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Season 9 – Episode 8 – The Best, the Worst, and “Why Are We Still Doing This?” AudioVideo Audio Video SUBSCRIBE:iTunesGoogleSpotifyAndroid Welcome to Season 9 Episode 8 of the Digital Insurance Pint! In this special retrospective, host Tom Reid attempts to herd cats once again, bringing you the finest outtakes, technical blunders, and questionable industry takes from the past season. Why a clip show? Because as Tom openly admits, they completely ran out of actual ideas, and both Gemini and Claude advised them to just pack it in and call it a day. Watch as the core panel gracefully dismantles each other’s dignities The post Season 9 – Episode 8 – The Best, the Worst, and “Why Are We Still Doing This?” appeared first on Digital Insurance Pint.

Season 9 – Episode 7 – Data Swamps & Tech Hopium AudioVideo Audio Video SUBSCRIBE:iTunesGoogleSpotifyAndroid Data swamps, tech “hopium,” and the looming broker apocalypse. The latest episode of the Digital Insurance Pint features guest Pete Tessier burning down the industry’s collective AI delusions. Hosts Jeff Roy, Tom Reid, Steve Earle, and Adam Mitchell clashed with Pete on everything from internal software coding to the exact timeline for small-broker extinction. The Big Debates: AI vs. Snake Oil: Pete claims the industry is stuck in a gold rush of “snake oil” vendors selling “hopium”. Jeff argues that brokers are just dumping ugly data into localized “data swamps” instead of fixing their workflows first. The “Build vs. Buy” Brawl: Pete thinks brokers should use their own internal sandboxes to test tools. Tom strongly disagrees with brokers attempting to build software. Adam essentially proved Tom right by admitting he used Claude to build a client map widget that temporarily left his entire client database wide open to the web —and that he’s currently $500k deep into an infrastructure build he hasn’t even been able to play with yet!  The 3-Year Apocalypse: Adam thinks smaller brokers can comfortably coast for 5 years without investing a dime. Pete aggressively shut that down, predicting insurance carriers will “absolutely obliterate small brokers” in 3 years because 27% of brokers already control 82% of Canadian business. Best Quote from the Episode: “Most of the large language models are the world’s best bullshitters. It sounds brilliant… and it’s absolute shit about something I happen to know a little bit about.” — Adam Mitchell Oh, and Tom pointed out that a Canada Revenue Agency AI chatbot was heavily criticized for being only 37% accurate—which sounds terrible until you find out human CRA employees on the phone only score 17% accurate. The bots are officially winning. The post Season 9 – Episode 7 – Data Swamps & Tech Hopium appeared first on Digital Insurance Pint.

Season 9 – Episode 6 – Super Soft – with Alister Campbell AudioVideo Audio Video SUBSCRIBE:iTunesGoogleSpotifyAndroid Riding the Insurance Rollercoaster: Market Cycles with Alistair Campbell Tom, Steve, Jeff and Adam dive into the thrilling world of insurance market cycles. Alister Campbell, CEO of PACCIC, takes us on a ride through the ups and downs of hard and soft markets, sharing insights that are as enlightening as they are entertaining. In this episode: Hard vs. Soft Markets: Discover why the insurance industry is like a rollercoaster, with thrilling highs and stomach-churning lows. The Soft Market Shuffle: Learn how insurers dance through soft markets, trying not to trip over their own rates. Hard Market Headaches: Explore the challenges of hard markets, where everyone’s scrambling for cover (literally). The Crystal Ball: Alister’s predictions for the future—spoiler alert: it involves less crystal and more spreadsheets. Broker Survival Tips: Practical advice for brokers to keep their cool and their clients happy, even when the market’s doing loop-de-loops. The post Season 9 – Episode 6 – Super Soft – with Alister Campbell appeared first on Digital Insurance Pint.

Season 9 – Episode 5 – Apocalypse Soon – with Alister Campbell AudioVideo Audio Video SUBSCRIBE:iTunesGoogleSpotifyAndroid In this episode, Tom, Steve, Jeff and Adam delve into the complexities of the Canadian insurance industry, exploring systemic risks like earthquakes and AI’s role in shaping future strategies. Alister Campbell, a seasoned insurance veteran and CEO of PASIC, shares invaluable insights on risk management, industry evolution, and the importance of human interaction in insurance. In this episode: The seismic risk facing Canada and why it remains a critical systemic concern The concept of a federal backstop modeled after US TRIA for catastrophic events The impact of climate change and AI on risk assessment, pricing, and operational efficiency The rationale behind risk-sharing frameworks like PACCIC and the importance of industry preparedness The post Season 9 – Episode 5 – Apocalypse Soon – with Alister Campbell appeared first on Digital Insurance Pint.

Season 9 – Episode 4 – AI – What is is good for ? AudioVideo Audio Video SUBSCRIBE:iTunesGoogleSpotifyAndroid The AI Takeover (And How to Survive It) Pour yourself a tall one and silence your notifications, because Tom Reid is back in the moderator’s chair, desperately trying to keep Jeff Roy, Adam Mitchell, and Steve Earle from talking over each other long enough to discuss the future. In this episode, the boys tackle the terrifyingly fast world of Generative and Agentic AI. It turns out AI is doing a lot more for underwriting and customer service than just writing mediocre poetry; it’s actually revolutionizing the industry. The crew breaks down why “business as usual” is a one-way ticket to extinction and why ignoring these tools is like bringing a fax machine to a space race. The banter stays high as the co-hosts dive into how AI-driven tools are actually making brokers look like they have their lives together. Jeff Roy shares how he’s using AI as a high-level consultant to handle the “boring stuff” while expanding his brainpower, while Adam Mitchell geeks out over the evolution of intelligent BMS and CRM systems. They argue that these systems aren’t just filing cabinets anymore—they’re becoming the brains of the operation, automating the grunt work and making data analysis actually… well, useful. If you’ve ever wondered if your CRM is smarter than you are, this is the segment that will probably confirm your fears. To wrap things up, the DIPP team gets real about the “Holy Grail” of insurance: clean data. They move past the AI hype to discuss the practical, non-nerd steps for integrating these layers into your brokerage today. From personalized marketing strategies that don’t feel like spam to “agentic layers” that might eventually replace your core systems, the guys lay out a roadmap for future-proofing your business before the robots take over entirely. Check out the first comment below to hear the full breakdown. Come for the tech tips, stay for the inevitable derailment. The post Season 9 – Episode 4 – AI – What is is good for ? appeared first on Digital Insurance Pint.

Season 9 – Episode 3 – Game Changer AudioVideo Audio Video SUBSCRIBE:iTunesGoogleSpotifyAndroid In the latest episode of the Digital Insurance Pint podcast, Tom, Jeff, Adam & Steve delve into a groundbreaking strategy developed by CSIO that promises to revolutionize the insurance industry. We explore how this new approach aims to eliminate duplication of effort and cost, enhancing connectivity between brokers and insurers. This initiative is not just a technological upgrade; it’s a strategic pivot that could redefine efficiency and collaboration across the sector. The conversation highlights the potential of this strategy to serve as the connective tissue that keeps the broker channel viable in an AI-first world. By centralizing connectivity and leveraging improved data flow, the industry can streamline processes, reduce costs, and ultimately deliver better value to consumers. This is more than an incremental improvement—it’s a transformative leap forward that could set a new standard for the industry. Join us as we discuss the implications and opportunities this presents for all stakeholders involved. The post Season 9 – Episode 3 – Game Changer appeared first on Digital Insurance Pint.

Season 9 – Episode 2 – Acera & Navacord – Deal of the Decade? AudioVideo Audio Video SUBSCRIBE:iTunesGoogleSpotifyAndroid Tom, Adam, Steve & Jeff dive into the recent acquisition of Acera by Navacord, exploring the implications for the insurance industry. With their usual mix of humor and candid insights, they discuss the consolidation trend, the role of private equity, and the cultural challenges of mergers. The conversation is peppered with “jokes”, a few personal anecdotes, and a heated debate on what it means to be a Canadian company in a global market. Check it out ! Takeaways Navacord’s acquisition of Acera marks a significant milestone in the insurance industry. Consolidation in the market raises questions about the future of smaller brokers. Cultural integration is crucial for the success of mergers and acquisitions. The insurance market is increasingly dominated by a few large players. Private equity plays a significant role in shaping the brokerage landscape. Employee ownership can be affected by large acquisitions. The future of large brokerages may involve more strategic partnerships and integrations. Market dynamics are shifting, with larger firms gaining more control. The post Season 9 – Episode 2 – Acera & Navacord – Deal of the Decade? appeared first on Digital Insurance Pint.

Season 9 – Episode 1 – Is Canada innovative enough? AudioVideo Audio Video SUBSCRIBE:iTunesGoogleSpotifyAndroid In this episode of the Digital Insurance Point podcast, hosts Tom, Jeff, Adam & Steve discuss the state of insurance innovation in Canada compared to the rest of the world. They explore the use of AI and machine learning in underwriting and claims, the challenges of telematics and usage-based insurance, the importance of enhancing customer experience through digitization, the impact of embedded insurance on brokers, and the role of InsureTech partnerships in driving innovation. The conversation highlights Canada’s position in the global insurance landscape and the need for continued investment in technology and innovation. Takeaways: Canada is lagging behind in insurance innovation compared to the US and Europe. AI and machine learning are being used in underwriting and claims, but their effectiveness is still debated. Telematics and usage-based insurance have not gained significant traction in Canada due to privacy concerns. Enhancing customer experience through digitization is crucial for the insurance industry. Embedded insurance poses a threat to traditional brokers by removing them from the purchasing process. InsureTech partnerships are becoming increasingly important for driving innovation in the insurance sector. The Canadian InsureTech community is growing, but it still has a long way to go compared to the US. The future of insurance will likely involve more integration of technology and human interaction. The post Season 9 – Episode 1 – Is Canada innovative enough? appeared first on Digital Insurance Pint.

In this episode of the Digital Insurance Point podcast, Tom, Adam, Jeff & Steve discuss the entrepreneurial journey of Samuel Bélanger-Lamoureux, co-president of Cemiar, an insuretech firm dedicated to improving efficiency in insurance brokerages.

Season 9 – Special TEC Summit 2025 AudioVideo Audio Video SUBSCRIBE:iTunesGoogleSpotifyAndroid Live from Montreal, it’s the Digital Insurance Pint Podcast ! The RCCAQ Tec Summit in Montreal was a raging success, featuring a ton of great content and the first ever DIPP Live podcast. Good news – if you didn’t join us in Montreal (you should) – you can still see the show. This power-packed live episode features Tom, your ever-insightful host, wrangling a panel of industry heavyweights: Jeff, Steve, and Adam! This wasn’t your average chinwag about deductibles; they dove headfirst into the tech tsunami reshaping the broker channel. From picking the year’s hottest tech advancements to debating the AI question (friend, foe, or just a fancy calculator?), they tackled the big questions. They pondered if brokers are now swimming in a golden ocean of Insurtech opportunities, or if it’s more like wading through treacle in a tech-laden swamp. And, of course, the burning question: data. Are brokers harnessing its mighty power, or still just using spreadsheets like glorified abacuses? In a nutshell, Tom, Jeff, Steve, and Adam served up a potent brew of insights, seasoned with their unique perspectives. They explored whether brokers are truly seizing the tech moment, or if legacy systems and a healthy dose of Canadian caution are holding them back. While the episode didn’t end in a fistfight over blockchain or a robot uprising, they did offer a compelling look at the future of the broker channel. Spoiler alert: optimism was in the air, though tempered with a healthy dose of realism about the challenges and changes ahead. Think of it as a professionally funny, yet genuinely insightful, debrief on navigating the Insurtech revolution – Canadian broker style, eh? The post Season 9 – Special TEC Summit 2025 appeared first on Digital Insurance Pint.

In this episode of the Digital Insurance Pint podcast, the DIPP crew is joined by Stephen Billyard, CEO of Billyard Insurance Group They discuss Stephen's journey in the insurance industry

In this episode of the Digital Insurance Point podcast, the DIPP crew discuss the evolution of the insurance industry, focusing on the innovative approach taken by Noel Fegali, CEO of Panda7.

The conversation delves into Carl's journey from Lebanon to Silicon Valley, the evolution of Gaya from a car-sharing platform to an insurance technology solution, and the challenges faced by insurance agents in the U.S.

In this episode of the Digital Insurance Point podcast, The DIPP crew and guests discuss the evolving landscape of insurance technology, focusing on Trufla's innovative products designed to enhance broker efficiency and client retention.

In this episode of the Digital Insurance Point podcast, the DIPP crew and guests discuss the evolution and application of AI in the insurance industry