What are the pros/cons of moving upmarket?

I've been an SMB/MM AE for the past 2.5 years and am exploring moving to more of an Enterprise role. I'm familiar with the longer sales cycle, etc. but would love to hear your experiences/pros/cons on the move.

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MMMGood

Celebrated Contributor

Senior Account Executive

Pros:
-Higher OTE/More income potential
-Bigger deals = greater glory landing needle movers for the company
-Advancing your career path
-Greater networking within Fortune 500 accounts

Cons:
-Higher quota
-Bigger deals = more riding on them, individually and for the company
-Greater scrutiny from leadership
-Higher stress
-Longer and more complex sales cycles

I say go for it.

CaneWolf

Politicker

Call me what you want, just sign the damn contract

Great list here. I'd also add as a con that you're probably going to notice how much more difficult prospecting becomes. It takes longer, it's harder to identify the decision makers, relationships matter way more, etc. It's absolutely worth making the move.

MMMGood

Celebrated Contributor

Senior Account Executive

Agreed. Org charts are much more complicated, and many times fluid.

Savagedoge

Tycoon

Account Executive

I’m all hears on the answers here too👂

wHaTyAgOtCoOkInG

Catalyst

Solution Consultant

Look at the manager of the enterprise team. Are they supportive and nurturing? Will they coach you on deal strategy? If so, do it, in the long run the highest earners in our space are enterprise. If the manager of that team is no good, be patient until they either have someone who is or you get head hunted. One thing I look for at enterprise; is the Enterprise leader the lowest earner on their team? If they are, you are in good hands. All the enterprise reps should be out earning their manager.

CuriousFox

WR Officer

🦊

So there's more scrutiny, red tape, and legal involved in Enterprise deals. The cycles run long, and the internal processes feel like they hold you back.

But once you get that commish check... 😏

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KlosingTime

What are the pros/cons of moving upmarket?

6 comments

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