Episode #160
May 1, 2025
From Help Desk to Executive Desk
with Chris Griffith from American Coastal Insurance Company and Skyway Underwriters
SPONSORED BY
Chris Griffith from American Coastal Insurance and Skyway Underwriters shares his expertise on going from the help desk to the executives desk. Discover how strong execution, smart frameworks, and leadership drive innovation without compromising quality or compliance.
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Introduction
In this episode of the InsurTech Geek Podcast, James Benham and Rob Galbraith sit down with Chris Griffith, President of American Coastal Insurance and Skyway Underwriters, to unpack an extraordinary career journey. From humble beginnings in technical support to leading an insurance company, Chris’s story is a powerful testament to resilience, learning, and the transformative power of technology in insurance.
This blog explores the major themes from the conversation: career development, the evolving role of AI, the power of no-code platforms, and why humility is a secret ingredient for success.
Career Paths Are Rarely Linear
Chris’s career began not in an executive boardroom but on a help desk, followed by a stint as a repo man — a job that taught him resilience under pressure. Eventually, a newspaper ad landed him a tech support role at DataStream, and the rest is history. His rise through tech roles, including Java development and database administration during the dot-com boom, gave him a front-row seat to the volatility and opportunity in tech.
Chris emphasizes that career trajectories are rarely straight lines. “You go from the help desk to manager to director to CIO — it wasn’t as clear as it sounds,” he noted. Career setbacks, such as the dot-com crash, were vital learning experiences that taught adaptability and persistence.
From Tech to Executive Leadership: Bridging the Gap
One of the major themes from Chris’s story is how technologists can transition into business leadership. His move from CIO to President didn’t happen by accident — it required a deliberate effort to deeply understand the business, not just the technology.
Chris’s advice: if you’re a technologist, don’t just build systems to specifications. Understand why the business needs what it asks for. This curiosity and business insight positioned him to influence decisions beyond IT, eventually stepping into COO and President roles.
Humility and Hard Lessons
In an industry often filled with fast-talking tech evangelists, Chris’s story is refreshing. He shared moments where mistakes (like accidentally deleting a live database) taught him humility and the importance of double-checking everything.
He also emphasized a key leadership lesson: “Dance like nobody’s watching, but write emails like they’ll be read in front of the Supreme Court.” In short, professionalism, caution, and emotional intelligence are as important as technical skill.
AI in Insurance: Assist, Not Replace
Chris and his team at American Coastal are keenly aware of AI’s potential — but also its limits. While AI tools can support underwriting by gathering information and highlighting outliers, human judgment remains critical, especially for complex risks like condos and apartment properties.
Rather than seeing AI as a replacement for underwriters, Chris views it as an accelerator — helping teams make decisions faster and with better information.
The Power of No-Code and Speed to Market
One standout achievement Chris discussed is launching an entirely new insurance product — apartments — in just six months with a seven-person team.
By leveraging a no-code platform rather than traditional heavyweight systems, they were able to skip lengthy development cycles and bring new products to market rapidly. This approach showcases the future for nimble Insurtech startups: agility over tradition.
Chris’s advice for anyone building new lines: “Don’t just follow what you’ve done before — go explore what’s new in the market.”
Conclusion
Chris Griffith’s career exemplifies the perfect marriage of tech savviness, business acumen, and relentless curiosity. In a time when insurance companies are navigating seismic shifts, leaders like Chris demonstrate that real innovation requires both expertise and humility.
Whether you’re starting your career at a help desk or launching the next great Insurtech startup, the lessons from this episode are clear:
✅ Master your craft.
✅ Understand the business.
✅ Stay humble and curious.
✅ Embrace new technology without losing sight of human judgment.