The company was established, based on business plan prepared by David Gundlach and Andrew Bowen, as "Hastings Direct" in 1997.

[4] In 2011 the company announced that 150 new posts would be created, with the first 60 to be recruited in January in the Bexhill, Hastings, Eastbourne, Brighton and Hove areas.

[7][8] In 2012, the company launched a usage-based insurance product under the Hastings Direct YouDrive brand.

[13] In August 2020 it was announced that the company would be acquired by a consortium of the South African business, Rand Merchant International, and the Finnish insurer, Sampo Group, for £1.7 billion.

[15] The company sponsored the Eastbourne International tennis tournament between 2003[16] and 2007[17] in a deal worth £350,000 per year.