We are looking for an experienced Staff Software Engineer (Flex) to accelerate our adoption of AI technologies across the technical organization.  This role will report directly to the Head of AI and Research. In this role, you will be responsible for developing AI technologies using generative AI (in particular LLMs) and machine learning. You will partner closely with data science, design, product and engineering to build new 0 to 1 features that are powered by AI.

What you’ll be doing as Staff Software Engineer (Flex):

• Lead key technical initiatives to enhance and expand Brightside’s telehealth platform.
• Design and scale high-performance, secure healthcare systems that comply with HIPAA and industry standards.
• Guide and mentor engineering teams, driving best practices in software development, CI/CD, and cloud infrastructure.
• Collaborate cross-functionally with product managers, designers, and clinicians to ensure that our platform meets real-world healthcare needs.
• Champion innovation by staying ahead of emerging technologies and proactively improving patient and provider experiences.
• Ensure data privacy & security, implementing best practices for encryption, authentication, and compliance.

Requirements:

• 8+ years of software development experience, with significant time in senior or lead engineering roles.
• Extensive hands-on experience in full-stack development with Ruby on Rails and React for web applications. As well as React Native for mobile development
• Deep expertise in cloud platforms (AWS, Azure, or GCP), including containerization, orchestration, caching, and CI/CD pipelines.
• Strong software architecture & performance optimization skills, ensuring scalability, reliability, and high-performance applications.
• Leadership experience in an engineering role (Tech Lead, Team Lead, or Staff Engineer), with a track record of mentoring engineers and fostering collaboration.
• Security & Compliance knowledge, including HIPAA regulations, secure authentication, encryption, and auditing practices in healthcare technology.
• Bachelor’s or Master’s degree in Computer Science (or related field) or equivalent professional experience.

Benefits:

• A competitive salary
• Fully paid for comprehensive health care (medical, dental, vision)
• Pet Insurance
• Life Insurance & Short / Long Term Disability
• 401k Plan
• Unlimited PTO and sick leave
• Parental Leave
• Work remotely and whatever schedule works best for you
• Additional memberships and perks

Work Environment & Culture:

At Brightside Health, you’ll join a fully remote, mission-driven team that values flexibility and impact. You’ll collaborate with professionals across engineering, product, and clinical teams, all dedicated to transforming mental healthcare. Our culture fosters continuous learning, empathy, and cross-functional collaboration.

We celebrate diversity and are committed to equal employment opportunities based on merit, competence, and performance. Research shows that underrepresented groups often apply only if they meet 100% of the listed criteria—we encourage women, people of color, and LGBTQ+ job seekers to apply even if they don’t check every box.

Compensation & Hiring Commitment:

Final offers are determined by multiple factors, including location, experience, and expertise. If you have questions about compensation bands, please ask your recruiter.

At Brightside, we recognize that building life-changing technology for mental health is both a responsibility and a privilege. We set high standards while ensuring every team member is valued, trusted, and empowered in an environment driven by inclusion and impact