Staysure

As Head of Content & Tone of Voice, I repositioned the UK’s leading travel insurer from reassurance-led and compliance-heavy to aspiration-led and culturally relevant.

The result was Dream Big – a new brand platform aimed at over-50s travellers, who are too often reduced to clichés: cautious, past their prime, risk-averse – even boring.

The song in our TV and radio ads captured the stereotype bluntly:

“You’re old, don’t be bold… Take up gardening, wrap up warm.”

In reality, our audience is energetic, enthusiastic, and actively planning their next adventure.

The platform was supported by a clear, joyful and commercially grounded tone of voice, rolled out across ATL, social, CRM and web.

I led the creative content strategy, built the TOV framework, and oversaw delivery across every customer touchpoint.

The Staysure ‘Dream Big’ rebrand

The Dream Big platform – repositioning a category

Travel insurance, particularly for over-50s, is generally functional and fear-based. But Staysure’s audience isn’t cautious; they’re adventurous and have a zest for life.

So we flipped the category narrative: from “stay safe” to Dream Big.

  • press ads

  • TV ad (playable)

  • social assets

  • homepage and website

  • birthday card

A joyful, current and helpful platform designed to reflect how over-50s actually see themselves.

TOV: the system behind the platform

A rebrand and TOV shift only works if that voice holds everywhere. I built this framework to make sure “Dream Big” translated consistently across every touchpoint – from press ads and CRM to social engagement and policy wording.

We summarised the voice in 3 words: joyful, current and helpful. The framework unpacked what that meant in practice.

Dos and don’ts

Every time I write TOV guidelines, I like to include a 1-page crib sheet giving dos and don’ts. Clients and employers find this very useful – because let’s face it, not every employee will constantly refer back to full TOV guidelines after the first read. It helps it land and stay front of mind.

New TOV: what good looks like, long form

Some before and after examples of how copy would look after the TOV refresh – in longer form here.

Everything gets the treatment – from social posts (which are pretty straightforward) to insurance policy wording. This is trickier, due to FCA and compliance regulations, but it’s still necessary to make sure a brand sounds consistent across the board.

I’ve deliberately chosen content that would usually get ignored.

Early ‘Dream Big’ ideation

Part of the joy of creating a new brand platform is the ideation work during the process. While I like the pun on ‘playa’ – being Spanish for ‘beach’ – for our international clientele, the banana hammock felt like a bit of a stretch (pun intended). So I buried it in the sand where it belonged.

Shouting about credentials

Brand proof and market position

Staysure is a multi-award-winning business. Officially the UK’s favourite travel insurance provider (9-time winner at the British Travel Awards at the time of writing), they seemed to lack a little cut-through compared to its competitors. So rather than 10 good reasons, I felt that 12 million good reasons – based on the number of customers we’ve insured – would be a good stat to lean on.

Staysure Expat

Pushing creative boundaries across the group

During my tenure, the business expanded its international presence. Alongside the core brand repositioning, I co-led creative work across other parts of the Staysure portfolio, encompassing ATL, web copy, bus decals and radio scripts. The brief was to grab the attention of an English-speaking audience in Spain with dashes of humour.