’I’d like to say a big thank you to everyone who has supported me,’ says departing top boss

By Miles’ cofounder and chief executive James Blackham has announced he will be leaving the business.

In an announcement on LinkedIn today (13 October 2023), Blackham, who helped launch the pay-by-mile insurtech in 2016, said he would be replaced by chief commercial officer Maddy Howlett.

Since By Miles was founded, it has sold over 100,000 policies and currently has around 50,000 customers – it also writes around £26m of gross written premium (GWP).

The firm was acquired by Direct Line Group earlier this year (25 April 2023) as part of the insurer’s plans to strengthen “digital-first” journeys for customers.

Blackham said watching By Miles “thrive with the benefit of their scale and support has been truly remarkable”.

“After six years, hundreds of thousands of members and over 500m miles insured, today is my last day at By Miles,” he said.

“I’d like to say a big thank you to everyone who has supported me and By Miles over the years, to the wonderful people at By Miles who have made it such a special place to work and to Direct Line Group who have welcomed us in this year.”


Successor Howlett joined the business in August 2021 after spending 18 years with British Gas.

She held several senior roles at British Gas, including head of commercial portfolio and head of customer experience and journeys.

Blackham felt she would do a “fantastic job” when taking over as the top boss.

“I’m handing the steering wheel to the amazing Maddy Howlett, who I know will do a fantastic job driving the business forward,” he added.