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Two reps. Same company. Same effort.
One closes a $50K deal.
The other closes a $100K deal.
Same hours. Same work.
One just gets paid double.
Most reps don’t think about this enough. They focus on closing deals… not maximizing them.
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SALES
Why selling bigger deals just makes sense
Take two reps at the same company with the same 10% commission.
Both spend 20 hours working on a deal from first call to close.
Rep A closes a $50K deal and makes $5K.
Rep B closes a $100K deal and makes $10K.
They gave the same effort and the same number of hours. But Reb B got double the paycheck.
This math is the single best argument for learning how to sell bigger deals. And the good news is that the bigger deal is often the better deal for your customer too.
Here’s how you can ethically sell bigger deals:
Anchor the Best Package First
On a recent deal of mine, the prospect mentioned a budget number early in discovery that I knew was going to be lower than the package they actually needed.
I just took a mental note of it. That wasn’t the time to push back on it or try to just justify a higher price.
A few calls later, when it was time to present pricing, I led with the biggest package, and didn’t have any other options on screen. All the bells and whistles, the add-ons, the freebies, every piece of value we could include was in there.
I walked them through it like it was the obvious choice, because for their use case, it was.
Then I showed the smaller package that fit their original budget. But by that point, they'd already seen everything the bigger package included, and they were anchored to it. The smaller one felt like a big downgrade.
This is the beauty of anchoring, and it's one of the most well-documented concepts in behavioral economics.
When Williams-Sonoma introduced a $429 bread maker next to their existing $275 model, sales of the $275 version nearly doubled. The expensive option reframed the cheaper one as a deal.
The same psychology works in reverse when you want the bigger package to stick. Show it first, let them sit with it, and then present the alternative.
The important part: I wasn't trying to force a bigger deal for a bigger commission check. I knew the bigger package was genuinely more valuable for what they were trying to accomplish. If the smaller one had been the right fit, I would have led with that.
Establish Value Before You Talk Price
The framing matters, but so does the timing. Gong analyzed 25,537 B2B sales calls and found that the top-performing reps consistently discuss pricing between the 40 and 49 minute mark of their calls. Average and low performers spread their pricing conversations evenly throughout the call.
The difference is that top reps spend the first 40 minutes building value. By the time they get to price, the prospect already understands what they're getting and why it matters. The number lands differently when you've already connected it to a real problem.
If you lead with price before you've established value, the prospect has nothing to anchor the number to. It just feels expensive.
But if you've spent 40 minutes showing them how this solves their actual problem, that same number feels justified.
Underselling Costs Everyone
When you sell someone the cheaper option, just because it's easier to close, you're often setting them up with something that doesn’t solve their problem or meet their expectations.
Data from SaaS churn benchmarks consistently shows that customers on higher-tier plans retain better than customers on lower-tier plans. They're more integrated, they get more value, and the switching cost is higher.
Selling the right package upfront keeps customers longer.
There's also a trust component. If your customer finds out six months later that there was a better option you didn't tell them about, that's a hard conversation.
But if you present the bigger package honestly, explain why you think it's the right fit, and let them make the call, you've done your job.
Even if they choose the smaller one, they respect that you gave them the full picture.
HEADLINES
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SOFTWARE
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That’s all for today.
Until next time,
Team B2B Whales