Ajit Jain has been a feature at Warren Buffett’s side since he left McKinsey & Co. to join Berkshire Hathaway in 1986, helping to grow the conglomerate’s suite of insurance businesses into a global powerhouse over the years.

Wall Street thought Berkshire had a lot of cash last year when the company had $189 billion of cash and cash equivalents on its balance sheet. But today, the conglomerate is sitting on a record $277 billion war chest -- a figure that equates to 27% of its current market capitalization.

Berkshire Hathaway sold Bank of America stock in nine straight trading sessions to close the month of August and into the start of September, resuming a sell-off that started in July when the bank's stock hit a two-year high.