Gregory joined John Poland Members’ Agency in 1986 looking after Names’ funds at Lloyd’s. In 1989 he joined Caudle Hilsum which merged with Scott Underwriting in 1992. In 1993 Scott Caudle Hilsum merged with R K Harrison to form Vantage where Gregory became a senior account Manager. In 1994 he joined Wren Underwriting (Brit Plc) as head of client liaison until the Members’ Agency wound up in 2000. In 2000 he joined HAL where he also sits on the Hampden Underwriting Research Committee.