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.

Rails Engineer

Company: Oddball

Location: Remote

Posted May 25, 2023

Oddball is looking for an experienced developer to help improve and build out backend code that interfaces with external systems. The company values learning, growth, and making a big impact, and is committed to delivering quality services to the Veterans Administration and the entire Veterans community.

Data Analyst

Company: Oddball

Location: Remote

Posted Apr 21, 2023

None Found

Subcontracts Manager

Company: Oddball

Location: Remote

Posted Jun 09, 2023

Oddball is seeking a Subcontracts Manager with extensive experience in government contracts. The role involves ensuring compliance with regulations, managing subcontractor relationships, negotiating agreements, and overseeing the subcontracting process. The ideal candidate should have a deep understanding of government regulations, strong analytical skills, and excellent organizational abilities. Unanet experience is a plus. The company offers competitive compensation, comprehensive benefits, and a fully remote work environment.

Senior Drupal Engineer

Company: Oddball

Location: Remote

Posted May 31, 2023

Oddball is hiring a Senior Drupal Engineer to work on a pivotal Federal program that is making a positive impact on millions of Americans' daily lives. The company values learning, growth, and making a big impact, and is looking for a highly skilled and experienced engineer to join their team.

React/Rails Engineer

Company: Oddball

Location: Remote

Posted Mar 29, 2023

Oddball is seeking a Full Stack engineer with experience in developing, testing, and debugging software solutions for the federal space. They value a calm, collected environment and a solid understanding of API design. The position offers a competitive salary, a tech stipend, and a continuing education stipend. Oddball is an Equal Opportunity Employer.

Java Engineer

Company: Oddball

Location: Remote

Posted May 25, 2023

Oddball is seeking a Java Engineer to build, improve, and expand their front and backend code for the federal space. The role involves writing code, developing tests, and debugging. The company values learning, growth, and making a big impact at a small company.

React/Rails Engineer

Company: Oddball

Location: Remote

Posted Mar 29, 2023

Oddball is a company looking for a Full Stack engineer with experience in developing, testing, and debugging software solutions for the Veterans Administration. They value a calm, collected environment and a solid understanding of API design. The role requires a Bachelor's Degree with 4+ years of experience, 4+ years with Rails, and a front-end JS framework. They offer a tech and continuing education stipend and are an Equal Opportunity Employer.

Product Manager

Company: Oddball

Location: Remote

Posted Apr 21, 2023

None Found

Node.js Engineer

Company: Oddball

Location: Remote

Posted Jun 06, 2023

Oddball is seeking an experienced developer to join their team and contribute to building and improving backend code for a high traffic node.js application. The ideal candidate should have 3+ years of Typescript/Node.js experience, 2+ years of PostgresSQL experience, and familiarity with REST APIs, complex node apps, and large-scale AWS infrastructures. The company values learning, growth, and making a significant impact in the federal space. They offer a fully remote position with comprehensive benefits, a tech & education stipend, and competitive compensation ranging from $100,000 to $150,000.

Project Control Manager

Company: Oddball

Location: Remote

Posted May 25, 2023

Oddball is hiring a Project Control Manager to assist with their fast-paced, high-growth team. The company values learning, growth, and making a big impact. They are looking for a go-getter who can help remodel their project control process and support financial analysis, risk mitigation, and revenue reporting.

UX Researcher

Company: Oddball

Location: Remote

Posted Apr 21, 2023

None Found

Operations Analyst

Company: Oddball

Location: Remote

Posted May 25, 2023

Oddball is seeking an operations analyst to work with the COO and program managers, establishing operational processes, ensuring compliance, and supporting business operations. The ideal candidate should be a self-starter with experience in government contracting, Unanet timekeeping system, and risk management. Oddball 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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