I wish I had read this several years ago. This is the kind of thing which everyone instinctively knows but somehow forgets with age, or ignores due to circumstances (like needing a job having just been made redundant). I swear that CEOs like the one mentioned here specifically prefer hiring those who are in need like this, with the predictable awful behaviours. Some people will get lucky, but I expect that they are the exceptions, not the rule.
Avoid startups where the CEO does / has done nothing but sales. Avoid them like the absolute plague that they are. If you are in such a place already, and you think things will get better, then I have a bridge to sell you. It is vanishingly likely that they won't, if only for the simple fact that the CEO has found a formula which works, and has no motivation to change it, and your best bet is to leave ASAP for the wider world which has infinitely more opportunity. (BTW, you won't succeed in changing such a "culture" for the better, so don't even think about it. I know you have.)
I could ramble on for several paragraphs, but BigJono has summed it up pretty concisely so I will proffer just this advice when sizing up CEOs and opportunities:
Remember, if there is any doubt, then there is no doubt.
As a counter example - I was at a startup where all the CEO did was sales. Everything worked really great.
I think the key here is is the culture pathological or not - not the specific role of the CEO. CEO can have good enough understanding of tech to do their job well even thought they are not elbows deep in it themselves.
Culture is important, but I think direction might be even more key.
If "sales" means "I spent 3 years talking to every customer in a particular industry, became keenly aware of a vacant niche, and now am looking to do something about it" I reckon it would be a very good thing.
If "sales" means "I saw that the crypto market is booming and want to get in on the easy money," it's not going to go well.
> Avoid startups where the CEO does / has done nothing but sales.
I worked for a small company where this was the case. The owner had been a sales person for a large online industrial web registry and decided he could be a middleman selling the companies websites that integrated with said registry. The job was fine, my paycheck bounced a couple times, but that’s the worst of it until after.
In my exit interview I had agreed to do some side work for them until they restaffed, and completed a decent number of sites in a short timeframe.
Then I got sick and ended up having emergency surgery - loaded with prescription drugs and largely out it, I passed a project back to them which I had put maybe 50 hours into and completed short of populating the final verbiage/copy specifying as much.
I offered to take half of the agreement since I wouldn’t be completing it. I got a polite “we’ll talk about it when you’re feeling better” from my former PM, wonderful person.
It was handed to one of their most junior developers, and according to people I knew at the company he told the owner I had done almost nothing on the project, the pages were blank. They literally just needed copy I hadn’t received yet! The entire backend was done!
When I got better and tried to get everything straightened out, they literally ghosted me. Ignored my calls and emails. I’d put a load of time into the project and wanted something for my efforts. I'd worked there for over five years, it felt so disrespectful at the very least.
I started copying more and more people at the company in my emails. In the end however my efforts were fruitless.
About a month after this ordeal, a developer I had managed took a job with my new employer. I received a letter threatening to sue me for stealing their employees. I had nothing to do with it. Our corporate lawyer analyzed our contracts and said they didn’t have a leg to stand on. He sent them an official response and sure enough nothing came of it.
They went into bankruptcy restructuring within the year, they’re still in business but I suspect I lost my right to try to collect with that.
I know the guy personally to this day. He's a super nice guy, he was just very green at the time. If I recall they threw out everything I'd built and started over.
Perhaps give them some flexibility if there's a technical co-founder as CTO.
It depends on what the startup is working on. If it's trying to sell into the enterprise I'd be a lot more confident in its future if the CEO is heavily sales-focused provided there's also a technical co-founder keeping things sane on the tech side.
That's what I thought. I thought that the character of one would balance the other out in this case. (Not that there is any guarantee, of course.) I was wrong.
> I swear that CEOs like the one mentioned here specifically prefer hiring those who are in need like this
This is absolutely a thing - it's the same mentality a pimp uses to identify and groom sex workers or other exploitative labor. The less stable/independent you are, the more control they can exercise over you etc
I know of a case when the salesman-CEO sold a freaking demo. (Helped the company to stay afloat, but the devs had to work hard to turn it into something of a product as fast as they could.)
Avoid startups where the CEO does / has done nothing but sales. Avoid them like the absolute plague that they are. If you are in such a place already, and you think things will get better, then I have a bridge to sell you. It is vanishingly likely that they won't, if only for the simple fact that the CEO has found a formula which works, and has no motivation to change it, and your best bet is to leave ASAP for the wider world which has infinitely more opportunity. (BTW, you won't succeed in changing such a "culture" for the better, so don't even think about it. I know you have.)
I could ramble on for several paragraphs, but BigJono has summed it up pretty concisely so I will proffer just this advice when sizing up CEOs and opportunities:
Remember, if there is any doubt, then there is no doubt.