Sr Director, Payments SRE

WEX•Chicago, IL
•$210,000 - $249,500

About The Position

WEX is seeking a senior technical leader to define and execute the reliability engineering vision for its payments platform ecosystem. The role focuses on high-volume, low-latency payment systems where reliability, scalability, efficiency, transactional integrity, and customer trust are critical. The Senior Director will lead cross-functional initiatives in observability, incident and problem management, automation, performance optimization, and capacity planning, while architecting resilient systems and proactive reliability strategies. The position provides strategic leadership across engineering, product, and platform organizations, influencing architecture and embedding SRE principles throughout the development lifecycle. It includes scaling reliability practices and tooling, mentoring engineers and engineering leaders, and fostering a culture of operational excellence, continuous improvement, and innovation. The organization uses modern technologies, AI, and automation in an agile, product-centric engineering model. The role also oversees SRE strategy and organizational growth across multiple payments domains, including business continuity, disaster recovery, and compliance. The Senior Director represents the SRE organization with executive stakeholders and in industry forums, and leads hiring strategy, headcount planning, and long-term team capability growth.

Requirements

  • 15 years of experience in software engineering.
  • 7 years of engineering management experience managing managers and individual contributors.
  • Deep experience in cloud-native architecture and large-scale distributed systems.
  • Deep expertise in system design, automation, and performance optimization.
  • Deep knowledge of Kubernetes, service meshes, and distributed tracing.
  • Hands-on experience with containerization and orchestration, including Docker and Kubernetes.
  • Experience with monitoring and logging platforms such as Grafana, ELK stack, Splunk, or similar.
  • Strong understanding of database reliability engineering, including MySQL, PostgreSQL, or NoSQL, and of networking and storage architectures.
  • Proven experience with highly available, low-latency systems and workloads requiring transactional integrity and consistency.
  • Excellent incident command and crisis management skills.
  • Strong experience with regulatory and compliance frameworks.
  • Exceptional leadership skills and a proven track record of driving reliability improvements.
  • Skill managing distributed teams and fostering psychological safety in high-stakes environments.

Nice To Haves

  • Understanding of PCI-DSS compliance and secure handling of payment data.
  • Experience monitoring payment flows and exceptions in real time, handling partner and payment-gateway integrations, and managing failure recovery and idempotency in financial transactions.
  • Familiarity with end-of-day reconciliation and cutoff schedules.
  • Deep AI/ML expertise for anomaly detection and predictive analytics in observability, with a track record of using AI to address significant Site Reliability and Operations problems.
  • Strong financial acumen in cost optimization and cloud-spend strategies.
  • Ability to align SRE practices with business goals and influence C-level executives on reliability strategy.
  • Track record of building and leading SRE organizations across multiple domains or product lines.
  • Ability to define and institutionalize reliability practices, including standardized SLOs, blameless culture, and incident communications.
  • Strong organizational and stakeholder-management skills across Engineering, Product, and Executive teams.
  • Recognized SRE thought leader with publications or conference talks.

Responsibilities

  • Set the organization-level SRE vision and strategy for reliability, observability, automation, and incident management.
  • Scale the SRE function across multiple payments domains, leading SRE managers and senior individual contributors.
  • Lead the development of solutions to reliability challenges in highly available, low-latency payment systems.
  • Promote a culture of reliability, operational excellence, blameless learning, and continuous improvement.
  • Ensure business continuity, disaster recovery, and compliance across the payments platform.
  • Build relationships with executive stakeholders and represent SRE in executive forums, reviews, and strategic planning.
  • Represent WEX in industry forums and conferences as a reliability engineering thought leader.
  • Drive hiring strategy, headcount planning, and long-term team capability growth.
  • Influence architecture and embed SRE principles across the development lifecycle.
  • Mentor engineers and engineering leaders, and scale SRE best practices.

Benefits

  • Health insurance
  • Dental insurance
  • Vision insurance
  • Retirement savings plan
  • Paid time off
  • Health savings account
  • Flexible spending accounts
  • Life insurance
  • Disability insurance
  • Tuition reimbursement
  • Quarterly or annual bonus eligibility for non-sales roles, subject to role and applicable plan
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