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.

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.

In technology it is VERY common as these exec recruiters are paid handsomely. 100K+ to find the right executive and place him/her at a company. These are not the low level recruiters spamming your inbox.

These people have a network, and know who has been where and for how long. After that 3/4/5 year mark, they start pinging people to let them know of interesting opportunities. That said, you DO want a good recruiter who's well respected.

I'd do your research on who some of the best are, and target them to work with. Perhaps people here can make suggestions?

Indeed, but I'd like to add that these recruiters are often penalised if the candidate leaves the business before a set period.

So they have a financial motive with not just placing a candidate, but also them staying there.

Interesting and obvious in many ways. The recruiters of course has all the interest in the world to deliver the right candidate. I would be interested if people have any recommendations in this regards as well.

Another opportunity you might consider is connecting with venture capital or private equity firm partners. They are constantly monitoring their portfolio of companies and at anytime may want to bring in someone with your significant experience to help scale their startups.

Another avenue you could try is cold-calling another executive and essentially selling yourself: https://www.forbes.com/sites/susanadams/2014/04/22/how-cold-...

Outside of technology, most companies usually find executives through their network - it's the safest way to be relatively assured that they won't be hiring wrong. If you're not into networking at a large scale, what about taking people out for coffee 1:1 and build the relationship that way?

It sounds like you've already made some people a decent chunk of change. Why not reach out to these same investors and tell them what you're looking for.

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.

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".

Food for thought... Whilst you might find the 'typical post-conference drinks to be incredibly tedious', you will find that this same thing (or something similar, in principle) will encompass part of being an exec at most businesses...

These businesses are looking for 100% the right person when filling these roles. And if you look like the right person, and they haven't yet filled it, then it won't matter when you apply.

But to answer your questions directly.

- I wouldn't waste yours and the other person time trying to force yourself to enjoy a conversation. Just chalk it up as one of your weaknesses when asked in an interview. - Yes there are specialist firms, and they typically have headhunters, and in my experience are quite good at finding candidates. - There is indeed a narrowing of the pyramid... Execs are at the very least highly motivated and highly intelligent. There are also very few jobs!

Reach out, either through a respected intermediary or directly, to CEOs of companies that are about to need executives but haven’t made a bunch of external executive hires yet. Get on their radar before they start their recruitment process.

Sure, this is networking of a sort, but taking a half hour to talk with the CEO of a company you might join is hardly a ‘forced conversation’.

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.

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.

Appreciate the advice, thank you.

This isn’t the most helpful answer but I’ve heard similarly to the sibling comment that most of the search for these roles happens through backchannels. There’s discussion around related topics in the app Blind.

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.

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.

Thanks a lot for asking this. I actually find myself looking somewhat in the same direction without really having found a clear path. But a lot of good answers here that I will look further into.

I just made my life a little more complicated by doing freelance development work and now in the short run probably will have to accept a major pay cut to prove myself in a VP/C* something role of a smaller company, until I would be able to break into larger firms and better pay.

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.

Taking some time off to purely focus on networking could be a good option. Networking is great fun when you have spare cycles. Networking when you have a full-time job - not so.

Maintaining a network when you have a full-time job is much easier than building one.

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.