The filing, which was submitted to the SEC on Tuesday, said that Guillen expected to sell 215,718 shares for $129 million that day, and that he offloaded 145,289 shares worth $89.6 million on June 14, and 90,111 shares worth $55 million on June 10.
Guillen, a former Mercedes engineer who was with Tesla since 2010, oversaw the company's entire vehicles business before being named president of the Tesla Heavy Trucking unit in March. He left the company on June 3.
The departure of Guillen, one of Tesla's top four leaders, including Chief Executive Elon Musk, has sparked market concerns about Tesla's future vehicle programs like the Semi electric truck and new batteries called 4680 cells.
Gordon Johnson, an analyst at GLJ Research, estimated that Guillen has cut his exposure to Tesla from 1.3 million shares a weak ago to about 150,000 as of Friday.
"Should TSLA be on the verge of technological and autonomous breakthroughs and breakout 2Q21E deliveries/earnings, as well as EV domination, why has what many assumed was the second most important person at the company (i.e., Jerome Guillen) sold $274mn worth of TSLA stock," he said in a report.
"It could raise some eyebrows for investors," Wedbush Securities analyst Daniel Ives said, adding that investors are going to watch closely to see if he sells more.
Stock options give employees and executives the right to buy their company's stock at a specified price for a certain period of time. When share prices rise above the exercise price, they can buy the stocks at discounted prices.
It was not immediately known how much Guillen paid to exercise the options.
(Reporting by Hyunjoo Jin, additional reporting by Jessica DiNapoli; Editing by Sonya Hepinstall and Steve Orlofsky)