They are a strange set up on account ownership, it becomes like real estate and reps sit on accounts for years - some people have built their career on 'owning' the right companies in the sytem - I got in 5 years ago so I've always benefited from this but the newbie's struggle to build a capacity of decent companies.
The stamping system for territories can be frustrating. Anything over 200 employees marked corp, seems unnecessary.
The product has been hard to sell to enterprise businesses - this is improving and HS's offering is getting more robust every month.
Sometimes Sales and Services don't see eye to eye but that has been the same where ever I've worked
There is not a lot of real hand raisers looking to talk to you about Hubspot, if you have the right attitude and take ownership of your pipeline this can easily over come but I remember being really surprised about the quality of top of funnel when I started.
They really try to make the culture positive, this could actually be in the Pro bucket if for some people. I become uncomfortable sometimes with some of the culture events as I don't know what to say or what the right approach should be on sensitive questions like race or politics. Some people like to have these discussions at work but I'd prefer to get on with the job.