Over the last 6 months, we have missed rent, missed billing customers, and missed paying all sorts of other things, including people. He refuses to hire a bookkeeper. Several other employees have approaches him as well, with similar results.
Not sure how big the company is, but this might be a sign that more than a book-keeper is the problem. There are a lot of startups that don’t hire an office manager, a do-everything administrative generalist who can everything from HR to finding a new office to accounting to payroll to scheduling, and more. This is a great job for someone non-technical who wants to get into a startup, they get to work directly for the CEO and see how the entire operation runs. If your CEO isn’t doing this stuff then he/she needs to find someone else who is reliable who can. Missing paying the people on your team is the last straw, and people will quit over it.