Insurance sector needs to show that it is ‘never too late’ for a second career

Among the many professionals that have spent decades working in the insurance sector, a common refrain is that once you’ve spent a couple of years in insurance, you never leave.

This is usually said with a wry, welcoming grin to newer staff, but the essential message is thus – insurance is such a good career that, while people may bounce around different employers, talent rarely finds a reason to leave the industry entirely. 

Analysis from insurance-focused LNJ Recruitment, published in 2025, found that while the average tenure with an employer in the UK insurance sector is just 2.8 years, 60% of professionals in the industry have been in insurance for over 10 years, with around 10% having stayed with on employer for more than 30.

The numbers are telling – and raise a broader question. In addressing the talent shortage, should the industry do more to attract professionals that have retired or moved on back to the sector?

Speaking to Insurance Times, Roger Flaxman, chairman at claims advocacy firm Flaxman Partners, quipped that after 50 years in insurance he had only just completed his apprenticeship.

Starting his career as a Lloyd’s broker and claims adviser in 1969, Flaxman spent much of his working life in the London market before he reached an inflection point 25 years ago, when he suffered a severe illness that forced him to restart his career at the age of 50.

Unwilling to retire from insurance broking and anticipating redundancy, he set out to launch his own independent advisory firm in 2000.

And, as a result, Flaxman feels strongly that there is a “massive talent pool” of experienced people aged over 50 who could be persuaded to share their expertise with the industry.

For a sector facing a looming succession gap rooted in an ongoing talent shortage, this could represent an untapped talent pipeline.

According to recruitment firm Hays UK’s insurance salary survey 2025, 84% of insurance employers experienced skills shortages over the previous year.

Similarly, in a report entitled ‘The talent shortage crisis’, published in April 2024, the Chartered Insurance Institute (CII) revealed that 25% of the UK insurance workforce will retire within the next decade.

For Simon Caplan, chief innovation officer at recruitment firm Arthur Financial, the consequence of this imminently retiring workforce is that “a lot of insurers are facing the risk of losing institutional knowledge”.

As these experienced professionals retire, he explained, the bigger picture is that they are “essentially taking those relationships, commercial judgement and knowledge with them”.

He continued: “It’s increasingly difficult to retain that because there are more people at the end of the spectrum in the market. There are other reasons why we have talent shortages, but that is one that I can foresee exponentially getting bigger.”

Giving back

As the population’s working lifespan extends, Flaxman explained that many people retiring from careers in insurance only realise they want to return to the industry when they start to “miss what they had”.

Alongside gaining a sense of purpose in returning to working life, he noted that there is a “humanitarian aspect” to using decades of industry experience to “give back to society” by mentoring clients and brokers.

Flaxman noted: “For example, I was involved with a local event last year which was going to be cancelled two days before because the broker said he couldn’t get insurance for the event to go ahead.

“Now, they’ve had insurance for 10 years and then suddenly the insurer says it [cannot be insured] because there’s an adverse risk. Somebody phoned me up and asked what to do and I knew exactly what to do.

“It was a mistake by the person in the insurance company where they misunderstood something and pressed the wrong button on the computer – so the computer said no. This happens all the time, more so with computerisation.”

This type of experience does not just come from a textbook, he continued, but comes from having seen the market cycle a few times, seeing real life examples and going through “a few bashings yourself that everybody goes through in a career”.

However, Michael Wilson, regional director and senior advocate at Flaxman Partners, who himself has worked in the insurance industry for over 40 years, added that this talent pool may need some persuading to return.

He explained those made redundant or retiring in their late 50s and 60s “might not have the confidence to do something with their knowledge, because they’ve never really considered that there’s anything special about it”.

“Maybe they just don’t realise that without some of the older people the context of insurance and why things are done in a particular way have been lost,” he continued.

“Some people might retire thinking ‘thank goodness’ I’ve put that behind me now. It’s only after they’ve become bored and disillusioned after a couple of years that they wish they’d done something else, but then they feel that it’s too late”.

Beginning again

Proving it is never too late to return to the insurance industry, Lucy Luckett, products and wordings associate at Willis Towers Watson (WTW), rejoined the sector after a 10-year hiatus.

Luckett began her insurance career at 17 as a claims handler at Commercial Union, where she spent a decade before leaving in 2001 to raise her children.

She returned to insurance in a part-time position at Covéa Insurance in 2011, where she worked as a claims handler and liability specialist before progressing to team leader.

Prompting her return to the sector was a change in circumstances when she separated from a partner, leading her to return to full-time work to regain financial independence.

In a five year whirlwind, Luckett took up several opportunities at different firms, including at equine broker KBIS, Partners& and WTW in positions where she gained experience in liability claims, developed as a broker in a claims environment and eventually landed in products and wordings.

She told Insurance Times that reaching a certain age gave her the “freedom as a woman” with grown up children to pursue these different roles, each of which she has taken new “experience from”.

And, she added that her experience transitioning from an insurer background into broking has given her an insight into “what insurers should be doing” to better support brokers and their clients.

She continued: “I’m not just that broker that shouts “this is what you should be doing”. I know [insurer] processes. I know what they should be looking for because I spent 30 years being an insurer, but I recognise the challenges of both.”

‘Commercial judgement can’t be downloaded’

One of the biggest challenges for broking specifically is that many account executives retire or leave the industry before they’re truly ready, simply because of the pace and pressure of the role.

This was the overarching view shared by Karen Weir, owner and founder at Weir Insurance Brokers, who explained that most of these professionals exiting the industry “still have so much to offer”, which could have a positive impact on the next wave of industry talent.

Weir said that she has seen a couple of experienced account executives that “spent years mentoring an account handler gradually step back as their mentee stepped up”.

The result is almost a role reversal, she explained, as the “experienced professional moves into a lower pressure nine to five role” while the next generation “takes the lead and accelerates their career”.

She added that this “win-win” for the industry could be made more lucrative on “short-term or project-based contracts”.

“Rather than losing decades of expertise overnight, we could tap back into that intellectual capital when it’s needed, giving businesses access to invaluable experience while offering seasoned professionals a more sustainable way to stay involved in the industry,” she continued.

“There’s simply too much knowledge walking out of the door for us not to find better ways to keep it within the profession.”

Similarly, Arthur Financial has seen a demand for senior leaders to return in mentor roles to develop and support their successors, Caplan noted.

Speaking to Insurance Times, he explained that this demand shows that “technical capability” and “commercial judgement can’t be downloaded”.

He continued: “Commercial judgement comes from people who’ve navigated the market for many years and seen market cycles, claims events, regulatory changes and organisational transformation.

“I can see these individuals being leaned on more and the market is receptive, but insurance is quite slow to react in general.”