ProSight Specialty Insurance

We made old-school insurance IT shiny and new.


ProSight Specialty Insurance’s managed hosting providers were becoming increasingly rigid and expensive to maintain, and policy renewals often overwhelmed the network.


They needed a secure, cost-effective way to manage their IT in a highly-regulated industry.


We proved the case for cloud and moved all of their applications and infrastructure to AWS, increasing performance by 40%, decreasing costs by 30% and allowing the firm to scale resources with demand.

ProSight Specialty Insurance serves the commercial property and casualty insurance market, focusing on niche industries such as media, entertainment, restaurant, construction, marine and oil and gas. The company, founded in 2009, is based in Morristown, New Jersey. ProSight Specialty Insurance’s written premium volume grew by over 40% annually in the last five years, and the firm holds over $370 million in policyholders’ surplus and over $1.2 billion in statutory assets.

IT challenge

The company had been managing its IT infrastructure through various managed hosting providers, which over time had proven increasingly rigid and expensive to maintain. Darryl Siry, the company’s Chief Digital Officer, began to investigate new options for managing IT in 2015.

ProSight had several issues it needed the new platform to address. The company required its remote users to VPN into a Cisco concentrator and then RDP into a Virtual Desktop to access network resources.  The process was difficult to manage and expensive to maintain. The company had no log management tools and no threat detection tools, so it also required a security solution with the new environment.

Siry, who also leads the IT department at ProSight, was convinced that moving to the cloud, particularly AWS, would be the right move. In his previous life as the founder of a Silicon Valley startup, he had positive experiences using AWS to host the company’s service. “I wanted to take a fresh view of technology and apply the Silicon Valley approach to IT. When I looked at the massive amount of money we were spending on servers, I wanted to find out whether AWS was ready for the enterprise and for highly-regulated businesses like ours.”

Siry attended AWS summits to educate himself on the AWS platform, where he was introduced to team members from 2nd Watch. He concluded that pursuing a cloud strategy was the best option for the firm, but he needed to test it and prove the concept to his senior management. Moving to the cloud would be a bold move for a company in the specialty insurance sector, which is very traditional in managing IT, according to Siry. The firm’s board expected a change, he says: “The board is sophisticated when it comes to tech, and they aren’t strangers to innovating.”

To ensure that AWS was the best cloud platform for the company, ProSight analyzed migration plans for moving both to AWS and to Microsoft Azure. The company found AWS would not only result in greater savings, but also offered more flexibility and sophisticated services while still being a viable platform for Windows and .Net systems.

2nd Watch Proof of Concept

ProSight needed to find a partner to help set up the POC, which would involve replicating four of the company’s corporate applications to the AWS environment. “We looked at some of the large consulting firms and system integrators, but it became evident to me that a lot of what they were saying was marketing babble. I wasn’t confident that they had deep technical understanding of the cloud. Meanwhile, 2nd Watch has grown up with AWS and they know the technology inside and out,” noted Siry.

The POC occurred in the fall of 2015, and the numbers proved valid: performance increases of more than 40% and 30% savings compared to using the existing managed hosting provider. Those numbers alone convinced the board at ProSight Specialty that moving to the cloud was a no-brainer. “Typical hosting providers today are not innovating and they are not focused on cost efficiency,” Siry remarks. “To compete in the digital world, you need partners that are innovative. Also, AWS continues to drive costs down.”

Moving ahead with the cloud

ProSight made the decision in June of 2016 to move to AWS with 2nd Watch facilitating the migration and managing the environment. With 2nd Watch help, the firm moved all of its applications, outside of Office 365, and infrastructure to the cloud. Included in the migration and configuration are a variety of Microsoft SQL Server versions (2008 – 2014), setup and configuration of SQL Server Reporting Services and SQL Server Integration Services as well as configuration of a SQL Server multi-subnet failover cluster.

The company has gained access to Amazon Workspaces, replacing both the Cisco client VPN and the Virtual Desktops with one easy-to-use Workspace. 2nd Watch security partner, Alert Logic Defender, collects server logs for analysis and monitor for threats to the servers, addressing ProSight’s security requirement.

Once migrated, ProSight needed additional expert cloud help in creating its first direct-to-consumer insurance portal, being the company’s first cloud-native, born-in-AWS application. 2nd Watch created repeatable design for all direct-to-consumer portals with a focus on customer experience and security. 2nd Watch also assisted with the IEM process with AWS as well designing and implementing some of the Amazon ELB, CloudFront and WAF components.

Benefits from 2nd Watch and AWS

Cost and performance: The proof of concept gave Siry confidence that his company will achieve measurable cost savings and performance benefits.

Managing workload spikes: Now, when major insurance policies hit renewal time for customers, those transaction workloads won’t overwhelm the network. On AWS, ProSight can fire up additional resources, particularly the CPU and I/0 optimized instances, to expedite processing during heavy workload times. “Our policy admin system architecture involves XML-heavy processing and that has been a bottleneck in the past, resulting in failed transactions for very large policy renewals,” Siry says. Unlike with their managed hosting providers, the insurance firm can ramp up and scale back infrastructure resources in tune with demand.

Workforce productivity: ProSight expects that better, more reliable performance of applications hosted on AWS will help increase productivity across the company.

Optimization of IT spend: ProSight’s 30% cost savings on IT infrastructure will now go toward supporting higher-level activities such as new customer-facing services.

“We’re fortunate in that our CEO really believes in technology as a differentiator in our space,” says Siry. “Most commercial insurers are old-school. Now, we are in the position to grow faster and smarter. 2nd Watch and AWS have been excellent digital transformation partners for our business, helping us get to that next level of competition.”

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