The operating system for insurance

bringing more than 20 years of experience at the intersection of applied mathematics, engineering, and business. A researcher, inventor, and entrepreneur, he combines the ability to develop foundational AI methods with the practical experience to build them into working businesses. Previously, he founded Data Clairvoyance Group and served as Chief Data Officer of Infogix, both of which were acquired, and held leadership roles at Bridgewater Associates and CNO Financial Group. He is also co-founder of Duo Dimensio (d2.ai), where his research focuses on AI models built directly on business data to support traceable, reliable decisions. The primary inventor on 11 granted U.S. patents, Reuben brings this breadth of experience to SecondSight’s work in underwriting, pricing, and portfolio management. He holds a B.S. in Microbiology from Indiana University and a Master of Finance and Economics from the University of Indianapolis.

bringing nearly two decades of experience in insurance and technology, with deep expertise in cyber risk, underwriting, and specialty insurance. Before joining SecondSight, he served as CEO of Ryan Financial Lines and Celerity Risk, leading businesses spanning cyber, professional liability, and financial lines. Previously, Jamie led underwriting for CFC Underwriting’s large corporate cyber facility and its technology and media practice.

He also held multiple leadership roles at AIG, including Head of Cyber, Technology and Media for Europe, the Middle East, and Africa, and helped develop the company’s international cyber product and strategy. His background combines hands-on underwriting expertise with experience building insurance businesses across international markets. Jamie holds a B.A. in Economics and History from Franklin & Marshall College.

Derek brings more than two decades of experience scaling technology and operations in highly regulated insurance markets. He joins SecondSight from Bloom Insurance, where he spent 17 years as Chief Operating Officer and later Chief Technology Officer, helping grow revenue from $5 million to $80 million. As CTO, Derek raised the capital to launch Ascend, a SaaS quoting and enrollment platform, and led its growth through SOC 2 compliance, a cloud migration, and expansion into mobile, voice, and individual marketplace products.

Dan joins SecondSight with deep operational and financial expertise across the startup ecosystem. Most recently, he served as Managing Partner at Zag Capital, a single-family office with investments in startups, venture capital, real estate, and services businesses. Previously, Dan spent a decade as an early operator at several high-growth startups, including AppNexus (Acquired), OrderGroove, and Rockerbox (Acquired). His experience includes establishing customer success and support functions from the ground up, developing client onboarding, engagement, and reporting processes, and building and leading teams through growth.

bringing more than a decade of experience advising clients on cyber risk and insurance. He began his career at JLT in London in 2012, broking complex cyber risks into the Lloyd’s of London market. James later moved to the US to help build out JLT’s cyber offering, guiding organizations through a rapidly evolving threat landscape. Following JLT’s acquisition by Marsh, he became one of the firm’s Northeast cyber leaders, managing a team of specialists and serving businesses across a broad range of industries and risk profiles. Throughout his career, James has focused on translating technical exposures into practical risk management and insurance strategies. At SecondSight, he brings together technology, data, and insurance expertise to give clients a more effective way to understand and manage cyber risk.

David’s years’ long insurance brokerage executive and client management experience is his North Star as he works with clients to imagine and build bespoke and effective solutions at SecondSight. For over a decade, David was a dedicated and fierce advocate for his clients - delivering on complex insurance brokerage and risk management consulting needs. He has built out and supported multiple teams focused on management liability, cyber, and property & casualty brokerage serving clients of all sizes and verticals. In his previous leadership roles, David was Woodruff Sawyer’s Vice President of Cyber, US Head of Cyber at McGill and Partners, and Head of Major Accounts for Lockton prior to that. David graduated from Arizona State University with a B.S. in Management.

He most recently served as COO of the Private Equity Practice at CAC Specialty, with prior senior roles at Willis Towers Watson in the M&A/Transactional Risk Practices, and within Lockton’s Financial Institutions Group. His diverse leadership background across all commercial lines of insurance allows him to develop differentiated growth strategies and scalable operating platforms for financial services organizations.

Kenny graduated magna cum laude from Babson College where he earned a Bachelor of Science in Business Administration and from Villanova University where he earned an MBA in Strategic Management

Doug brings nearly 20 years of insurance experience to the role, having worked at major carriers including AIG, The Hartford, Travelers, and Chubb. Most recently, he built a $3M book of business from scratch in 18 months as a broker at Anzen.

Doug also acts as a forward development engineer, using AI to turn ideas into solutions, keep teams moving, and help guide projects through build and implementation.