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

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

#1

Post by exogeny »

Hi! Long time lurker.

After a six or seven year career spanning different generalist tech roles (everything from product designer to front-end engineer to platform developer), I founded a startup, raised seed, and sold for a 5x return. Yay.

I've spent two years at my acquiring company, mostly making sure that our IP gets integrated and has a good home. It's clear however that the acquiring company is not a growth company by any means, and I find myself incredibly stifled by the slow pace, the lack of vision, and frankly, the denial about the situation.

I report into to our CPO, but have found myself unable to find a realistic vector for also becoming a C*O in the company, as he is unlikely to leave as a founder and they do not appear all that interested in exploring alternatives that might cause his role to be diminished or otherwise carved up. I likely wouldn't be all that interested in sticking around anyway, given the cultural problems I mentioned above.

As I look out into the job market, I'm concurrently finding myself being a week late to opportunities. By that I mean, by the time I find them and/or a recruiter reaches out to me, a candidate is already deep in the process. It's frustrating, and I'm finding myself wondering if my long-standing aversion to networking is causing me to miss these opportunities, as I assume that most of these jobs are filled with internal recommendations from people within the professional network of the other executives.

(I should note that I'm actually an extrovert by personality, and have a..decent-to-good sized network within my industry. I just find networking and the typical post-conference drinks to be incredibly tedious.)

I'm at a bit of a loss for how to accurately phrase the question, but hopefully some of you will understand where I'm coming from. Is the right move simply to suck it up and pretend to enjoy forced conversations? Is there a recruiting firm who is actually somewhat good at handling generalist/entrepreneur types? Or is this just the narrowing of the pyramid as you get closer to the top?

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

#4

Post by twunde »

There are some recruiting firms that specialize in executive recruiting. That may be an option for you and is worth exploring. Another option is to reach out to some of the tech recruiting firms and let them know that you're looking for an exec position (director/VP/CPO/whatever) and to reach out if they see one. I've occasionally seen those pitched. You may also want to look at consulting firms, as those can turn into executive positions if the hiring company wants to keep you.

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

#5

Post by brianwawok »

exogeny wrote: post #3
sharemywin wrote: post #2

why not start another company? if your going to network why not network for a co-founder. and/or a bigger team. I imagine you could get a seed round again.

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

You made no savings from the 5x sale?

It is a lot easier to have a less stable job if you have a few mil in the bank.

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

#6

Post by quickthrower2 »

brianwawok wrote: post #5
exogeny wrote: post #3

Earlier quoted context omitted.

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

You made no savings from the 5x sale? It is a lot easier to have a less stable job if you have a few mil in the bank.

What does 5x mean? How is that millions?

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

#7

Post by exogeny »

brianwawok wrote: post #5
exogeny wrote: post #3

Earlier quoted context omitted.

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

You made no savings from the 5x sale? It is a lot easier to have a less stable job if you have a few mil in the bank.

Sure, I have lots of savings. But I also have children who will want to attend college, a mortgage, a lovely wife who is pursuing her non-mercenary interests and whole host of other reasons that make it fiscally possible yet not preferable for me want to do it again right now.

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

#8

Post by exogeny »

twunde wrote: post #4

There are some recruiting firms that specialize in executive recruiting. That may be an option for you and is worth exploring. Another option is to reach out to some of the tech recruiting firms and let them know that you're looking for an exec position (director/VP/CPO/whatever) and to reach out if they see one. I've occasionally seen those pitched. You may also want to look at consulting firms, as those can turn in…

That's helpful, thank you. I should also state that I previously may have been too prideful to look into something like that in more depth, but I'm increasingly concluding that viewpoint is silly.

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

#9

Post by rdiddly »

exogeny wrote: post #3
sharemywin wrote: post #2

why not start another company? if your going to network why not network for a co-founder. and/or a bigger team. I imagine you could get a seed round again.

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.

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

#10

Post by ericd »

quickthrower2 wrote: post #6
brianwawok wrote: post #5

Earlier quoted context omitted.

You made no savings from the 5x sale? It is a lot easier to have a less stable job if you have a few mil in the bank.

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.
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