Friends with Benefits: Episode 2 – The One with John from Workday: Decluttering Benefits, Proving ROI, and the Truth About Data

Benefits are bloated. Data is broken. ROI is murky. But people still need support that works.

About the guest

John Whitaker,
Senior Director of International Benefits at Workday

John leads strategy and delivery across global markets. With decades of experience at the intersection of HR, benefits, and data, John brings a pragmatic, people-first lens to reward strategy. He’s passionate about simplifying complexity, challenging industry buzzwords, and building benefits that actually work for businesses and their people. In this episode, John brings his signature candor to topics like decluttering bloated benefit stacks, redefining ROI, and why admin that just works is more valuable than most shiny new features.

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Summary

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In this episode of Friends with Benefits, we're joined by John Whitaker, Senior Director of International Benefits at Workday. From decluttering bloated benefit portfolios to the real reasons wellbeing ROI is so hard to prove, John brings a refreshingly honest view of what actually matters in the benefits space. We cover global cost pressures, benefit duplication, the data gaps still holding us back, and why sometimes the best employee experience is just making things work.

Tune in for practical insights, hard truths, and a few benefit confessions you won't forget.

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Topics on the table:

  • Why decluttering your benefits stack matters more than ever
  • The truth about ROI: why most models don’t work
  • How to simplify without sacrificing impact
  • Personalisation vs standardisation: where the balance lies
  • Data challenges that slow benefits teams down
  • The gap between admin and strategy
  • How to make benefits feel meaningful and visible
  • What great UX looks like in employee experience
  • Confessions and lessons learned from the field

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03:00 – Why having more benefits isn’t better

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“People aren’t asking for more—they’re asking for better.”

John, Senior Director of International Benefits at Workday

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07:40 – Wellbeing fatigue & lack of results

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“Wellbeing budgets have grown, but outcomes haven’t. That should worry us.”

John, Senior Director of International Benefits at Workday

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12:00 – Budget ≠ impact

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“We’ve thrown budget at the problem without solving the delivery.”

David, COO and co-founder at Ben

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14:00 – Personalisation over standardisation

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“Standardisation is easy. Personalisation drives impact. But it takes work.”

John, Senior Director of International Benefits at Workday

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19:00 – Data gaps still hurt decision-making

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“We’re still dealing with data silos that make basic reporting a nightmare.”

Carl, VP of Benefits Design at Ben

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23:00 – Admin vs. strategy

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“More often than not, benefits teams are buried in admin—not designing experience.”

John, Senior Director of International Benefits at Workday

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30:00 – The problem with proving ROI

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“We ask teams to prove ROI with tools that don’t even track engagement properly.”

David, COO and co-founder at Ben

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33:00 – Living your values through benefits

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“Our benefits reflect our culture. They’re how we say ‘you matter’ in real terms.”

John, Senior Director of International Benefits at Workday

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38:00 – Cutting costs without cutting care

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“There’s a misconception that cutting benefits saves money. It rarely does.”

Carl, VP of Benefits Design at Ben

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42:00 – Benefit confession

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“I once approved a pilot benefit I didn’t understand…because the vendor was persuasive. Never again.”

John, Senior Director of International Benefits at Workday

Listen to the podcast on Spotify, Youtube, Apple Podcast.

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