Pippa Scaife is Director of Digital Advertising at Sky Media. Before joining Sky Media, she held senior commercial roles at NBCUniversal, CNN International, and The Box Plus Network.
Who is your digital hero?
My digital hero is Rob Bradley, SVP of Digital at CNN, and one of the most forward‑thinking leaders in global digital media.
What has he done to win hero status in your eyes?
Rob Bradley earns hero status because he doesn’t just lead digital, he embeds it.
While I was at CNN, he led major transformations in product, audience development, data strategy and social distribution, but almost more important than that, he made digital thinking a core part of every sales conversation, not an optional add‑on. He ensured commercial teams didn’t just understand digital but genuinely believed in it, creating a culture where everyone felt part of the transformation journey.
His leadership blends commercial vision, editorial respect and a deep understanding of innovation, a combination that’s rare, and very powerful.
How has his heroism helped drive digital?
Rob’s leadership helped shift CNN from “digital as a channel” to “digital as a mindset”, and I think it set a pace that a lot of businesses have followed.
- Embedding digital into every sales narrative, ensuring it was seen as central to growth.
- Championing experimentation across formats, platforms and audience experiences.
- Driving data-led thinking both and off platform to strengthen commercial outcomes.
- Bringing teams along with him, making change feel shared rather than imposed.
He proves that digital transformation succeeds when leadership and product innovation evolve together.
What are the biggest challenges in digital that need another hero to solve?
Right now, we need to continue to evolve what sustainable monetisation within such a fragmented ecosystem looks like. It’s not easy to crack the multi-channel consumer in a way that feels cohesive and additive to an advertiser. Part of that challenge is navigating the dependence on third‑party platforms that businesses increasingly have, while protecting direct relationships.
The players who figure out how to do this first will have a massive advantage and it will drive benefits across the industry.
There is also the need to build around a responsible, transparent use of AI, especially in content and advertising. It is so easy to get distracted by all of the promises of AI without really weighing up the risks vs. rewards.
There is a challenge here to prioritise, and focus on problem solving as opposed to chasing novelty. We need to ensure that AI is applied where it genuinely enhances outcomes, protects trust, and drives meaningful value rather than simply adding complexity.
To really crack these challenges, the industry need leaders with courage, clarity and the ability to unite teams around a shared digital purpose.
What is your most heroic personal achievement in digital so far?
My most heroic achievement was working across the onboarding of CTV apps onto the PlayStation 4 — including iPlayer, YouTube, My5 and Lovefilm.
It was near the start of my media career, so I feel really lucky to have been part of one of the first mass rollouts of connected TV infrastructure in the UK, as it signalled a major shift in how audiences would engage with streaming services.
One of the most exciting elements for me was negotiating the onboarding of Sky’s NOW TV service, which even then was a platform defined by bold innovation and agile thinking. Looking back, it’s a full‑circle moment: my career has now brought me to Sky, where I’m helping the business continue to lead the industry, by, amongst other things, rolling out a programmatic transformation across our BVOD inventory.
It feels like the same spirit of innovation, but now I’m on the inside.
