met Sarah.
Sarah is a VP at a major startup. Her deal could have put me way over my quota. I needed this!
But Sarah is the buyer from hell. She’s prickly, rude, and super technical.
Even though she was fake, I could feel my cortisol rising.
I would try to answer her questions, but she would always say my answer wasn’t specific enough. My technical sophistication simply didn’t match hers.
Try as I might, I was never able to sell to Sarah. She actually called me an “amateur” and hung up.
I’m glad I never have to speak to this jerk again!
But Sarah taught me something useful. I don’t need every single buyer.
I never sold her a dime’s worth of software, but I still crushed my quota. Take that, Sarah!
Wrap-Up
Using Vaporsell gave me new empathy for anyone in sales. Selling is friggin’ hard.
My biggest takeaway: you can’t sell to every buyer the same way.
Some buyers, like John, want a quick rundown. Others, like Sarah, want you to go deep.
In the end, the main thing that helped me was practice.
This makes me want to prioritize founders that have experience in sales. They’ll be better at closing customers and at fundraising, too!
Try Vaporsell and improve your sales skills. It’s better to lose a fake deal than a real one!
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