You're smart to ask this question now, because in my experience things often do go bad between business owners and their CFO or top accountants. The biggest culprit is an owner who's demanding more from his or her accounting team than those people are qualified to handle. When I go into companies to help with CFO-level needs, I'm often welcomed with open arms by controllers who have been beat up for months, even years, over expectations that are impossible for them to meet.
Bookkeepers are trained to collect and enter transactions into your accounting system, then produce an income statement and a balance sheet. Controllers can produce financial statements and conduct some basic analysis, such as areas of the business where costs are out of control or where savings can be had. A CFO takes those reports to make strategic insights for the company and figure out how to pay for them, which may involve preparing the paperwork to secure financing. If you're expecting more from people than what they're trained to do, guess what? You're banging your head against the wall.
The disconnect often starts right at the beginning. I've heard many business owners say they're looking for a CFO. When I ask about the proposed salary, I'm astounded by the low numbers that are typically tossed out. In most industries, a CFO with more than 20 years of experience and a CPA or MBA can expect compensation starting at $250,000, plus benefits, bonuses and stock options. Similarly, good luck finding a controller with high-level accounting education, who may also be a CPA, for less than $100,000.
In my experience, as companies grow, the finance department is usually the next-to-last function to get adequately built up with expanded systems, updated processes and the right people. (The last is usually human resources.) I believe that investing in accounting people and systems should be an integral part of growing your business. Otherwise you risk losing financial control.
Granted, as a CFO, I'm biased toward spending money to get the right person for the job. If you skimp in this department, you may think you're getting a deal, but the bookkeeper you keep pressing to do controller-level tasks won't see it that way.