Since early June he's sold $50 million worth of shares in over 70 transactions, mostly in the $51-$58 price range, according to records kept by Insidertrading.org.
These were all scheduled transactions, meaning they were planned in advance and are not in reaction to something going on at Salesforce.com. He is clearly just cashing out of some of his stake.
And, even with the sell-off, it hasn't affected his stake much. Benioff started with over 40.8 million shares and, as of the last two transactions on August 1 (20,000 shares, for just under $1.1 million), he still had nearly 40.1 million shares left.
Salesforce.com declined comment when asked why he's been selling so much.
As we previously reported, this is (or at least was) out of character for him. While other top executives routinely cash out of their stock options, month after month, year after year (Sheryl Sandberg for instance), Benioff didn't sell any shares in 2013, according to Insidertrading.org, nor did he schedule any other transactions prior to June of this year.
And it's not because the stock is on some kind of high. The stock is doing well but hit a high of $67 back in March before the sell-off.
It could be to free up money for other investments, or to help him pay his charity commitments. For instance, in April, he and his wife, Lynne, made a second $100 million donation commitment to UC San Francisco for children's hospitals in San Francisco and Oakland.
In any case, sometimes we do stop and marvel at how quickly a CEO tech billionaire can lay his hands on $50 million. He merely sells a tiny portion of his stock.