Senior Cloud & Infrastructure Engineer

Tokio Marine Highland; Chicago (IL); Hybrid; USD 125,000 - 150,000; Full time

Job summary

Tokio Marine Highland is seeking a Senior Cloud & Infrastructure Engineer to design, modernize, and support our cloud and hybrid infrastructure with AWS at the center. This hands-on role requires deep AWS expertise and a strong understanding of how cloud works with on‑premises systems like VMware and Windows Server/AD.

You will collaborate across teams to deliver secure, scalable solutions. The position is hybrid and based in Chicago, IL, with 2–3 days in the office weekly, and offers a base

Qualifications

• 7+ years of progressive experience in cloud and infrastructure engineering, including hands-on AWS.
• Experience designing, securing, and optimizing AWS cloud environments in enterprise settings.
• Strong understanding of hybrid infrastructure and on-premises integration (VMware, Windows Server/AD, networking).
• Scripting and automation experience (PowerShell) and infrastructure-as-code practices.
• Experience leading cloud migrations, modernization projects, and complex technical initiatives.
• Strong troubleshooting, analytical, and cross-functional collaboration skills.

Responsibilities

• Design, implement, and optimize secure, scalable AWS infrastructure.
• Support and advance the hybrid environment, integrating AWS with on‑premises tech (VMware, Windows, networking).
• Lead cloud migrations, modernization initiatives, and lifecycle management.
• Develop infrastructure automation using PowerShell and IaC technologies.
• Implement and maintain security and resiliency controls (IAM, monitoring, backup, DR, patching).
• Monitor health, troubleshoot complex issues, and provide senior-level guidance.
• Partner with multiple teams to design and deliver technology solutions.
• Participate in scheduled after-hours maintenance and on-call rotation.

Skills

AWS cloud engineering

Hybrid infrastructure

PowerShell

VMware

Windows Server/AD

Networking

Security and resiliency

Collaboration & communication

Education

Bachelor's degree in IT or related field

Tools

Terraform

Python

AWS CloudFormation

Git-based workflows

Job description

Tokio Marine Highland is seeking a Senior Cloud & Infrastructure Engineer to help design, modernize, and support our cloud and hybrid infrastructure, with Amazon Web Services (AWS) at the center of the role.

This is a hands‑on engineering position for someone who brings strong AWS experience along with a solid understanding of how cloud environments integrate with traditional infrastructure. You’ll work across cloud engineering, infrastructure automation, security, resiliency, and modernization while partnering closely with Infrastructure, Security, Data & Analytics, and Application teams.

The role also supports our broader hybrid environment, including VMware, Windows Server/Active Directory, networking, Azure, Microsoft 365, backup, and disaster recovery, but the primary focus is AWS cloud engineering and operations.

Key Responsibilities

• Design, implement, and optimize secure, scalable, and highly available AWS cloud infrastructure.
• Support and advance TMH’s hybrid infrastructure environment, ensuring reliable and secure integration between AWS and on‑premises technologies, including VMware, Windows Server/Active Directory, and enterprise networking.
• Lead and contribute to cloud migration, infrastructure modernization, lifecycle, and optimization initiatives that improve performance, availability, security, and cost efficiency.
• Develop infrastructure automation using PowerShell and infrastructure‑as‑code technologies to improve provisioning, consistency, and operational efficiency.
• Implement and maintain cloud and infrastructure security and resiliency controls, including AWS Identity and Access Management (IAM), monitoring, backup, disaster recovery, patching, and vulnerability remediation.
• Monitor infrastructure health and performance, troubleshoot complex cloud and infrastructure issues, and provide senior‑level technical support and guidance.
• Partner with Infrastructure, Security, Data & Analytics, Application teams, and other stakeholders to design and deliver technology solutions that support business and operational needs.
• Participate in scheduled after‑hours maintenance and on‑call rotation as needed.

What You'll Bring

• Typically 7+ years of progressive experience in cloud, infrastructure, systems engineering, or a related technology discipline, including at least 3 years of hands‑on AWS engineering and administration experience.
• Strong hands‑on experience designing, supporting, securing, and optimizing AWS cloud environments in enterprise production environments.
• Strong understanding of hybrid infrastructure and how cloud integrates with on‑premises environments, including experience with VMware, Windows Server/Active Directory, and enterprise networking.
• Hands‑on experience with infrastructure automation and scripting, particularly PowerShell.
• Working knowledge of cloud and infrastructure security and resiliency practices, including identity and access management, monitoring, patching, vulnerability remediation, backup, and disaster recovery.
• Experience leading or independently delivering cloud migrations, infrastructure implementations, upgrades, modernization initiatives, or other complex technical projects.
• Strong troubleshooting, analytical, communication, and collaboration skills, with the ability to work effectively across technical teams and business stakeholders.
• Bachelor’s degree in Information Technology, Computer Science, or a related field, or equivalent relevant professional experience.

Preferred Qualifications

• Experience with Microsoft Azure cloud environments and Microsoft 365 services, including Entra ID.
• Experience with infrastructure‑as‑code and automation technologies such as Terraform, Python, AWS CloudFormation, or Git‑based workflows.
• Experience with enterprise backup, disaster recovery, and monitoring solutions, including Veeam and AWS Backup.
• Experience providing operational support for Snowflake environments, including access management, monitoring, troubleshooting, or AWS integration.
• Relevant cloud or infrastructure certifications, such as AWS Certified Solutions Architect – Associate, or AWS Certified SysOps Administrator – Associate.

Additional Job Details:

This hybrid position is based in Chicago, IL, with an expectation of 2–3 days in the office each week.

The base salary range for this role is $125,000–$150,000 annually. This range reflects a good‑faith estimate of pay at the time of posting. Actual compensation will be determined based on factors such as experience, skills, knowledge, education, and internal pay equity.

Work Authorization

Candidates must be legally authorized to work in the United States. This position is not eligible for employer‑sponsored work authorization now or in the future.

About Tokio Marine Highland

Tokio Marine Highland is a managing general agency that offers distinct specialty risk management solutions, including private flood, fine art, specialty property, real estate investment, and lender‑placed insurance.

Founded in 1962, Tokio Marine Highland is a wholly owned subsidiary of Tokio Marine Kiln (TMK), a leading specialist insurance underwriting business operating in the Lloyd’s insurance market and part of one of the world’s largest insurance groups, Tokio Marine. As one of the largest Lloyd’s syndicates, TMK benefits from Lloyd’s financial strength, including an A+ rating from AM Best.

Tokio Marine Highland has office locations in Chicago, IL, Frisco, TX, Miami, FL, New York City, NY, and South Pasadena, CA. For more information, visit our website at www.tokiomarinehighland.com.

Tokio Marine Highland, LLC (TMH) is an Equal Opportunity Employer. TMH’s success depends heavily on the effective utilization of qualified people, regardless of their race, ancestry, religion, color, sex, national origin, sexual orientation, gender identity and/or expression, disability, veteran status, or any characteristic protected by law. As a company, we adhere to and promote equal employment opportunities for all.