CMO option grant

I'd be surprised if a company like you described would be asking this question. The question to ask isn't "what percentage" but rather "how much value" to give.

Ultimately, rather than determining a percentage of ownership, you should be determining a dollar figure of value that you think the role is worth, then offer them that value as a combination of cash and shares.

You mention 4 rounds of financing... based on that financing, you should be able to determine a share price for the company. So, as an example, if you determine that the share price was $1/share, and you want to give the person $100k in cash and $100k in shares, then you'd be giving them 100k shares as part of their compensation package.

This is, however, an exceptionally rudimentary example. You'd need to balance a few other questions as well:

• How many shares do other executives have?
• Are you sure you want to use shares, rather than share options?
• Over what time period would the shares vest?
• Are you issuing the shares from treasury or an existing compensation pool?

Best of luck!