Backstory: I built and tried to sell what the competition built. My customers didn't care.
Mistake #9: I tried to upsell fancy features.
We watched the competition.
They shipped a feature, we shipped it too.
To stay relevant, I thought…
Then we went to our customers: "We built a new thing. Want to buy it?"
It sounded good on paper.
It wasn't right for their use case or their business.
So they said no. Or worse, nothing.
I believed upselling meant selling more.
What it produced:
Good: We looked relevant next to the competition.
Bad: Every "new thing" call made the next call feel like a pitch.
Bad: Had no proof it will help them. Did not sell.
Bad: Made us look the same as the competition.
Here's what I missed:
You don't upsell. You diagnose and recommend.
And you have to earn the right to recommend.
Upselling is push. You built a feature, now you go find someone to sell it to.
Recommending is pull. The customer has a number that isn't moving, and the right feature finds him.
Same product. Opposite direction.
Selling from service means the sale is an act of helping.
You focus on what the buyer needs, not on your quota.
You sell a promise and trust, not a thing.
You diagnose before you recommend.
And sometimes the recommendation is "don't buy this."
That's what makes the next recommendation believable.
Solution: We only recommended what the data proved worked, when they needed it.
Example: SMS notifications.
They got opened. They got read. And lost and stolen packages went down.
So when a customer's problem was delivery issues, that's what we recommended. Not a cool feature. A number.
Every feature we presented had to pass two questions:
Is it appropriate for their needs, not just their use case?
Will it improve KPI x, y, z?
Timing mattered as much as the feature.
If it changed their operations, they needed time to train their team and test if it works in their workflow. So it came with a testing and implementation plan.
Right functionality, right time. That combo was everything.
Why this works:
Expansion sales = No lead cost. No long sales cycle. No competitor in the room.
Just a customer who already trusts the data you're showing him.
When we needed to hit quota, we didn't chase new logos.
We upsold what existing customers actually needed, when they needed it.
After EasyPost acquired the company, WeSupply became part of the expansion sale strategy to their existing clients.
Same strategy.
We knew who to help and how, positioned it correctly, and sold it where it fit.
A great vertical was healthcare, where they needed shipment and delivery tracking for their certifications and compliance.
WeSupply grew exponentially post-acquisition on this strategy.
The results:
Expansion became our biggest revenue driver
Quota got hit on the accounts we already had
Customers bought what we recommended, because it came with a number
How to replicate it:
Understand the customer and their needs, not just their use case
Tie the upsell to a quantifiable success KPI. Nobody buys a cool feature that doesn't move a number.
Get the timing right. If it changes their operations, bring a testing and implementation plan.
Come from service. Recommend what helps. Say no when it doesn't fit.
You're done when every recommendation you make names the KPI it moves and the date it lands.
He recommends what the data already proved, and the number carries the authority.
That's a system, not luck.
Secret Sauce: Don't upsell. Recommend what the data proves, when they need it.
Sell from service.
Best,
Virgil
PS: Mistake #10: I thought I was the only one who could sell it.