justsomegirl

Senior AE

Acclaimed Answer

Valued Contributor

I hate Enterprise sales

Why does it seem like every sales rep aspires to become an Enterprise rep? 🤔

Like it's the holy grail or something.

I used to think the same thing... Gotta get promoted to Enterprise rep. Gotta get that prestige. Gotta get that bread. 💰

Then I did. And I HATED IT!

The sales cycle is SO freaking long! I don't want to have to keep you & nineteen other people in your company engaged for two years. None of you are going to remember the conversations we already had .... how are we going to handle your unique use-case? The same way we talked about doing it TEN other times in the past two years, Cheryl. 🙄

Don't get me wrong - I hate transactional sales even more! I realize we just barely met & you don't know anything about me, my company or my product - but I need you to buy this thing from me. Right. Now.

For me, my ideal sales cycle is 30-45 days. Long enough to build a relationship with the prospect & ensure they will get value out of my product ... but not so long that our menses have synced up.

What's your ideal cycle?

👑 Sales Strategy

31

44 comments

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CoorsKing

WR Officer

18

Retired King of the Coors Knights

Personally, I am the opposite. I like the grind of Ent sales, it is like a chess match. I enjoy navigating the account and slowly building a compelling case and grooming champions.

But to your point, I know plenty of people that enjoy shorter, more transactional cycles.

Beauty of Sales, is you can do what you like the best! And make killer money in any segment if you do well.

CuriousFox

WR Officer

5

🦊

They play checkers while we play chess 💯

CoorsKing

WR Officer

10

Retired King of the Coors Knights

I like to think I play chess, but sometimes it feels like all I can do is connect four lol.

Salespreuner

Big Shot

0

Regional Sales Director

TRUE THAT!

Rallier

Politicker

5

SDR Manager and Consultant

I was just thinking about this today. And I think I've realized it's only the goal because you can make significantly more money. I absolutely hate the red tape, the boring corporate people, legal, and all the other nonsense that comes with multiple stakeholders.

saygrace

Valued Contributor

0

Sales Executive

Sounds like a headache

RandyMoss

Politicker

1

Account Executive

It is, but when you get a PO for a deal that you've been meticulously working for two years...MAN that rush feels good

CaneWolf

Politicker

5

Call me what you want, just sign the damn contract

We all go after the Enterprise crown early because that's how we're wired as salespeople. We see the shiny crown of Enterprise sales in our early days and are like "oh, that's gonna be me." I did the same thing. It's to each their own.

@Rallier - To your point about money, I think it probably balances out in the long run unless you just pop off every year in ENT (unlikely). If you're killing it in mid-market and making 1.5x-3x OTE, I gotta imagine you'll make the same as an ENT rep who has really good and really bad years.

I prefer the mix of both personally. Give me a whale but also some quicker wins with companies I can get to know a bit more.

dealdaddy87

1

CEO & Founder

This. In my experience you can find both in Enterprise (depending on the product of course).

You'll ideally have 1-2 whales you're building for the longer term but then a handful than can move in anything from 2-6 months.

funcoupons

WR Officer

4

👑

I prefer mid market. A sales cycle of 2-3 months is my ideal.

RedHotCheetos

Good Citizen

3

Business Development Representative

I feel you. Personally for me, Mid-Market is better. Less stakeholders, smaller sales cycle, and there’s usually a *ton* more prospects to go after. This all depends on industry of course.

Chep

WR Officer

3

Bitcoin Adoption Specialist

Yea enterprise is a grind

Maximas

Tycoon

1

Senior Sales Executive

Certainly it is.

CuriousFox

WR Officer

3

🦊

I love it. The long game. The strategy. The quick cunning decisions. The adrenaline rush when you WIN. 🦊

Broncosfan

Politicker

2

Account Manager

I will never be good enough for enterprise sales and I’m 100% ok with that. I much prefer short sales cycle but the correct answer to your question of why people like Enterprise sales is money.

Salespreuner

Big Shot

0

Regional Sales Director

Money, network and indeed getting used to long game ✅

0

Enterprise Account Executive

don't put yourself down. It's not you won't be good enough, it is a different skill set and mind set. You prefer shorter sales cycles.

SADNES5

Politicker

1

down voters are marketing spies

I run in the 2-4+ year cycle. I do miss the easy "quick wins". But there is something so satisfying of aligning the stars and getting the signatures done is the BIGGEST rush.

It's a long game, but then again, Business Development is... just that. Create, Capture, Grow, Enhance.

Abydocomist86

1

Client Manager

I like the longer cycle, if (and this is a big if) the company I work for is realistic about their sales cycle and properly aligns it with the companies that are a good fit for their product. I think the biggest problem in sales today is that misalignment

Lumbergh

Politicker

0

Sr Account Exec

100%. Aka management that expects 6 month sales cycles and million dollar deals

0

Enterprise Account Executive

Completely agree. Huge disconnect between market reality of the sales cycle and highly unrealistic expectations by the company. Add in Marketing that doesn't understand the needs of the AE to make things even harder.

MsTech

Executive

1

Business Development Executive

I love enterprise sales. It's a chance to learn a lot about a company, their development, and uncover opportunities. The way to navigate through that without getting too frustrated, is to be in a position of offering multiple products/services for the different areas of need. If all you have is 1 card, the odds are not in your favor.

Wolfof7thStreet

Valued Contributor

1

AE

Just curious, is the pay ceiling higher for Enterprise than SMB/ MM at your company? I feel like this is a lot of rep's motivation to drive for enterprise

Blue_Turtle

Opinionated

0

sdr

Enterprise pay ceiling is usually the highest at most companies.

TheJoker

Fire Starter

1

VP of Sales

I lead and get messy as a player-coach in Enterprise, Telco, and Government sales with sales cycles of 9 months to 2 years. I prefer to be a conductor of an orchestra filled with rare talent rather than a soloist. I made that choice for me, but everyone needs to their own way. Leading a deal-specific virtual team to success in a complex account is my gold. Still, I have seen strategic sales guys / lone wolves kill it up and down and all around. I love green too, so mammoth hunting became my thing - still, rabbit hunting keeps me fed while on the hunt. Do what you love.

(Couldn't get any more analogies in there!)

Willygggg

Good Citizen

1

Founder

I’m enterprise. Not because I’m great at sales. Probably the reverse. I was never a natural. I’m not pushy. And I want to know people. I’m enterprise because if I had to sell fidget spinners id get fired. Anyone else feel this way?

paddy

WR Officer

1

Director of Business Development

Ideal cycles are about 1-2 months. I used to sell to large media/entertainment conglomerates and navigating those was like running through a mine field. Not ideal for me.

Trinity

WR Officer

0

BusDev

I actually enjoy enterprise sales. I don't enjoy SMB and never had experience selling into mid-market (though I heard it's harder).

saygrace

Valued Contributor

0

Sales Executive

Great perspective here.

sktech

Executive

0

Sales Advisor

The SLED space is very similar but typically with a lower contract value compared to Enterprise.

Sokeen22

0

Client Partner - Digital

This is an interesting post and I think about this a lot. I’ve sold very transactional products and hated it. But now I’ve made a jump to strategic ent accounts and the long transformational sale is stressing me out a lot more than those quick 10k deals.

MRRforBreakfast

0

Account Exec

Problem is, Ent is where the nice unicorn deals happen where a rep makes $100k+ off one deal and then everyone chases the dream.

For me, MM is the balance of working on nice chunky deals that don't take a year of my life to close but also some nice short cycle deals that close quickly and build momentum

Lumbergh

Politicker

0

Sr Account Exec

Hear, hear. And the management team starts judging you like some 7 figure deal is gonna come out of the first deal too...midmarket is a good sweet spot as they have money but not a total shit purchasing process and they move faster than a glacier. Worst thing about enterprise is losing your champion 12 months into a cycle and having to start all over again. Of course that’s no excuse for not closing the deal!

0

Enterprise Account Executive

or when the CIO leaves mid-purchase process and the new CIO wants to start from the beginning. I ended up closing that deal but took a lot of work with the new CIO, heavily backed up by my champion and technical champion.

LostAngeleno33

Old School Bravo

0

VP Sales

Never enjoyed SMB as much, like the strategy and big win with enterprise sales. And haven't worked a full Friday in a decade.

Bensonwade

Good Citizen

0

Enterprise Account Executive

If something takes 9 months to a year to purchase, that means it is critical and strategic to the company. Needing many people to get involved means it is touching many parts of the organization. It isn't just about the sale, it involves validation, integration, migration and successfully bringing into production.

You truly get the opportunity to make a meaningful impact on your customers. They are equally invested in making the partnership successful. Also, land and expand. Once you break-in, there is a license to hunt AND you have one of the best references possible, another division.

Ent sales is essentially a project manager that helps the company buy and implement something they otherwise would have a challenge to figure out without your guidance.

nomdeguerre

Executive

0

Account executive

Probably because it pays better. Friend of mine is in mid-market and crushing it, but his base sucks and they don't pay him enough in comms... he is closing way more logos than I do but I still outearn by a mile.

Allisce

Tycoon

0

Account Executive

This is why I have resisted a move to Mid Market after years at the top of the board. I don't want to close a couple deals a year. I love the pace where I am just wish it paid better and the company placed more value in int

Rigeyyy

Opinionated

0

Account Executive

Haha it’s all about the recognition people love to move to the totem pool even if it didn’t make Sense

sketchysales

Politicker

0

Sales Manager

I feel you if you are just getting started in that area of sales but when you have established yourself and have several deals running through, you are always closing deals. It just takes time to begin with where it feels like the cycle is taking forever.

The biggest rewards are in this area of sales.

JuicyKlay

Celebrated Contributor

0

AM

yeah you're right, enterprise is way overrated.

JoshtheOps

Contributor

0

Sales Intelligence Manager

It's all fun and games until your champion gets fired :(

Machine

Politicker

0

Enterprise AE

Fair points. I enjoy a healthy mix. Give me 5-10 whale accounts to work on strategically for 1-2 years and grow while bringing in 10-20 deals during the year at a quicker pace.

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