Vantaggi
The previous CEO and developer partner created a good product. The existing customer base is fairly loyal, and may support the company for some time. There are some good, smart people there. Benefits are decent.
Svantaggi
The company is in a precarious position because it offers essentially one product, which was built up organically for 25+ years. It has thousands of features. Maintaining this mountain of technical debt is likely to become infeasible in the near future. The company's future relies on rebuilding its software using new technology, but the development effort faces serious impediments; 1. There is no technical lead or manager. 2. The non-technical CEO does not trust developers and makes decisions for emotional reasons. 3. There are very few requirements, because no business analyst has ever been hired. 4. Visible results are prioritized over good architecture, refactoring, unit testing, etc. 5. Morale and productivity are damaged by backward views, e.g. "Code shouldn't go to QA with defects" and "If it takes more than a couple days, it's being done wrong". 6. An inexplicable choice to cling to the original obscure, creaky DB and jungle of a "schema". I estimate that these factors reduce development efficiency by 80% There is no performance review process. The value of my work was almost never recognized. My level of stress was very high much of the time.