I understand your frustration, because I am going through a similar phase, looking for a new job without references after many years not having to. I've also been rejected after what I thought to be very successful interviews, without real feedback on how I fell short.

I believe one or more of following factors are at play, keeping in mind that one company would not be the same as next:

- people have high bars for experienced hire, you can't just be smart and get things done, but also be able to wow the hiring manager/committee in some way.

- related to point 1, someone with 5 years of experience will have a difficult time evaluating someone with 15.

- if engineering expertise is hard to interview for, leadership skill is even harder. And companies are definitely more cautious when hiring for leadership roles.

- there are a LOT of people wanting to join those top startups, so competition is fierce, and there is less pressure to hire a good but not amazing candidate.

- interviewing is a skill in itself, just because you had so much experience does not mean you can ace interviews without preparation, especially with high expectation/competition positions. You should sit down and think hard how you can best demonstrate your experience in an interview.

- lastly, it's actually quite easy to fell into a good job that makes getting next one harder, especially if that project was a failure, or uses an outdated technology.

Isn't it also possible that it's always been an insiders club & you've only recently started being an outsider?

What you are describing could be attributed to a component of SV thats long existed. Ageism.

Hello,

I went through something similar. As a self-taught software engineer with a business background from a not great school, the hiring process at most large companies is specifically built to prevent people like me from getting in the door.

What you are encountering is the "gatekeeper layer" of these major tech companies. I call this "the front door." To put it mildly: The front door of tech is configured to reject everything that doesn't match some unrealistic perfect ideal of a genius savant engineer. To summarize Gandalf's general disposition towards flaming Balrogs:"Thou shalt not pass!"

Why is the focus on rejection and not acceptance?

There are three reasons. First, everyone wants to work at Google, Facebook etc. and there are a lot of unqualified people coming in. Second, these companies can't afford to grow at the rate at which they can gain talent. If Google were to hire a tiny fraction of the people applying to them every day, they would rapidly grow far beyond a size which makes sense. Third, they are very strategic about which directions they plan on growing in. They would rather acquire talent in groups focused in strategic topics like automotive than bother letting in single general-purpose individuals based on some brain teasers. Fourth, the actual volume of truly qualified people is even too high! The big companies can't afford to hire every qualified person who actually wants to work for them in some cases.

Therefore, anyone who possesses a diversity of skills beyond pure programming should completely avoid the front door, it isn't going to value your whole person (as you have seen).

Instead, you need to be using the "side door." That means you go and find people who you like (want to work with, resemble, build interesting stuff you like to use) and approach them personally and sit down with them like a regular human being and talk about building cool shit together.

If you are really great, people will recognize your greatness and they will help you get in the door.

Using the side door is about creating your own interview process rather than letting someone else define your interview process for you. Shoot high. Pick people who can hire you or have influence directly over hiring decisions. You don't need the gatekeepers.

It's always been yes and no. It's class-based.

Yes, the management class (or officer class) is for the pedigreed elite. You're trying to join the manager class and they have a line out the door of people with pedigree. What school did you go to? Yeah, so why would they pick you...they're themselves incompetent so why would they use competence as the criteria? VCs invest almost exclusively invest in this class and so the cycle continues.

The technical class (or soldier class) does all the actual work and so they have to be competent. This is almost entirely meritocratic in Silicon Valley. Anyone even moderately competent can get well paying some job, even if it's not at one of the big adtech companies like Google/Facebook that can afford to mostly require pedigree from even their soldiers.

What's neat about Silicon Valley is that anyone of the technical class can simply promote themselves to the manager class given sufficient effort and luck. This alone is what makes it so special. It's very rare but it does happen.

Connections can always make a difference, but are not everything. Here are a few thoughts on your scenario:

>>> The things I think are hurting me are that I'm not great at whiteboarding

I don't know about that. I have a friend who stopped an interview when asked to whiteboard and instead referred the panel to review github together, they ended up hiring him.

>>> it's hard to summarize the scope and impact of what I've done as CTO growing a team from 2 to 16 engineers

That is more likely to be the issue. Find a way to explain your value, what you did, and what you can do.

My two cents is that your skillset is not quite the right match for the companies you are interviewing at, and so it's going to be tougher to find a position. Not impossible but you'll have to interview around a lot more and have a good reference (as you suggest. Basically to get a stretch position you need an "in.") The easiest jobs to get are those where you are essentially doing exactly the same thing you did before, in a similar space. So - a company doing related work, of similar size (less than 15 engineers.) It sounds like you are interviewing at much larger companies than places you have experience as a tech lead at - and it is a different skillset. Large-scale experience IS different. Tech leads at a large company do different kinds of work than a CTO at a startup. A lot of the work is around working with other tech leads, and working with cross-functional leads across the company who have growing teams of their own, managing politics, scaling etc. Figuring out communication structures, reporting up and across and so on. Other on HN could elaborate on this better than I can. To get this kind of job you have to convince the interviewers that you can work well in a huge company as a tech lead even though you haven't done that before. Find ing someone who can vouch for you in that respect (a VC, executive at the company etc) will help you get there. Good luck

I had a similar experience recently with a well funded startup. There is no doubt that I can do the job well, as I helped with one of their engineers as a vendor. I corrected one of their components several times, when my contact there reached out to me for advice.

But my resume wasn't bulletproof (decent school, some job hopping) and I didn't express the requisite awe about their product or technical tasks (I gave my assessment that they have a good business plan but should expect modest growth, and the engineering tasks needed would be tedious to anyone honest). That's all I can think of, because I sure as hell didn't answer any questions incorrectly.

Also, for all my efforts, they ghosted on me afterwards.

I think you're right - it is an insider's club. Looks like you have pretty solid credentials. Unfortunately the corporate-capitalist system has more than enough resource (despite their whining about STEM shortages - debunked here: http://spectrum.ieee.org/at-work/education/the-stem-crisis-i...) to enable them to play around with people and cause this soul-searching angst. Stories like yours break my heart and make me fear the future.

To play Devils's advocate here:

"My experience is great and perfect and in demand and they just can't see it"

Have you considered that you may not be presenting your experience the best way? You said you grew a team from 2 to 16, over what period of time? A month? A year? Expanding a team by 14 people over a month is very different experience than doing it over the course of a year. Perhaps instead of framing your experience as "I have what you're looking for" you can frame it as "I haven't done exactly what you are looking for but I am ready to step up to it."

Speaking as someone completely on the outside of your situation it's possible that the people doing the interviewing are looking for X and your offering them Y and telling them it's X. This may make them feel like you don't really know what they are looking for.

Once again, I'm just trying to look at your situation form the other side. I'm not trying to belittle your experience.

No.. but it is a tribe, "are you one of us" e.g. white boarding + algorithm/data structures. You may have better luck at slightly larger companies that are past the startup phase. Buy a whiteboard and have some (CS) friends over, practice. My experience has been that "experience" doesn't matter as much as the fundamentals do and being a nice reasonable person. The experience and degree get you the interview... the fundamentals land the job.

When explaining your accomplishments, put them in context they can understand. This isn't technical specific (unless shared) but rather at the more abstract (business) level.

There's the interview kickstart guy on here too. He runs a course that gets you in shape. You get interviewed by employees at the big companies which can only help. Triplebyte here also does a pre-screen for YC companies.

Good luck!

Apart of interviewing as a skill that can be improved, do not overthink your situation, it may be much simpler than that: getting chosen and hired from the unemployed pool is much more difficult than jumping ship while being employed. Your failure, if you want to use this term in this context, may be being unemployed, especially true in tinderised environments aka startups and/or very young workforce. Your best shot is probably restart a bit lower in the ladder and therefore make your way up again from within.

I'm a Brazilian guy with no experience in SV or the US market for that matter but with some experience working and hiring people. I have one question for you and forgive me if it sounds blunt, but it's an honest question.

How come that after 16 years in the same market you have no reference or contact with people in a position to help you find a job?

I find it very hard for a person with so many accomplishments to not have a single contact to vouch for you or that wants to work with you. Have you thought about it?

Olá! Interessante notar que é brasileiro porque também sou.

To answer your question, of course I have references, amazing references even, just not anyone inside the companies that I'm applying to. One of the weird things is how none of these companies even care about my references, everything boils down to a series of 45-minute 1:1 interviews.

Opa!

What I meant is, none of the people you know has asked you to come work with/for them?

I have some 12 years of experience and after my first gig I never had to take an interview and go through hiring process again.

Now I'm working as an H1B in the US and even this happened because of someone I worked a few years before. No interview or weird process except for the VISA thing.

And I don't think I'm an exception. What I learned is that people usually build a network of people and work with them most of their life.

Well a big part of this is that I'm trying to get into slightly larger companies than I've been at in the past, and the companies are brand name SV companies with very high standards where they tend to have pretty rigid hiring processes even for referrals. I know a handful of people at these companies, but none of them are hiring managers, and none of them are from my most recent two jobs (ie. the last decade) to be able to vouch for my recent experience. Also, out of a 16 year career, only 5 of those years were in SV, the other 11 were split between London and US flyover country, so my network is pretty dilute in SF.

Truth be told though, I haven't reached out to much of my network because I don't just want any random job to pay the bills, I am looking for a specific kind of company and experience. If it keeps going like this though I will probably need to broaden my selection.

I think it is not about SV, but about CTO level positions..

So you did get an offer from 1? 1 in 10 is not that bad?