Jobs at Oddball
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.
Senior Drupal Engineer
Company: Oddball
Location: Remote
Posted Dec 05, 2023
Be advised, actual offer details are determined by job category, job location, and candidate skill level. Define and implement Drupal site structure, content types, taxonomies, and workflows. Benefits: Fully remote Tech & Education 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. Evaluate and recommend modules, themes, and third-party integrations to enhance Drupal functionality. Drupal certifications (e.g., Acquia Certified Developer) are a plus. Guidance on recommended modules, themes, and third-party integrations to enhance Drupal functionality. Proficiency in PHP, JavaScript, HTML, CSS, and other relevant web technologies. In alignment with state legal requirements. Experience collaborating with stakeholders to gather requirements, propose technical solutions, and estimate effort for Drupal projects. Strong understanding of Drupal's core concepts, architecture, and contributed modules.
Technical Lead
Company: Oddball
Location: Remote
Posted Feb 29, 2024
Oddball is seeking a Technical Lead to lead a team of engineers and designers on a pivotal Federal program. The role involves planning, executing, and directing the team, requiring strong communication skills, Agile environment experience, and in-depth knowledge of APIs. The company values learning, growth, and making a big impact in the federal space. Benefits include remote work, comprehensive benefits package, and a competitive salary range of $100,000 - $150,000.
VP of Engineering
Company: Oddball
Location: Remote
Posted Dec 14, 2023
Be advised, actual offer details are determined by job category, job location, and candidate skill level. United States Wage Range: $180,000 - $230,000 In alignment with state legal requirements. This includes setting expected skill levels, setting the number of “rungs” on the career ladder, and establishing mentoring capabilities within the company Overseeing the interview screening process for all engineering candidates Participating in determining engineers’ eligibility for rotation and promotion Supporting and guiding Tech Leads in both managerial and technical aspects in support of their programs Publishing or organizing content that communicates Oddball’s engineering achievements and processes Building programs to train and assess growing engineers Implementing agile methodologies and working with client’s to do so Building technical strategies and assessing tech opportunities and skill sets that can help us increase our performance Building multiple software development lifecycles for client needs Influencing and driving change with federal clients Provide thought leadership both within the company and to customers Possibility of travel required to represent the company at client meetings and/or conferences Our ideal candidate would have experience: Working as a federal government contractor Building partnerships to drive change in the government space Providing guidance to and assisting other engineers that do not report directly to them Acting as the technical lead on a large federal government program Mentoring and growing fellow engineers Being comfortable spending more time managing and overseeing engineering efforts rather than participating in regular “hands on keyboard” coding Participating in initiatives focused around company growth and increasing business Using strong communication skills and the ability to use these skills to foster collaboration Communicating with government customers and possess a consultant mindset Managing DevOps transformations and cloud migrations Being part of an ATO process at the federal level with IT Security Requirements: 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 remote Tech & Education 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. A range for the included position is listed below. What you'll be doing: Guiding program teams to adopt consistent solutions to engineering and technical problems, and encouraging technical consistency across programs Acting as a technical liaison across the company and help connect the technical “dots” for different programs/customers Working with Program Managers to provide guidance and ensure programs are delivering optimal technical value to our clients and meeting contracted goals/objectives as needed Establishing the career paths for the engineering practice area. 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] Compensation: At Oddball, it’s important each employee is compensated competitively and fairly. The VP of Engineering will be the primary individual responsible for ensuring high-quality engineering in federal projects at Oddball working with and providing guidance to our 100+ Engineers spread across multiple government programs. We are hiring a VP of Engineering to our team to help scale and build out our engineering capabilities in our federal practice. 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.
IT Administrator
Company: Oddball
Location: Remote
Posted Mar 02, 2024
Oddball is seeking an IT Administrator to build and manage their IT infrastructure, ensuring security compliance, and developing IT policies. The role involves managing budgets, leading IT personnel, and handling support requests. The ideal candidate should have proven experience in IT administration, strong knowledge of IT systems, networks, cybersecurity, and cloud services. They should also have experience with budget management, familiarity with compliance regulations, and excellent problem-solving skills. The company offers a fully remote position, comprehensive benefits, and a competitive salary range of $70,000 - $110,000.
HR Generalist
Company: Oddball
Location: Remote
Posted Dec 08, 2023
Be advised, actual offer details are determined by job category, job location, and candidate skill level. 3+ years of experience in human resources, payroll, and/or operations Experience with HRIS systems Benefits: Fully remote Tech & Education 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. Administer leave programs, including but not limited to FMLA, ADA, and other statutory or company-specific leaves. In alignment with state legal requirements. Perform other duties as assigned Requirements: Must be a US Citizen and able to work domestically Bachelor's degree in Human Resources, Business Administration, or related field. Guide employees through the leave application process, ensuring proper documentation and compliance. A range for the included position is listed below. What you'll be doing: Maintain compliance with federal, state, and local employment laws and regulations, and recommend best practices; review policies and practices to maintain compliance Process and manage end-to-end payroll cycles, ensuring accurate and timely disbursement of employee salaries, wages, bonuses, and other compensation. United States Wage Range: $60,000 – $80,000 Assists with performance evaluation process and training.
DevOps Engineer
Company: Oddball
Location: Remote
Posted Dec 23, 2023
Oddball is seeking a DevOps Engineer to join a pivotal Federal program, aiming to improve the daily lives of millions of Americans through quality software. The role involves working with great DevOps engineers, creating CI/CD jobs, infrastructure with Terraform, Ansible playbooks, and tools. The ideal candidate should have extensive experience with config management tools, AWS environments, Terraform, CI/CD scripts, web technologies, Linux, and SQL architecture. Oddball offers a fully remote position with comprehensive benefits, flexible PTO, and a competitive salary range of $100,000 - $155,000.
VP of CMS Operations
Company: Oddball
Location: Remote
Posted Dec 14, 2023
Be advised, actual offer details are determined by job category, job location, and candidate skill level. Effective communication skills, both verbal and written, to interact with stakeholders at all levels. Identify and mitigate operational risks, including compliance, contractual, and security concerns. Experience working on responding to government proposals as well as have demonstrated success organically growing programs during program execution Requirements: Must be a US Citizen and able to work domestically Must be able to attain low-level security clearance Education: Bachelor’s degree or higher (masters preferred) Benefits: Fully remote Tech & Education 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. Strong organizational agility and the ability to thrive in a dynamic, fast-paced environment. Continuously assess operational processes, identify bottlenecks, and implement process improvement initiatives to enhance efficiency, reduce costs, and increase productivity. Collaborate with the finance department to develop and manage the operations budget, ensuring cost control, resource allocation, and financial efficiency. In alignment with state legal requirements. Excellent leadership and people management skills, with the ability to inspire and motivate teams, as well as the ability to effectively have difficult conversations when necessary. Strong analytical and problem-solving skills, with the ability to think strategically and develop innovative solutions.
Engineering Manager
Company: Oddball
Location: Remote
Posted Oct 24, 2023
Oddball is seeking an experienced Engineering Manager to lead a multidisciplinary team in delivering high-quality products to federal partners. The role involves managing, mentoring, and growing a large team, with a focus on architectural and people management. The ideal candidate should have 10+ years of experience in leading large teams, 10+ years in programming and project management, and 7+ years in architecting high-level solutions. The company values learning, growth, and making a significant impact in the federal space.
Test Engineer
Company: Oddball
Location: Remote
Posted Dec 05, 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 In alignment with state legal requirements. What you'll be doing: Responsible for guiding, testing and implementing modern QA practices and principles for a pivotal Federal program Oversee and handle all blackbox/manual testing; test a variety of products while managing the QA plan and strategy, potentially across multiple teams Guide and implement strategies to help engineering and leadership make quick and decisive decisions Build and implement test reports, communicating the results to multiple stakeholders Work with leadership to bring QA as a whole solution, not just one step in the process Make decisions based on strategy and context, and roll out changes as needed to boost efficiency What you’ll bring: A proven track record of Quality Assurance work with the above experience in supporting large scale programs Strong verbal and written communication skills directed at both technical and non-technical audiences Comfort with managing multiple ongoing engagements and parallel work streams Capable of taking direction from senior leadership and translating into concrete next steps and actions Experience working in Agile environments Requirements: 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 remote Tech & Education 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. A range for the included position is listed below. 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] Compensation: At Oddball, it’s important each employee is compensated competitively and fairly. We are hiring a Test Engineer to work on a pivotal Federal program that is making a positive impact on millions of Americans' daily lives. 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 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.
UX Designer
Company: Oddball
Location: remote
Posted Dec 05, 2023
Be advised, actual offer details are determined by job category, job location, and candidate skill level. Adaptability when working with, and in, existing design and UX systems. Requirements: Must be a US Citizen and able to work domestically Must be able to attain low-level security clearance Education: Bachelor’s Degree preferred Benefits: Fully remote Tech & Education 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. Compensation: At Oddball, it’s important each employee is compensated competitively and fairly. In alignment with state legal requirements. A demonstrated facility with creating and using prototypes, wireframes, user interviews, data points, etc. Experience working in Agile development environments. A range for the included position is listed below. Experience working with Git Version Control. United States Wage Range: $90,000 $140,000
Senior Test Engineer
Company: Oddball
Location: Remote
Posted Oct 28, 2023
Oddball is seeking a Senior Test Engineer to join their team and contribute to a significant Federal program. The role involves guiding and implementing modern QA practices, overseeing blackbox/manual testing, and communicating test results to stakeholders. The ideal candidate should have a proven track record in Quality Assurance, strong communication skills, and experience in Agile environments. Oddball values learning, growth, and making a substantial impact in the federal space. They offer competitive compensation, comprehensive benefits, and a fully remote work environment.
Backend Engineer
Company: Oddball
Location: Remote
Posted Dec 16, 2023
Be advised, actual offer details are determined by job category, job location, and candidate skill level. The ability to write code that is a pleasure for other engineers to read and understand The ability to speak and write in terms that non-developers can understand clearly, whether it be in a conference call, blog post or support email Requirements: 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 remote Tech & Education 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. What you’ll be doing: Collaborate with CMS and other stakeholders to analyze and design software solutions Work on developing applications from specifications decided upon by the team Perform or direct revisions, repairs, or expansion of existing programs to increase operating efficiency or adapt to new requirements Consult with managerial, technical, and business personnel to clarify program intent, identify problems, and suggest changes Assist other software developers by analyzing user needs and designing software solutions Support the systems that have been built Identify problems uncovered by testing or customer feedback and corrects problems Participate in team agile ceremonies (daily scrum meeting, refinement, retrospectives, sprint planning) Skills/Requirements: Modern Technical Skills: GoLang, React (familiar with), Javascript (familiar with), Web Services (REST, JSON), AWS, Jira, Confluence, GitHub Industry: AWS exposure/experience; Certification a plus Typescript/Node.js experience a plus Solid verbal and written communication skills, problem solving skills, customer service and interpersonal skills. United States Wage Range: $100,000 – $140,000 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] Compensation: At Oddball, it’s important each employee is compensated competitively and fairly. A range for the included position is listed below. We are hiring a Node.js Engineer to work on a pivotal Federal program that is making a positive impact on millions of Americans' daily lives. 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 value learning and growth and the ability to make a big impact at a small company.