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Ask HN: How do you get over the executive wall?

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Re: Ask HN: How do you get over the executive wall?

#11
Contact people from your network and tell them exactly what you are looking to do.

If you really do have friends from the industry who honestly and truly believe in you and want to see you do better it is a great place to start.

Also, marketing yourself as a generalist/entrepreneur is a bit of a red flag. Chief "Big Idea Guy" is a tough title to get from the outside and without some serious bona fides.

I'd suggest taking a little time to really think about what your industry needs to grow in the next few years and map out a VERY specific strategy.

Then find a company who could benefit from that knowledge. It will at least give you more to talk about when you sit down for an interview.

If you can't be a specialist in practice be one in strategy.

Good luck.

Re: Ask HN: How do you get over the executive wall?

#12
post #10

Earlier quoted context omitted.

What does 5x mean? How is that millions?

I read it as they sold for 5x their seed valuation, which is typically at least a few million, and is occasionally as high as $15M.

Yes, this is correct; we returned 5x the value to our investors. Apologies for the inelegant wording.

Re: Ask HN: How do you get over the executive wall?

#13
post #9
post #3

Earlier quoted context omitted.

Good question. Different risk tolerance than before; wife, kids, mortgage.

That sounds like an argument for the "slow pace" that you bemoan as a trait of the acquiring company. Slow growth and low risk go together. It's not a bad thing.

Good point - maybe what I'm looking for is the middle ground, to the extent that it's possible. I'd enjoy the stability of a slightly larger company, without the slowness and bureaucracy of a large one.

I think my wheelhouse would be a Series B and above growth trajectory company that is looking to flesh out it's founding team with established and experienced execs. Seems like a needle in a haystack.

Re: Ask HN: How do you get over the executive wall?

#14

Contact people from your network and tell them exactly what you are looking to do. If you really do have friends from the industry who honestly and truly believe in you and want to see you do better it is a great place to start. Also, marketing yourself as a generalist/entrepreneur is a bit of a red flag. Chief "Big Idea Guy" is a tough title to get from the outside and without some serious bona fides. I'd suggest ta…

Helpful feedback on it being a red flag - I think that skillset has worked for me in the two capacities I've used it in; first, being a utility player for an early-stage company and second, as an entrepreneur. How that fits into something that isn't either of those two poles is a challenge.

Good advice though, thank you for the thoughtful response.

Re: Ask HN: How do you get over the executive wall?

#15
post #13
post #9

Earlier quoted context omitted.

That sounds like an argument for the "slow pace" that you bemoan as a trait of the acquiring company. Slow growth and low risk go together. It's not a bad thing.

Good point - maybe what I'm looking for is the middle ground, to the extent that it's possible. I'd enjoy the stability of a slightly larger company, without the slowness and bureaucracy of a large one. I think my wheelhouse would be a Series B and above growth trajectory company that is looking to flesh out it's founding team with established and experienced execs. Seems like a needle in a haystack.

I really think your network is the way to go here. Contact VC funds you've worked with, pitched to, or are otherwise connected with and talk to them about portfolio companies. As someone mentioned, recruiting/headhunting firms are usually on the lookout for executives as well.

Definitely not a needle in a haystack with a bit of networking. I have a similar story (not even as impressive as yours - 2x return to investors on an acquired seed-stage startup) and in 1-2 months of networking have plenty of inbound from Series B companies looking for VP/C-level folks.

Re: Ask HN: How do you get over the executive wall?

#17
post #15
post #13

Earlier quoted context omitted.

Good point - maybe what I'm looking for is the middle ground, to the extent that it's possible. I'd enjoy the stability of a slightly larger company, without the slowness and bureaucracy of a large one. I think my wheelhouse would be a Series B and above growth trajectory company that is looking to flesh out it's founding team with established and experienced execs. Seems like a needle in a haystack.

I really think your network is the way to go here. Contact VC funds you've worked with, pitched to, or are otherwise connected with and talk to them about portfolio companies. As someone mentioned, recruiting/headhunting firms are usually on the lookout for executives as well. Definitely not a needle in a haystack with a bit of networking. I have a similar story (not even as impressive as yours - 2x return to investo…

Appreciate the advice, thank you.

Re: Ask HN: How do you get over the executive wall?

#18
post #14

Contact people from your network and tell them exactly what you are looking to do. If you really do have friends from the industry who honestly and truly believe in you and want to see you do better it is a great place to start. Also, marketing yourself as a generalist/entrepreneur is a bit of a red flag. Chief "Big Idea Guy" is a tough title to get from the outside and without some serious bona fides. I'd suggest ta…

Helpful feedback on it being a red flag - I think that skillset has worked for me in the two capacities I've used it in; first, being a utility player for an early-stage company and second, as an entrepreneur. How that fits into something that isn't either of those two poles is a challenge. Good advice though, thank you for the thoughtful response.

I in agreement with jsonderulio, but think of it this way. Just because you may end up doing a lot of "Big Thinking Generalist" work, it may be a difficult sell to go in thinking that title would exist.

Are you a good fit as CPO, CTO, etc and then the your capabilities as "Big Idea Guy" can be leveraged from those positions.

Think about it another way, how many company CEOs or Boards have ever thought "What we need is an Big Idea Guy".

Re: Ask HN: How do you get over the executive wall?

#19
my 2 cents, you're either going to have to be so successful on your own that people are trying to pry you away from your own goal... or you're going to have to hit it lucky.

Unless you've found yourself "a week late" on dozens of opportunities, I'd just keep trying until you get a reasonable sample size.

Re: Ask HN: How do you get over the executive wall?

#20
It can take months to fill executive level positions.. and even then dealing with unknowns on both sides hence a bias for filling from within.

Reach out to a few head hunters. Professional ones you feel comfortable with, avoid recruiters, and build a relationship with them.

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