Job Description: Title: Senior Software Development Engineer in Test (SDET 5) Team: Patient Experience - MediFind Engineering Location: Remote Canada (Priority given to those in EST or CST timezone regions) Why This Role Exists At Phreesia, we're transforming the healthcare experience through intelligent, AI-powered solutions that help patients connect with the care they need. As our MediFind platform continues to evolve with Voice AI agents and large language model (LLM) technologies, ensuring these systems are reliable, accurate, and scalable has never been more important. We're looking for a collaborative and proactive Senior Software Development Engineer in Test (SDET 5) to help define the future of quality engineering for AI-enabled healthcare applications. In this role, you'll lead testing strategies for Voice AI agents and LLM-powered workflows while leveraging AI to accelerate your own testing processes. Working alongside engineers, architects, product managers, and operations teams, you'll help embed quality into every stage of the development lifecycle, ensuring AI-driven features are safe, observable, and ready for production. If you're excited about shaping testing strategies for AI-powered systems while using AI as a force multiplier in your own work, this is an opportunity to make a meaningful impact on healthcare innovation. What You’ll Spend Your Time Doing Lead quality for AI-powered experiences. Design and maintain automated test strategies for Voice AI agents, LLM-powered workflows, and cloud-native applications, ensuring reliability, accuracy, scalability, and performance. Build automation that scales. Develop and enhance automation frameworks, integrate testing into CI/CD pipelines, and continuously improve quality processes to deliver fast, reliable feedback. Validate complex distributed systems. Perform end-to-end, API, UI, integration, and performance testing across microservices, event-driven architectures, and cloud platforms. Leverage AI to improve engineering efficiency. Use AI-assisted tools to accelerate test design, data generation, exploratory testing, coverage analysis, and defect investigation while proactively identifying quality risks. Partner to deliver production-ready software. Collaborate with engineers, architects, product managers, and operations teams to troubleshoot issues, monitor application health, participate in code reviews, and ensure high-quality releases. Raise the quality bar. Mentor junior SDETs, champion testing best practices, and drive continuous improvements across automation frameworks, tooling, and engineering processes. What Makes You a Great Fit You don’t need to check every box — but this role will feel energizing if you: Have deep experience building automated test frameworks for complex, distributed applications using C#, TypeScript, and modern testing tools such as Playwright or Selenium. Enjoy testing AI-powered products, including Voice AI agents and LLM-enabled workflows, while using AI-assisted tools to improve quality engineering. Have strong expertise in API, integration, UI, regression, and performance testing within cloud-native environments using AWS, Azure, or GCP. Are comfortable working with CI/CD pipelines, containerized applications, microservices, and modern cloud technologies including Docker and GitLab CI/CD. Thrive in collaborative Agile teams, partnering with engineers and product leaders to build reliable, scalable software. Enjoy mentoring others, driving continuous improvement, and raising engineering quality across the organization. We Do Have A Few Requirements To Check Bachelor's degree required, preferably in Computer Science. 8+ years of experience in Quality Assurance or as a Software Development Engineer in Test (SDET) supporting complex, distributed systems. Recent hands-on experience testing AI-powered products, including Voice AI agents and LLM-enabled workflows, while using AI-assisted tools to improve quality engineering. 5+ years of professional programming experience using C# and TypeScript, including building and maintaining automated API and integration test suites. 2+ years of team leadership experience. Where You’ll Work This is a remote role in Canada, preferably those in ET/CT time zone regions. You'll work closely with cross-functional engineering teams in a collaborative, cloud-first environment focused on delivering reliable AI-powered healthcare experiences. Why Phreesia Phreesia is on a mission to make healthcare more human, connected, and efficient. Our SaaS platform powers digital patient intake, engagement, and care experiences for healthcare organizations across the country, helping patients access care while enabling providers to work smarter. We're proud to be: A five-time Modern Healthcare Best Places to Work winner Recognized on the Bloomberg Gender Equality Index Deeply committed to inclusion, innovation, and employee growth Compensation & Rewards Annual Base Salary of $130,000 - $145,000 CAD, depending on qualifications. A comprehensive Total Rewards package designed to support your whole life — not just your work. Disclosure: This posting is to fill an existing vacancy. Who We Are: At Phreesia, we’re looking for smart and passionate people to help drive our mission of creating a better, more engaging healthcare experience. We’re committed to helping healthcare organizations succeed in an ever-evolving landscape by transforming the way healthcare is delivered. Our SaaS platform digitizes appointment check-in and offers tools to engage patients, improve efficiency, optimize staffing, and enhance clinical care. Phreesia cares about our employees by providing a diverse and dynamic work environment. We’re a five-time winner of Modern Healthcare Magazine’s Best Places to Work in Healthcare award and we’ve been recognized on the Bloomberg Gender Equality Index. We are dedicated to continuously improving our employee experience by launching new programs and initiatives. If you thrive in a culture of recognition, value inclusivity, professional development, and growth opportunities, Phreesia could be a great fit! Top-rated Employee Benefits: Remote First: 100% Remote work + home office expense reimbursements+ monthly reimbursement for cell phone, internet and wellness. Top of market rewards: Competitive compensation Take time when you need time: Flexible PTO + company holidays Top class healthcare benefits: Variety of healthcare benefits for you and your family (and your pets!) starting day one Care about your families: Generous top-up for parental leave benefits Support personal development: Continuing education and professional certification reimbursement Connecting in person: Various offsite events and activities for team to connect and meet in person, to support team building and engagement. Giveback to community: Local in-person volunteer events, and give back programs to our communities. Recognition and perks: We have a company wide recognition tool (Phireworks) to celebrate milestones, recognize achievements and strengthen your bond with your teams. You can accumulate points and redeem them for a wide catalogue of items! Diversity and inclusive environment: At Phreesia, all employees are encouraged to bring their authentic self to work, feel supported and perform at their best. We have a variety of Employee Resources Groups (ERGs) which bring together individuals from a wide range of backgrounds, experiences and perspectives, and seek to foster a sense of shared community and empowerment for employees who share a common social identity, such as gender, race, ethnicity, and sexual orientation. Opportunity to join an Employee Resource Group. Learn more here: https://www.phreesia.com/workforce/ Disclosure: Phreesia uses certain automated tools, including artificial intelligence, to support the assessment of applicants for this position. We strive to provide a diverse and inclusive environment and are an equal opportunity employer. At Phreesia, we’re transforming the patient experience and giving healthcare organizations the capacity to do more—and we need smart, innovative problem-solvers to help us get there. Phreesians have a wide range of backgrounds—you don’t need to be a healthcare expert or a technology geek to succeed on our team. We’re looking for talented, diverse individuals who want to make a difference in healthcare. Phreesia welcomes and encourages applications from people with disabilities. Accommodations are available on request for candidates participating in the selection process.