It's not you

Weeding out crappy sales jobs + getting your emails seen

Chris Dankowski
December 15, 2024

A client of mine we’ll call Leon has been going through it and is struggling to decide if sales is for him.

Here’s what Leon has been going through. This may sound familiar…

- Laid off due to COVID

- Hired into a new job. The manager who hired him left right after he started. His new manager was a first time manager and resorted to relentless micromanaging. He left after 9 months for something new.

- Starts a new role at a highly regarded fast growing startup. They get acquired 3 months later. The acquiring company ends up letting everyone go after 6 months.

- Decides to work at an early startup as their founding AE so he can get in on the ground floor and work his way up anddddddddd….. He gets RIF’d in 2023.

- The company he’s at now doesn’t really excite or challenge him. He’s like something different, but he’s scared.

His resume looks terrible.

It’s not his fault.

I’ve listened to his calls. He’s a great seller.

His problem is that his picker is off.

How do you develop a good job picker?

You need to understand the different sales environments at companies as it relates to how they are funded, size, and the personas they sell to.

For instance, a PE backed company is going to have a short term focus, so there’s going to be a lot of pressure to perform.

Conversely, a Bootstrapped company is committed to slow growth over the long haul, and would provide more stability. The downside would be lack of resources and advancement opportunities.

If finding the right fit is important to you, you need to develop an Ideal Employer Profile that includes funding type, size, and buyer persona.

Once you have that, you can find companies that fit that profile and begin to network your way in with confidence.

Tactical Sales Tip

More and more, email prospecting is becoming a negative-sum game.

You have to do everything possible to optimize for deliverability and visibility.

There are a million things to optimize, and subject lines are one that i'd consider low hanging fruit.

The data is pretty clear that shorter is better for subject lines.

That said, if you talk to buyers, relevance and originality is what catches their eye and gets your email seen.

A short, unique, and relevant subject line can make or break your email outreach.

There are tons of ways to approach this, and the frameworks in this video is just one.

@dankow.ski
More and more, email prospecting is becoming a negative-sum game. You have to do everything possible to optimize for deliverability and vi... See more

Feeling like Leon? Give my career strategy course a try:

Curious how we could work together?

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