Anna Wilson-Jones is the actress in StaySure's 2026 'Dream Big' TV advert. StaySure confirmed her involvement on their official Instagram account (@staysuretravelinsurance) on 31 December 2025, asking followers "Did you spot Anna Wilson-Jones in our TV ad?" The role is also listed on her IMDb profile under Other Works with a 2026 date.
Wilson-Jones is a British actress born in Surrey in 1970, best known for playing Lady Wilhelmina Coke in the ITV period drama Victoria. She has also worked across theatre, film and television since the early 1990s. The 'Dream Big' campaign launched on Boxing Day 2025 during ITV's The Masked Singer.
Who is Anna Wilson-Jones?
Anna Wilson-Jones has been a working British actress since the early 1990s. Her best-known role is Lady Wilhelmina Coke in the ITV historical drama Victoria, where she appeared opposite Jenna Coleman. Other television credits include Hotel Babylon, Mistresses, Monarch of the Glen and Holby City. She has also worked extensively in theatre, with stage roles in productions at the Royal Court and the National Theatre.
She was born in Surrey, England, in 1970. The StaySure 'Dream Big' commercial is one of her most prominent 2026 commercial appearances and now sits on her IMDb profile alongside her drama work.
The 2026 ‘Dream Big’ campaign
The advert is part of StaySure's 'Dream Big' campaign, which launched on Boxing Day 2025 during ITV's The Masked Singer. The 90-second TVC, titled 'Where The Sun Don't Shine', carries the strapline "as your age gets bigger, so should your dreams" and deliberately challenges ageist stereotypes about the over-50s travel market.
According to The Stable, the commercial shows older adults "scaling mountains, zip-wiring, sneaking home at sunrise, jet-skiing and nightclubbing" rather than the usual gentle imagery associated with senior travel insurance advertising. David Morley, StaySure's chief marketing officer, told the publication: "Our market are fed up with the cliches and assumptions made about aging. The idea of 'being old' is old fashioned."
Wilson-Jones fits that brief. Insurance brands typically cast recognisable character actors rather than celebrities, and a CV like hers, theatre-trained, established in British TV drama, registers as trustworthy and capable without overshadowing the product itself.
Why StaySure named her on Instagram
Brands often keep commercial cast lists quiet because of non-disclosure clauses that come standard with casting agency contracts. StaySure broke that pattern for 'Dream Big' with the Instagram post on 31 December 2025, six days after the TV launch. The reveal appears deliberate: by naming Wilson-Jones publicly, StaySure converted the casting itself into a small piece of campaign press, useful for a brand that wants the ad to be talked about rather than just watched.
It also reflects a difference in tone from StaySure's previous TV ads. The 2018 'Worth Doing Right' campaign featured Scottish actor Robert Cavanah (Doctors, Casualty) and openly credited him on their campaign page. The 2026 effort sits in the same tradition: cast someone with real screen credentials and let people know who they are.
Previous StaySure campaigns
StaySure has used different creative approaches over the years. The 2018 'Worth Doing Right' commercial was shot in Rome and compared bespoke tailoring to personalised travel insurance. The intermediate campaign, 'Putting the sure in travel insurance', was produced by Happy Hour Productions and licensed Take That's song 'Sure'.
Some older online sources mention Judi Dench or Michael Caine in connection with StaySure. Neither appears in the current 2026 campaign and neither has been linked to the brand in StaySure's own communications.
What StaySure’s brand strategy says about the casting
StaySure has won Best Company for Travel Insurance at the British Travel Awards every year from 2016 to 2025, according to its Dream Big campaign page. It holds more than double the five-star Trustpilot reviews of any other UK travel insurance provider. The brand is not trying to disrupt the market; it is trying to own it.
The 'Dream Big' campaign is designed to future-proof that dominance by appealing to younger over-50s (the 45 to 60 demographic) who do not yet see themselves as "old". Wilson-Jones, in her mid-fifties and visibly active in the ad, is exactly that target persona made flesh. The casting is not incidental; it is the message.
The advert is available to watch on StaySure's website and their YouTube channel. The campaign runs throughout 2026.
Comments
0 comments
Loading comments…