Episode summary
This one’s a deliberate tangent. Not away from insurance, but out to the place where the industry comes together to argue, learn, sell, build… and occasionally rethink itself.

My guest is Bill Harris, co-founder and Chief Customer Officer of InsureTech Connect (ITC) — the largest gathering of insurance innovation in the world. We talked about how ITC started (including the very “sliding doors” origin story), what it takes to build something at that scale, why the pandemic actually accelerated the need for face-to-face community, and what Bill hopes his legacy is beyond “the conference guy in Vegas.”

What we cover

• Bill’s early ambition to be a news anchor, and the moment that dream changed
• The real origin story of ITC — and why Bill says it wasn’t even his idea
• Building the first ITC in roughly 180 days (yes, really)
• Why the 1-to-1 meeting zone became the “most valuable real estate” in the expo hall
• The year ITC almost didn’t go ahead — and the weight of that decision in 2017
• When ITC shifted from “a big event” to part of the industry’s innovation infrastructure
• Post-pandemic: why community came roaring back, and why ITC accelerated
• Bill’s take on signal vs noise (and the “AI sticker” problem)
• What success at ITC actually looks like for founders and leaders: connections, conversations, network
• Designing an experience that works for everyone from solo founders to carrier CEOs
• The content responsibility: how ITC topics can shape Q4 planning and next-year budgets
• Bill’s legacy: being remembered as a connector and bridge builder

Links / where to find Bill & ITC

• ITC Vegas: vegas.insuretechconnect.com
• Bill on LinkedIn: Bill Harris (ITC Vegas)

If you enjoyed this episode…
Share it with someone who’s never been to ITC but keeps saying they’ll go “next year.” And if you’re going in 2026, come say hello — we might just do Humanizing Insurance live from Vegas.

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.

Engineering Communities: Paolo Cuomo

When Paolo Cuomo planned for a life designing and building tangible things - bridges, buildings, “real stuff” - he didn’t expect to fall for an industry that makes nothing you can touch. But in the grey areas of specialty risk and the human handshake of EC3, he found something else: a place where engineering discipline meets portfolio uncertainty, and where communities change careers.

In this episode, Paolo (Executive Director, Gallagher; co-founder of Instech London; Lloyd’s Lab founding team) traces the path from Imperial College engineering to McKinsey problem-solving to building businesses and communities that have shaped today’s insurance ecosystem. We talk about the real origins of “InsurTech” (and why he still loves “Instech”), London’s “unfair advantage” of proximity, and the very human reason insurance matters: it quietly enables progress - ship voyages, chip factories, sprinkler retrofits - then steps out of the spotlight.

We also get personal: the cost of doing too much, what a real priority list looks like, and why Paolo is calling 2026 “the Year of Paolo.” Underneath it all is a builder’s mindset: lay better foundations, connect people who should meet, and measure success by what stands years later.

In this conversation

• Engineering vs. insurance: structure, uncertainty, and where they clash, and complement
• Why more data sometimes adds confusion (lessons from the first InsureTech wave)
• Instech London’s beginnings, the hashtag wars, and the power of community
• London’s proximity effect: why EC3 creates serendipity other hubs can’t easily replicate
• MGAs as the innovation chassis: letting humans + tools ship value faster
• Insurance as quiet social good: sprinklers, cyber posture, and enabling big bets
• Focus, boundaries, and “The Year of Paolo”: doing fewer things, better
• Legacy: builder of communities, businesses, and relationships that last

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.

Changing Perspectives: Simon Hayes

When markets softened and box-ticking took over, Simon Hayes didn’t chase “cheapest.” He doubled down on stories that change perceptions.

From Royal Marines officer training to aviation broking at Lloyd’s, Simon learned early that insurance is a people business. The real leverage wasn’t a rate card, it was narrative: helping underwriters see the full picture, turning “distressed risk” into understood risk, and partnering beyond price.

Years later, a brutal redundancy could have closed the book. Instead, Simon started again, founding NextGen Communications, becoming a go-to voice for insurers and InsurTechs who needed more than press releases. He rode the early InsurTech wave, sat with founders who had product but no profile, and built campaigns that earned attention where it counts: with buyers.

This conversation is about resilience, relationship capital, and pride; about telling the truth well enough that the industry can stand up at a dinner party and say, “We oil the wheels of the world,” without apology.

Simon reminds us that PR, at its best, is not spin, it’s stewardship of trust. Claims are acts of restoration. Brand is the promise you keep when no one is watching. And the most durable growth still comes from helping first.

Whether you build products, place risk, or lead teams through change, this episode is a quiet masterclass in finding your value, showing your work, and staying human when the spreadsheet says otherwise.

What we cover

• Royal Marines to Lloyd’s: the people skills that outlast process
• Aviation broking and the “soft market” epiphany: stop selling cheapest, start selling partnership
• Storytelling that moves markets: closing the gap between Zimbabwe Airways and its peers by changing perception with facts
• PR as perception change (not vanity metrics): where outcomes actually matter
• Diversity then and now: why the market feels different, and what’s still missing
• Redundancy, reinvention, and the power of your network when the ground shifts
• InsurTech accelerators, funding waves, and how NextGen became a go-to in the niche
• Practical comms for insurers & InsurTechs: what to invest in when budgets are tight
• Pride at the dinner party: making the case for being in insurance
• Life beyond the inbox: small global teams, travel, golf dreams, and building a business you actually like

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 m

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.