Eric Schmidt is to sell 5.8% of his stock in Google, valued at about $326.7m (£200m), the company said in a filing to US financial regulator, the Securities and Exchange Commission.
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Eric Schmidt has also been awarded $100m in stock and stock options, the first since he joined the company around a decade ago.
Mike Davis, senior analyst at Ovum, said the company was awarding Schmidt the payout for taking Google from a garage start-up into a multi-billion profit company during his ten-year tenure.
"The share cash-in could be due to Schmidt knowing something we don't, but he is probably just looking for a really good retirement," added Mike Davis.
Under the leadership of Schmidt, Google has branched into several new markets such as mobile devices with its Android operating system and the enterprise market with Google Apps. "The company certainly hasn't been resting on its laurels," said Davis.
During his time at the company, Schmidt has amassed 9.2 million Google shares, worth $5.8bn.
In his new role Schmidt will focus on deals, partnerships, customers and broader business relationships, while Larry Page will lead product development and technology strategy, the company said in a statement last week.