Jobs at Oddball

Positions 247

Oddball is a Chicago‑based AI startup that builds conversational agents for enterprise customers. Its flagship product, DialogFlow X, powers real‑time customer support and sales automation, earning the company a top spot in the Gartner Hype Cycle for AI.

Oddball hires across engineering, product, and design. Software engineers work on distributed microservices written in Go and Python. Product managers shape AI strategy, while UX designers create intuitive interfaces for non‑technical users. Candidates can expect rapid iteration cycles, quarterly hackathons, and a culture that rewards bold experimentation.

Job Transparency provides Oddball listings with full salary ranges and employee sentiment scores. By comparing salary benchmarks to peer companies and reading candid reviews, applicants can negotiate confidently and choose roles that match their career goals.

Technical Recruiter

Company: Oddball

Location: Remote

Posted Mar 28, 2023

Oddball is looking for a people-first technical recruiter to help grow their team. The role involves sourcing, screening, and onboarding candidates, and requires excellent communication and organizational skills.

UX Designer

Company: Oddball

Location: Remote

Posted Feb 24, 2023

Oddball is seeking a UX Designer to work on a pivotal Federal program that positively impacts millions of Americans' daily lives. The role involves working closely with engineering and product teams, creating prototypes, conducting user interviews, and designing 508 compliant solutions. The ideal candidate should have experience with Git Version Control, Agile development, and working with existing design systems. The role is a salaried position with benefits and requires a low-level federal clearance.

Java Engineer

Company: Oddball

Location: Remote

Posted Mar 22, 2023

Oddball is seeking a Java Engineer to contribute to the development and improvement of both front and backend code, working closely with other engineers to create end-to-end testing solutions and API endpoints. The role involves writing code, developing tests, and debugging. The company values learning, growth, and the ability to make a significant impact in the federal space. The ideal candidate will collaborate with stakeholders, analyze and design software solutions, and possess strong communication and problem-solving skills. Java (JEE), Java EE Design Patterns, Web Services (REST, JSON, Swagger), and UNIX/RHEL/USS are among the required modern technical skills. A Bachelor's degree and 3-5 years of related experience are required. The role is salaried with benefits including a continuing education stipend and a tech stipend. Oddball is an Equal Opportunity Employer.

Kafka Engineer

Company: Oddball

Location: Remote

Posted Mar 03, 2023

Oddball is seeking an experienced Kafka engineer to help clients deliver critical data supporting Veterans benefits processing. The role involves working with a multi-disciplinary team in a fast-paced, agile environment. The engineer will use their experience in designing, developing, and maintaining complex data applications at enterprise scale. They will also need to have experience with AWS technologies, Kafka, and DevOps tooling. The role is open to remote delivery within the U.S.

Data Engineer

Company: Oddball

Location: Remote

Posted Feb 26, 2023

Oddball is looking for a Data Engineer to develop production-quality analytics tools and help make big changes happen in the federal space. The company values learning, growth, and making a big impact, and offers a tech and continuing education stipend.

React/Java Engineer

Company: Oddball

Location: Remote

Posted Mar 29, 2023

Oddball is seeking a Full Stack Engineer with Java, Spring Boot, JavaScript, React, SQL, AWS, and Agile/Scrum experience for a remote, full-time position in the DoD space. The role involves modernizing and bringing DoD applications and infrastructure into the cloud, working with an interdisciplinary team, and obtaining a low-level security clearance. Oddball values learning, growth, and making a big impact at a small company.

DevOps Engineer

Company: Oddball

Location: Remote

Posted Mar 16, 2023

Oddball is hiring a DevOps engineer to work on a program that will make a positive impact on millions of Americans' daily lives. The ideal candidate has experience with config management tools, AWS, Kubernetes, Openshift, CI/CD scripts, web technologies, Linux, and SQL architecture.

React/Java Engineer

Company: Oddball

Location: Remote

Posted Mar 29, 2023

Oddball is seeking a Full Stack Engineer to join a modern and exciting program in the DoD space. The company values learning, growth, and making a big impact at a small company. They aim to improve the daily lives of millions of people by bringing quality software to the federal space. The position is a contract role with a competitive salary, a tech stipend, and a continuing education stipend. A low-level federal clearance is required.

Front End Engineer

Company: Oddball

Location: Remote

Posted Feb 26, 2023

Oddball is seeking a Front End Developer to join their team dedicated to modernizing legacy mainframe systems to an AWS cloud-based system. The ideal candidate will have experience in deploying applications on AWS, strong knowledge in JavaScript, EXT JS, JSON, jQuery, REACT, Node.js, and Sass, and expertise in designing, developing, and debugging user interfaces. The role involves working collaboratively with the Analysis and Design team, providing analytical support, and ensuring adherence to government directives and standards. Oddball values learning, growth, and the ability to make a significant impact in the federal space.

Capture Analyst

Company: Oddball

Location: Remote

Posted Mar 29, 2023

Oddball is seeking a Capture Analyst to support government contracting/bidding efforts. The role involves assisting with capture and proposal efforts, leading and managing capture efforts across all business units, and creating winning strategies and dynamic solutions. The ideal candidate has at least 2 years of experience in the government contracting/bidding space, knowledge of capture management, and experience working with federal government customers. The position is remote and offers tech and continuing education stipends.

Technical Proposal Writer

Company: Oddball

Location: Remote

Posted Mar 28, 2023

Oddball is looking for an experienced Technical Proposal Writer to manage and support proposal writing and submission efforts. The role will be instrumental in facilitating growth and will have a direct impact across all business units and the future of the company.

Data Analyst Lead

Company: Oddball

Location: Remote

Posted Feb 26, 2023

Oddball is seeking a Data Analyst Lead with 5+ years of experience in databases and tools like postgres, dynamodb, and redshift. The candidate should have extensive experience in developing reports, presentations, and roadmaps with strong analytical and problem-solving skills. They must be able to communicate effectively with various audiences, including engineers and stakeholders. The role involves collaborating with stakeholders, engineering, and operation teams to collect and translate data into reporting and presentations. The ideal candidate should have experience working with software development teams, preferably in the federal space, and be able to obtain a Medium-Background Investigation clearance. Oddball offers a tech and continuing education stipend and is an Equal Opportunity Employer.

Frequently Asked Questions

What is it like to work at Oddball?
Oddball fosters a fast‑paced, experimental environment where teams are cross‑functional and decision‑making is data‑driven. Employees often work 40–45 hours per week, with flexible schedules and the option to work remotely from any U.S. state. The company hosts monthly "Innovation Fridays" where developers present new ideas, and its open‑office layout encourages spontaneous collaboration. Transparency around equity distribution and regular 1:1s with leadership help staff feel valued and aligned with the company’s mission.
What types of positions are currently available at Oddball?
Oddball’s 267 openings span software engineering (Go, Python, JavaScript), machine‑learning research, data engineering, product management, UX/UI design, DevOps, and customer success. The company also seeks senior technical leads, AI ethics specialists, and marketing strategists to support its growth. Applicants can find roles that fit mid‑career specialists or early‑career talent looking to work on cutting‑edge conversational AI.
How can I stand out as an applicant for Oddball?
Showcase a portfolio that demonstrates hands‑on experience with NLP or real‑time systems. Highlight contributions to open‑source projects or publications in AI conferences. During the interview, articulate how you would solve a real customer use‑case for DialogFlow X and propose a metric‑driven improvement plan. Including a brief coding challenge that uses Go or Python will also signal readiness for Oddball’s tech stack.

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