Executive Team
Mike Rosenbaum joined Guidewire as Chief Executive Officer in 2019. Since Mike’s arrival, Guidewire has cemented its position as the leading cloud platform serving the P&C insurance industry, growing cloud adoption by over 500%, tripling cloud revenue, and expanding the Guidewire partner ecosystem to become the largest in P&C insurance.
Mike’s focus on delivering value for customers, coupled with his “ship, shipmate, self” approach to prioritization, continue to shape the industry-leading platform, applications, and content trusted by insurers globally. Prior to Guidewire, Mike led product management and go-to-market strategy for core CRM products at Salesforce and served in the US Navy as a submarine officer.
John leads Guidewire’s Global Sales, Delivery Services, and Customer Success organizations. He is an accomplished senior executive with more than 25 years of experience in driving high-growth teams to shape and deliver industry transformation. As head of the $4B+ North America Business Unit at Capgemini, John led a global team of professionals in delivering innovative solutions that support the strategic growth of the world’s leading brands. Previously he had led the Capgemini Insurance Business Unit, overseeing the expansion of Capgemini’s global insurance business. He began his career with eight years at Accenture.
As Chief Financial Officer, Jeff is responsible for Guidewire’s financial operations, which includes FP&A, accounting, investor relations, facilities, and procurement. He contributes to strategic planning and helps assess risks and opportunities. Previously, Jeff oversaw company financials as the Vice President of Finance at Guidewire. Prior to that, he was the Chief Financial Officer at GoodData and Vice President of Finance at Rally Software. Jeff began his career as an investment banker focused on the software industry.
Winston is responsible for Guidewire’s worldwide administrative functions, including human resources, business technology, recruiting, legal, and corporate services. He also manages Guidewire’s corporate and compliance matters, as the company’s General Counsel and Secretary. Prior to Guidewire, Winston served as EVP, General Counsel, and Secretary at Infogroup and also worked at WilmerHale, an international law firm. Winston served as a clerk to Judge Bruce Selya on the US First Circuit Court of Appeals.
As Guidewire’s Chief Customer Officer, Christina helps customers to realize optimal value through their journey with Guidewire. Previously, Christina led cloud sales strategy globally at Guidewire, leveraging her commercial and operational cloud experience. She brings deep consulting knowledge to Guidewire programs as well as SaaS proficiency from her 15 years at Capgemini. Christina also spent four years on the executive leadership team of Virtustream, the mission-critical cloud company of Dell Technologies.
Brigette McInnis-Day is the Chief People Officer of Guidewire, bringing over 25 years of experience leading HR, operations, and organizational transformation at UiPath, Google Cloud, SAP, and Mercer. She is recognized for advancing inclusion, scaling global teams, and embedding AI and automation into HR to drive business growth. Brigette holds a Master’s in Industrial/Organizational Psychology and was named one of the Top 50 Women Leaders of Philadelphia (2024).
Brian leads Guidewire’s global marketing efforts, including demand generation, branding, and communications. Brian joined Guidewire in 2006, and during his tenure the company has been recognized as an industry-leading brand serving customers in more than 30 countries. He previously was Vice President of Marketing for PeopleSoft’s supply chain division and held marketing leadership and product marketing roles at Ketera, Ariba, and Tradex. Brian serves on the board of directors of Betterview, an insurtech that provides a geospatial predictive analytics platform for P&C insurance.
Diego has held numerous executive positions overseeing technology and product development in the San Francisco Bay Area, India, and Europe. In his role at Guidewire, he drives design and strategy to implement engineering goals that address the needs of P&C insurers, such as the requirement to rapidly bring new and differentiating insurance products to market. Prior to Guidewire, Diego served as Vice President of Software Development and Vice President of Product and Engineering at SAP Labs. He began his enterprise software career at Baan in the Netherlands.
David leads Guidewire’s Global Sales, Inside Sales, and Solution Sales organizations. David is a proven senior executive with deep domain expertise in driving high performance organizations that focus on customer success. He also has vast experience working with customers across many industries on their cloud transformation journey. David has held several senior leadership positions at SAP & Salesforce. Most recently, David was the former Senior Vice President (SVP), Financial Services and Banking for North America Cloud and Technology at Oracle. In this role, he helped customers identify value and drive collaborative strategies to best meet their business goals in moving to the cloud.
