The cons essentially come down to management, specifically the owner and the CTO.
In public, and in the big all-hands meetings, the owner says all the right stuff, and sounds pretty cool. The problem however lies in his attitude during work. To say it's horrible is being generous. He's got a very negative attitude, and is difficult to deal with on work issues. When he comes in, any greeting to him is usually received with a grunt at best - and that's if he's "cheerful" that day. Asking for input on a project can become very adversarial. After only a couple interactions after I started, I was worried - I wasn't sure why, but I was pretty sure he didn't like me. As time passed, I realized I wasn't singled out - that's how he talks to most everyone. Even folks on his inner circle have called him out on it, but it doesn't change. Worse yet, he has made disparaging comments about employees - within earshot of other employees. That's the pinnacle of uncool and pure poison to a positive morale. It was best to have technical discussions when he wasn't around, as he would interject himself into the conversation and contribute nothing but negativity, stilfling innovation and critical thinking. He had no capability of constructive criticism, only snide remarks.
As for the CTO, you quickly get the impression that he's someone who's not fully confident in his own abilities, so tries extra super hard and overcompensates. He has a presentation that he does about himself that essentially boils down to "look how great I am and all the cool things I do", and it's frankly kinda painful to watch. How do you know he wrote a book? Don't worry, he'll tell you. How do you know he worked at Princeton? Oh, don't worry. You'll hear it until it becomes a running joke. If trying too hard to sound legit was the only problem, he'd be mildly annoying, and if he did a good job as a leader, that would be tolerable. Unfortunately, that's not the case. He talks - constantly and at great length - and very rarely listens. He promises routine one-on-one meetings - and never delivers. Annual reviews are always late. Mine was over two months late, and that wasn't bad - others were well past that. Some folks actually had to put the review on his calendar and force the issue just so they could get the review done. At my review, he spoke about 90% of the time, and there were several things that I wanted to raise during the meeting that just didn't have time because he just... kept... talking. Amusingly enough, he often says that he wants folks to talk to him, and that it's an important part of the job - but when you try to talk to him, you wind up getting talked at, not having a discussion. You also get the feeling that when you are talking... he's not listening as much as he's politely waiting for his turn to talk at you again. I've actually had him ask a question that I had JUST answered - proving that he was paying absolutely no attention to what I was saying. Subsequently, you're less inclined to talk to him as you've learned that it won't be much except a lecture in his philosophy.
He also doesn't seem to trust the people who report to him, and so insists on being involved in far too many decisions, which winds up delaying important projects for far too long. It's pretty clear to see that he's under significant stress and that he's trying to do too much. Considering the owner's attitude towards everyone else, I can imagine the CTO's job is no picnic, but his approach is just making it worse for everyone. TThe original casual startup culture is dying slowly, being replaced by a culture which is far more corporate, with more and more meaningless buzzwords and fad ideas being piled on. People are becoming more and more unhappy, but staying on because of the perks.
Even before I left, I often said of the job that I've never had a job that I both loved so much - and yet put me under so much stress. The perks wind up being a form of "golden handcuffs", and you wind up convincing yourself that "it's not that bad" because other aspects of it are so good. It's not until you leave and find a place with really good management that you truly appreciate just how bad it was.
How can the company be so bad and still be #7 on the best places to work in PA? Because we would latch onto the good things, the things that showed us what it could be, and we tried not to focus on the bad things, the things that were killing us inside. We got on the bandwagon and bragged about how great our job was to everyone who would listen, maybe in the hopes that it was actually true, maybe trying to convince ourselves, maybe just trying to focus on the positive. Having worked in a corporate environment, it's not hard to be in this laid back environment and think it's all that. That carries through to surveys, where you answer maybe a bit too positively because you're trying so hard to view it in the positive light - you really want it to be true.
That's what is really tragic about this company. In so many ways, it is such a fantastic company, filled with great people who want to do great work and have fun and make some really cool stuff happen... and it's constantly soured by a negative owner and a CTO who seems to be far, far over his head. It could be so - SO very amazing. Another core value is "Create remarkable experiences" - notice how they don't say good experiences - just remarkable. I certainly had plenty of remarkable experiences in my time there. I just wish more of them were positive.