re: Tough career decision

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Good salespeople make TERRIBLE operations people.

I was Fortune 500 sales- and badass at it. So much so I worked for the brand President before I left to go out on my own.

Operations is my weak point- and everyone on my management team now tells me “We gotta get the salesman out of you somehow”

Only you know if you can make this jump. But it’s TOTALLY opposite of what you’re doing now.

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I would say I'm an average salesperson unless it's a product I personally believe in. I'm a bad BSer

Personality wise, operations would probably fit me better which is really the only reason I'm considering it.

You aren't responding to the things that matter, Healthcare and savings. You could 50/50 hit it big with start up...but if owner isn't offering you a true competitive comp it is a very bad decision to move.

How much growth is there for you really at the small gig? If you don’t share the same last name as the owner, it probably isn’t what you think it will be.

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You aren't responding to the things that matter, Healthcare and savings. 

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My in laws use a Christian medical debt sharing program that they really like, they've made multiple claims and said it's way better/cheaper than insurance and it'd cost me about $1k more annually than what I pay now through my current employer.

Retirement savings and matching are where I'd be losing but the owner says they do plan to offer that very soon.

No timeline as of yet though.

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no benefits

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Keep repeating to yourself.

Won't be the answer you're looking for, but only you know the answer to this question and you've likely already decided on it.

If you're asking, my gut tells me you are looking for an out from the big company. I can likely relate as someone who worked at a Fortune 50 as a top sales rep at the same age. Just turned 30. Making assumptions, but assume you're tired of the bureaucracy from said Fortune 500. Too many reports. Too many team huddles/calls. Don't feel like you're making an impact. Seems like all my 25-35 year old sales buddies hit this feeling.

The small jump to operations may work. I have seen it work for good friends of mine. I will say though, everyone that did and did it successfully, left analyst or data type roles to to be operators not sales. It's a different beast.

It will be more work. If your fortune 500 is paying your company car, letting you work remote, and you have a good boss, sticking around may not be the worse. If you're set on leaving, you're young enough to go try for 18-24 months and at worst, jump right back into big corporate if it doesn't pan out. There's always BD roles there.

I left Fortune 50 for a smaller company with 300 people. I couldn't be more pumped about it and the vibe change is noticeable from day 1.

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The cons are no benefits, newish company, a lot of uncertainty. Pros are a ton of opportunity for future growth, the chance to have a lot of effect on the company, and it's a majority work from home position. Starting pay would be basically the same. I enjoy what I do now and like the people I work with but the challenge of helping build a business sounds very intriguing to me. I like the owner well and we seem to have similar views and thought processes about the future direction of the company.

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I was in a steady enjoyable job with about 2k employees when an opportunity with a very small company.

Tiny raise at the time but is great now.

Money aside, working for a small company and being an integral part of all the business is so much more rewarding than being a replaceable cog in the machine.

There’s stress to building a small business especially when times are lean but being a part of a team that can be agile and doesn’t have a bloated bureaucracy has been incredibly rewarding.


If I died at my last job, they’d pass a card around to sign and that would be the end of it. The job would be posted before I was in the ground. If I died at this company I know my boss would take care of my family.

It worked out for me but everybody and every job is different.