What is the right timing for investment rounds?

No simple answer exists other than “before you need it.” In general, the longer you wait to raise any round of investment,

Some advisors would tell you to always raise more than you need because you have probably been overly optimistic in many of your predictions. Some advisors would tell you to always raise less than you need (i.e., be as lean as you possibly can be) because your company's valuation will always be higher later and you can raise less expensive money later. Only you can make this decision.

For additional details, see blog post, When Should You Ask for Investments?

Related Question:

How do I change the date of an investment round?