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Oddball

SDVOSB digital modernization for federal services

Vice President of Engineering

Full-Time
$170k - $250k+ Annual stipend + 401(k) match
Expert
Washington, DC, USA
HybridMust be located in the DMV area and work in the Rosslyn, Virginia office three days a week.
Engineering ManagementEngineering Leadership

About the job

Requirements
  • At least 7 years of experience in software engineering, systems architecture, or technical leadership roles.
  • Deep understanding of architecture concerns, including performance, scalability, security, reliability, and observability.
  • Experience across multiple technologies, including cloud platforms such as AWS, Azure, or GCP, containerization, microservices, and distributed systems.
  • Experience with infrastructure as code, continuous integration and continuous delivery, and deployment pipelines.
  • Experience deploying applications to production environments.
  • Ability to explain architectural trade-offs to engineers, product stakeholders, and leadership.
  • Ability to translate strategic objectives into actionable technical roadmaps.
  • Experience leading and managing engineers and helping raise technical maturity.
  • Must be authorized to work in the United States.
Responsibilities
  • Lead the technical vision and manage a small team of engineers.
  • Set architecture standards and work with product managers to deliver scalable, reliable, and future-proof products and tools.
  • Define the lab's technical vision and support growth and sales efforts.
  • Implement ideas through agile experimentation and delivery cycles.
  • Perform other related duties as assigned.
Desired Qualifications
  • Prior experience designing and securing federal systems, including FedRAMP, Authority to Operate (ATO), or zero-trust systems.
  • Certifications or background in architecture frameworks such as TOGAF.
  • Experience designing systems that incorporate both artificial intelligence/machine learning and non-machine-learning components.
  • Direct experience delivering artificial intelligence/machine-learning systems in production at scale, with a focus on trust and explainability.
  • Prior experience in startups or fast-moving environments where building and iterating quickly is required.
  • Prior experience working with government as a contractor or federal employee.

About the company

Oddball helps federal agencies modernize citizen-focused services by delivering end-to-end digital solutions—from design through deployment—using scalable software that supports both the public and government workforces. Its teams fuse user-centered design with technical execution, combining UX research, development, and operations practices like CI/CD and cloud migration to produce deployable software. As an SDVOSB-certified, veteran-owned partner, Oddball differentiates itself through a full-stack, end-to-end service with an emphasis on citizen needs and enterprise-grade delivery. The goal is to improve government services for citizens and boost workforce efficiency through reliable, maintainable software and continuous delivery.

Company Size

201-500

Company Stage

Grant

Total Funding

$1.5M

Headquarters

Washington DC, District of Columbia

Founded

2015

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Simplify's Take

What believers are saying

  • August 2026 Baumgartner targets CMS and HHS expansion, enlarging Oddball's federal health wedge.
  • September 2026 SEC cloud-support win added $4.8 million and validates competitive strength.
  • March 2026 veteran-notification modernization shows scalable AWS delivery across millions of monthly transactions.

What critics are saying

  • SEC work concentrates revenue; losing the BPA recompetes by 2028 would hit hard.
  • BEDAP ended August 18, 2026, exposing renewal risk across VA and HHS workloads.
  • Falfurrias ownership increases pressure for faster growth, exits, and margin discipline.

What makes Oddball unique

  • SDVOSB status and remote-first delivery position Oddball inside federal set-aside buying channels.
  • Human-centered design plus DevSecOps underpins its citizen-service modernization brand.
  • Recent hires Baumgartner, Ciesielski, and Rose deepen federal health, architecture, and transformation expertise.

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Benefits

  • Remote Work Options
  • 401(k) Company Match
  • Unlimited Paid Time Off
  • Paid Holidays

Growth & Insights and Company News

Headcount

6 month growth

25%

1 year growth

25%

2 year growth

25%
PR Newswire
Oct 7th, 2026
Oddball appoints Kathy Klapacz as chief operating officer

Oddball, a digital services agency focused on government technology modernisation, has appointed Kathy Klapacz as chief operating officer. Klapacz brings 20 years of executive leadership experience in federal programs and technology organisations, including work with the Centers for Medicare & Medicaid Services, Department of Health and Human Services, and Defense Health Agency. Throughout her career, Klapacz has led federal portfolios exceeding $100 million and managed organisations of more than 400 personnel. Her experience includes overseeing large-scale technology modernisation initiatives, cloud transformation, and operational strategy. As chief operating officer, Klapacz will oversee operational strategy and execution whilst strengthening collaboration across delivery, engineering, and growth. She holds an MBA from the University of Maryland University College and a Bachelor of Science in Industrial Engineering from Penn State University.

SBIR.gov
Sep 13th, 2026
Awards | SBIR

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GovCon Wire
Aug 21st, 2026
Paul Baumgartner joins Oddball as Federal Health VP.

Paul Baumgartner joins Oddball as Federal Health VP. * Oddball has tapped Paul Baumgartner to lead federal health * Baumgartner brings more than 18 years of federal health experience to the role * The 2026 Healthcare Summit will explore AI, healthcare delivery and more Paul Baumgartner, a federal health technology executive, has joined digital services provider Oddball as vice president of federal health. As federal health agencies pursue modernization and expanded digital service delivery, government and industry leaders will gather at the Potomac Officers Club's 2026 Healthcare Summit on Dec. 3 to discuss artificial intelligence, digital tools and other modernization priorities aimed at improving healthcare access. Sign up now to join the conversation shaping the future of federal health delivery. What are Baumgartner's responsibilities at Oddball? In a LinkedIn post published Wednesday, Oddball said Baumgartner will lead Oddball's growth strategy across the federal health market, with a focus on expanding partnerships with the Centers for Medicare and Medicaid Services, the Department of Health and Human Services and other federal health organizations. Baumgartner said he is excited to help grow the company's federal health business. "I'm excited to help grow our Federal Health business by partnering with agencies to accelerate mission delivery, support their evolving priorities, and deliver measurable outcomes for the people they serve." Who is Paul Baumgartner? Baumgartner is a federal health technology executive with over 18 years of experience supporting federal health agencies on mission outcomes through modern technology, product delivery and enterprise-scale execution. According to his LinkedIn profile, he most recently served as a business development executive at General Dynamics Information Technology. Before GDIT, he spent more than a decade at SemanticBits, where he served as vice president of digital health and director of business development. He also served as senior manager of operations controls and bioinformaticist at Gene Logic. The James Madison University graduate holds a master's degree in bioinformatics and computational biology.

GovCon Wire
May 5th, 2026
Oddball appoints Agata Ciesielski, Drake Rose to executive leadership roles.

Oddball appoints Agata Ciesielski, Drake Rose to executive leadership roles. Oddball has added Agata Ciesielski and Drake Rose to its executive leadership team. Ciesielski will serve as vice president of architecture, while Rose will lead as vice president of digital transformation, the McLean, Virginia-headquartered company said in a LinkedIn post Monday. Agencies are rapidly adopting AI and automation to secure their systems against cyberthreats. Join the Potomac Officers Club's 2026 Cyber Summit on May 21 to hear directly from government leaders how new technologies, including AI, are changing the cyber landscape. Sign up today. Who is Agata Ciesielski? Ciesielski brings extensive experience in artificial intelligence and federal technology modernization. She previously led AI-driven transformation efforts at the Department of Homeland Security within the Office of the Chief Information Officer, where she helped optimize a $7 billion annual technology acquisition process and delivered scalable AI capabilities through DHSChat product lines, generating cost savings and efficiency gains. Her background also includes roles at the National Science Foundation and the White House Presidential Innovation Fellows program, where she supported AI strategy development across multiple federal agencies. In addition, she founded Tethics to help organizations deploy AI and data in a legal and ethical manner and worked as a senior AI solutions manager at C3 AI. At Oddball, Ciesielski will help advance Oddball Labs, the company's innovation arm focused on scaling AI capabilities to support federal systems. Who is Drake Rose? Rose brings more than a decade of experience delivering user-centered digital platforms across defense and commercial sectors. He most recently supported the modernization of Air Force command and control systems during his tenure at Kessel Run, where he held product leadership roles. He also held the role of senior product specialist at S&P Global. Earlier in his career, he served as an infantry mortarman section leader in the U.S. Marine Corps. At Oddball, Rose will be in charge of efforts to advance digital transformation initiatives, applying his experience in product development and platform delivery to improve government digital services and drive adoption of modern technologies.

Oddball
Mar 6th, 2026
Improving Veteran outreach through DevOps tools and AWS cloud infrastructure.

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.