Security Engineer

Improving Veteran outreach through DevOps tools and AWS cloud infrastructure. March 6, 2026. Oddball modernized a federal platform using AWS cloud infrastructure and DevOps tools for Continuous Integration and Continuous Delivery (CI/CD), including Infrastructure as Code (IaC) to meet complex requirements and deliver secure, real-time, multichannel communication to Veterans. Problem Statement/Definition The legacy platform was built on 100+ on-premise servers and could not sustainably manage the rapidly increasing workload of critical Veteran notifications. Oddball was tasked with migrating and modernizing these on-premise servers to a highly scalable, and automated AWS infrastructure using modern DevOps tools. Proposed Solution & Architecture As part of its multi-year modernization effort, Oddball implemented a mature DevOps culture and an architecture based on core cloud-native and automation principles. Continuous Integration and Continuous Delivery: Oddball, Inc. established a fully automated delivery pipeline to ensure every code change was automatically tested and deployed, reducing the risk of human error and increasing the speed of development cycles. Oddball, Inc. used GitHub Actions to automate its CI/CD workflows, which allowed its development team to automate workflows from code commits and pull requests to deployment and updates. To ensure a scalable, serverless container environment, Oddball, Inc. used Amazon Elastic Container Registry (ECR) to store, manage, and deploy Docker container images and OCI artifacts, and then used Amazon Elastic Container Service (ECS) Fargate to run the containerized applications. In addition, Oddball architected a new AWS Python-based workflow into the pipeline which was designed to send SMS notifications to Veterans, and enhanced the existing Flask application to send notifications during a defined timeframe, both minimizing disruption to the delivery process. Infrastructure-as-Code (IaC) and Cloud Native Services: Its architecture and cloud-native services were implemented using anIaC approach, which allowed Oddball, Inc. to manage AWS resources in a programmable and predictable manner. Oddball, Inc. leveraged AWS Lambda for serverless, event-driven processing (e.g., translating opt-in data, consuming payment events), and Amazon noSQL DynamoDB to translate opt-in data via integrations, consume payment events, and track eligible notifications. Oddball, Inc. also used Amazon SQS to send messages between components with no data loss, and AWS Application Load Balancers (ALB) ensure high performance and minimal latency. Observability and Feedback Loops: Oddball, Inc. utilized AWS CloudWatch to provide deep observability across the entire technology stack, offering real-time logging, metrics, and custom alarms to alert its team to the system's health. Amazon PinPoint and Amazon Simple Email Service (SES)/Simple Notification Service (SNS) were utilized not just for email and SMS notification delivery, but also to track user engagement and delivery status, providing Veteran usage data back to development teams for continuous iteration. DevSecOps and Security Automation: Oddball, Inc. integrated security practices directly into the automated delivery pipeline using AWS Identify Access Management (IAM) to securely control access to the system, and adhering to the principle of least privilege by managing users, groups, roles, and permissions across the entire automated environment. Also, the deployment into AWS GovCloud DocDB simplified security and compliance management, including its Authority to Operate (ATO), and allowed the team to focus on secure configuration and automation efforts. Oddball, Inc. iteratively rolled out each modernization in close communication with its stakeholders and clients to avoid disruption and minimize deployment issues. Ultimately, its DevOps culture allowed Oddball, Inc. to enable AWS to build, operate, and maintain performant, reliable software that powers millions of notifications per year. This includes crucial Veteran outreach for appointment reminders, vaccine outreach, surgery notifications, prescription shipment tracking, emergency events, and beyond. Outcomes & Success Metrics * Sustained system error rates below 0.02%, validating the effectiveness of the automated testing and CI/CD quality gates. * Automation and the CI/CD pipeline have enabled more frequent and reliable code changes * Achieved P95 latency at <0.16s for notifications, ensuring a performant application and reliable UX * On average, Oddball, Inc. can securely send 14 million SMS notifications each month * A DevOps culture has allowed its modernization efforts to increase Veteran outreach success, 214 million texts, 27 million emails, and counting * Proactive monitoring via CloudWatch and IaC allows teams to rapidly identify, resolve, and roll back issues, minimizing downtime and improving resiliency of the system. * Modernized Flask app processes 6 million monthly events overnight * Administrators can rapidly configure important healthcare notifications Total Cost of Ownership Analysis Performed Throughout the modernization, Oddball reduced total cost of ownership by replacing fixed-capacity systems with managed, pay-as-you-go cloud services and by utilizing DevOps practices. By building on managed and serverless primitives (e.g., ECS Fargate, Lambda, SQS, SES/SNS) and pairing those with Infrastructure as Code, automated CI/CD pipelines, and robust observability practices, Oddball, Inc. converted hard infrastructure costs and maintenance labor into more measurable operating expenses. This architecture enabled high-throughput, low-latency delivery at scale while minimizing re-platforming costs, accelerating feature delivery, and ensuring sustainable operations for millions of Veteran healthcare notifications annually. Lessons Learned * Continuous Feedback Loops: Oddball, Inc. leveraged Amazon PinPoint and AWS CloudWatch to establish comprehensive monitoring and logging. This accelerated business innovation through continuous feedback loops between Veterans and developers, allowing the development team to quickly iterate on services based on real-time Veteran usage and system performance data. * Single Sign-On (SSO) Integration: Integrating SSO into a serverless ECS environment highlighted the importance of a true DevOps culture, requiring close collaboration between its development, operations, and external SSO teams to successfully adapt legacy services to modern architectures. * Containerization in Cloud Environments: When deciding on a container orchestration solution, Oddball, Inc. found that using AWS services like ECS with Fargate for serverless container management simplified scaling and resource allocation, allowing teams to focus on development instead of day-to-day infrastructure work. * Serverless Infrastructure: By choosing a fully serverless architecture for all AWS resources, Oddball, Inc. streamlined ATO management, and significantly reduced long-term maintenance labor and infrastructure risk, so costs directly match fluctuating notification volumes.

Why did Rob Silverman win the 2026 Wash100 Award? Since joining Oddball, Silverman has positioned the company as a fast-growing, innovation-focused government contractor capable of competing with bigger, more established firms on major programs. Under his leadership, Oddball secured a key IT support task supporting the Securities and Exchange Commission and was awarded its first full and open contract with the Defense Health Agency. The company also earned a position on the Missile Defense Agency's Scalable Homeland Innovative Enterprise Layered Defense, or SHIELD, indefinite-delivery/indefinite-quantity vehicle potentially valued at $151 billion. Additionally, Oddball, through its Oddcore joint venture with Wilcore, is providing the Department of Veterans Affairs with chatbot services under the Strategic Partners for the Reinvention of U.S. Healthcare, or SPRUCE, contract, easing the process for veterans seeking help in accessing government services. As CEO, Silverman has overseen the implementation of Oddball's Corporate Curve 2 strategy, which aims to scale next-generation capabilities and strengthen corporate infrastructure. The establishment of Oddball Labs is a key element of the strategy designed to accelerate innovation and co-develop solutions alongside federal customers. The company is preparing to open a new Oddball Labs facility in Arlington, Virginia, that will support collaboration among government clients, technology vendors and academic partners. Oddball, with the backing of private equity firm Falfurrias Management Partners, is also pursuing strategic mergers and acquisitions to expand capabilities and client access while maintaining cultural alignment. The company continues to invest in areas such as artificial intelligence and machine learning, user-centered design and secure software delivery. In a recent Executive Spotlight interview, Silverman described the company's trajectory as a growth inflection point, stating that Oddball is no longer up and coming; it is "already 'here' in the market and looking to grow to even new heights." Who is Rob Silverman? Silverman has been the CEO of Oddball, a federal digital modernization services company, since November. Prior to joining Oddball, he spent over 23 years at Booz Allen Hamilton, most recently serving as an executive vice president. During his tenure, he led initiatives across defense, civilian and health markets, developing expertise in analytics, digital transformation and mission execution. It was also during his time at Booz Allen Hamilton that he earned his first Wash100 for spearheading defense technology innovation to support U.S. warfighters and for promoting allyship across industry. Earlier in his career, the executive also held roles as a research fellow at LMI and an analyst at KPMG. In addition to leading Oddball, Silverman serves as faculty at Johns Hopkins University's Whiting School of Engineering. What is the Wash100 Award? Launched in 2014, the Wash100 Award 100 honors the 100 most influential leaders in government contracting and the federal sector. The award is handed annually to honorees who are selected through a competitive evaluation process that looks at their leadership, innovation, vision and impact on the GovCon landscape over the past year and their potential to reshape the federal mission in the years to come. The 2026 Wash100 Award underscores Executive Mosaic's recognition of Silverman's leadership during a pivotal stage of growth for Oddball and his broader impact on federal digital transformation efforts. Executive Mosaic congratulates Rob Silverman on his 2026 Wash100 Award. The 2026 Wash100 popular vote competition is underway. Support Rob Silverman and make your voice heard at Wash100.com. Share the Post:

McLean, Virginia-based Oddball, a custom software development and consulting company, ranked #1 in this year's medium-sized Top Workplaces for Engineers list.