A new report has claimed that Direct Line has been holding talks with Winslow

Direct Line Group has approached Aviva’s Adam Winslow about becoming its new top boss, according to a report.

Late on Saturday night (19 August 2023), Sky News claimed that the group had been holding talks with Winslow about succeeding Penny James and taking up the role of chief executive.

James stepped down from the position earlier this year (27 January 2023), with Jon Greenwood moving into the role on an interim basis.

According to Sky News, it is not yet clear whether Winslow would take the role of chief executive.

The publication also stated that it was unclear whether other candidates remained in talks with Direct Line.

Both Aviva and Direct Line Group declined to comment when approached by Insurance Times.


Winslow joined Aviva in January 2021 as chief executive of international markets before leading its UK and Ireland general insurance practice.

Reports of him being courted by Direct Line came after the group saw its profits nosedive in 2022 after it was hit by the highest level of claims from major weather events since it listed a decade ago.

In a trading update earlier this year (14 March 2023), the insurer revealed its full year underlying gross written premiums (GWP) fell 3.2% to £2.97bn last year.

Of this GWP, £2.09bn was generated via own brand policies, although premium from this sector fell 5.5% year-on-year.

While the firm grew GWP for its motor direct own brands in Q1 2023 by 4.3% year-on-year, it warned that it had experienced further adverse claims development in respect of late 2022 and early 2023 in motor, particularly in relation to damage.

“This is expected to put pressure on earnings in 2023 including from prior-year reserve releases,” the firm said.

Later in the year (29 June 2023), the group was also instructed by the FCA yesterday to go back through motor total loss claims settled between 1 September 2017 and 17 August 2022.