Oddball

Oddball believes that the best products are built when companies understand and value the things they are working on. We value learning and growth and the ability to make a big impact at a small company. We believe that we can make big changes happen and improve the daily lives of millions of people by bringing quality software to the federal space. We're looking for a Proposal Writer to join our dedicated Proposal team, where you’ll own the content strategy and production of our responses to government Requests for Proposals (RFPs), Quotes (RFQs), Information (RFI), and other external deliverables to support the opportunity lifecycle. What you'll be doing: Lead content planning, writing, graphics ideation, peer reviews, and editing across proposal volumes and artifacts, including but not limited to: technical approaches, management, corporate experience, staffing, vendor-written Performance Work Statements, oral presentations, and technical challenges. Work with the proposal, business development, capture, solutioning, and operations teams to clear blockers to developing compliant, responsive, and compelling proposals. Interview subject matter experts to extract (not simply transcribe) technical information and distill it into clear, persuasive, and differentiated narrative and concepts for graphics. Act as an ambassador of the Proposal team, Growth team, and of Oddball: manage peer, cross-functional, executive, and external relationships to ensure consistent input, alignment, and buy-in to the proposal process. Demonstrate disciplined and ethical use of AI as an extension of your own thinking and ability to produce winning content, never as a substitute for it: arguing against your own draft, shifting feedback left based on evaluation criteria and company standards, and running down sources so you can stand confidently behind every word on the page. Meaningfully contribute to improving the writing practice, proposal function, and broader Growth team at Oddball. What you’ll bring: Proven experience leading proposal volumes for U.S. federal government clients across multi-phase and quick-turn efforts. Exceptional writing skills with the ability to sell complex technical concepts and our value proposition to all buyer personas/stakeholders. Familiarity with U.S. federal agencies (civilian and defense), with experience writing proposals for VA, CMS, SEC, and DoW preferred. Strong understanding of federal contracting including the FAR, contract vehicles, and the opportunity/business development lifecycle. Demonstrated fluency with key concepts in government technology today, including: agile, human-centered design, DevSecOps, cloud infrastructure, product management, etc. The drive to excel under deadline pressure and in collaborative cross-functional environments Communication and persuasion skills, whether you’re interviewing a SME from the driver’s seat, offering peer-to-peer feedback, or presenting to leadership. Intellectual curiosity about the work Oddball does and how we put Oddball in the best position to win more work. A genuine passion for how what we do as a company improves the lives of the people we serve. Requirements: Applicants must be authorized to work in the United States. In alignment with federal contract requirements, certain roles may also require U.S. citizenship and the ability to obtain and maintain a federal background investigation and/or a security clearance. Education: Bachelor’s degree Benefits: Fully remote Tech Stipend Comprehensive Benefits Package Company Match 401(k) plan Flexible PTO, Paid Holidays Oddball is an Equal Opportunity Employer and does not discriminate against applicants based on race, religion, color, disability, medical condition, legally protected genetic information, national origin, gender, sexual orientation, marital status, gender identity or expression, sex (including pregnancy, childbirth or related medical conditions), age, veteran status or other legally protected characteristics. Any applicant with a mental or physical disability who requires an accommodation during the application process should contact an Oddball HR representative to request such an accommodation by emailing hr@Oddball.io Compensation: At Oddball, it’s important each employee is compensated competitively and fairly. In alignment with state legal requirements. A range for the included position is listed below. Be advised, actual offer details are determined by job category, job location, and candidate skill level. United States Wage Range: $110,000 – $140,000

Oddball believes that the best products are built when companies understand and value the things they are working on. We value learning and growth and the ability to make a big impact at a small company. We believe that we can make big changes happen and improve the daily lives of millions of people by bringing quality software to the federal space. This position is contingent upon contract award. As a Key Personnel role, the selected candidate will be asked to sign a letter of intent and may be invited to participate in oral presentations or pre-award activities as part of the proposal process. We're looking for a Program Manager to join our CMS team, serving as the single point of accountability for a Medicare Part A claims processing program supporting millions of beneficiaries. What you'll be doing: Serve as the primary point of contact to the Contracting Officer and COR for all aspects of the task order Own staffing, cost management, and performance reporting across O&M and modernization workstreams Maintain visibility into program health, risks, and dependencies across the full contract Build and sustain strong relationships with CMS stakeholders and the prime contractor Represent Oddball at program-level meetings, reviews, and reporting sessions What you’ll bring: Proven program management experience on large-scale federal IT contracts Experience managing cost, schedule, and performance on complex multi-workstream programs Familiarity with CMS, Medicare, or federal health IT environments is a strong plus Experience working as a subcontractor in a prime/sub teaming arrangement is a plus Experience managing delivery in an Agile environment, including sprint coordination and release planning Thrives in a remote, collaborative environment and genuinely enjoys working across matrixed teams Communicates clearly and openly with both technical teams and senior government stakeholders Performs other related duties as assigned. Requirements: Applicants must be authorized to work in the United States. In alignment with federal contract requirements, certain roles may also require U.S. citizenship and the ability to obtain and maintain a federal background investigation and/or a security clearance. Education: Bachelor’s degree Benefits: Fully remote Yearly stipend Comprehensive Benefits Package Company Match 401(k) plan Flexible PTO, Paid Holidays Oddball is an Equal Opportunity Employer and does not discriminate against applicants based on race, religion, color, disability, medical condition, legally protected genetic information, national origin, gender, sexual orientation, marital status, gender identity or expression, sex (including pregnancy, childbirth or related medical conditions), age, veteran status or other legally protected characteristics. Any applicant with a mental or physical disability who requires an accommodation during the application process should contact an Oddball HR representative to request such an accommodation by emailing hello@Oddball.io Compensation: At Oddball, it’s important each employee is compensated competitively and fairly. In alignment with state legal requirements. A range for the included position is listed below. Be advised, actual offer details are determined by job category, job location, and candidate skill level. United States Wage Range: $125,000 – $175,000

Oddball believes that the best products are built when companies understand and value the things they are working on. We value learning, growth, and the ability to make a big impact at a small company. We believe that by bringing quality software to the federal space, we can make big changes happen and improve the daily lives of millions of people. We’re looking for a Delivery Manager to join our VA team, keeping delivery moving on the products that power the authenticated Veteran experience across VA.gov. What you'll be doing: Partner with Product Managers and engineering teams to plan, prioritize, and deliver high-quality software on schedule Facilitate Agile ceremonies including standups, sprint planning, refinement, retrospectives, and sprint demos Track delivery progress, surface risks early, and keep stakeholders informed and aligned Help break down product initiatives into actionable, well-scoped work for engineering teams Collaborate with Product Owners on roadmap planning, backlog prioritization, and release planning Coordinate across teams in the broader VA.gov ecosystem to manage dependencies and keep efforts aligned Write clear reports and updates that communicate the value the team is delivering to clients and leadership Foster a team environment built on accountability, clear communication, and continuous improvement What you’ll bring: Experience managing software delivery in an Agile environment, ideally on federal programs Familiarity with VA.gov platform conventions or similar federal digital services is a plus Strong facilitation skills — you can run a room, keep things moving, and bring out the best in a team Ability to work across disciplines, translating between technical teams and non-technical stakeholders Comfort with ambiguity — you know how to create structure and clarity without having all the answers upfront Experience with project and collaboration tools such as Jira and Confluence Thrives in a remote, collaborative environment and genuinely enjoys working closely with a cross-functional team Communicates clearly and openly, whether writing a status report, running a retro, or escalating a blocker Performs other related duties as assigned Requirements: Applicants must be authorized to work in the United States. In alignment with federal contract requirements, certain roles may also require U.S. citizenship and the ability to obtain and maintain a federal background investigation and/or a security clearance. Education: Bachelor’s degree Benefits: Fully-remote Annual stipend Comprehensive Benefits Package Company Match 401(k) plan Flexible PTO, Paid Holidays Oddball is an Equal Opportunity Employer and does not discriminate against applicants based on race, religion, color, disability, medical condition, legally protected genetic information, national origin, gender, sexual orientation, marital status, gender identity or expression, sex (including pregnancy, childbirth or related medical conditions), age, veteran status or other legally protected characteristics. Any applicant with a mental or physical disability who requires an accommodation during the application process should contact an Oddball HR representative to request such an accommodation by emailing hr@oddball.io Compensation: At Oddball, it’s important each employee is compensated competitively and fairly. In alignment with state legal requirements. A range for the included position is listed below. Be advised, actual offer details are determined by job category, job location, and candidate skill level. United States Wage Range: $90,000 – $115,000

Oddball believes that the best products are built when companies understand and value the things they are working on. We value learning and growth and the ability to make a big impact at a small company. We believe that we can make big changes happen and improve the daily lives of millions of people by bringing quality software to the federal space. We're looking for a Digital Solutions Architect to join our Oddball Labs team, developing and designing the technical solutions that win federal contracts and establishing a library of products and solution patterns that work for our broad federal customer base. What you'll be doing: Support pre-RFP capture through solution whiteboarding, customer meetings, and concept development Partner with capture managers, architects, designers, product partners, and engineers to explore new ideas and technical approaches build compelling narratives and supporting visuals Support continuing capture, proposal, and pricing efforts throughout the qualification and response submission cycle Lead the architecture, design, and build on software solutions ranging from prototypes to production systems Deconstruct RFPs, PWS/SOWs , and Section L/M criteria to drive compliant, responsive technical solutions Write and contribute to technical volumes including architecture, DevSecOps, data strategy, and AI/ML approaches Ensure solutions align with federal IT standards including NIST 800-53, FedRAMP, FISMA , and Section 508 Build and maintain a library of products, reusable solution patterns, technical approaches, and past performance mappings Stay current on federal digital services trends, AI/ML regulation, and govcon procurement dynamics Write clean, maintainable, well-tested code and help establish good engineering practices within Labs Performs other related duties as assigned What you’ll bring: 7+ years in IT or software engineering with at least 3 years in a solutions architect or technical lead role supporting federal proposals Proven track record developing winning technical solutions for government clients Deep understanding of Agile delivery methods, DevSecOps principles, and AI/ML model lifecycle Familiarity with FAR, IDIQ/BPA structures, and federal evaluation criteria Comfortable with AWS, Azure, Google Cloud , and cloud-native architecture patterns Strong written communication skills — you can translate complex technical ideas into clear, compelling proposal language Thrives under deadline pressure, across teams, and in ambiguous environments Communicates clearly and openly, whether leading a whiteboard session or writing a technical volume Strong general software engineering experience with the ability to work across different tech stacks Comfort operating in ambiguous problem spaces with evolving requirements Experience designing and building modern applications, services, or platforms Requirements: Applicants must be authorized to work in the United States. In alignment with federal contract requirements, certain roles may also require U.S. citizenship and the ability to obtain and maintain a federal background investigation and/or a security clearance. Education: Bachelor’s Degree Benefits: Fully remote Tech & Education Comprehensive Benefits Package Company Match 401(k) plan Flexible PTO, Paid Holidays Oddball is an Equal Opportunity Employer and does not discriminate against applicants based on race, religion, color, disability, medical condition, legally protected genetic information, national origin, gender, sexual orientation, marital status, gender identity or expression, sex (including pregnancy, childbirth or related medical conditions), age, veteran status or other legally protected characteristics. Any applicant with a mental or physical disability who requires an accommodation during the application process should contact an Oddball HR representative to request such an accommodation by emailing hello@Oddball.io Compensation: At Oddball, it’s important each employee is compensated competitively and fairly. In alignment with state legal requirements. A range for the included position is listed below. Be advised, actual offer details are determined by job category, job location, and candidate skill level. United States Wage Range: $150,000 – $215,000

Oddball believes that the best products are built when companies understand and value the things they are working on. We value learning and growth and the ability to make a big impact at a small company. We believe that we can make big changes happen and improve the daily lives of millions of people by bringing quality software to the federal space. We're looking for a Full Stack Engineer to join our CMS team, building the APIs and interfaces that power tools helping shape healthcare policy for millions of Americans. What you'll be doing: Build and maintain user interfaces using React and TypeScript Design, develop, and maintain backend services and APIs in Go Consume and interact with GraphQL APIs via Apollo Client Collaborate across frontend and backend to shape data endpoints and API contracts Write clean, well-tested, maintainable code that other engineers enjoy working with Participate in code reviews, architecture discussions, and Agile ceremonies Ensure interfaces meet federal accessibility standards including Section 508 and WCAG What you’ll bring: Hands-on experience with React and TypeScript on the frontend Experience building backend services in Go Experience with GraphQL and Apollo Client Solid understanding of API design and how frontend and backend systems interact Familiarity with Docker , Git , and Cypress or similar testing frameworks Experience with PostgreSQL or similar relational databases is a plus Comfortable working in a federal or regulated environment Thrives in a remote, collaborative Agile environment and genuinely enjoys working closely with a cross-functional team Communicates clearly and openly, whether in a code review or a conversation with a non-technical stakeholder Performs other related duties as assigned Requirements: Applicants must be authorized to work in the United States. In alignment with federal contract requirements, certain roles may also require U.S. citizenship and the ability to obtain and maintain a federal background investigation and/or a security clearance. Education: Bachelor’s Degree Benefits: Fully remote Annual Stipend Comprehensive Benefits Package Company Match 401(k) plan Flexible PTO, Paid Holidays Oddball is an Equal Opportunity Employer and does not discriminate against applicants based on race, religion, color, disability, medical condition, legally protected genetic information, national origin, gender, sexual orientation, marital status, gender identity or expression, sex (including pregnancy, childbirth or related medical conditions), age, veteran status or other legally protected characteristics. Any applicant with a mental or physical disability who requires an accommodation during the application process should contact an Oddball HR representative to request such an accommodation by emailing hr@oddball.io Compensation: At Oddball, it’s important each employee is compensated competitively and fairly. In alignment with state legal requirements. A range for the included position is listed below. Be advised, actual offer details are determined by job category, job location, and candidate skill level. United States Wage Range: $100,000 – $135,000

Oddball believes that the best products are built when companies understand and value the things they are working on. We value learning and growth and the ability to make a big impact at a small company. We believe that we can make big changes happen and improve the daily lives of millions of people by bringing quality software to the federal space. We’re looking for an Applied AI / Machine Learning Engineer to design, build, and deploy practical AI-powered solutions that solve real-world problems. This role focuses on applying modern ML and GenAI techniques in production systems — from experimentation and prototyping through deployment, evaluation, and iteration. You’ll work closely with engineers, designers, and product stakeholders to turn ambiguous problems into scalable, reliable AI-driven capabilities. This is a hands-on engineering role for someone who enjoys shipping, learning quickly, and balancing technical rigor with real-world constraints. What you'll be doing: Design, develop, and deploy machine learning and AI-powered features into production systems Apply supervised, unsupervised, and deep learning techniques to structured and unstructured data Build and evaluate models for tasks such as classification, ranking, prediction, NLP, or anomaly detection Develop and integrate GenAI solutions (e.g., LLM-based workflows, retrieval-augmented generation, agents) Translate business and user needs into ML problem statements, metrics, and experiments Implement data pipelines and feature engineering workflows to support model training and inference Evaluate model performance, bias, drift, and reliability; iterate based on results Collaborate with software engineers to integrate models into APIs, services, and user-facing applications Contribute to architecture decisions around model serving, scalability, and cost optimization Document approaches, assumptions, and tradeoffs to support maintainability and knowledge sharing What you’ll bring: Strong foundation in machine learning concepts, including model selection, training, validation, and evaluation Experience building and deploying ML models in real-world applications Proficiency in Python and common ML libraries (e.g., PyTorch, TensorFlow, scikit-learn) Experience working with large language models, embeddings, and prompt-driven systems Familiarity with data processing tools and workflows (e.g., Pandas, SQL, Spark, or similar) Understanding of software engineering best practices (version control, testing, code reviews) Ability to reason about tradeoffs between accuracy, latency, cost, and maintainability Strong communication skills and comfort working in cross-functional teams Performs other related duties as assigned Bonus if you have: Experience working in innovation, R&D, labs, or exploratory engineering teams Experience deploying models to cloud platforms and managing inference at scale Familiarity with MLOps practices such as model monitoring, CI/CD for ML, and experiment tracking Experience contributing to architectural discussions or technical strategy Location: Hybrid/Remote. Candidates must be located in the DMV area (DC, Maryland, Virginia) and able to participate with in-office collaboration. Requirements: Applicants must be authorized to work in the United States. In alignment with federal contract requirements, certain roles may also require U.S. citizenship and the ability to obtain and maintain a federal background investigation and/or a security clearance. Benefits: Fully remote Annual stipend Comprehensive Benefits Package Company Match 401(k) plan Flexible PTO, Paid Holidays Equal Opportunity Employer/Protected Veterans/Individuals with Disabilities: Oddball is an Equal Opportunity Employer and does not discriminate against applicants based on race, religion, color, disability, medical condition, legally protected genetic information, national origin, gender, sexual orientation, marital status, gender identity or expression, sex (including pregnancy, childbirth or related medical conditions), age, veteran status or other legally protected characteristics. Any applicant with a mental or physical disability who requires an accommodation during the application process should contact an Oddball HR representative to request such an accommodation by emailing hr@oddball.io The contractor will not discharge or in any other manner discriminate against employees or applicants because they have inquired about, discussed, or disclosed their own pay or the pay of another employee or applicant. However, employees who have access to the compensation information of other employees or applicants as a part of their essential job functions cannot disclose the pay of other employees or applicants to individuals who do not otherwise have access to compensation information, unless the disclosure is (a) in response to a formal complaint or charge, (b) in furtherance of an investigation, proceeding, hearing, or action, including an investigation conducted by

Oddball believes that the best products are built when companies understand and value the things they are working on. We value learning and growth and the ability to make a big impact at a small company. We believe that we can make big changes happen and improve the daily lives of millions of people by bringing quality software to the federal space. We're looking for a Power Platform Developer to join our CMS team, supporting a low-code modernization effort that helps federal programs run more efficiently. What you'll be doing: Build and maintain solutions using Microsoft Power Platform including PowerApps and Power Automate Work across frontend and backend development as needed to support the broader product Collaborate with product managers, designers, and stakeholders to translate ambiguous requirements into working solutions Troubleshoot complex issues independently and drive problems to resolution without hand-holding Contribute to code reviews and engineering standards across the team What you’ll bring: Strong general engineering background — we care more about your fundamentals than a specific stack Experience with or willingness to learn Microsoft Power Platform and PowerApps Comfortable working with data and backend systems Senior-level problem-solving instincts — self-driven, resourceful, and comfortable with ambiguity Thrives in a remote, collaborative Agile environment and genuinely enjoys working closely with a cross-functional team Communicates clearly and openly, whether working through a technical problem or aligning with stakeholders Performs other related duties as assigned Requirements: Applicants must be authorized to work in the United States. In alignment with federal contract requirements, certain roles may also require U.S. citizenship and the ability to obtain and maintain a federal background investigation and/or a security clearance. Education: Bachelor’s Degree Benefits: Fully remote Annual Stipend Comprehensive Benefits Package Company Match 401(k) plan Flexible PTO, Paid Holidays Oddball is an Equal Opportunity Employer and does not discriminate against applicants based on race, religion, color, disability, medical condition, legally protected genetic information, national origin, gender, sexual orientation, marital status, gender identity or expression, sex (including pregnancy, childbirth or related medical conditions), age, veteran status or other legally protected characteristics. Any applicant with a mental or physical disability who requires an accommodation during the application process should contact an Oddball HR representative to request such an accommodation by emailing hr@oddball.io Compensation: At Oddball, it’s important each employee is compensated competitively and fairly. In alignment with state legal requirements. A range for the included position is listed below. Be advised, actual offer details are determined by job category, job location, and candidate skill level. United States Wage Range: $100,000 – $135,000