The one size fits all sales career hoax

A case for NOT promoting into enterprise sales

Chris Dankowski
November 01, 2024

Just told a friend to leave enterprise sales and move down to SMB, and it was 100% the right thing to do.

Giphy

He's been in enterprise for 6 months, and here's what he's told me about it...

it's sooooo tedious
everyone is overcomplicating everything
I have sooooo many BS meetings for pipeline reviews, commit calls, account planning

His old manager approached him with an offer to come back to work for him and keep his enterprise base salary.

He wanted my input.

I told him it's a no-brainer for him.

He gets to make great money, doing something he loves.

There's this thing in SaaS sales that we need to move away from.

This idea that enterprise sales is the be all end all indicator of success and aptitude.

Chasing that, and trying to conform to that model is making a lot of people miserable in their careers.

Be true to yourself!

Get real about what excites you and what feels right, and then pursue those things with an energized passion.

The money will come.

I’ve been hard at work on a career strategy course specifically for sales reps, and one of the exercises is to granularly and clearly define the exact job that you aspire to promote into within the next 5 years.

The output looks like this:

It says: “In 5 years, my goal is to be a Mid-Market Sales Executive at a Large PE backed company selling Marketing software”.

The more specific you can be in regards to segment, role, company size, company funding type, and the persona you wish to sell to, the greater your chances of finding a perfect fit sales job.

Lilhelper Perfect Fit GIF by Lil Helper Cloth Diapers

Gif by LilHelper on Giphy

Tactical Sales Tip for November

You’ve got to get ahead of “Let’s circle back after the holidays” season NOW… like right now!

You need to have a call with the Champion on all your open Opps to map out who from the buying team is going out on PTO, when they’re going to be out, and what they need to get done before leaving to ensure them being gone doesn’t stall the deal.

What you’re going to find is that they have a lot less time to work through their evaluation and procurement than expected.

You’re going to create urgency, and you’re going to do it in a way that’s organic and not pushy.

I have the entire play mapped out for you in a previous post.

Have a great November!

Go vote if you haven’t already!

The one size fits all sales career hoax

Subscribe to keep reading

Reply

Keep Reading