Good Morning and happy almost-long-weekend. Labor Day weekend is coming up, which means about half of America will be checked out by 2 PM tommorow. Heads up, there won’t be a Follow Up on Tuesday because I’m getting married this weekend. Apparently, that takes priority over writing a B2B sales newsletter. We’ll be back next Thursday, freshly married and ready to serve up the internet’s best B2B sales sauce. Now, let’s get into today’s Follow Up. (:

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In 2014, three college students started Handshake to help other students find jobs.

Over the next decade, they built a network of 18 million students and alumni across 1,500 universities.

That business was solid. But it wasn’t a rocket ship.

Then AI labs started looking for educated people to review data, test models, and correct their answers.

Handshake already had 3 million graduate-level workers, including more than 500,000 PhDs. So it turned that network into Handshake AI.

Their CEO, Garrett Lord, said the new business hit $50 million in revenue in four months and is on track for $100 million in its first year.

Some people would call that luck. And they would be right.

But Handshake has spent ten years getting ready to be lucky.

Sometimes you just have to stick around long enough to get “lucky.” And that’s how a lot of sales careers work.

So today, we’re breaking down what happens when you stay in one industry and let your career compound.

Compounding happens when every return gets added to the original investment. Future returns are earned on the larger total.

At first, the difference looks tiny. When you give it enough time, the gap gets ridiculous.

Sales careers compound in a similar way.

The knowledge you gain this year makes next year’s lessons easier to understand.

Things like a customer introducing you to another. Or a former teammate bringing you into their next company.

Eventually, your experience starts producing opportunities that effort alone can never create.

4 assets in your career will drive most of those returns…

Every new job comes with a reset. There’s no way around it.

You have to learn a new product, new systems, new coworkers, and everyone’s favorite… new internal politics. You also lose the trust you built inside your old company.

But some parts of your career will travel with you.

Let’s take a cybersecurity rep as an example. If they join another cybersecurity company, they need to learn a new product.

But they already know the buyers, competitors, common threats, and how companies buy security tools. They may even know people they can call on day one.

The bigger reset happens when you change companies, industries, and deal types all at once.

From the example above, if that same cybersecurity rep joins a new company selling software to real estate agents, they’ve got to learn a lot of things from scratch.

I think this is part of what the job-hopping debate misses. Hiring managers want to see that you stayed at one company for 3-5 years (which is a good metric).

But they should also ask whether each move you made built on your experience or made you start over.

Andy Kofoid is the president of global field operations at Databricks. He recently wrote that short stays are a red flag when he hires people.

He likes to see people stay at a company for 4 to 5+ years.

One short job is fine, but a long list of short jobs is not.

Hiring a sales rep takes time and money. The company has to train you and wait for you to build a pipeline. So your manager wants to know you will stay long enough to see a return on their investment in you.

But there are also good reasons to leave after one year. Like an impossibly bad territory, a weak product, a terrible manager, or a layoff that you have no control over.

Good hiring managers understand that. And it’s easy to explain a short stay when you also have a longer stay on your resume.

There’s one thing pretty much every sales leader agrees on: You should not spend 5 years trapped in a bad job just to make your LinkedIn profile look good.

Staying has an opportunity cost too. Like accepting below-market pay, or selling a weak product, or waiting for a promotion that will never come.

But when you stick around a company or industry long enough, your odds of getting lucky are better.

Back to the example of Handshake from the beginning… they spent a decade building a network before the AI boom made that network wildly more valuable.

You can’t plan for luck, but you can stack your odds of getting lucky.

Check out The Follow Up Guy on LinkedIn.