What size company would you rather work for? Why?

Still new to the sales world, but I've worked at a F500 & a small start-up environment (current role).


I thought I hated the amount of structure at the F500, but when you're literally building the structure out at a new company, the lack of direction can sometimes feel daunting.


What are your pros & cons for working at different size companies?

What size company would you rather WORK for?

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TheRealTommyCallahan
Arsonist
2
President of Callahan Auto
I worked for a startup 2 times and both went public. I saw both go from startup to corporate culture. I much prefer the startup experience. It is crazy fast paced and also not a lot of direction but I love that freedom part of it. In the corporate world you usually are told how to do your job and if you don't do it their way they won't like you. At least that was my experience. 
BossBitch
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Account Executive
I've had the same experience. I prefer startup.
MoonDog349
Valued Contributor
1
Sales Manager
This has been a huge internal question for me recently. I'm at a ~700 person company now that likes to say we act like a startup when in reality the company is 16 years old... So it's BS. 

I haven't worked at a start-up yet but my biggest question as an AE is, how many other tasks will I be tasked with outside of selling? If I am doing something that contributes to my own deals or my team's deals, that's fine.  I don't want to be tasked with doing things for the company that don't contribute to my commission check because they haven't hired a person to do said task. 

IMO this is the only upside to a slightly larger company. Corporate culture mostly sucks but wearing a sales hat and ONLY a sales hat is part of the whole SaaS sales life cheat code for me (great money, easy hours, no grad school, etc). 

I think I draw the line at a company the size of mine. I wouldn't work for a bigger company than this ever again. 
CaneWolf
Politicker
2
Call me what you want, just sign the damn contract
@Kmcrey They all fucking do that "we act as a startup". I've done the startup thing 2x coming from established companies both times. I'm gonna be honest, it was not fun. Way too much shit isn't codified and just gets done on the whims of the leadership. The CEOs often can't let go of sales and are way into minutiae rather than the big picture stuff to do.

I'm personally a fan of the midsize. 300-2000 people seems to be my sweet spot.


Edited to make this make more sense.
MoonDog349
Valued Contributor
0
Sales Manager
Agreed... but, 2000 is big. I like a private equity backed 300-900 person company. the sweetest spot
CaneWolf
Politicker
1
Call me what you want, just sign the damn contract
The problem with the PE angle (which I've done and can be good) is that the quotas SKYROCKET.
MoonDog349
Valued Contributor
0
Sales Manager
I never realized that was a PE thing factoring into it.... Now that I think about it, mine is north of $900k this year and the PE seems to be getting ready to sell us off in 2022. Good stuff man
CaneWolf
Politicker
0
Call me what you want, just sign the damn contract
My quota doubled in 2 years...
newbie
Good Citizen
1
BDR (Big Ducks Rock)
Great points here @Kmcrey, my comp plan is directly tied to how much revenue we bring in. If I have to spend a bunch of time doing other tasks that I'm asked to complete, that takes away the time I can spend actually booking meetings and selling and yanno, making money! 
MoonDog349
Valued Contributor
0
Sales Manager
Right? I don't mind if my base and variable don't match but I'd need a significantly higher base to be working on tasks that don't retire quote. 
Beans
Big Shot
1
Enterprise Account Executive
Pre-IPO, but established customer base and more importantly, high level backing.
Salespreuner
Big Shot
0
Regional Sales Director
Well chosen. +1
funcoupons
WR Officer
0
👑
SMB/Mid Market. I feel it's the best of both worlds...you get some of the freedom that startups offer but with a higher degree of job security and at least a rough framework of people having their shit together. 

Enterprise companies have too many managerial layers and red tape and start ups are too disorganized/unstable to be appealing to me.
BossBitch
Politicker
0
Account Executive
At my third startup. Love it. Love the fast pace. You learn so much and a lot of room for career advancement. I went from no sales experience to enterprise in 3 years because of being aligned with startups. 
CoastLife
Good Citizen
0
Large Enterprise Sales
I'm a big fan of the start-up phase but it is completely different than even a well established company with 500+ people. 

Figure out what makes you thrive. 

Bigger companies tend to have their processes figured out. Territories, commissions, pricing structure, sales tools etc are all in place. 

If you want to move from BDR - MM AE - Ent AE - Sales leader, a bigger company might be the place for you.

If you love solving problems that might have nothing to do with your job, improving processes, helping shape what sales looks like at your company, then consider start up. But it is not easy. Career and growth paths can often look very different.
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