The pair join as the insurtech starts its ’next important expansion phase of markets’

UK insurtech Ripe Thinking has made two key senior appointments as it surpasses 300,000 customers.

The senior team will see Rob Styring join as chief financial officer and Simon Trott join as chief operating officer.

The pair have previously worked together leading Towergate Direct – the broker’s specialist retail division – with Trott as its chief executive and Styring as its finance director. 

Paul Williams, Ripe Thinking’s chief executive, said: “Styring and Trott join as we start our next important expansion phase of markets, products and superior delivery to our customers.”

Growth and success

Styring joins from Kingsbridge Group, where he held the position of chief financial officer, having formerly been a finance director for PIB Group, Thistle Insurance and Towergate.

Meanwhile, Trott was chief operating officer of legal specialists NAHL Group and previously held senior roles at RKH Group and Towergate.

Williams said: “Their expertise will help drive our continued success and the growth we know is possible. The whole Ripe team is excited to be working with them.”

The appointments reinforce the Manchester-headquartered company’s position as one of the UK’s largest insurtech companies providing easy-to-access insurance to leisure, lifestyle and SME customers.

This milestone marks a 50% increase in customers in less than three years, reflecting the ability of Ripe to offer products and services to power the growth.

 

The 2025 Insurance Times Awards took place on the evening of Wednesday 3rd December in the iconic Great Room of London’s Grosvenor House.

Hosted by comedian and actor Tom Allen, 34 Gold, 23 Silver and 22 Bronze awards were handed out across an amazing 34 categories recognising brilliance and innovation right across the breadth of UK general insurance.
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