Oliver Winkenbach

General Manager, Data Applications @ Guidewire | InsurTech & Cloud Strategy | AI & Data Products | Ex-McKinsey

New York City Metropolitan Area

About

I help insurance companies transform how they operate, compete, and grow — through cloud technology, data, and AI. As General Manager of Data Applications at Guidewire, I lead the strategy and growth of our data business, working at the intersection of enterprise software, insurance, and AI. Before stepping into this GM role, I spent over four years driving go-to-market strategy for Guidewire Cloud — helping insurers navigate one of the most significant technology shifts in the industry. Earlier in my career, I spent 8 years at McKinsey & Company advising financial services, insurance, and technology leaders on digital transformation, Lean IT, and operating model redesign. I also had the privilege of building operations at Oscar Insurance during its high-growth phase, where I stood up new capabilities in claims technology, payment integrity, and provider operations from the ground up. I'm particularly energized by the role of AI and data in reshaping the insurance industry — a topic I explored in a recent World Economic Forum publication on organizational transformation in the age of AI. Based in New York. Always open to connecting with operators, investors, and innovators working at the frontier of InsurTech and enterprise AI.

Experience

  • Guidewire Software (8 yrs 9 mos)
    • General Manager - Data Applications
      Sep 2025 - Present · 10 mos

      General Manager of Guidewire's Data Applications business, responsible for strategy, product go-to-market, and growth of the data portfolio across Guidewire Cloud. • Defined and executing the multi-year strategy for Guidewire's Data Applications business, including market positioning, pricing, and partnerships • Leading cross-functional initiatives to accelerate cloud adoption and data-driven decision-making across Guidewire's global insurer customer base • Driving strategic growth programs spanning product, sales, and customer success to expand the data business within the Guidewire Cloud ecosystem • Co-author of a World Economic Forum publication on organizational transformation in the age of AI (March 2026)

    • Senior Manager
      Sep 2023 - Aug 2025 · 2 yrs

      Led go-to-market strategy and execution for Guidewire Cloud and Guidewire Cloud Solutions, driving cloud adoption across the global insurance industry. • Developed and owned the GTM playbook for Guidewire Cloud Solutions, including messaging, sales enablement, and market segmentation • Partnered with product, sales, and customer success teams to accelerate pipeline and conversion for cloud solutions • Contributed to Guidewire's transition from on-premise to cloud-first — one of the most significant business model shifts in the company's history

    • Principal, Product Go To Market
      Jun 2019 - Sep 2023 · 4 yrs 4 mos

      Responsible for go-to-market strategy & execution for Guidewire Cloud and Guidewire Cloud Solutions

  • Senior Manager (Technology & Operations) at Oscar Insurance
    Jul 2016 - Aug 2017 · 1 yr 2 mos

    Joined Oscar Insurance during its high-growth phase to build and scale technology and operations capabilities across Claims, Provider Relations, and Payment Integrity. • Built and launched an in-house claims examination and payment integrity team from scratch, establishing the processes, tooling, and talent base to identify and recover payment discrepancies at scale • Redesigned end-to-end claims processing, complaints handling, dispute resolution, and accounts receivable workflows — reducing cycle times and increasing accuracy across a rapidly scaling operations org • Led the reorganization of member complaints and provider disputes teams (~25 team members), driving toward faster resolution and improved provider and member experience • Defined requirements and designed new internal and external applications (including a provider-facing portal) to streamline workflows and reduce manual intervention • Built out provider-facing metrics, dashboards, and reconciliation reporting — enabling higher visibility and increased self-service for provider partners • Established a knowledge management framework (SOPs, policies, supporting documentation) that accelerated new team member onboarding and enabled faster operational scaling • Managed vendor selection and outsourcing of document management activities, freeing internal capacity for higher-value work

  • McKinsey & Company (8 yrs)
    • Associate Principal
      Jan 2016 - Jul 2016 · 7 mos

      Served as Associate Principal with a focus on IT transformation, Agile operating model design, and Lean operations for financial services and insurance clients. • Redesigned the IT organization and operating model of a major financial institution, creating the structural and governance conditions for a successful transition to Agile software development practices • Led multiple waves of a Lean IT transformation for a major financial services company, driving measurable improvements in delivery speed, cost efficiency, and organizational capability

    • Engagement Manager
      May 2014 - Dec 2015 · 1 yr 8 mos

      Led client engagements across financial services, insurance, and high-tech, managing teams and delivering impact across strategy, digital transformation, and IT operations. • Led digital transformation strategy for a major financial services client, defining the roadmap and operating model to compete in an increasingly digital landscape • Drove Lean IT and operations transformations for insurance and financial services clients, redesigning processes and governance to improve efficiency and scalability • Advised a high-tech client on business unit strategy, strategic partnership management, and project portfolio prioritization — helping align investment with growth priorities • Managed IT organization design, governance, and strategy engagements for financial services and insurance clients navigating regulatory change and technology modernization • Delivered a finance transformation engagement for a major communications company, redesigning core financial processes and reporting structures

    • Senior Associate
      Oct 2012 - Apr 2014 · 1 yr 7 mos

      Delivered client work across Lean IT, service operations, and IT organization design for financial services and insurance clients in the US. • Led Lean IT and operations engagements for financial services clients, identifying and eliminating waste in technology delivery and operations processes • Advised on IT organization, governance, and strategy for financial services and insurance clients undergoing regulatory and technology transformation • Supported service operations redesign engagements, improving end-to-end delivery performance and client satisfaction

  • Visiting Associate at The Boston Consulting Group
    Feb 2007 - May 2007 · 4 mos

    - Private Equity (Financial services)

  • Summer Intern at EADS
    Sep 2006 - Oct 2006 · 2 mos