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.

Program Manager

Company: Oddball

Location: Remote

Posted Jun 23, 2023

None Found

Delivery Manager

Company: Oddball

Location: Remote

Posted Jul 26, 2023

Oddball is seeking a Delivery Manager with 3-5 years of experience in project and delivery management, particularly in agile environments. The role involves overseeing project delivery, leading teams, and ensuring high-quality output. The company values learning, growth, and making a significant impact in the federal space. They offer a competitive salary, comprehensive benefits, and a fully remote work environment. Oddball is an equal opportunity employer.

Lead Security Engineer

Company: Oddball

Location: Remote

Posted Jul 01, 2023

Oddball is seeking a Lead Security Engineer to work on a pivotal Federal program that positively impacts millions of Americans' daily lives. The role involves working with other engineers to ensure compliance with regulatory frameworks, aiding in renewal of an existing Authority to Operate (ATO), and implementing security guidelines and features within a government environment.

Lead Project Finance Control

Company: Oddball

Location: Remote

Posted Jun 19, 2023

None Found

DevOps Engineer

Company: Oddball

Location: Remote

Posted Jun 10, 2023

Oddball is a company that values learning, growth, and making a big impact at a small company. They are hiring a DevOps Engineer to work on a pivotal Federal program that is making a positive impact on millions of Americans' daily lives. The candidate should have in-depth experience with config management tools, experience working with AWS environments, and the ability to create and support Terraform. They should also have skill in developing and improving CI/CD scripts and services for development and deployment. The company offers a fully remote work environment, a tech and education stipend, comprehensive benefits package, and company match 401(k) plan. They are an equal opportunity employer and do not discriminate against applicants based on various characteristics. The compensation range for the position is $100,000 - $155,000.

Product Support - Tier 1

Company: Oddball

Location: Remote

Posted Jul 01, 2023

Oddball is looking for experienced Tier 1 Support to help improve, troubleshoot and support incidents and outages for their growing product. The role involves working with engineering and management teams to oversee the delivery of numerous applications and providing production support to VA customers.

Product Support - Tier 2

Company: Oddball

Location: Remote

Posted Jun 28, 2023

None Found

Product Manager

Company: Oddball

Location: Remote

Posted Jul 22, 2023

Oddball is a rapidly growing, technically focused company seeking a experienced, data-driven, delivery-focused Product Manager to lead engineering efforts and deliver for federal clients. The ideal candidate will have 4+ years of full product lifecycle experience, experience leading and managing cross-functional agile teams, and a proven ability to solve problems with development teams. Federal work experience is preferred.

Data Designer

Company: Oddball

Location: Remote

Posted Jun 22, 2023

None Found

UX Researcher

Company: Oddball

Location: Remote

Posted Jul 22, 2023

Oddball is seeking a UX Researcher to work on a pivotal Federal program that positively impacts millions of Americans' daily lives. The role requires extensive experience with UX research, strategic thinking, and ability to work in Agile development environments. The company values learning, growth, and making a big impact at a small company.

Azure DevOps Engineer

Company: Oddball

Location: Remote

Posted Jun 19, 2023

None Found

Front End Engineer

Company: Oddball

Location: Remote

Posted Jul 11, 2023

Be advised, actual offer details are determined by job category, job location, and candidate skill level.United States Wage Range: $100,000 – $150,000 Working hand in hand with other engineers in developing end-to-end testing solutions and API endpoints and services, day to day work will involve writing code, developing tests, and debugging.What you’ll bring:5+ years of Javascript experience, specifically using React and Sencha Ext JSWorked with CI/CD pipelines and with cloud computing services, including AWSExperience working in an Agile/Scrum environment with sprints and daily stand-upsAbility to work with an interdisciplinary team of engineers including data scientists, UX, product and software engineersStrong communication skills along with the ability to work well as a team and enjoy constantly learning and adapting are highly desirableRequirements:Must be a US Citizen and able to work domestically Must be able to attain low-level security clearance Education:Bachelor’s Degree Benefits:Fully remoteTech & Education StipendComprehensive Benefits PackageCompany Match 401(k) planFlexible PTO, Paid HolidaysOddball 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. In alignment with state legal requirements. 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 [email protected]:At Oddball, it’s important each employee is compensated competitively and fairly. A range for the included position is listed below. 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 are hiring a Front End Engineer to work on a pivotal Federal program that is making a positive impact on millions of Americans' daily lives.What you'll be doing:We are hiring a Front End Engineer to join a modern and exciting program in the VA space. We value learning and growth and the ability to make a big impact at a small company. Oddball believes that the best products are built when companies understand and value the things they are working on.

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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