Typical comp shape
CTOs usually earn founder equity with 83(b), or executive rsu + psu. Common employers include Early and growth-stage startups, Public tech companies. Early-stage CTOs often hold large founder ISOs where 83(b) elections and QSBS eligibility dominate tax planning.
What Kentucky changes
In Kentucky, every RSU vest, NSO exercise, and ESPP purchase carries 4% state tax on top of federal. For a senior cto with $300k+ of equity income, the state layer routinely adds $25-45k to the annual bill.
Planning cadence
For a cto in Kentucky, the three planning windows are: after each RSU vest (withholding check and sell-vs-hold), before any ISO exercise (AMT model at federal only), and in Q4 (estimated tax top-up to clear the safe harbor).