Senior Software Engineer, Assurance

About this role

<p><strong>Job overview:</strong></p> <p>Omada Health is on a mission to bend the curve of chronic disease. Our programs help people make behavior changes to improve their health and their lives.</p> <p>We are a virtual-first healthcare and technology company looking for an experienced Senior Software Engineer to join our agentic systems team, powering our AI Transformation efforts across Engineering, Product, and Design.</p> <p>Our team sits within the Architecture &amp; Infrastructure department, inside of the larger Engineering org. Our mission is to define and deliver how internal Omadans use AI to build, test, and operate software safely and effectively. This group provides the patterns, tools, and infrastructure that make AI-augmented work secure, measurable, and accessible to every engineer, PM, and designer.</p> <p>This team is new, and is poised to build useful things. We are at the forefront of AI Transformation work at Omada, and we are leading the way towards a near future, where we can orchestrate agentic software development with quality built in by design.<span style="font-weight: 400;"><br></span></p> <p><strong>About you:</strong></p> <p>You are confident in your capabilities. You are good with people, and have led a life and career full of positive relationships. You are motivated by multiplying the impact of others through thoughtfully designed tools and workflows. You enjoy working at the intersection of infrastructure, application development, and human-centered tooling, and you’re comfortable owning ambiguous problems end-to-end.&nbsp;</p> <p>You have strong software engineering fundamentals, are fluent with modern AI tooling and APIs, and are curious about how agentic systems are changing the way we plan, build, test, and operate software. You value communication and empathy as much as technical depth, and you like to collaborate directly with internal customers to understand real workflows and pain points.</p> <p><strong>Your impact:</strong></p> <ul> <li>Design and build software testing tools that integrate with engineers’ day-to-day environments (e.g., Claude, VS Code, GitLab, Datadog, internal documentation, Slack chatops).</li> <li>Build and maintain automated test infrastructure that supports mobile, web, and backend engineering teams.</li> <li>Define AI-augmented software testing patterns and quality gates in our release management system</li> <li>Instrument and monitor AI usage, performance, and cost to help the team and engineering leadership understand our impact and our organizational maturity.</li> <li>Collaborate with security, compliance, and infrastructure teams to ensure that AI workflows are designed to handle PHI and other sensitive data safely.</li> <li>Create reusable examples, templates, and internal libraries that make it easy for teams to adopt AI-powered quality workflows</li> <li>Contribute to training, documentation, and office hours that help engineers, PMs, and designers become confident automated test users and partners.</li> </ul> <p><strong>You will love this job if you:</strong></p> <ul> <li>Enjoy working on tools and systems that enable other teams to deliver better software, faster.</li> <li>Thrive in environments where you can operate cross-functionally and influence architecture, development, and deployment workflows.</li> <li>Like to collaborate with Platform, Application, and IT teams to improve reliability and observability.</li> <li>Love to mentor and learn from your teammates – training and collaborating with developers to write great code and solve problems together.</li> <li>Believe that quality is everyone’s responsibility, and enjoy helping others succeed</li> </ul> <p><strong>Requirements for this role:</strong></p> <ul> <li>6+ years of experience in a Software Engineering or SDET role</li> <li>Recent hands-on experience with agentic model harnesses and automated test orchestration&nbsp;</li> <li>Strong experience building and maintaining automated tests and Gitlab CI/CD workflows</li> <li>Experience with at least one modern test automation framework (e.g., Playwright, Appium, Cypress)</li> <li>Deep knowledge of versatile programming languages (e.g., Ruby, Javascript, Shell/Bash, Python)</li> <li>Familiarity with mobile app testing, API testing, and web testing</li> <li>Experience integrating and maintaining third-party QA and monitoring tools</li> <li>Ability to collaborate cross-functionally, translate real-world workflows into technical requirements, and communicate tradeoffs clearly.</li> <li>Brilliant communication and documentation skills</li> </ul> <p><strong>Bonus points for:</strong></p> <ul> <li>Experience building Slack apps, chatops tooling, or similar conversational interfaces for internal teams.</li> <li>Familiarity with observability tools and practices to track AI usage, reliability, and cost over time.</li> <li>Practical experience managing infrastructure on AWS with Terraform</li> <li>Familiarity with AWS cloud infrastructure and secure-by-default patterns for handling secrets, credentials, and sensitive data.</li> <li>Background working in healthcare or other regulated industries where PHI/PII handling, auditability, and compliance are critical.</li> </ul> <p><strong>Benefits:</strong></p> <ul> <li>Competitive salary with generous annual cash bonus</li> <li>Equity grants</li> <li>Employee stock purchasing plan (ESPP)</li> <li>Remote first work from home culture</li> <li>Flexible Time Off to help you rest, recharge, and connect with loved ones</li> <li>Generous parental leave</li> <li>Health, dental, and vision insurance (and above market employer contributions)</li> <li>401k retirement savings plan</li> <li>Lifestyle Spending Account (LSA)</li> <li>Mental Health Support Solutions</li> <li>...and more!</li> </ul> <p>It takes a village to change health care. As we build together toward our mission, we strive to embody the following values in our day-to-day work. We hope these hold meaning for you as we