EPISODE · Sep 24, 2025 · 39 MIN
Will Ross: The Federato Playbook — RiskOps, Appetite, and Winnability for Profitable Growth
from Scouting for Growth · host Sabine VdL
On this episode of the Scouting For Growth podcast, Sabine VdL talks to Will Ross, Co-Founder & CEO of Federato, and if you’re an underwriting transformation leader—drowning in Excel, stale pilots, and disconnected data sources—this episode is for you. Will Ross isn’t here to sell you hype. He’s here to show what it looks like when AI actually delivers: faster quotes, better decisions, happier underwriters, and measurable results before the next board meeting. KEY TAKEAWAYS Thinking back to when Amazon released the Echo with Alexa and a bunch of us bought them and took them apart to figure out how it worked reminds me of how Wild West the early days of AI was a decade and a half ago. Now any undergraduate student taking computer science will have some exposure to AI. One of the first things they might learn is how to do simple tasks like that on very little computational resource. I love jumping into our products like that to understand how they work. Break down what AI means: There’s an idea of intelligence or grasping a concept or knowledge, then there’s artificial – doing something in place of a human. You can take it a step further and look at ‘generative’ – generating a thing, or predictive – predicting a thing, agentic – giving it agency and allowing it to complete a task. What is it that humans do today and, theoretically, what could humans do if they had unlimited time to do their jobs? For underwriters, the process is similar across many line of business: you analyse an exposure, loss history and loss control to come up with a rate perspective, etc. Where can AI systems interact with that process? BEST MOMENTS ‘One of the things I think is really scary with AI today is its perpetuation of news cycles and how fast it spreads.’ ‘No matter how sceptical people are, the vast majority of people are already using these technologies to do their jobs. By bringing them into the room, making them aware of what this technology does, and letting the interact with it, that’s a powerful thing.’ ‘There are going to be jobs that change, but we shouldn’t think about it as AI replacing our jobs, we should think about it as someone using AI to do our job who will replace us.’ ‘What we call AI today will change and change again because it always has; Deep Blue used to be called AI and is now called a chess simulator.’ ABOUT THE GUESTS William Ross is a product and operations leader obsessed with solving the toughest problems in insurance with a mix of pragmatism, speed, and machine learning. As a core member of the Federato leadership team, Will focuses on one mission: turning underwriting from a slow, manual grind into a dynamic, data-driven advantage. At Federato, Will is helping specialty and commercial carriers build resilience and growth into their underwriting operations, showing chief underwriting and transformation officers that AI doesn’t need to be another failed pilot—it can be the competitive edge that secures market share today. LinkedIn ABOUT THE HOST Sabine VanderLinden is a corporate strategist turned entrepreneur and the CEO of Alchemy Crew Ventures. She leads venture-client labs that help Fortune 500 companies adopt and scale cutting-edge technologies from global tech ventures. A builder of accelerators, investor, and co-editor of the bestseller The INSURTECH Book, Sabine is known for asking the uncomfortable questions—about AI governance, risk, and trust. On Scouting for Growth, she decodes how real growth happens—where capital, collaboration, and courage meet. If this episode sparked your thinking, follow Sabine VanderLinden on LinkedIn, Twitter, and Instagram for more insights. And if you’re interested in sponsoring the podcast, reach out to the team at [email protected]
What this episode covers
On this episode of Scouting For Growth, Sabine VdL sits down with Will Ross, Co-Founder & CEO of Federato, for a straight-talking conversation every underwriting transformation leader needs right now. If you’re drowning in Excel sprawl, stalled “innovation pilots,” and disconnected data sources, this episode delivers what most AI conversations don’t: clarity, practicality, and measurable outcomes. Will isn’t here to sell hype. He’s here to explain what AI looks like when it actually works—helping carriers quote faster, decide smarter, and give underwriters their time (and sanity) back. From AI “Wild West” to enterprise reality Will reflects on the early days of AI—when Alexa first launched and curious tech minds took devices apart just to understand what was inside. Back then, AI felt like the Wild West. Today, it’s mainstream. Any computer science student has exposure to it, and AI capabilities that used to require heavy resources are now accessible at scale. That shift matters because it’s changed what’s possible for insurers—not someday, now. What “AI” actually means (and why definitions matter) One of the most useful parts of this episode is Will’s breakdown of AI in plain English: Artificial = doing something in place of a human Intelligence = grasping knowledge or concepts Then you have different “modes” of AI: Predictive AI (predicting outcomes) Generative AI (creating content) Agentic AI (taking action and completing tasks) For enterprise leaders, this matters because too many initiatives fail at the starting line: teams buy tools before they’ve defined what type of AI they actually need. Underwriting isn’t broken — it’s bottlenecked Will reframes underwriting work in a way executives will recognize instantly. Across most commercial lines, underwriters follow a repeatable process: assess exposures, loss history, and controls, then arrive at a rate perspective. The real question isn’t whether underwriters know how to underwrite. It’s: what could they do if they had unlimited time? This is where AI becomes a force multiplier—supporting risk analysis, surfacing signals faster, and removing manual grind so underwriters can focus on judgment and deal quality. The mindset shift leaders must drive Will addresses the uncomfortable truth: jobs will change. But the real risk isn’t “AI replacing people.” It’s people using AI replacing people who don’t. That’s not fearmongering—it’s competitive reality. And Will makes an equally important point: most people are already using these tools at work, whether leadership has sanctioned them or not. The most effective move? Bring AI into the room. Let teams interact with it. Build awareness and confidence through real use—not policy documents. The caution: speed without discernment creates risk Will also flags a growing concern: AI can accelerate misinformation and amplify news cycles faster than ever. That’s a warning for insurers where trust, accuracy, and decision accountability are non-negotiable. Why this episode matters This episode is a call to action for underwriting and transformation leaders: stop chasing AI theater and start building underwriting advantage. Because the future carrier winner won’t be the one with the biggest tech stack. It will be the one that helps underwriters make better decisions, faster—with proof on the scoreboard before the next board meeting.
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Will Ross: The Federato Playbook — RiskOps, Appetite, and Winnability for Profitable Growth
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