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Interview: Simon McCulloch, Chief Commercial Officer, Staysure

Travel Insurance
31 Oct 2025 | Editorial Team
Featured in ITIJ 298 | November 2025
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Illustration of a man holding a data sheet on health

Mandy Langfield speaks to Simon McCulloch, Chief Growth Officer for UK-based insurer Staysure, about the company’s latest policy adaptations and enhancements

What’s your background in the insurance industry, and how did you come to your current role with Staysure?

I started my career in the retail banking and mortgage industry, and this led to me running a home insurance business for Countrywide in the mid-2000s. I saw the emergence of comparison sites as a game-changer and joined Compare the Market in 2011, initially leading the money team and then in 2012 becoming Director of Insurance, responsible for the P&L of all their insurance products. In 2016, I became Commercial Director, looking after all demand and supply-side partnerships, focusing on expanding the panel of providers, commercial revenue growth, and pricing competitiveness.

In 2020, I joined HSBC as Global Head of Digital for Wealth and Insurance, leading on projects to grow insurance sales for all wealth and insurance product categories across 64 markets, with a focus on improving digital experiences, online share of sales, and launching new propositions.

The role of Chief Growth Officer at Staysure came up in 2023, in which I’m accountable for the Group’s growth businesses, which includes ROCK (partnerships), PayingTooMuch (travel insurance comparison), price comparison distribution (Avanti Go, Insurefor, BigBlue), expat and international markets. Insurance has a unique draw as it’s set apart from other financial products as it directly impacts on people’s lives – it’s about protection, reassurance, and being there when it matters most, which makes the work feel genuinely meaningful.

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Staysure has enhanced its medical travel cover so that customers awaiting a diagnosis can still be protected for their already diagnosed conditions. Previously, these individuals faced significant exclusions or were left with limited cover options. What prompted this move by the company?

As with everything we do, this change was driven first and foremost by our customers. The growing number of people on UK National Health Service waiting lists too often find themselves in a sort of insurance limbo, where they’re unable to obtain meaningful travel cover because they have symptoms under investigation. We wanted to offer a more compassionate and flexible solution that protects what is known about a customer’s medical situation, rather than penalising those who are waiting for answers.

How difficult was it to persuade the underwriter to cover these risks?

Introducing cover for diagnosed conditions while excluding undiagnosed symptoms was a nuanced underwriting conversation. It has taken a combination of collaboration and strong data to show that this segment could be insured responsibly. Our partners recognise the need to support customers facing diagnostic delays, and together we’ve found a way to build safeguards into the product while making sure it meets important demands.

Now you’ve made this bold move, do you think other UK travel insurers will follow suit?

As customers’ awareness grows around what different policies do and don’t cover, they’ll start to ask tougher questions of their providers. It’s likely the industry will continue to evolve in this direction, but we’re proud to be among the first to have taken action.

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Looking at claims data, what proportion of the claims you pay each year are for medical versus baggage, cancellation, etc?

Claims type

Avg %, 2023–24

Baggage

7.7

Cancellation

42.0

Medical

34.3

Travel delay

11.6

Other

4.4

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Are claims costs increasing faster than premiums?

Medical inflation is still a major cost driver. Treatments abroad have significantly increased in price in recent years, particularly post-Covid, and fluctuating exchange rates can amplify that. At Staysure, we strive to price fairly for our customers amid cost pressures, and we’re working hard to keep our products sustainable through smart underwriting.

How can the industry engage more with customers to explain the issue of medical declarations and tease the right information out of them at the point of sale? Are the current questions people are being asked not good enough?

Medical screening needs to be simple, though definitely not simplistic. It’s just as much about how we ask questions as about the questions themselves. The language has to be straightforward, and it helps to have explainer prompts on screen alongside digital interfaces and chatbots that adapt to customers’ questions and answers. At Staysure, we’ve worked hard to make this part of the journey feel accessible and comprehensible, so that customers aren’t drawn to under-declare or disengage.

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What trends is the company seeing with regard to single-trip versus annual trip purchases,
and senior travel habits in termsof length of trip and Europe versus worldwide destinations?

Single-trip policies continue to take the lead, making up around 55% of all sales across our brands, compared to 45% for annual multi-trip cover.

When it comes to destinations, Europe dominates our customers’ preferences. Spain (including the Balearics and Canary Islands) is by far the most popular destination, followed by Greece, France, Portugal, and Italy.

We’re also seeing most customers booking their travel insurance within two months of departure, with the eight to 60-day window being the most common lead time across both Staysure and Avanti products. That said, a sizeable share – more than 29% for Staysure and 35% for Avanti – book more than 60 days in advance, indicating a growing segment of customers planning longer or more significant trips well ahead
of time.

Partnerships with online travel agents, airlines, banks, comparison websites, and insurance brokers are just some of the ways in which insurers are able to increase their reach in the market; which ones does Staysure believe have the best long-term benefits?

Direct-to-consumer remains core for us, but we’re expanding strategically. The recent launch of Avanti Go on MoneySuperMarket marks the first time we’ve brought one of our flagship brands to price comparison websites, allowing us to broaden access to specialist cover for older travellers and those with pre-existing medical conditions. As habits shift, we’re going to see smart digital partnerships, particularly in the price comparison website space, playing an increasingly important role alongside trusted direct channels.

If you could change one thing about the UK’s travel insurance market, what would it be?

It would be brilliant to see more consistency in how pre-existing medical conditions
are treated across the market. At the moment, two products might look similar on the surface but perform very differently when it comes to medical cover. That can confuse and disadvantage customers at the point of claim, so a more standardised framework would go a long way towards supporting transparency.

What do you enjoy most about your role with Staysure?

What I enjoy the most about my role is being part of a business that’s not only a leader in travel insurance but is also constantly pushing the boundaries of what’s possible in the industry. There’s a real sense of purpose in helping people (especially those with pre-existing medical conditions) travel with confidence, and it’s exciting to be part of a company with such a clear, ambitious direction. The pace of innovation, combined with the opportunity to shape how we support customers around the world, makes it a genuinely inspiring place to work.

Cover of the magazine ITIJ

November 2025
 Issue

In this issue of ITIJ we look at current travel patterns to and from the US and Europe, take a close look at the Italian healthcare system, and examine how insurers are adapting policies and coverage to manage weather-related challenges.

Read full issue
Travel Insurance
31 Oct 2025
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Editorial Team

The Editorial Team updates the ITIJ website daily, and works on features for the print edition. With expert industry knowledge and years of experience in writing about complex travel insurance issues, the Editorial Team is ready to investigate and report on the topics that matter most to ITIJ's readers.

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