[balls187]

The rub with startups is that leadership may not have experience with developing careers.

From what you've written, it seems like you really don't have a lot of experience developing careers either, which is one reason to bring in an experienced engineering manager. It's not a knock on your skillset managing a 10 person team and delivering. Just a realization that management isn't something you can just quickly learn on the job.

My advice: have a discussion with whomever the new engineering manager is, and explain your career aspirations and the current dilemma you have.

[itsbonczek]

Agree with this advice. You should talk to your manager and work out a plan to achieve your career goals within the company. This is a significant part of your manager's job responsibilities, and assuming they are good a good manager, then they will be more than happy to work with you on this. You are obviously an important part of the organization and if they have any common sense, they will want to retain you. And if, for some reason, it turns out there is no good way to grow within the organization, then start weighing the pros and cons of leaving.

Also, remember that transitioning into a management role is an advancement only if you want to be a manager. It's a career change, and is not suited for everyone. This is why many tech companies have pure developer track advancement opportunities.

[voidlogic]

As employee #2 he should be talking to (presumably, his friend), the CEO, regardless of who his manager technically is.

[briandear]

Exactly. If he doesn't have an open line with the CEO, then I would leave, assuming I have some percentage of options that had vested. I would stick around long enough to vest, then go start your own thing or be a cofounder of something.

I know this situation well. I am employee #1 in a 55 person company and I feel like I might as well be employee 55. But, since I'm remote, I can do my thing, write code, and generally be left alone while getting paid regularly. So being cut out of the loop does have some advantages, especially if you're remote.

[balls187]

> I'm remote, I can do my thing, write code, and generally be left alone while getting paid regularly. So being cut out of the loop does have some advantages, especially if you're remote.

There is the opposite end too. I joined a 100 person company, and some early founding employees were clearly resting and vesting, while I was working nights and weekends to iterate and replace prototype software written by early team members. I was grateful for the company they built, but was curious why they had an entitled approach to their positions.

Software is meritocracy based, not loyalty and tenure.

As employee #1, in what ways do you think you should be treated differently than the other employees?

[_3u10]

Software might be about meritocracy but power is not.

It's not entitlement so much as ownership, they don't feel they are entitled to 5% of the company, they own 5% of the company.

Depending on how much equity they have collectively they might be able to fire the CEO if push comes to shove.