James Wynn
Passionate Technologist | Technical Leader | Software Engineer
I’m a seasoned technical leader and engineer with over a decade of experience building high-performance, distributed systems in Java on Kubernetes and cloud environments. I excel in fast-paced environments where I can apply my skills in systems architecture, modern DevOps practices, and team leadership.
As a technical leader, I’ve managed cross-functional, full-stack DevOps teams and implemented modern engineering practices like GitOps (FluxCD), OpenTelemetry for observability, and modular Gradle plugin systems to streamline builds. I’ve also led cloud migrations (to and from Azure), built internal tooling for deployment and report pipelines, and decommissioned large-scale legacy systems after successful client migrations.
I thrive on complex technical challenges, troubleshooting intricate issues, and learning how new technologies can improve systems and processes. I’m especially interested in working with a small, principled organization — preferably nonprofit or public-benefit — that builds tools people actually use and care about, contributes to FOSS, and values privacy, autonomy, and transparency.
Skills & Expertise
- Java
- Python
- JavaScript
- Go
- Rust
- C/C++
- OpenAPI
- OAuth2 / OIDC
- Azure
- AWS
- Docker
- Podman
- Kubernetes
- k3s
- k3d
- PostgreSQL
- MariaDB
- Microsoft SQL Server
- Oracle
- Redis
- CI/CD
- GitOps (FluxCD)
- GitHub Actions
- Azure DevOps
- Spring/Spring Boot
- Gradle
- Custom Gradle Plugins
- Maven
- OpenTelementry
- Prometheus
- Grafana
- Tempo
- Loki
- Splunk
Professional Experience
Custom solutions and technology.
Led the design, development, and delivery of a performance-critical, highly flexible portfolio storage platform for financial applications. Architected from the ground up to support scale, stability, and extensibility across multiple product lines.
- Designed a distributed microservices architecture using modern Java and Sprint Boot, deployed to Kubernetes across environments.
- Implemented a hybrid multi-tenant architecture with MSSQL databases distributed across multiple servers, offering both single-tenant and shared models.
- Integrated Redis for fast, in-memory delivery of priority data.
- Integrated with OAuth2 and bespoke entitlements systems for secure, granular access control.
- Onboarded and supported multiple downstream products, adapting the platform to the varied data and entitlement needs.
- Established robust test coverage, including unit, integration, functional, and performance test suites.
- Conducted regular performance testing and monitoring to ensure system stability and scalability under load.
- Championed engineering best practices, driving clean code, observability, and continuous improvement.
Led the design, development, and delivery of a robust, scalable portfolio processing platform, purpose-built to support complex, rule-driven financial workflows across diverse clients.
- Managed a cross-functional team through full lifecycle delivery – from architecture to production rollout and support.
- Architected a suite of orchestrated Spring Boot services deployed to Kubernetes, built on Spring Batch / Spring Cloud Data Flow backed by RabbitMQ message queues.
- Designed and implemented a custom Groovy-based DSL to enable flexible, user-defined processing rules without code changes.
- Developed a web-based UI for monitoring pipeline execution and inspecting outputs, improving operational visibility and user autonomy.
- Streamlined the build and deployment pipeline to maximize developer efficiency and reduce release overhead.
- Provided direct support to internal users as they developed and deployed configuration packages, ensuring fast feedback and high adoption.
- Leveraged Microsoft SQL Server for durable, high-volume transactional storage.
Contributed to the modernization and cloud migration of a microservice-based AI platform to improve scalability, maintainability, and performance across cloud environments.
- Refactored and migrated complex Node.js services to Spring Boot, improving reliability, performance, and observability.
- Containerized services and deployed the platform to Kubernetes clusters on AWS, increasing scalability and portability.
- Ported the platform from IBM Cloud to Google Cloud and AWS to support broader deployment strategies and client requirements.
- Enhanced AI pipelines and routines to improve model execution, integration, and automation across services.
Led the architecture and delivery of a job orchestration platform that unified modern and legacy portfolio processing tools into streamlined, maintainable pipelines.
- Designed and implemented an Airflow-based orchestration system to coordinate complex, multi-step financial workflows across heterogeneous processing systems.
- Developed supporting microservices for managing and deploying pipeline rules, configurations, and execution metadata.
- Deployed the full system to Kubernetes for scalability, reliability, and ease of management in production environments.
- Enabled consistent and observable execution across legacy and modern platforms, reducing operational complexity and improving maintainability.
Designed, built, and delivered a lightweight, high-efficiency portfolio processing engine tailored for on-premises client deployment.
- Architected and developed a containerized Java/Spring Boot application with YAML-driven processing rules for maximum configurability and minimal operational overhead.
- Created a highly efficient, resource-conscious system optimized for client-specific environments with limited infrastructure.
- Delivered a fully config-driven solution, enabling rapid adaptation to varying data formats and business rules without code changes.
Designed, developed, and maintained a microservice-based platform with a modern user interface to enhance usability and efficiency across legacy portfolio processing tools.
- Architected a modular Spring-based backend to abstract and manage complex legacy systems behind clean service boundaries.
- Built tailored front-end interfaces for specific user workflows, including process monitoring, file access, rule configuration, and data quality management.
- Enabled users to inject custom rules to address edge cases and data anomalies without requiring code-level changes.
- Deployed to a custom on-premises cloud infrastructure
- Significantly improved user experience, operational transparency, and system flexibility across multiple teams.
- Leveraged Oracle database server
Designed and delivered custom libraries for their payment processing platform for iOS and Android.
Brought on post-acquisition to stabilize, document, and decommission a complex legacy portfolio management platform, successfully migrating all clients to modern systems.
- Investigated and reverse-engineered undocumented systems built in C#, C++, and MSSQL to produce technical documentation and ensure operational continuity.
- Designed and implemented a new deployment system, reducing release time from a 9-hour, multi-person process to a 20-minute single-operator task.
- Built automated tools to compare output between legacy and modern platforms, rapidly identifying data and processing discrepancies.
- Developed a reporting pipeline to automate report generation on the legacy platform and deliver them through the new system during the migration period.
- Successfully migrated all clients to the new platform and fully decommissioned the legacy system, improving maintainability, performance, and supportability.
Designed, architected, and developed a single-player 3D educational game with a custom-built engine, aimed at helping K-12 students explore academic and career pathways in a simulated high school environment. Managed a cross-disciplinary team composed of both professionals and students.
- Built a custom game engine in C++ using open-source libraries, supporting real-time 3D graphics and modular game logic.
- Implemented a Lua-based scripting system for dynamic gameplay and educational interactions, enabling rapid iteration and content updates.
- Developed a hybrid UI system using HTML, JavaScript, and CSS for flexible, web-style interfaces integrated into the 3D game environment.
- Enabled character customization, academic and social simulation, and in-game assessments aligned with educational goals.
- Integrated gameplay telemetry to track player decisions and progress across academic, financial, and social metrics for teacher review.
Led the development of a 3D educational multiplayer game designed for K-12 students, targeting ultra-mobile PCs (UMPCs) with significant performance constraints. The game was featured at GDC 2008 in San Francisco.
- Architected and developed a client-server multiplayer system in C++ using RakNet, supporting up to 16 players per world.
- Designed and implemented a custom 3D game engine optimized for low-power devices, leveraging FOSS libraries and efficient rendering techniques.
- Developed Lua-based scripting support for flexible and interactive educational gameplay across subjects including math, bioscience, chemistry, and geography.
- Created Flash-based UI elements to enable rich, interactive interfaces within the game environment.
- Built gameplay telemetry systems for tracking student progress.
- Managed a cross-disciplinary team of professionals and students across art, testing, and engineering disciplines.
- Deployed across UMPC devices in classroom environments to support immersive, game-based learning experiences.
Education
Norman, OK USA
Minors in Math and Japanese.
Recommendations
It’s been my honor to work with James for over 13 years on complex projects of strategic importance, in which he has overperformed and inspired others to do the same.
As a colleague, James is a superior software developer with excellent engineering sensibility, who communicates clearly and professionally. His drive and his broad experience are an asset to any team he’s on. I’ve known James to rapidly deliver value in new contexts, over and over.
As a leader, James guides teams in choosing robust architectures and establishing best practices. Those choices have made his teams especially productive.
I wholeheartedly recommend James Wynn as a senior software engineer and as a leader.
I had the opportunity to work with James for more than 14 years at MSCI, including several years where he was part of my team. During that time, James consistently demonstrated strong technical expertise and a thoughtful approach to problem solving.
Across multiple initiatives, he played key roles in improving and modernizing critical systems. Early in our time together, he helped automate what had been a multi-person, evening-long release process into a single-person task that could be completed in minutes. On HedgePlatform, he contributed to modernizing the application stack by helping to introduce Spring Boot–based microservices, and later served as the lead developer for the microservice layer on OMPS (One MSCI Portfolio Service).
James brings a deep understanding of enterprise systems and a proven ability to deliver robust, scalable solutions. He would be a strong technical asset to any team looking for depth in architecture and implementation.
James is an outstanding software engineer and a true leader. We initially hired him part time when he was a student. His work was so outstanding that we hired him full time when he graduated. He has lead a team of student software engineers to produce a unique educational game engine. His software design and implementation is outstanding. Our team could not get along without him.
James is an exceptionally talented programmer and in addition has natural communication and leadership skills. As a lead developer at the k20 Center he managed to build and foster a spirit of team work that went a long way towards helping us achieve our common project goals.
He has excellent problem solving skills and in my work with him I have not witnessed a programming challenge he wasn’t able to raise to. Last but not least, he has great understanding and knowledge about many aspects of the process of developing a videogame, including non-programming ones such as different hardware platforms, networking, and 3D graphics.