The War Room

How long did it take for you to go from mid-market to enterprise sales?

I've been with my company for around 2.5 years selling in the mid-market space. Average deal size is around $90k ARR - my largest deals have been with publicly traded organizations topping out at around $200k ARR. OTE is $180k and I did around $210k last year. I'm really eager in taking that next step into the ENT space but they've only promoted one MM rep to ENT thus far and seem to be hiring only externally for other ENT positions - to make matters worst, those that are coming in are coming in from other MM roles.

For those of you that have successfully made the pivot from MM to ENT sales, how long did it take for you to do that?

What were the deal sizes you working in MM compared to what you are working on in ENT today?

How does your OTE compare in ENT today vs your previous MM roles?

When you made the pivot from MM to ENT, was it with the same organization or did you have to look else where to break into ENT?

Also, would love to hear from any MM sellers that have strategically chosen to stay in MM vs moving up to MM.

P.S this is my first post here so I hope I'm doing this right.

๐ŸŽˆ Mentorship
โ˜๏ธ Software Tech
Notable Contributor
Director Sales and Market Development
Hey, good post and yeah you did it fine. Lot of questions though so let me try and answer them.ย 

I think as a top producer in MM you need to tell your manager your plan, get a meeting with Director/VP of enterprise and get on their radar. Their answer will give you yours to stay or look elsewhere.ย 

OTE will add $25k base and probably $50k Commish, but remember less deals will close in Ent vs MM so you may be living off base for a quarter or 2 then pay for a semester of kids college the next quarter. Harder to budget but super fun when that check hits

Should take 2 years (maybe less depending on team size and company size, we have 30 sales reps and 15 Ent 15 MM)

I was able to move up in same company but followed my above advice, put myself on radar and they watched me perform the next year and signed me
WR Officer
Senior Account Executive
Have you had the conversation with your manager? Discuss your plan, passion, and next steps to get there?

Also have you looked at openings at other companies?
Enterprise Sales for Hackers
Mid Market vs. Enterprise Prospecting
SMB to mid market prospecting