1. HIGH Turnover rate! Haven't been able to grow past 24 employees since every time they hire one person, two people quit.
2. Flaky product. The software goes completely down about once a week and with every release bugs are introduced. As front line of customer support, get used to lying and saying to the clients "We haven't had reports of any issues but let me send this over to the development team". Also, get ready to explain the difference between a URL and the address bar. You will get that "problem" about five times a day.
3. Terrible "benefits". The medical benefits are essentially catastrophic coverage for which you have to pay a huge portion of the premium. Stingy with time off, only 5 sick days and 10 pto days. No stock options or even a match on 401k. But you do get beer on Friday and an endless supply of chips!
4. Family business. Questionable qualifications of upper management, not a coincidence that everyone with a VP title is related to the President.
5. Bad "management" (this is just about the Operations/Customer Success management team). The best words to describe the management in this department are passive aggressive, unprofessional, gossipy and hostile. As there are no goals or annual reviews, management is unable to track any real metrics but instead your value to the company is based on if the manager personally likes you or not.