Alan Demers spent 24 years at Nationwide, building a career in claims, leadership and innovation before stepping out to found InsurTech Consulting.

In this episode of Humanizing Insurance, we talk about what claims teaches you about people, pressure and decision-making, and why it remains one of the most misunderstood parts of the industry. Alan reflects on a career spent largely inside one organisation, what loyalty and longevity can give you, and the moments when staying in one place can make you wonder what you might be missing elsewhere.

We also explore leadership at scale, the reality of trying to build the “claims of the future”, and what Alan sees now from outside the insurance machine that he could not see when he was inside it. It is an honest conversation about innovation too: not the conference version, but the real thing, with all the bureaucracy, delay and frustration that comes with trying to change a complex industry.

This is a conversation about careers, conviction, claims, and the humbling experience of starting again after years at the top of a large organisation.

In this episode:

• How Alan found his way into insurance through claims
• Why claims is far more nuanced than many people realise
• What 24 years at one company gave him, and what it may have cost
• The tension between loyalty, longevity and moving to grow
• What leadership looks like when you are responsible for thousands of people
• How close the industry has really come to building the “claims of the future”
• What insurers still get wrong about innovation
• Why external networks matter more than many people think
• What it feels like to leave corporate life and build something of your own

Humanizing Insurance is bought to you by Daniel Grimwood-Bird. It's a passion project, driven by the evergreen phrase 'Insurance is a people industry'.

Through each conversation, we explore the stories, experiences, and ideas that make our world of insurance more human - from the pioneers and innovators shaping its future to the quiet leaders who hold its traditions together.

This podcast exists to remind us that behind every policy, premium, and claim is a person, someone making decisions, taking risks, and protecting what matters most.

If these stories resonate with you, please follow the show, leave a review, and share it with a colleague or friend who still believes in the people side of this business.

You can also connect with Daniel on LinkedIn to continue the conversation, recommend guests, or request a topic that you'd like to know more about.

Humanizing Insurance — one conversation at a time.

Tony Cañas is one of insurance’s most distinctive voices: recruiter, podcast host, community builder, and, increasingly, magician.

In this episode, Tony joins Humanizing Insurance to talk about the winding route that took him from wanting to work in computer science to falling into insurance after the 2009 crash, building Insurance Nerds and Profiles in Risk, and eventually rediscovering a childhood love of magic.

What could have been a conversation about novelty becomes something much deeper. Tony reflects on authenticity, the performance of professionalism, the power of silence, and the ways both magic and insurance depend on perception, trust, and human psychology. He also makes a passionate case for insurance as a fascinating, meaningful career and argues that the industry has done far too little to educate consumers about what insurance is actually for.

It is funny, unusual, and thoughtful in equal measure, and a reminder that sometimes the most interesting people in insurance are the ones bold enough to stop wearing the uniform.

What listeners will get from this episode

• Tony’s route into insurance after the financial crash
• how Insurance Nerds and Profiles in Risk came to life
• the story behind the top hat, the flaming wallet, and the return to magic
• what magic teaches about attention, silence, and human psychology
• why insurance should be an experience business
• why consumers still misunderstand insurance
• why insurance is not boring, and never has been

Humanizing Insurance is bought to you by Daniel Grimwood-Bird. It's a passion project, driven by the evergreen phrase 'Insurance is a people industry'.

Through each conversation, we explore the stories, experiences, and ideas that make our world of insurance more human - from the pioneers and innovators shaping its future to the quiet leaders who hold its traditions together.

This podcast exists to remind us that behind every policy, premium, and claim is a person, someone making decisions, taking risks, and protecting what matters most.

If these stories resonate with you, please follow the show, leave a review, and share it with a colleague or friend who still believes in the people side of this business.

You can also connect with Daniel on LinkedIn to continue the conversation, recommend guests, or request a topic that you'd like to know more about.

Humanizing Insurance — one conversation at a time.

In(surtech) Vogue: Rory Pyke

Rory Pyke didn’t plan to work in insurance.

He studied graphic design, interned at Vogue, built a custom trainer business (complete with a Dragons’ Den application), bought property in St Helens, and was on the verge of opening a wine bar before COVID changed everything.

Today, he’s VP Global Partnerships at Insurtech Insights, sitting at the centre of the global insurtech ecosystem and helping shape the conversations that bring insurers, founders, and technologists together.

In this episode of Humanizing Insurance, Rory shares what that journey looked like, and what it’s taught him.

We talk about:

• being an “extroverted introvert” and learning to step onto big stages
• handling imposter syndrome when interviewing senior industry leaders
• why the best conversations balance insight and inspiration
• what startups and insurers often misunderstand about each other
• the story behind the Insurtech Run Club and healthier ways to network

We also get into something more personal: the reality of walking into a room full of strangers, the temptation to leave, and how community and shared experiences can make the industry feel a little more human.

Because behind the conferences, the panels, and the partnerships, this is still an industry built on people.

Humanizing Insurance is bought to you by Daniel Grimwood-Bird. It's a passion project, driven by the evergreen phrase 'Insurance is a people industry'.

Through each conversation, we explore the stories, experiences, and ideas that make our world of insurance more human - from the pioneers and innovators shaping its future to the quiet leaders who hold its traditions together.

This podcast exists to remind us that behind every policy, premium, and claim is a person, someone making decisions, taking risks, and protecting what matters most.

If these stories resonate with you, please follow the show, leave a review, and share it with a colleague or friend who still believes in the people side of this business.

You can also connect with Daniel on LinkedIn to continue the conversation, recommend guests, or request a topic that you'd like to know more about.

Humanizing Insurance — one conversation at a time.

David Cabral has worked across more corners of insurance than most of us will ever see - Bermuda, the UK, Europe, Asia, Africa, and the Americas - spanning claims, underwriting, leadership, and now senior advisory work at the Bank of England.

In this conversation, David shares why he believes claims is the best place to start any insurance career, how he deliberately built breadth through “sideways moves” (often without pay rises), and why insurance companies miss opportunities when they obsess over product instead of risk management.

We also talk about what it really takes to enter new markets well, how local nuance gets lost when head office exports a one-size-fits-all approach, and why the simple question “What do you need?” can unlock better products, better pricing, and deeper client trust.

Towards the end, David reflects on what he’d do differently if he started again — and why his curiosity is increasingly pulled towards microinsurance, development economics, and building models that serve communities properly.

In this episode:

• Why claims teams understand the contract better than almost anyone
• The hidden cost of being “product-first” instead of “risk-first”
• How to build a career through knowledge, not titles
• What changes when you move from CEO/CUO roles to strategic advisory
• Why “listening locally” is the real unlock for international growth
• The quiet case for microinsurance beyond parametrics

Humanizing Insurance is bought to you by Daniel Grimwood-Bird. It's a passion project, driven by the evergreen phrase 'Insurance is a people industry'.

Through each conversation, we explore the stories, experiences, and ideas that make our world of insurance more human - from the pioneers and innovators shaping its future to the quiet leaders who hold its traditions together.

This podcast exists to remind us that behind every policy, premium, and claim is a person, someone making decisions, taking risks, and protecting what matters most.

If these stories resonate with you, please follow the show, leave a review, and share it with a colleague or friend who still believes in the people side of this business.

You can also connect with Daniel on LinkedIn to continue the conversation, recommend guests, or request a topic that you'd like to know more about.

Humanizing Insurance — one conversation at a time.

Risk, Liability & Event Insurance with Freddie Sparrow

What happens when a music festival founder becomes an insurance entrepreneur?

Freddie Sparrow is the co-founder of Vento Insurance, a specialist event insurance broker serving festival organisers, conferences, trade shows and the wider events supply chain. Before launching Vento, Freddie ran a 5,000-person music festival — managing venues, contractors, ticket sales, cashflow, weather risk and the legal responsibility of thousands of attendees.

In this episode of Humanizing Insurance, we explore the real risks behind live events and how those experiences led Freddie into underwriting, broking and eventually building an event insurance business.

We cover:

• Event insurance and cancellation risk
• Public liability insurance for festivals and live events
• Cashflow, ticket sales and operational exposure
• Weather risk and “acts of God”
• Underwriting vs broking — what’s the difference?
• COVID cancellations and the underinsurance gap in the events industry
• Building a specialist insurance startup

Freddie’s journey runs from music promoter to reinsurer at TransRe, broker at Acrisure, and now founder of Vento Insurance — bringing discipline, lived experience and trust to a sector that learned the hard way what happens when coverage isn’t in place.

If you work in insurance, event management, live production, risk management or are building a business in a volatile industry, this conversation will resonate.

Because whether you’re running a festival or an insurance company, one truth remains:

The show must go on.

Humanizing Insurance is bought to you by Daniel Grimwood-Bird. It's a passion project, driven by the evergreen phrase 'Insurance is a people industry'.

Through each conversation, we explore the stories, experiences, and ideas that make our world of insurance more human - from the pioneers and innovators shaping its future to the quiet leaders who hold its traditions together.

This podcast exists to remind us that behind every policy, premium, and claim is a person, someone making decisions, taking risks, and protecting what matters most.

If these stories resonate with you, please follow the show, leave a review, and share it with a colleague or friend who still believes in the people side of this business.

You can also connect with Daniel on LinkedIn to continue the conversation, recommend guests, or request a topic that you'd like to know more about.

Humanizing Insurance — one conversation at a time.

Ola Jacob – Director of Business Development, Global Parametrics

Insurance has a storytelling problem.

Not because what we do isn’t meaningful — but because we don’t always explain it in human terms.

In this episode, I’m joined by Ola Jacob from Global Parametrics. We start where we always do — with the person. From dreaming of an Ironman-style “Jarvis life” to studying Human Computer Interaction and becoming an insurance scholar at UCL, Ola’s journey into the industry was intentional, curious, and entrepreneurial from the beginning.

What follows is a conversation about purpose, prevention, and people.

Ola explains parametric insurance in its simplest form:

“When a precondition is met, a pre-agreed payout is made.”

But we go deeper than definitions.

We talk about:

• Why insurance, at its heart, is simply a promise to pay
• How parametric is evolving from filling protection gaps to enabling pre-emptive risk management
• Why entrepreneurship absolutely exists inside insurance — if you’re willing to look for it
• The quiet economic ripple effect of a well-handled claim
• And how we bring more young people into an industry that touches every business in the world

One of the standout moments comes when Ola suggests that insurance may have accidentally positioned itself like a religious institution — held to impossible standards and judged harshly when it falls short.

His alternative?

Maybe we’re closer to action heroes.

Not perfect, not glamorous, but steady, dependable, and there when it matters most.

If we told that story better, perhaps the next generation would see what we see.

Humanizing Insurance is bought to you by Daniel Grimwood-Bird. It's a passion project, driven by the evergreen phrase 'Insurance is a people industry'.

Through each conversation, we explore the stories, experiences, and ideas that make our world of insurance more human - from the pioneers and innovators shaping its future to the quiet leaders who hold its traditions together.

This podcast exists to remind us that behind every policy, premium, and claim is a person, someone making decisions, taking risks, and protecting what matters most.

If these stories resonate with you, please follow the show, leave a review, and share it with a colleague or friend who still believes in the people side of this business.

You can also connect with Daniel on LinkedIn to continue the conversation, recommend guests, or request a topic that you'd like to know more about.

Humanizing Insurance — one conversation at a time.

What do wartime staff magazines, colonial underwriting rates, and a forgotten female trailblazer reveal about the history of insurance?

In this episode of Humanizing Insurance, I’m joined by Mollie Horne, archivist at Aberdeen Group, to explore what insurance archives uncover about the people behind the policies.

We step into Second World War staff magazines, read letters from employees on active service, and revisit the London office destroyed during the Blitz - where only an envelope of ash from the policy safe survived. We discuss how duplicate ledgers were preserved during wartime, what historic “extra rates” books reveal about underwriting and social assumptions, and how internal sports like the Davidson Cup reflected company culture across offices in London and Edinburgh.

We also spotlight Edith Beesley, one of the first women in insurance management, who flew to Paris on business in 1920 and challenged expectations in a male-dominated industry.

Finally, we look forward. As insurance becomes increasingly digital, we explore why electronic records may be more fragile than the paper ledgers that have survived for centuries — and what future archivists might struggle to recover from our era.

Behind every policy is a person. And insurance history, at its heart, is social history.

Humanizing Insurance is bought to you by Daniel Grimwood-Bird. It's a passion project, driven by the evergreen phrase 'Insurance is a people industry'.

Through each conversation, we explore the stories, experiences, and ideas that make our world of insurance more human - from the pioneers and innovators shaping its future to the quiet leaders who hold its traditions together.

This podcast exists to remind us that behind every policy, premium, and claim is a person, someone making decisions, taking risks, and protecting what matters most.

If these stories resonate with you, please follow the show, leave a review, and share it with a colleague or friend who still believes in the people side of this business.

You can also connect with Daniel on LinkedIn to continue the conversation, recommend guests, or request a topic that you'd like to know more about.

Humanizing Insurance — one conversation at a time.

Episode summary
In this episode of Humanizing Insurance, Daniel Grimwood-Bird sits down with Tim McCosh, Founder and CEO of Yokahu — an MGA and digital marketplace for worldwide parametric natural catastrophe and extreme weather risk insurance. Tim shares the very human reality of building a startup while becoming a new dad to twins, his unexpected route into insurance, why he left broking after years in the market, and the lessons that forced Yokahu to rethink its original approach.

We unpack what parametric insurance really is (“if X then Y”), why Yokahu is aiming to become an infrastructure layer for the market, and what’s changed in the industry — from the early “is this even insurance?” conversations to today’s push for innovation through Lloyd’s Lab. Along the way, Tim gives a candid view on why insurance change takes time, why product-market fit is harder than it sounds, and why he’d still tell his kids: yes, work in insurance.

What you’ll hear about

• Becoming a dad of twins while scaling a startup — “hard mode” leadership
• From rural Scotland to the Lloyd’s market: how Tim stumbled into insurance
• Why broking can feel reactive — and why Tim couldn’t do “another 30 years”
• Parametric explained in plain English: the logic and the value
• Why SMEs are the missing middle for parametric (not personal lines, not sovereign/corporate)
• The biggest early mistake: building what carriers would offer vs what customers wanted
• The cultural and structural blockers to innovation (value chains, slow onboarding, proof points)
• Lloyd’s Lab, interconnected InsureTech, and why the revolution may arrive faster than expected
• Tim’s five-year view: better certainty for customers, and what success would change

Guest
Tim McCosh — Founder & CEO, Yokahu

Host
Daniel Grimwood-Bird — Host, Humanizing Insurance

Humanizing Insurance is bought to you by Daniel Grimwood-Bird. It's a passion project, driven by the evergreen phrase 'Insurance is a people industry'.

Through each conversation, we explore the stories, experiences, and ideas that make our world of insurance more human - from the pioneers and innovators shaping its future to the quiet leaders who hold its traditions together.

This podcast exists to remind us that behind every policy, premium, and claim is a person, someone making decisions, taking risks, and protecting what matters most.

If these stories resonate with you, please follow the show, leave a review, and share it with a colleague or friend who still believes in the people side of this business.

You can also connect with Daniel on LinkedIn to continue the conversation, recommend guests, or request a topic that you'd like to know more about.

Humanizing Insurance — one conversation at a time.