The One with Will from Halfords: Why Benefits Lost Their Way — and How to Get People to Care Again
About the guest

Will Winter Smith is the Reward Director at Halfords, leading benefits strategy for over 13,000 colleagues across the UK and beyond. With two decades of experience in retail and financial services, he brings a no-nonsense, commercially smart approach to engagement, value, and communication — and isn’t afraid to call out what doesn’t work.
Whether it’s rethinking private medical, applying marketing tactics to reward comms, or experimenting with AI, Will makes one thing clear: if people don’t understand it or feel it, it doesn’t matter.

Summary
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In this episode of Friends With Benefits, we sit down with Will Winter Smith, Reward Director at Halfords, to explore why traditional benefits strategies are no longer landing with today’s workforce. From private medical that “lost its way” to too many bolt-on products and confusing comms, Will shares a refreshingly honest look at what’s broken — and what actually gets people to engage.
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Topics on the table:
- Why private medical benefits have “lost their way”
- Breaking down real barriers to access and engagement
- Cutting through the noise of too many products and platforms
- Why “we’re retailers to our colleagues”
- Communicating benefits like marketers, not administrators
- Making tough ROI calls and stopping what doesn’t work
- How AI fits in (if at all) for reward teams
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00:00 — Engagement Is Key
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"Engagement is key to everything that we do."

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“I think private medical has lost its way a little — measuring it and reporting on it is something that, frankly, a lot of the folks we talk to find really difficult.”
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03:00 — Private Medical Has Lost Its Way
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“Private medical has lost its way a little. How much does it really help with that immediacy of need?”
“There’s a really high barrier to entry. What we really want is to be able to pick up the phone or see a GP downstairs in your office, get help straight away, skip the NHS queues. But the reality is very different.”

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08:00 — Product Overload and Noise
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“Every insurance broker, every provider — it feels like everyone’s trying to offer some kind of wellbeing solution. One of the challenges employers have is: which one do you recommend?”
“It’s really about how we use communication to help colleagues navigate the wealth of information out there.”

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16:00 — Benchmarking and the Same-Same Trap
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“I think it’s important to point out that most organizations we talk to are benchmarking what everyone else is doing. You end up with all these same-same programs.”
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17:00 — We’re Retailers to Our Colleagues
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“Effectively, as reward professionals, we are retailing to our colleagues.”
“When I talk to my own colleagues about things like Cycle to Work — which is very relevant for Halfords — our ambition here is to sell bikes.”

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21:00 — Guerrilla Marketing and Disruptive Moments
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“What you’ve really got to do is make your communication stand out. How can you really wow your colleagues?”

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“Word of mouth is super powerful. When colleagues talk about a positive experience, it spreads.”
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25:00 — ROI and Knowing When to Stop
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“If you’re not seeing utilization, especially for some benefits, you’re going to upset some people. But again, you design for most, not all.”
“If it isn’t working and it’s expensive — stop it.”

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“Benefits is an interesting world. There are very few industries where companies spend so much money — 10 to 15% of payroll in many cases — and then have to push comms to get people to actually engage with what they’re spending on.”
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31:00 — AI Is Like Teaching a Toddler Origami
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“AI is like trying to teach a toddler origami. One minute you’re close to a swan — and then it decides it likes the boat and sticks with the boat.”
“What role does AI play? Because it will exist.”

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38:00 — Culture and Trust Around AI
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“Some pretty strong comments have been made — things like, ‘I’m not really interested in what ChatGPT has to say about it, I’m more interested in your view.’”

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