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.

Python Engineer

Company: Oddball

Location: Remote

Posted Aug 08, 2024

Oddball is hiring a Python 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 self-motivated and detail-oriented team player.

CMS Solutions Architect

Company: Oddball

Location: USA

Posted Jul 07, 2024

Oddball is seeking an experienced growth leader to serve as Solutions Architect within their Growth team to support Federal Government proposal efforts. The ideal candidate will develop and translate capture strategy and technical and operational delivery capabilities into compelling and compliant proposal content, and will work cross-functionally to understand architecture needs by multiple business units.

Lead Accessibility Engineer

Company: Oddball

Location: USA

Posted Jul 18, 2024

Oddball is hiring a Lead Accessibility Engineer to work on a federal program that makes a positive impact on millions of Americans' daily lives. The company values learning, growth, and making a big impact, and offers competitive compensation and benefits.

Senior Pricing Analyst

Company: Oddball

Location: USA

Posted May 30, 2024

Oddball is seeking a Senior Pricing Analyst to lead pricing efforts for pivotal Federal programs. The role involves developing pricing models, leading strategy reviews, collaborating with cross-functional teams, and ensuring compliance with regulations. The ideal candidate should have a finance or related degree, 5+ years of pricing analysis experience, and proficiency in financial modeling and Excel. Oddball offers a fully remote position with competitive compensation, comprehensive benefits, and a flexible PTO policy.

Java Engineer

Company: Oddball

Location: USA

Posted Aug 07, 2024

Oddball is hiring a Java 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 offers competitive compensation and benefits.

COBOL Developer

Company: Oddball

Location: USA

Posted May 10, 2024

Oddball is seeking a COBOL Developer to join a pivotal Federal program, aiming to enhance the lives of millions of Americans through quality software. The role involves working closely with leadership, architecting modernizations, and implementing engineering guidelines. The ideal candidate should have extensive experience in mainframe programming, project management, and software development. Knowledge of healthcare business processes, advanced debugging tools, and various databases and platforms is highly valued. Oddball offers a fully remote position with comprehensive benefits, a tech & education stipend, and competitive compensation. The company is committed to equal opportunity employment and fostering a culture of learning and growth.

Senior Data UX Analyst

Company: Oddball

Location: USA

Posted Jun 07, 2024

Oddball is hiring a Senior Data UX Analyst for a pivotal Federal program that aims to improve the daily lives of millions of Americans through quality software. The role involves developing and maintaining a robust framework for UX metrics, conducting in-depth data-based analyses, and collaborating with UX designers and product managers. The ideal candidate should have a Bachelor's degree in a relevant field, 8+ years of experience in data analysis with a focus on UX research and visualization, and proficiency in tools like PowerBI, DataDog, SQL, and Excel. Familiarity with cloud platforms and experience in healthcare or a related industry are preferred. The company offers a fully remote position, comprehensive benefits, and a competitive salary range of $100,000 - $140,000.

Lead UX Designer

Company: Oddball

Location: USA

Posted Aug 04, 2024

Oddball is hiring a Lead UX Designer to work on a pivotal Federal program that is making a positive impact on millions of Americans daily lives. The role requires extensive experience with UX research, design, and prototyping, as well as the ability to think strategically and work in Agile development environments.

Product Owner

Company: Oddball

Location: USA

Posted May 12, 2024

Oddball is seeking a Product Owner to work on a significant Federal program, aiming to enhance the lives of millions of Americans through quality software. The ideal candidate will collaborate with management, engineering, and operations teams to design, create, and deliver products for federal clients. Key responsibilities include leading cross-functional agile teams, managing JIRA backlogs, mitigating scope creep, and ensuring products solve client problems. Federal work experience is preferred, and the role requires US citizenship, low-level security clearance, and a Bachelor's degree. Benefits include full remote work, an annual stipend, comprehensive benefits, and a 401(k) match. Oddball is an Equal Opportunity Employer.

Delivery Manager

Company: Oddball

Location: USA

Posted May 10, 2024

Oddball is hiring a Delivery Manager to work on a pivotal Federal program that is making a positive impact on millions of Americans' daily lives. The role requires experience in project management, agile development, and team leadership, with a focus on delivering high-quality projects on schedule.

CMS Solutions Architect

Company: Oddball

Location: USA

Posted May 03, 2024

Oddball is seeking an experienced growth leader to serve as Solutions Architect within their Growth team. The ideal candidate will develop and translate capture strategy and technical and operational delivery capabilities into compelling and compliant proposal content. They will work cross-functionally to understand architecture needs by multiple business units, own the entire architecture development process, and lead the development of solutions with technical and customer domain experts. The candidate should have over 10 years of experience in IT solution delivery and a significant role in Federal proposals, skilled in advanced technical solutions, and expert in linking strategy with execution. They should be open to diverse perspectives, knowledgeable in Agile HCD and DevSecOps cultures, and have a proven track record in responding to complex Federal IT proposals.

Senior D

Company: Oddball

Location: remote

Posted Jun 06, 2024

Oddball is seeking a Senior Data UX Analyst for a remote position. The role involves developing and maintaining a framework for UX metrics, creating PowerBI reports, conducting data-based analyses, and collaborating with UX designers and product managers. The ideal candidate should have a degree in a relevant field, 8+ years of experience in data analysis with a focus on UX research and visualization, proficiency in tools like PowerBI, SQL, and Excel, and familiarity with cloud platforms. Experience in healthcare or a related industry is preferred. The company offers a fully remote position, comprehensive benefits, and a competitive salary range of $100,000 - $140,000.

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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