dwightyouignorantsale

Account Executive

Valued Contributor

Larger deals, less wins OR more transactional, more wins?

I am an enterprise sales rep who has only sold at one company. Our sales cycles are anywhere from 6-18 months and even our best reps close 3 deals, at most, per year.

Our longer sales cycles are fantastic financially...when they close. However, I have went 8 months without closing a deal. The feeling of constantly showing up empty handed can get to you.

I'm curious what life is like in a role where you get monthly, if not weekly, wins. Does the feeling of winning outweigh the need to work way more deals for the same pay? For the reps who have done both roles - transactional and longer enterprise deals - which do you prefer and why?

Best type of deal for $$, effort, and sanity

Attached poll

6+ month cycles, higher ARR per deal, lesser wins transactional, more wins, lower ARR per deal give me any kind of deal plz

*Voting in this poll no longer yields commission.

🚀 Career Goals

☁️ Software Tech

14

28 comments

Sort by:

funcoupons

WR Officer

7

👑

I like something in the middle. Not transactional but not 12+ months. I like a 1-3 month cycle, closing a few deals per month.

dwightyouignorantsale

Politicker

1

Account Executive

That sounds pretty dreamy, not going to lie.

CuriousFox

WR Officer

4

🦊

I love the thrill and excitement of Enterprise selling. Always have.

dwightyouignorantsale

Politicker

1

Account Executive

I do too. The various complexities of each deal are equally stressful and exciting.

rubberducky

Politicker

3

SAE

Did very transactional sales (1 day to 1 month). Money was nice, but the administration sucks!

dwightyouignorantsale

Politicker

1

Account Executive

Wow I didn’t even think about that part. That in and of itself would make me want to run from transactional sales 😅

FattySnacks

Politicker

2

Senior Account Executive

I would do unspeakable things to close a fucking deal right now…

dwightyouignorantsale

Politicker

0

Account Executive

you and me both

hh456

Celebrated Contributor

1

sales

We get about one deal a month, sometimes they fall in but our cycles are really long too. But with how contracting works it just generally lands that way.

I'd honestly take anything I can get. If I can get five in a month, great, if I get one, great. Keep showing up, that's the key to success.

dwightyouignorantsale

Politicker

0

Account Executive

Keep showin up is all we control!

chubbspeterson

Politicker

1

Business Development

I'm full cycle, which I like because it's best of both worlds. You get the daily little wins of setting meetings, and then the bigger more meaningful ones when I actually close, which is typically 2 - 8 months from the first meeting.

dwightyouignorantsale

Politicker

1

Account Executive

Nice. I’m assuming you do some sort of SDR/AE combined role? How do you focus on prospecting vs working later stage opps?

chubbspeterson

Politicker

1

Business Development

Exactly, and it took a while for me to find the balance, mainly carving out time to make cold calls, but now I've got a pretty solid routine down, and having the balance between the two breaks up the day nicely.

chubbspeterson

Politicker

0

Business Development

fucking great user name by the way haha

dwightyouignorantsale

Politicker

1

Account Executive

thank you thank you. one can never go wrong with The Office quotes

CaneWolf

Politicker

1

Call me what you want, just sign the damn contract

I have a $2.8M beast right now. I would really like that to close.

Unclemo

1

Enterprise Account Executive

Smaller deals typically come with micro-management on daily activity with lots of pressure and you will always have to be thinking 3 months out. Longer Deals deals are annoying at times. This is where you have to appreciate the mini wins (I.e. legal finished redlines, RFP submitted, moved to next round of RFP, etc.) Outside of closing longer sales cycles are extremely valuable if you are building close relationships with your contacts. If they leave or if you leave that’s another potential opportunity to close a large deal at a different company. Rambling here took a 5 hour energy but hope this helps.

dwightyouignorantsale

Politicker

0

Account Executive

This is a very good and way undervalued point. I, and I’m sure along with many other enterprise reps, definitely need to focus less on that last, big close and celebrate more of the little closes, like the items you mentioned. Very good outlook.

Trynblegendary

Executive

0

Enterprise Account Executive

You’re right. A lot of micromanaging with the smaller deals, keeps you active but sucks when you’re striking out. Nothing more intense than you and legal reviewing a GSA for the 797th time working the long enterprise deals.

Upper_Class_SaaS

Politicker

0

Account Executive

This is also up to your descretion. Depends on what the % is you are getting paid out on

dwightyouignorantsale

Politicker

0

Account Executive

Financially, my current role and deal structure is great. It definitely gets tough on mental health though when it’s been 6 plus months without a win. Sometimes I wonder if getting paid less per deal, but closing more deals, would help my overall outlook on work.

CaneWolf

Politicker

0

Call me what you want, just sign the damn contract

I'm going to teach a class on less vs fewer for the WR.

dwightyouignorantsale

Politicker

1

Account Executive

one day I’ll learn to have decent grammar…. one day

CaneWolf

Politicker

0

Call me what you want, just sign the damn contract

Let me assure you that you are far from the only offender in this community.

DungeonsNDemos

Big Shot

0

Rolling 20's all day

Quite the mix so far. I think having the transactional ones in-between larger enterprise sales will help keep your winning spirits up, but obviously they pay much less.

OldDogNewTricks

Opinionated

0

Sales guy

I've done transactional sales, where the guns will close a deal every 1-2 days... mid market deals with a 2 week-3 month sales cycle... and enterprise 3-12 month sales cycle

I like mid market personally as you're closing high 5 and into 6-figure deals (that pay well), regularly enough that you feel that grit, that edge of confidently closing.

dwightyouignorantsale

Politicker

1

Account Executive

I was formerly mid-market and really enjoyed the companies I worked with. It was somewhat of a tough sell though because my company’s product is very tailored towards enterprise and we didn’t necessarily have a MM product until recently. It is a great spot to be though.

mitts2

Politicker

0

Account Executive

I'm in a nice middle ground where most of my book is lower ACV (compared to other reps in my company) but I close more deals and more quickly (1 - 3 months). Pretty standard SMB / Commercial stuff. The frequent satisfaction / more consistent commish is nice.

That said, I've had a few diamonds in the rough where the deal ends up being huge ACV and takes longer (6-8 months). There is no feeling that compares to closing a whale. Full body chills, butterflies in your stomach. Its fucking awesome.

I'm trying to move up a level next year so. Ican get more of the latter. Carrying a bigger number is more stressful but damn does it feel good to close something big.

Bravado is a community of trusted sales professionals endorsed by their customers.

Products

The War Room Jobs Salary Guide Tech Sales U

Company

About Us How It Works Blog Bug Bounty

Contact

© 2024 Bravado Inc. All rights reserved.

Privacy Policy Legal and Privacy Center Sales Jobs

If you are hired as a contract sales rep by a Bravado customer, we may ask you to prove access to the employee email account provided to you by that customer. This data will be shared with customers to track your sales productivity; customers can use this data to confirm you meet the minimum activity requirements to pay out your ramp stipend and commission.