Senior Director, Benefits SRE (Boston)

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 understanding of failover recovery architectures - Active-Active, Active-Passive.
• Understanding of Benefits domain such as claims processing, eligibility lookup success rate.
• Understanding of incident impact awareness on members and providers.
• Experience working with compliance frameworks such as HIPAA, SOC 2, or HITRUST.

About WEX

WEX is a global leader in financial technology solutions, helping businesses navigate complex payment ecosystems with cutting-edge digital innovation. Our Benefits division is committed to transforming the benefits experience through modern, reliable, and scalable technology.

Why Join WEX?

• Impact: Lead the transformation of a mission-critical business division and drive meaningful change in benefits technology.
• Growth: Opportunity to shape and scale a modern SRE organization with executive sponsorship.
• Innovation: Work with cutting-edge cloud and reliability technologies in a high-performance engineering environment.
• Culture: A collaborative and inclusive workplace that values diversity, learning, and career development.

The base pay range represents the anticipated low and high end of the pay range for this position. Actual pay rates will vary and will be based on various factors, such as your qualifications, skills, competencies, and proficiency for the role. Base pay is one component of WEX's total compensation package. Most sales positions are eligible for commission under the terms of an applicable plan. Non-sales roles are typically eligible for a quarterly or annual bonus based on their role and applicable plan. WEX's comprehensive and market competitive benefits are designed to support your personal and professional well-being. Benefits include health, dental and vision insurances, retirement savings plan, paid time off, health savings account, flexible spending accounts, life insurance, disability insurance, tuition reimbursement, and more. For more information, check out the About Us section. Pay Range: $207,000.00 - $275,000.00