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It's a two-edged sword for sure.
The good:
Lots of room for creativity, innovation, and change. But as others mentioned, this depends on the company culture.
Less red tape because of the shorter line up the organization.
Faster promotion track if the company grows and you've already established yourself. You can also get a huge payout if the company is acquired in the future.
The bad:
Possibly not as organized vs a company with an established support group (admin, payroll, HR, etc.).
People having to perform multiple roles due to having fewer personnel.
As a counter to the 2nd bullet in the pro section, having to deal directly with top management means you're more exposed to politics.
Possibly lower pay. But you said they've been around for 2 decades so maybe they're paying well, and I'm sure you've considered the pay already.
A pro in my book. I like the diversity of work rather than getting pigeon-holed into some very niche little task that I would have to do day in and day out.
For sure, but it depends if you actually want to do the additional work assigned to you. It's all good, until you're being asked to do some administrative stuff like help Jen from accounting on company finances because it's tax season. Or finish some paperwork for the lease on the building the company is renting. Or sales/marketing stuff like reaching out to a customer to sell additional features, when you're a backend developer. Or provide technical support when you aren't supposed to be customer-facing.
There's nothing like some droll task like stuffing some envelopes to get your mind off that problem you've been wrestling with.
But yeah, this all is highly dependent on the company and the work expected of you. I was thinking more along the lines of not wanting to have to do devops all day every day. While I do like that work, I much prefer when I also get to do other work like architecture, programming, db design, etc.
Yeah, this is what happened to me. Went in with a 50/50 business analysis & programming role, and now I'm having to do marketing, customer service, project management, documentation, all-of-the-above because we're understaffed. Great from an entrepreneurial standpoint to learn a wide-range of skills, but I don't enjoy it, and I don't have control over my workday.
I really like this list. But another thing is job security. Generally the larger the company the more likely it is to continue existing.
This is more important for VC-funded startups that are more likely to run out of cash than continue existing, but is still true of established profitable companies.
Man, I have all of those cons at in an org that has 20,000 people.....
Also there may be very good coworkers or very bad coworkers, you'll probably work closely with either.
And things will probably be a lot more informal.