Started as a Content Marketing Manager interview and developed into a potential Head of Marketing hire. The first interview was with the recruiter. The second interview was with the Chief of Staff. The third interview was with the CEO. The first and second interviews were great. I enjoyed speaking with the Chief of Staff (Rob) and after the interview, I felt confident that I could trust the leadership at the company. The third interview is where everything changed. The CEO (Jonathan) completely changed my mind about this company. As we began the interview, I had an opportunity to ask Jonathan a direct question to which he responded "holdon, let's focus on you. We are interviewing you, not the other way around". Interviews are a two-way conversation where the candidate is learning about the company and vice-versa. It should always be an open conversation. We moved on and Jonathan started to ask about my freelance work. He asked if I would be willing to reel back on freelance work if I was hired. I answer stating I'm open to this and have 1 client that's on a 6 month retainer. He responded by stating that's a "yellow-flag" for him. He then proceeds to say that whoever gets this job needs to grind, think about this job 24/7, and shouldn't be focused on anything else. He began to voice concerns about commitment, loyalty, solely because I am currently freelancing. I attempted to share that my client is contracted for a very small project with low hours but Jonathan actually cut me off saying "don't try to convince me". Jonathan proceeds to say "If I'm offering a salary, benefits, stock options, this should be your 100% focus". It's important to know that at this point, a job description had not been created for this role and none of the above-mentioned items were actually "on the table". There is not a single company/organization who has the jurisdiction to tell you what to do (or not do) in your spare time. The idea this CEO can try to tell a candidate that they can only work him is completely out of line. To summarize the remainder of the RED-FLAGS that a candidate should be aware of, I'll share some feedback that I received from an ex-employee. While doing my research, I noticed that many previous employees (middle to senior managers) had less than 1-year tenure before they left this company. I reached out to many individuals and they all shared similar feedback. 1) Jonathan has no boundaries. He expects you to be working before and after you leave the office. A 40-hour work week is not respected here. 2) Jonathan is a micro-manager. From top to bottom all things will be micro-managed and the closer you get to Jonathan, the worse it gets. This is especially worrisome as you consider growth at this company. The more you grow, the more you are micro-managed. 3) Proximity to the CEO (Jonathan) is the main driver for people to leave. Senior leadership has experienced heavy turnover for the past couple of years and all feedback points to issues working with the CEO. The word "toxic" was used to describe working here and I would recommend any candidate to research past employees and learn from their experience before working here.