Why you're bummed out with your career

How to change that + A hack to get job interviews NOW

Chris Dankowski
January 19, 2025

You need to be able to answer these 6 questions in order to have a solid career strategy…

What is the perfect sized company for me to work at?
What sales role is the best fit for what I enjoy and excel at?
How long should it take you to get that role?
How is my ideal employer funded?
What segment is the best for me to sell to?
Who is the ideal persona for me to sell to?

Knowing where you align to each of these 5 points will give you the ability to define your career strategy in terms like this…

“In 5 years I will be the VP of Enterprise Sales at a mid-sized PE backed sales engagement software company focussed on selling to leaders in sales and sales ops.”

Or this…

“I will be a Mid-Market AE at a large publicly traded martech company that sells to CMOs and VPs of Marketing within the next 5 years.”

To do this, you have to understand the pros/cons between all of the following…

Selling at a small, mid, or large sized company
Selling at VC backed, PE backed, bootstrapped, and publicly traded companies
Selling to HR, Marketing, Sales, IT/Security, Finance/Accounting, B2C, and Legal
Selling to Consumers, SMB, MM, Enterprise, and Strategic
Being a BDR vs. AE vs. CSM/AM vs. Manager vs. Director vs. VP/CRO vs. Retention/Renewal Rep

Knowing all of this will give you clear direction in your career, and will enable you to be able to define the “why” behind your career strategy.

There are a couple of ways to gain the knowledge necessary for this exercise:

real world experience
research online
ChatGPT
my “Elevate Your Sales Career” course

You have to do things differently to get a sales job in 2025.

Recruiters are getting too many applicants.

Initial screening is by AI and looks for a matrix of very specific keywords and experience.

Then the recruiter hand selected from a big stack who they're going to talk to.

Your chances suck!

Still get that referral in from a current rep, but follow that up with a connection request to the VP of Sales and all the other sales leaders there.

Spend a week or so interacting with their content, and then start calling and emailing.

Give them a taste of your prospecting chops.

I promise you that the majority of sales leaders will love it and will talk to you.

Why you're bummed out with your career

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