‘A movement’: How insurer Staysure is empowering over-50s to ‘dream big’

Insurance provider Staysure is on a mission to change perceptions of over-50s travel.

By injecting humour and looking to disrupt the way older audiences are represented in advertising through “can do” language, the insurer wants its ‘Dream Big. Staysure’ brand platform to set a precedent as it expands into new markets.

When CMO David Morley joined the Staysure Group – which also includes Petgevity and Avanti – 11 months ago he remembers thinking the firm was “missing a trick”. Morley believed Staysure’s marketing should reflect the lives its customers have lived.

“The way that older people are presented, I find dreadful. It’s appalling. The industry is really lazy, so we decided to do something about it,” he says.

According to Morley, Staysure’s latest work is better described as “a movement” rather than a campaign. The platform launches with a humorous TV advert on Boxing Day (26 December) and bespoke song ‘Where The Sun Don’t Shine’, highlighting that people of any age can travel and adventure. The idea is to target customers who want to get out and enjoy life. Morley wants Staysure’s whole customer base to feel seen.

“We want everybody to feel secure and reassured that no matter what they want to do, whatever their travel ambitions, they can achieve them because they’ve got Staysure on their side,” he says.

When testing the advert, some people – particularly “older women” – burst into tears as the advert made them feel “recognised”, Morley recalls.

Over third of public say older people ‘negatively stereotyped’ in ads

The new platform is part of a wider shift away from direct response and towards “storytelling”.

Alongside the TV ad, the campaign will span a range of channels, including radio, digital and, for the first time, influencer work. It is also the first time Staysure has produced a fully integrated brand platform. Morley also wants to make the song in the advert “famous”.

The Boxing Day launch is intentional as it is a “key moment” for travel booking.

“We want to be part of that consideration mindset, so it’s the right environment to pop up in,” he states.

Morley explains the category is growing, with more people being diagnosed with medical conditions and falling into Staysure’s audience. The insurer has no upper age limit and offers cover to people with pre-existing medical conditions.

Effectiveness will mainly be measured though spontaneous brand awareness via quarterly brand tracking, which also covers a range of other metrics such as penetration and usage.

Morley explains his C-suite peers are “committed” to the change in strategy, “rebalancing the plank” between brand versus response, with commercial targets being monitored on a daily basis.

Wider goals are to grow brand affinity and brand advocacy, with the Staysure CMO claiming he “doesn’t worry” about competition.

“What I worry about is my customers. That is our obsession within the organisation,” he says.

The way that older people are presented, I find dreadful. It’s appalling. The industry is really lazy, so we decided to do something about it.

David Morley, Staysure

The customer response and how much they choose to “participate” in the platform, such as through entering competitions, will be closely monitored.

“I’m a great believer that the strength of a great idea is how far it can travel before you have to put media money behind it. Media drives awareness, absolutely. But that doesn’t in itself change how people feel. It’s the messaging that changes how people feel,” he adds.

Going forward, Morley is using the brand platform as a basis for marketing across the group and he sees the concept “growing arms and legs”, as Staysure looks to expand into new channels.

Next year, the brand plans to expand into the US and Asia, meaning the platform will be executed in the UK first. The idea is to develop “a winning formula”, which can launch at pace into new markets. Last month, the company also opened in Ireland, with two other European markets set to be live in the first quarter of 2026.

“We intend to bring what we’ve been doing for the UK consumers in the last 21 years to the world. We want to become the biggest specialist travel insurance brand in the world,” says Morley.

The CMO is thinking about the “impact” the work has on customers and how that translates into business performance. While Staysure is the “mothership” brand, with regards the wider group there will be a “theme” that informs the storytelling push. Morley also believes in the importance of distinctiveness and making each brand stand out within its own market.

“What are we? Why are we different? Why are we better? And why should customers care? If we can answer those basic questions, then you have a go-to-market strategy that will enable you to win,” he says.

Best of both worlds

Prior to joining Staysure – his first brand-side marketing role – Morley worked in agencies for 32 years. When Digitas was Bronner Slosberg Humphrey, he was part of the UK startup team. Morley also spent time at Havas and Crazy Horse, before 19 years at Iris, rising to chief client officer.

During his agency days, his work was mostly focused on looking at the problems the team had to solve through its brand and marketing. With his own consultancy Trebla, Morley looked more at the “diagnostic elements”.

After having worked with Staysure via his consultancy and prior to that at Iris, Morley recalls a phone call with the firm’s founder and CEO Ryan Howsam in December 2024. Within 15 minutes, Howsam persuaded Morley to give up running his own business and come “help him transform the group”.

Howsam told Morley the group needed a “transformation”, a diagnostic mindset and “to know what brilliant brand work looks like”.

“You don’t get a good outcome if you don’t diagnose the right problem,” says Morley.

“That philosophy for me is really important, which is why I’m really proud of where we’ve got to with this piece of work, because it identifies a problem and it’s a human truth.”

He sees the insurance sector as offering a “tapestry of opportunity” as the “enabler of life”, with Staysure allowing customers to do things they may not have before, such as meeting their grandchildren in Australia.

We want to become the biggest specialist travel insurance brand in the world.

David Morley, Staysure

Working in a regulated industry such as financial services has been an “eye-opener” for Morley, who wants to reflect the regulatory responsibilities “in the right way” through brand and marketing.

He describes his team at Staysure as “the most talented bunch of people [he’s] ever worked with”.

“This perception that agencies hold all the talent and clients don’t is absolute nonsense. I have been so impressed with the quality and calibre of talent,” Morley states.

“It is part of my job, and my fellow colleagues on the C-suite, to create the right environment for that talent to thrive and part of that is completely new operating models, different ways of working.”

The team are currently looking at how data automation and AI can improve the customer experience, for example by helping consumers with medical questionnaires. Morley describes the experience of working in the sector as “humbling”, with some customer calls the team listening in on reducing them to tears.

“We’re dealing with flesh and blood [people], who are quite vulnerable at times and we have a duty of care. That duty of care goes beyond the regulatory commitments into just how we operate as a business,” he says.

With this in mind, it is important Staysure’s communications strike the right tone. Morley doesn’t want the brand to be “too earnest and too worthy”, and is keen for customers to feel like the firm “gets them”.

“We care a lot. We need that to come through in our communications as well, with the right tone, with the right cheekiness, a little bit of a smile,” he adds.

The Staysure CMO describes his job as the “best of both worlds” as he experiences the “rigour and the inside track on marketing through the customer lens”, but also the “pace, the dynamism, the excitement of working in an agency environment”.