Ask HN: Career crossroads | Hacker News Reader

Ask HN: Career crossroads

3 pointsanon0987658 comments

HN,

I'm faced with my first major career move, and I need some unbiased advice.

I have two options:

1) be a leader (but non-exec) in a very sexy (very early) B2B startup run by high-caliber people in an industry I love, working with people who share my philosophy and principles. Decent equity (but high likelihood of dilution because it's quite a capital-intensive business), solid pay raise and significant responsibility increase relative to my current position.

2) be an exec (make two jumps in title), nearly double my salary, and get a solid amount of equity at a non-sexy but already established company that is a former leader in its industry but has grown more slowly lately bc of poor execution the last few years. I have worked with the recently-hired (new) exec team in the past and I trust them, but our philosophies are different, and I know I'll bear additional stress (I know I'll be stressed anywhere) related to our deep-seated disagreements. All that said, because they trust me, I'll have instant credibility on the exec team and with their (very well-known) investors.

What's your advice?

1) Most start-ups fail. If you join that start-up and it fails, leaving you looking for another job, are you okay with that? Is that an outcome you can live with?

2) Chronic stress is very bad. Can you set aside your philosophy and avoid stress by being genuinely okay with following someone else's philosophy during working hours regardless of whether it's the philosophy you would have chosen?

This says it all - "run by high-caliber people in an industry I love, working with people who share my philosophy and principles". No brainer.

I will suggest picking option 2. Executive position and title at an established company (assuming relatively well known company in segment) will go a long way in your future executive career growth. I wouldn't be surprised that after staying in the role for 6 months, you will start getting contacts from executive recruiters for executive positions at other companies. Also, being in executive position you will most likely interact with BoD and other investors. At exec level, you need connections to move up and sideways.

The chance of B2B startup becoming big and stay independent are low. Most such startups get acquired by larger established companies in the segment. Executive position at startup doesn't typically equate with executive position at acquiring established company. As a non-exec at startup who might have been reporting to an exec at startup, you most probably will be demoted and reporting to someone non-exec in this situation at acquiring company. You will lose any professional cachet in executive recruiting or moving into executive role.

Mark Suster's Is it Time for You to Earn or to Learn? is among the "solved problem" essays I've come across on HN.

http://www.bothsidesofthetable.com/2009/11/04/is-it-time-for...

Good luck.

Thanks for that. I came to post this article, not by Suster but enthusiastically endorsed by him:

http://blog.eladgil.com/2015/03/career-decisions.html

Edit: typo

The way you worded 1) shows that you prefer it, so you should do that. Simple. :)

A couple of areas to consider in making your decision--

Which opportunity presents the bigger professional stretch?

Given the pace of this business-- people change jobs/companies every few years; which experience do you anticipate will give you the best leverage and most options?

Ask for an exec-level title if you pick #1. In an early stage startup, it's easy to get. It makes it harder for them to hire someone over you later.

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