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Enterprise sale that takes too long to close VS Several small fast closing deals?

Which one would you go for?
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*Voting in this poll no longer yields commission.
๐Ÿฐ War Stories
๐Ÿ‘‘ Sales Strategy
8
CuriousFox
WR Officer
+11
Needer of Life Alert
In a perfect world you'd be able to sprinkle in a few fast small deals while you work on the Enterprise whales.ย 
Ace
Arsonist
+9
CEO
This would be ideal
JuicyKlay
Politicker
+9
AM
If only we all had managers who would let us do this!ย 
User1234567
Politicker
+5
User1234567
This would be amazingย 
ARRisLife
Politicker
+3
Account Executive
I work at an org where we have a good mix, I could be working a decent size 6 figure deal which equates to a quarterly number as well as some quarters I get there from a handful of smaller deals.

I think balancing both is best- I get really anxious if my quarter is riding on one deal, so I work everydeal like its worth everything to me. (because it really is)

The glory and credit from the big deals is pretty great though.
Ace
Arsonist
+9
CEO
That makes sense. Some people talk about focus. You know kinda where you keep your focus on 1 deal and see the end through it and not diversify because if it's taking the same effort then why not close a big deal.

But I agree your point. I think that balance is the key too
ARRisLife
Politicker
+3
Account Executive
Probably depends on the situation; but from my experience you *should* be able to balance a few balls in the air... even some of my more demanding larger deals, there's time when you've done your steps and theres time for other deals so while I agree you shouldnt be stretching yourself too thin and making a large deal suffer you should be able to swing a bit of both!
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User1234567
Politicker
+5
User1234567
this sounds great - good pointsย 
ZebraStripe
Opinionated
+1
Sr Sales Director
As someone who is now working in a pure enterprise sale that takes forever, the healthy mix is where you want to be.ย  My last role was more the small fast closing, and that wasn't viable either.ย  Like @CuriousFoxย said, getting those small fast closers to take you through to the next big win is the holy grail.ย  Right now I'm really struggling with motivation on deals that aren't moving at all and have no end in sight.
JuicyKlay
Politicker
+9
AM
Agreed especially when youโ€™re starting an enterprise role with no preexisting pipeline and 12-18 month cycles.ย 
HarryCaray
Notable Contributor
+14
Regional VP
Feel like this poll might be a little biased haha.ย  "takes too long to close"
Ace
Arsonist
+9
CEO
How fast was your closing of a big enterprise sales? Just curious.ย 
beerisforclosers
Politicker
+8
Account Manager
I'm a notorious whale chaser, what can I say... But I do my best to keep the small sales moving just in case.
Ace
Arsonist
+9
CEO
Has one affected the other in any way ?
poweredbycaffeine
Politicker
+7
Bean Juice Drinker | Sales Savant
My org has a well-defined ICP, but as we move upmarket we are starting to see larger deals. What we found was that the larger deals often move at a higher rate of velocity than our ICP deals because they have a budget, a clear buying process, and have likely defined a scope/need far before engaging with us. That said, our reps stay focused on a good mix of both because your incremental growth comes from smaller deals while bigger deals validate upmarket strategy and are not meant as the meat of our pipeline.
Ace
Arsonist
+9
CEO
That's great to know. A lot of orgs don't have the ICP defined and that really messes a lot of things up
PhlipOut
Politicker
+6
Account Executive
I didn't vote as I've done both. the huge and slow Enterprise deals (7 figs, 18 month cycles) which are great if/when they come in. but can be a bit boring day to day if you have a small territory.

so I went to my current job which is a lot faster although i think too much. Chasing tiny deals day in and day out is not amazing at this stage, and distracts from longer term whales (distracts management that is)

pros and cons, but as someone once said.. it's important to figure out if you're a sprinter or a marathon runner. Do what excites you! you can get paid at both
ZebraStripe
Opinionated
+1
Sr Sales Director
Really curious on your thoughts on staying motivated (and busy) when you are purely chasing enterprise.ย  I don't have a 'small' territory, it's LA, but the target clientele are very large, and we already have business with a lot of the other major players.ย  There are only so many emails I can send to the same decision makers at the same 10 companies.
PhlipOut
Politicker
+6
Account Executive
Same I had maybe 12 accounts and limited roles within them to sell to.

It's hard. Need to focus on the bigger picture and step away from measuring success in small increments.ย 

You can still drive awareness within multiple contacts. Do more custom work which requires reading annual reports, Google alerts etc..

Good luck!
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km
nr
+53
kmelnichenka , ย  Broncosfan , ย  nreskin ย  and 53 people voted
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