Pros
This place has pushed me in a lot of ways -- it's almost overwhelming the number of different skills, tactics, knowledge, frameworks, etc. that I could choose to focus on and learn from my colleagues, customers and prospects.
I love the autonomy, I love the opportunity to move around internally and work cross-functionally. If you are comfortable seeking out opportunities and taking big jumps in your career, this is the place to do it.
Brian Halligan, Dharmesh Shah and JD Sherman are some of the most transparent (and very different from each other!) leaders I've ever worked with. The fact that we have access to their thoughts, concerns, vision, etc. in REAL TIME and at our fingertips at any minute means we can all do our jobs that much better.
Plus - you can't beat the community, friendship, and honestly, family that you meet here. I spend more time with my co-workers than my actual family, so they better be good people. And let me tell you - they are.
Some highlights over the years -- I've worked with executives who have opened doors for me and written recommendations that I would never have even met in person at a different company. I've had a diverse set of mentors that seem to have fallen in my lap -- something I never found though sought at other companies. I take classes every year that HubSpot pays for to help me add to my skillset and my value to this (or any other) company. I work when I want, where I want, and have a team to support me. I have a manager whose #1 goal is to see me get promoted and succeed, whether it's on her team or not. I have equity as a top performer. I get to travel globally to meet customers and speak at events.
Cons
Things have certainly changed over the course of the past half-decade (what company doesn't when going from 300-1500+ employees that rapidly?) We've retained our culture but our processes and day-to-day workflows have certainly changed. This isn't a con so much as a result of growth that any employee must learn to adapt to at any growing company. If you're thinking of joining -- know that you are NOT joining a startup. The culture feels like it, but experience in a larger company and how to navigate throughout an org will be a huge value add.
You're never going to get paid the highest salary at HubSpot. It's just not the case, but there is huge opportunity and benefit outside of your annual salary. Read the last paragraph of my Pros section -- if you care about money more than these things, you may find this as a con at HubSpot.
