Upland Capital Group offers a diversified portfolio of excess and surplus lines (E&S) casualty, property, and specialty insurance products, with an initial focus on excess casualty products distributed through select wholesale brokers. The company was established in 2020 and initially announced its launch in January 2021. It is funded through an equity investment of up to $200 million from Newlight Partners LP (Newlight), a growth equity investor, and an additional investment from the company's executive management team. The company is rated A-VIII by AM Best. It has taken a cloud-first approach, with a focus on being secure, nimble but disciplined, and avoiding the "IT Shuffle."

A Certified and Proactive Leader

Dave McKenna is the VP of Information Technology and Chief Information Security Officer with Upland Capital Group. With this role, he has full accountability for building the insurance technology, operational and regulatory, from the ground up. He has spent time in both government and private companies. Prior to Upland Capital Group, he was the Chief Technology Officer for the Massachusetts Cannabis Control Commission with full accountability of all systems and security for the Commission. He has a Ph.D. in Information Technology with research focused on the security of IoT devices, MS in IT Management, and BS in Computer Info-Systems. Dave has various certifications, including Certified Information Security Manager (CISM), Certified Data Privacy Solutions Engineer (CDPSE), and Project Management Professional (PMP).

Trust is The Key to Business Success

As a technology leader, Dave knows when to listen and provide advice where appropriate. He believes that having complete alignment with an organization is essential, and asking questions is a way to get there. Cyber security demands a delicate balance between defending the network and allowing employees flexibility with technology to do their jobs. One achievement Dave had was building a government technology stack from nothing. This build required secretary-level approval, a conscious view of the security of information from medical (HIPAA), criminal (CJIS), employee, licensee, etc. The subject areas were endless, and the implementation was quick (less than six months), and there was an immediate benefit when the COVID-19 pandemic hit.

This implementation allowed all employees to leave work on Friday and start work the following Monday with no impact on operations (including the call center). Traveling through the past experiences, Dave learned to trust expertise, to trust people, decide and implement quickly with purpose.

Stepping Up Against the Challenges

Much of Dave's career was surrounded by understanding how to influence the right people, make the right decisions, and being confident in the result. In many organizations, there are challenges and differing opinions around whether technology is suitable for the organization. Dave says, "Early on, there will be many ideas, and they all will seem easy." On that note, he had to learn that there is a balance between easy implementation, data, and security. Often these areas are separated. By aligning these practices, he was able to be more successful.

"There is a lot of focus on Zero Trust, which enables trusting but verifying to gain authentication. However, once the user is in, we need to analyze, learn, and assess (ALA) their activity to strengthen cyber defense. To trust a user now extends beyond authentication." he adds.

Essential Leadership Qualities for Tech Leaders

Dave said that balance, confidence, education, and persistence are the key traits of a strong, successful leader. A leader needs to balance the needs of the organization, provide solutions in which he or she is confident, stay educated on ubiquitous security topics, and be persistent in his or her decisions. He also mentioned that a leader must have a purpose to proceed.

Implementation of Cloud-Based Operations

Innovation requires commitment and a deep understanding of the organization's appetite for risk, especially concerning technology and security. Introducing something new is not a complex topic. Aligning the innovative topic with practicality is another. Dave said that at Upland Capital Group, he and his team had a healthy respect for innovation. They have set the foundation for innovation by implementing a fully cloud-based operation, which allows for quick adjustments to our overall technology strategy. By enabling this type of environment, everyone can implement solutions with advanced security considerations quickly and gain adoption almost immediately, says Dave. This also allows more proof-of-concept design quickly, which gains traction for innovative ideas—being innovative means constantly evaluating the processes and challenging the teams to do better. This can be with a blend of technology and process. Staying innovative means one is no longer debating technologies that make sense.

An Expanded View on Disruptive Technologies

Dave believes that an IT leader or a CISO is expected to know far more about technology solutions than five years ago. Disruptive technology solutions are increasing cloud adoption, streaming data, IoT, automation, and AI. A CISO has to understand all the potential vulnerabilities each technology might introduce. In addition, leadership expects quick risk mitigation solutions. Essentially, the CISO (and team) has to be embedded in the majority of projects that involve information to drive the deployment of security solutions rapidly.

A Sneak Peek- Adoption of Industry-Leading Technology and Tools

Upland Capital Group has a promising future with its use of technology. The team has an intense focus on data, analytics, and decisions. Upland Capital Group is a cloud-based organization in a position to adopt industry-leading technology and tools in near real-time. Cyber security in the finance sector has evolved into an executive seat at the table for the CISO.

Embracing New Technology

Dave advises the emerging CISOs to keep an open mind, entertain new technologies, and focus more on enabling a rapid deployment environment that supports innovation quicker while keeping threats at bay. Start by asking how (e.g., how will this solution impact the posture against threats), as opposed to jumping to solutions. The future of cyber security is human and behavioral at the core. Be a partner, learn new things, be more than a CISO, be a utility person that brings technology solutions that consider security, says Dave.