Exercise early, sell everything
Does not transfer — and is backwards hereSchnitzer gives up 39 months of option life and takes an immediate ordinary-income hit because he has no alternative: in a US public company the spread is taxable at exercise regardless of whether he sells. His “sell 100% of net” rule is the rational response to a tax event he cannot defer.
A Canadian-controlled private corporation is the opposite case. Where options are over CCPC shares, the employment benefit under the stock-option rules is generally deferred until the shares are disposed of, not when the option is exercised — and the shares may also start the clock on capital-gains treatment and on the qualified-small-business-corporation holding tests. Copying the Travelers behaviour inside a CCPC throws away the single largest structural advantage you have.