Some experiences with this in my personal capacity: You want someone who has a working style which is compatible with your working style. There are a surprisin

Some experiences with this in my personal capacity: You want someone who has a working style which is compatible with your working style. There are a surprising number of accountants who cannot reliably receive a folder that has been Dropboxed to them. Some of them are good accountants... for other people. If you are e.g. an email person, you do not want a phone person accountant. You want an accountant where neither of you are annoyed with the other's expectations with regards to timeliness of replies to emails. You want someone who is capable of understanding the fundamental nature of your business. They don't have to be able to _operate_ the business, but they need to _deeply_ grok the mechanics of the business, because accounting is a facts-intensive profession and they need to understand your facts to apply GAAP and IRS procedure (etc) to them. You can be a great small business accountant without knowing what the difference between SaaS, Github Enterprise, and Microsoft Word is; you cannot be a great accountant for a software company without being able to understand the differences in those three products. You want someone who is generally good at accounting. Like any other profession, there is a competence curve. Don't hire the people at the left end of the competence curve. You want someone who is good at being a professional, partly because that will make interfacing with them easier and partially because a portion of the services of an accountant is to suit up occasionally and say "I am an accountant." to third parties. You want someone who can cause the appropriate reaction there. (Most commonly tax agencies, but there are a variety of potential counterparties, for example e.g. mortgage lenders, prospective landlords, immigration agencies if that is relevant to you, business counterparties, etc.) Some of y'all might have interesting situations, and very interesting situations often counsel having a specialist. A particular interesting situation which I have in my life is that I'm an American who lives in Japan; that fact substantially complicates accounting for my businesses or personal life, both with regards to tax preparation and with regards to just giving good financial advice, and I get far better results working with people who specialize in international clients than I get with (presumably) skilled accountants who are willing to work with international clients but don't wake up and breathe the US Japan Social Security Totalization Agreement. More relevantly to HNers, I think that you probably have special circumstances if: you do a material amount of investing in things that your average dentist does not, you own a material amount of equity, the character of your life is intrinsically international, etc. (Running a business is its own flavor of complication.)