Senior Director, Benefits SRE

About the Team & Role

We are seeking a Senior Director of Site Reliability Engineering (SRE) to lead and mature our SRE function for the Benefits product line. This leader will play a pivotal role in ensuring the scalability, reliability, and operational excellence of our platforms while spearheading SRE collaboration on our Benefits Modernization initiative. This role demands deep technical expertise, strategic leadership, and a passion for building high-performing teams that bridge software engineering and system reliability.

Key Responsibilities

Strategic Leadership & Transformation

• Lead the SRE function for Benefits product line, defining vision, strategy, and best practices aligned with business goals.

• Oversee SRE collaboration on the Benefits Modernization initiative, ensuring reliability, observability, and operational efficiency in our next-generation platform.

• Champion a "Reliability as a Product" mindset, integrating SRE principles into the engineering culture across the division.

• Drive SRE adoption of modern infrastructure, cloud-native architectures, and DevOps best practices to improve resilience and speed of delivery.

Operational Excellence & Reliability

• Define and implement Service Level Objectives (SLOs), Error Budgets, and operational KPIs to continuously improve system reliability, performance, and recoverability.

• Establish automated monitoring, observability, and incident response processes to proactively detect and resolve issues.

• Drive incident management and problem management processes, ensuring effective root cause analysis and remediation.

• Foster a culture of blameless postmortems and continuous learning, turning incidents into opportunities for improvement.

Collaboration & Cross-Functional Leadership

• Partner with Product, Engineering, Architecture, Security, and Infrastructure teams to embed reliability into the software development lifecycle.

• Influence engineering teams to adopt best practices for high-availability, scalability, and fault tolerance in application design.

• Ensure SRE plays a critical role in migrating legacy systems to modern cloud-based architectures as part of the Benefits Modernization program.

• Work closely with business stakeholders to balance reliability investments with feature delivery and customer needs.

Team Leadership & Talent Development

• Build, mentor, and scale a high-performing SRE organization, fostering a culture of ownership, innovation, and technical excellence.

• Implement a talent strategy to attract, retain, and develop employees in SRE principles and modern operational practices.

• Encourage a collaborative and inclusive work environment, driving engagement and alignment across distributed teams.

Required Qualifications

• 15+ years of experience in software engineering, reliability engineering, DevOps, and/or cloud infrastructure roles.

• 7+ years of leadership experience, managing large-scale engineering or SRE teams.

• Deep expertise in SRE principles, including SLIs, SLOs, error budgets, and incident management.

• Strong background in cloud platforms (Azure, AWS, GCP) and Kubernetes-based architectures.

• Hands-on experience with observability tools (Datadog, Prometheus, Grafana, OpenTelemetry, etc.).

• Proven track record leading large-scale transformations, especially in regulated industries such as healthcare, benefits, or financial services.

• Strong understanding of CI/CD, Infrastructure as Code (Terraform, Pulumi), and security best practices.

• Experience working in high-growth, Agile environments, driving cultural and process change.

• Exceptional communication, stakeholder management, and executive-level presentation skills.

Preferred Qualifications

• Experience in healthcare, insurance, or benefits technology.

• Knowledge of modern software architectures, microservices, and distributed systems.

• Deep