At Collective Health, we’re transforming how employers and their people engage with their health benefits by seamlessly integrating cutting-edge technology, compassionate service, and world-class user experience design.
We’re looking for a Lead Software Engineer to join our Developer Experience team. This team builds and maintains the critical internal tools and platforms that enable our engineers to move quickly, safely, and confidently. From owning our CI/CD systems, to designing core internal libraries, to ensuring observability with Honeycomb, we exist to make every engineer at Collective Health more productive.
As a Lead Engineer, you’ll drive complex cross-functional initiatives, set technical direction, and partner with engineering leadership to define how we build software at scale. You’ll mentor engineers, lead design discussions, and ensure that our internal developer ecosystem is robust, reliable, and delightful to use.

WHAT YOU’LL DO

• Lead the design, implementation, and rollout of key cross-functional projects that improve engineering productivity.
• Own and evolve our CI/CD platform, ensuring reliability, speed, and scalability.
• Utilize working knowledge of AI-powered developer tools (e.g., Copilot, Cursor) and actively contribute to AI adoption in development and operational aspects.
• Define and maintain standards and best practices for our core internal libraries, frameworks (Java/Spring Boot, TypeScript, Go, Python), and AI enabled systems
• Partner with infrastructure and product engineering teams to improve developer workflows, testing strategies, and release pipelines.
• Drive observability initiatives across services using Honeycomb and other tools.
• Mentor and guide engineers, fostering a culture of technical excellence and collaboration.Advocate for the developer experience across the company, influencing technical decisions at all levels.

TO BE SUCCESSFUL IN THIS ROLE, YOU’LL NEED

• 8+ years of professional software engineering experience, with at least 1+ years in a technical leadership role.
• Strong technical expertise in at least one of our core languages (Java, TypeScript, Go, or Python); experience with Spring Boot is highly desirable.
• Experience with distributed systems and cloud-native development (AWS, Kubernetes, etc.).
• Familiarity with Honeycomb, OpenTelemetry, or other observability platforms.
• Proven experience designing and scaling CI/CD systems and developer tooling.
• Deep understanding of modern software engineering practices (testing, observability, deployment strategies, etc.).
• Experience leading complex cross-functional projects, balancing trade-offs, and aligning stakeholders.
• Strong communication and mentorship skills; able to influence without direct authority.
• Passionate about improving the craft of engineering and enabling others to do their best work.