In this episode of AI Heroes & Headaches, host Vivienne Wei talks with Alex Schmelkin, Founder and CEO of Sixfold, the AI platform built for insurance underwriters. Alex dissects how the wave of generative AI is forcing the traditionally slow-moving insurance industry to modernize quickly. He explains the shift from traditional risk assessment to near-autonomous underwriting agents, and why boards are asking tough questions about competitive threats. Beyond the technology, Alex emphasizes the importance of balancing AI adoption with maintaining a healthy, enjoyable work culture - stressing that fun, music, and community connection are vital for generating the creative ideas needed to navigate the AI era.
🔑 Expect to Learn

Why insurance is one of the most AI-disruptible industries today.

How Sixfold’s AI underwriting agents are transforming productivity for insurers.

The importance of CEO involvement in successful AI transformations.

How AI can be both a threat and a partner in workforce transformation.

Key mistakes and lessons in rolling out AI systems within large enterprises.



⌛ Episode Breakdown with Timestamps
[00:00:00] - Opening Thoughts: The Insurance Industry & AI's Tipping Point: Intro to the insurance sector's risk of stagnation and the need for transformation.
[00:02:05] - Alex's Journey from Fashion to Insurtech: How Alex moved from public policy and e-commerce into founding an AI startup focused on underwriting.
[00:03:30] - Founding Sixfold: The $7 Trillion Opportunity: Insight into Sixfold’s inception, vision, and mission to modernize underwriting with AI.
[00:09:00] - AI Agents in Action: From Copilots to Doers: The shift from analysis-only tools to AI agents that autonomously handle underwriting tasks.
[00:12:15] - Measuring Impact: Efficiency & Premium Growth: The key business metric - gross written premium per underwriter - and how Sixfold boosts it.
[00:15:00] - Aging Workforce & AI as a Talent Multiplier: How AI addresses the challenge of 30% of senior underwriters retiring in the next five years.
[00:17:33] - Leading Change: CEO Buy-In Is Non-Negotiable: The pivotal role of executive leadership in driving successful AI transformation.
[00:20:00] - Mistakes & Learnings: Why Accuracy Measurement Matters: The early misstep of not quantifying AI accuracy and how that changed.
[00:22:17] - Elevating Underwriting Managers with AI: How mid-level leaders use AI for real-time portfolio strategy and guidance.
[00:25:50] - Final Thoughts: One Thing You Must Do as a Startup CEO: Alex’s top advice for AI founders and how to bring fun and balance into startup life.
🔗 Follow the guest, Alex Schmelkin:
👉 LinkedIn: https://www.linkedin.com/in/schmelkin/

🔗 Follow Sixfold:
👉 LinkedIn: https://www.linkedin.com/company/sixfold-ai/
👉 Website: https://www.sixfold.ai/
🔗 Follow the host, Vivienne Wei:
👉 LinkedIn: https://www.linkedin.com/in/weivivienne/
👉 Website: https://www.theviviennewei.com/
👉 Facebook: https://www.facebook.com/vivienne.c.wei
🔗 Listen to AI Heroes & Headaches on your favourite platform:
👉 YouTube: https://www.youtube.com/@theviviennewei
👉 Spotify: https://open.spotify.com/show/6VdE8SqhZhhLHexxzx3gfB?si=f74b0ad0bf2549e4
👉 Apple Podcast: https://podcasts.apple.com/us/podcast/ai-heroes-headaches/id1832607443
#AIInInsurance #Insurtech #GenerativeAI #StartupLeadership #UnderwritingRevolution #AITransformation #VerticalAI #FutureOfWork

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