The company has done an excellent job of creating a positive environment for women, but this can lead to double standards. In the office, women make sex jokes of the same nature that you'd expect most women only to make in private with their female friends. It's generally understood that if a male employee were to make similar jokes, he'd be fired.
Most tech companies err on the side of not hiring an employee they're on the fence about, in the belief that it's more detrimental to the company to make a bad hire, than it is beneficial to make a good one. HubSpot wants to ensure it doesn't miss out on a rockstar developer. The way it reconciles these two competing interests is by hiring anyone the company could go either way on, but also firing them if, for any reason, it isn't working out after 3-6 months. What this means is it's possible to be hired by the company, placed in a situation in which it's impossible for you to succeed through no fault of your own, and fired three months later. In my case, I was placed on a team in which the tech lead was out recovering from surgery and the person who was supposed to be helping me was unavailable. After six months I was fired without the company ever trying me on a different team.
What Dan Lyons wrote about the company only caring about the bottom line is very true. The managers do listen, but only to large numbers. As an individual, you matter very little. I worked 10 hour days and on weekends to compensate for the absence of management I was given. I suggested pairing me to work with someone from another team for just a few days and it was ignored. People knew I was struggling, but not a single one ever offered to help me. The only management I was given was being told that anonymous members of my team had assumed I wasn't doing work, and because the team is more important than the individual, it was my job to figure out how to get them to stop. When I was fired, I saw a very different side of one of my managers. This was someone who was largely respected in the company and regarded as a sensitive, helpful manager. I was told I didn't have common sense and that I didn't belong in the field. I've since gone on to lead projects at major companies and be courted by some of the biggest names in tech, but once the company decides it doesn't need you, you see its real side.
The company's approach to management is very passive aggressive. They might hold a meeting telling everyone they don't want them to feel they have to work too long, but privately you'll be told you're underperforming and you need to get your productivity up.
Even though the company does take steps to create a feeling that you're around friends, the truth is many of the people will show a different side of themselves once you're no longer with the company. Only one person from the company has kept in touch.
The reputation about being the best place to work in Boston is largely hype that the company has created. During the years I've worked in Boston, the only people I've met who wanted to work for HubSpot were college students who bought into the hype. By contrast, I know several seasoned developers who know about this company's reputation and don't want to work here. Everyone in Boston knows someone who knows someone who got overworked by the company and either was fired, or quit.
Once you leave the company you'll meet multiple people who tell you they felt the same way as Dan Lyons but were less vocal about it, etc.