The 6 magic questions

If you're in sales, there are 6 questions you need to have answers to in order to have a failure proof career strategy…

1. What is the perfect sized company for me to work at?

2. What sales role is the best fit for what I enjoy and excel at?

3. How long should it take you to get that role?

4. How is my ideal employer funded?

5. What segment is the best for me to sell to?

6. 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 something in terms like these…

“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, or publicly traded companies

• Selling to HR, Marketing, Sales, IT/Security, Finance/Accounting, B2C, or Legal

• Selling to Consumers, SMB, MM, Enterprise, or 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.

A lot of coaching clients who come to me because they keep picking the wrong companies, and their resumes make them look like job hoppers, are unable to define their career mission with this granularity and it's what's driving that turbulence.

It turns out that I’ve been following Scott Leese on Linkedin for over 11 years which is nuts!

He thinks so, too!

Was great to finally speak with him and talk about finding your niche in sales, and saying fuck it to the default BDR to AE to Enterprise AE to Manager career path that we tend to default to.