Adam Winslow, Direct Line

Before joining Direct Line Group, Winslow was CEO of UK and Ireland general insurance at Aviva, where he played a pivotal role in driving growth and operational excellence, which was no doubt what turned the heads of DLG’s board when they were looking for a successor for Penny James.

After seeing off a bid from Ageas at the start of 2024, he quickly hired a team – including a few of his former Aviva colleagues, most notably finance director Jane Poole – to deliver the greater operational efficiency he feels is essential to ensure the company becomes “the customers’ insurer of choice.” 

At half year results, Winslow announced the group had delivered strong premium growth and returned to profitability, demonstrating the actions taken were beginning to make a difference, which must have turned the heads of the top team at his ex-employer Aviva.

On 23 December, DLG’s board announced it was recommending the offer from Aviva of £2.75 per Direct Line Group share be accepted – a significant uplift from the £2.02p share price when Winslow joined on 1 March.

The offer won the backing of both sets of shareholders at the start of this year, and the deal is now just awaiting regulatory approval. 

While the finer details of the mega merger of these two brands is being finalised, Winslow is pushing ahead with plans to drive Direct Line Group back to consistently posting profits he outlined last July.

Given that for 2024, operational profit stood at £205m, a huge £316.6m improvement on the year before, which was helped by a much improved motor performance, he clearly seems to have got the group back on the right track.

Direct Line launched three new branded motor insurance products on Compare the Market in December 2024, produced two new apps, and signed a deal with Apple allowing Green Flag to be the first UK breakdown brand to offer roadside assistance via satellite.

Reconfirming its commitment to diversity, equity & inclusion, under Winslow the group earned recognition as the 12th most inclusive UK employer in the Inclusive Top 50 UK Employers index, and supported more than 11,000 disadvantaged young people through its Community Fund.

The group also made significant progress on its environmental, social and governance commitments in the last year and remains on track to deliver its operational and investment science-based targets.

It has improved its Carbon Disclosure Project (CDP) score by two levels to a B, earned AAA rating from MSCI, and achieved a 9% reduction in Scope 1 and 2 emissions compared to 2023.

Additionally, 95% of DLG’s accident repair centres now use hydrogenated vegetable oil, dramatically cutting emissions from its recovery fleet.

The group is also accelerating its transition to cleaner energy, converting three more paint spray booths from gas to electricity.

What next

Turning from a greener world to what the future could hold for Winslow, as DLG becomes part of Aviva it is worth noting that in the past he served as CEO of Aviva’s international businesses, overseeing operations across multiple markets.

His CV also includes leadership roles at AIG, where he was CEO of global life insurance, and CEO of AIG Life UK.

As the dust settles on Aviva’s mega merger with DLG, it will be interesting to see if the life side of the sector entices him back, and whether he sticks with these shores or heads overseas.

Winslow holds a master’s degree in European Business from ESCP Business School in Paris and a bachelor’s degree in history with French from York University, so language is no barrier and he is certainly capable of powering any business across the globe.

However, given what he has achieved to-date in his career, he is certainly a contender for replacing his former boss Aviva Group CEO Blanc at the top of a future Post Power List if he sticks with the general insurance side of the market following the merger of DLG and Aviva.

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