Staff Site Reliability Engineer

WEX; Chicago (IL); On-site; USD 121,000 - 151,000; Full time

Benefits offered by this job

Health insurance

Dental insurance

Vision insurance

Retirement plan

Paid time off

Health savings account

Flexible spending accounts

Life insurance

Disability insurance

Tuition reimbursement

Job summary

WEX is seeking a Staff Site Reliability Engineer to lead reliability initiatives across the platform and drive AI-enabled operations. You will architect scalable systems, define best practices, and mentor teams while shaping a resilient, observable, and efficient infrastructure.

You will collaborate across product and platform teams, oversee capacity planning, and build self-healing capabilities. A strong track record in large-scale systems, Kubernetes, and AI-driven automation is essential for

Qualifications

• 8+ years of experience in large-scale system reliability.
• Expertise in cloud platforms and automation frameworks.
• Hands-on with AI-enabled operations and AI agents is a plus.

Responsibilities

• Architect and oversee mission-critical systems focusing on availability and scalability.
• Define and enforce SRE best practices across teams.
• Lead cross-functional initiatives to improve reliability and efficiency at scale.
• Serve as a technical advisor on reliability, architecture, and risk.
• Develop capacity planning and load testing strategies.
• Design self-healing and auto-recovery mechanisms.
• Drive cloud cost optimization without compromising reliability.
• Design, build, and govern AI agents to automate workflows.
• Integrate AI ecosystems into SRE/platform workflows.
• Apply AI security and governance controls.

Skills

Large-scale reliability

Cloud platforms

Kubernetes

Service meshes

Distributed tracing

Incident response

AI in operations

Automation

Tools

Grafana

ELK stack

Splunk

OpenTelemetry

Jaeger

Prometheus

Docker

Job description

About The Role

We are looking for a highly motivated, high-potential Staff Site Reliability Engineer (SRE) to join our team as a technical leader and drive transformative impact across WEX’s platform reliability and operational excellence.

About The Role

We are looking for a highly motivated, high-potential Staff Site Reliability Engineer (SRE) to join our team as a technical leader and drive transformative impact across WEX’s platform reliability and operational excellence.

This is a particularly exciting time to be part of the SRE function at WEX. Our diverse product ecosystem supports a wide array of customer businesses and generates rich, complex telemetry across applications, infrastructure, and platforms. Ensuring these systems are scalable, observable, and resilient is critical to unlocking business value and customer success.

As a Staff SRE, you will play a pivotal role in shaping the reliability engineering strategy at WEX. You’ll architect and lead efforts that improve availability, performance, and efficiency at scale, driving initiatives across observability, automation, incident management, problem management, capacity planning, and performance optimization. You’ll be hands‑on in building foundational tooling and frameworks while also acting as a multiplier, mentoring engineers, aligning cross‑functional teams, and influencing platform decisions with a strong reliability lens.

You’ll also help define how WEX applies AI to reliability engineering, building agents and reusable skills that automate high-TOIL work, integrating safely into our AI ecosystem, and establishing security and operational guardrails so intelligent automation is trustworthy, measurable, and scalable. Our team embraces agile development, a strong product mindset, and modern engineering practices, including AI‑assisted operations and intelligent automation.

You’ll take on some of the most complex, high‑impact challenges at WEX, supported by a team of highly skilled engineers and technical leaders invested in your success and growth.

If you’re a senior technical leader passionate about building reliable systems, leading through influence, and making a meaningful impact with AI‑enabled operations, this is a fantastic opportunity for you.

What You’ll Do

• Architect and oversee the implementation of mission‑critical systems with a focus on availability, scalability, and operational excellence.
• Define and enforce SRE best practices and operational standards across engineering and platform teams.
• Lead cross‑functional initiatives to enhance system reliability, performance, and efficiency at scale.
• Serve as a technical advisor for engineering leadership on reliability, architecture, and operational risk.
• Develop capacity planning and load testing strategies that proactively identify and mitigate scalability risks.
• Design self‑healing and auto‑recovery mechanisms that reduce manual intervention during failures.
• Drive cloud cost optimization and budgeting initiatives without compromising reliability.
• Design, build, and govern AI agents and reusable skills that automate operational workflows and reduce TOIL.
• Evaluate and integrate AI ecosystems, including models, agent frameworks, orchestration, tooling interfaces, and evaluation practices, into SRE and platform workflows.
• Apply AI security and governance controls, including least‑privilege tool access, secure data and prompt handling, auditability, and safe automation boundaries.
• Lead AI‑enabled initiatives for incident response, runbook automation, anomaly detection, and capacity/performance insights, with clear measurement of TOIL reduction and reliability outcomes.
• Mentor engineers on production‑grade agentic solutions and help embed AI into day‑to‑day reliability practices.

What You’ll Bring

• 8+ years of experience with a focus on large‑scale system reliability.
• Expertise in system architecture, cloud platforms, and automation frameworks.
• Deep knowledge of Kubernetes, service meshes, and distributed tracing.
• Experience with monitoring and logging platforms (Grafana, ELK stack, Splunk, etc.).
• Knowledge of containerization and orchestration (Docker, Kubernetes).
• Experience designing high‑availability, fault‑tolerant architectures.
• Strong understanding of database reliability engineering (MySQL, PostgreSQL, NoSQL), plus networking, databases, and storage architectures.
• Excellent incident command and crisis management skills.
• Hands‑on experience building AI agents and skills/tools that integrate with operational systems (APIs, observability, ticketing, CI/CD).
• Working knowledge of AI ecosystems and agent architectures, including orchestration, tool calling, context/memory, evaluation, and human‑in‑the‑loop patterns.
• Practical understanding of AI security and governance for production use, secure permissions, data leakage prevention, secrets handling, and guarded autonomous actions.
• Demonstrated ability to reduce TOIL with AI by automating repetitive operational work and delivering measurable efficiency and reliability gains.

Nice to Have

• Experience with multi‑region and multi‑cloud deployments.
• Deep expertise in scalable microservices and event‑driven architectures.
• Strong experience with advanced observability tools (OpenTelemetry, Jaeger, Prometheus).
• Leadership in driving large‑scale SRE transformations.
• Experience designing and developing AI agents, skills, and copilots for SRE/platform engineering, including evaluation and safe rollout practices.
• Familiarity with enterprise agent platforms, skill registries, and observability for AI/agent workflows.
• Ability to influence engineering culture and process improvements, including adoption of AI‑assisted operations under change control, safety, and audit requirements.

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: $120,600.00 - $150,900.00