Free tool
Cutting Board Size Calculator
Enter your longest knife and your counter depth and this suggests a board size that fits both.
How this works
The rule of thumb is a board several inches longer than your longest blade, so the tip and heel never hang off the edge, and a depth that leaves some counter free in front of it. Larger jobs get extra length.
Sources: USDA FSIS: Cutting Boards and Food Safety for board hygiene.