Pain - you shouldn't hire a new accountant until your current accountant is unable to complete their work in a normal workday. You ask your accountant to work a couple extra late nights and start looking for another accountant. Wait until the pain has reached its peak, then relieve it. In the meantime, there's a waiting period to put a job posting out, wait for responses, interview people, do background checks, hire them, let them give 2 weeks notice at their current place, and then train them. From the date you decide to hire a new accountant, you may be putting extra stress on your existing team for another 5-6 months.