Michael Bright, chief executive of Independent Insurance, this week increased his stake in the company by buying another 391,000 shares.
This takes his total shareholding in Independent to 6.1%.
At the same time, deputy managing director Phil Condon bought 261,000 shares, giving him a 1.64% stake.
Together they spent £1.5m, paying 244p a share – though the purchases failed to buoy the shares which slipped 16% on Monday.
Last Tuesday, Independent unveiled its results showing that pretax profits fell by 33% to £61.5m.
Personal lines suffered a loss of £6m, though gross earned premium in the motor account grew 18% to £21m.
Despite the drop in shares, the view of insurance analysts was that Independent was undervalued.
Later this year, the company plans a raft of internet ventures.