This former lawyer was scared of selling. Here’s how he closes million-dollar deals.

Good Morning. If you spend all day selling and somehow still want a side hustle, there’s an app for that. Whatnot is a live shopping platform where people sell everything from clothes to collectibles on camera. And a new article found one seafood seller who did $20,000 in a single livestream. Yes, seafood. Bought by strangers on the internet. On a livestream. Maybe it’s time to turn on the camera and try to sell that pile of stuff in your garage. Now, let’s get into today’s Follow Up. (:

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Jon Sobel was a corporate lawyer before he got into sales.

And those first few sales calls scared him. “I thought it was something you needed superpowers to do,” he told us.

A pretty inconvenient belief when you have software to sell…

Jon co-founded Sight Machine, which sells AI software to manufacturers. He found himself selling to big companies, with lots of people involved in the buying decision.

His time as a lawyer gave him something to work with, because he knew how to prepare for tough questions, think through his answers, and stick to claims he could back up.

But he still had to learn what made someone want to buy from him.

That’s when Jon and his team decided to visit 50 manufacturing facilities. 

And on those trips, they realized the factories had automated data that wasn’t connected and required a data scientist to access. 

Without this data, plant managers had to rely on gut instinct to make big decisions about running the facilities.

They kept hearing about the same problems. So they built software to help plant managers use the data their factories were already collecting.

I wanted to understand how a lawyer with no sales background got big companies to buy a brand new product. Here’s what I learned from our conversation with Jon.

Early on, a prospect asked Jon if Sight Machine could use a 3D model to test how a machine would work.

Jon said, “No, we don’t do this.”

He explained that Sight Machine uses live factory data to predict how production will run. Then he added, “Let’s work together to find someone who can.”

The company loved it, and they found a partner for the 3D model together.

When Sight Machine was small, Jon and his team showed a prospect work they’d done for the company that referred them to the prospect. They wanted to prove they could do the job.

They had permission to share it, too.

But it ended up scaring the prospect.

Seeing another company’s work made them worry about how Sight Machine would treat their own information.

I get why Jon’s team thought it would help. You’re a small company trying to win business. Showing someone what you’ve already done seems like a pretty reasonable move.

But the buyer has to picture being your customer. In this case, that meant thinking about where their own information might end up.

Unfortunately, Jon and his team lost that sale.

He learned that you need to explain what you’re allowed to share and how you decide what stays private. Having permission matters. So does making those limits clear to the person looking at the work.

On another project, Sight Machine expected to work with a customer for three years and bring in millions of dollars.

The team determined that the person within the client’s organization who was responsible for rolling out the technology to their plants was against the project.

“Instead of confronting what was happening, we just kept trying to work at it,” Jon said.

Then, the whole thing blew up: that key person kept on delaying the project.

Looking back, Jon says they should have dealt with the problem in the first month or two.

They expected that project to last three years. (And as you can guess, it didn’t…)

Today’s newsletter was written by Nic Conley & Lily Hartman