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Dear Quota Team,
I work for a startup. It’s the first time in my life I’ve worked for one, and to say the learning curve is steep would be a huge understatement. I was brought on less than a year ago to head up and build out the sales team. Before this, I was a VP of Sales for a well-established (non-public) tech company.
Here’s the problem: the CEO! I don’t know if there is literally something wrong with this guy psychologically, but in the last several months, he’s been a complete disaster. When he first brought me on, he seemed fairly normal. Friendly and competent-seeming, though he did do a lot of name-dropping which I thought was a bit weird.
But I bought into the vision, and joined. And in the last six months, he’s been super erratic, and oftentimes MIA. He comes into the office (our engineering staff is remote but we’re mostly in-person), a few days a week, stays for an hour or two, then says “I have to go to my attorney’s office,” or something similar and then leaves. He also used to talk a ton about fundraising prospects, but that has pretty much subsided over the last few months.
And on top of all that, he is constantly on my case about hitting wildly unrealistic numbers that our product is not even close to justifying. At this stage, we should basically be working with our existing customers to evolve the product and make it sticky as possible before going upmarket, but this CEO is literally asking why we’re not landing Fortune 500 deals. It’s kind of nuts.
Is it possible that I agreed to work for a literal crazy person, or do you think this is just an early-stage thing. I have read a lot about eccentric CEOs being able to grow their companies into unicorns, but I have a sinking feeling that this guy is not eccentric, he’s just a moron. What are your thoughts?
Frustrated on the East Coast
We can’t tell you whether your CEO is crazy, because none of us were smart enough to become psychologists. But we have collectively worked for (and started) enough startups to know that he sounds checked out – or worse.
The erratic thing is a red flag, but necessarily a flashing alert signal. As you pointed out, there are plenty of erratic and capricious CEOs who take their companies to great heights, though they’re not usually the type of people others enjoy working for.
What really worries us is that the CEO isn’t showing up at work, and isn’t out fundraising or selling clients instead. If he’s just hanging out with his lawyer or going to the gym, or the bar, then that isn’t the kind of person who is going to lead the company to success.
And if his chances of raising another round of funding to keep the company going have dried up, then he might feel like the walls are closing in and might be trying to avoid taking the responsibility or breaking the news. Our advice (with the caveat that we don’t know the full situation): find another role. This company might work out, but it’s not looking so good.