As chief digital officer of ProSight Specialty Insurance, Darryl leads the Core IT and Digital teams. Siry also held executive roles at ProSight, Tesla Motors, and Fireman’s Fund/Allianz; founded and led a small business PR services software startup and worked at Mercer Management Consulting. He has a BA in Economics from Brown University. He was interviewed for the Novarica Update in 2018.

Matt Josefowicz, Novarica: What are your top priorities for the next six to 12 months?

Darryl Siry, ProSight: The largest one is building and evolving our direct-to-consumer small commercial platform. Our recent launch is just the first step in the evolution. We’re starting small with one target segment, and we’ll be expanding over coming months. Our objective is to learn as we go, evolving both the technology and product offering.

MJ: What was the process like for designing the direct product and customer experience?

Darryl Siry, chief digital officer, ProSight Specialty Insurance
Darryl Siry, chief digital officer, ProSight Specialty Insurance

DS: The key was that we had to build a team that could do design, user experience, and development all together. What we want is to build a lasting core competency in digital, not just complete a digital project.

MJ: What was the most interesting or surprising lesson for you?

DS: The most interesting thing to me, having been involved in full-stack Web development and having had a lot of experience on core systems, was that I really didn’t appreciate how much you have to architect your middle API layer to support a great digital experience. We had to build the API layer as if it was a product. We wanted to build not just for this project, but to meet requirements for coming years and to be able to plug in with other platform partners.

MJ: What should people know about building out that layer?

DS: You look at core systems and you hear the marketing language that says “we have an API.” That may be true, but it’s not sufficient. We quickly learned you have to build an API for the API. To the extent that the API for a system is reflective of the systems’ business process flows, that may not support the flows of the digital experience you’re building. If your goal is to create a simple, enjoyable experience for end customers, that may require a lot of complexity behind the scenes.

You can’t take complex products and deliver them in a simplified way. You really need to rearchitect the product end to end. You can’t just take an old product off the shelf and shove it through the Internet. It’s an entirely different business model, not just a channel.

MJ: How has that mindset affected the design of your IT organization?

DS: We completely reorganized in September when we set out to do this. Just treating this as an IT project wouldn’t get us there. We had to set up as a product organization with the ability to iterate rapidly based on market feedback. We split IT: core IT including infrastructure, security, and development was put under one senior executive, and then we built out a digital organization with digital engineering, UX, product management, and digital marketing. We think it’s distinctive to have marketing, UX, and design all reporting to an “IT” executive. Without that unified digital team, it’s much harder to deliver an effective digital product and experience.

MJ: How have your teams leveraged the Novarica relationship?

DS: The publications are very timely and relevant, but our ability to reach out and get the best current thinking on our specific topics is extremely valuable. I think we’ve also found it very valuable to attend the events. They’re structured in a way that really promotes open and honest conversations with peers in a way that’s very difficult to do.

This article has been reprinted with permission from Novarica.

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