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 cloud and on-premises infrastructure with AWS at the center. The role demands hands-on AWS expertise, strong networking fundamentals, and the ability to troubleshoot complex issues across cloud and on-premises environments.

You will lead cloud migrations, develop infrastructure automation, and ensure security, resilience, and cost efficiency while collaborating with multiple teams.

Qualifications

• 7+ years of progressive experience in cloud/infrastructure roles with hands-on AWS
• 3+ years of hands-on AWS engineering and administration experience
• Strong networking experience including routing, switching, firewalls, VPNs, DNS/DHCP, VPC connectivity
• Experience with infrastructure automation and scripting (PowerShell) and related tools
• Experience leading or delivering cloud migrations and modernization initiatives
• Excellent communication and collaboration with cross-functional teams

Responsibilities

• Design, implement, and optimize secure, scalable AWS cloud infrastructure
• Support and advance hybrid cloud/on-premises infrastructure (VMware, Windows Server/AD)
• Troubleshoot enterprise networking across AWS and on-premises environments
• Lead cloud migrations and modernization initiatives for performance and cost efficiency
• Develop infrastructure automation using PowerShell and IaC technologies
• Implement security, monitoring, backup, DR, patching, and vulnerability remediation
• Monitor health and provide senior-level technical support and guidance
• Collaborate with Infrastructure, Security, Data & Analytics teams to deliver solutions
• Participate in after-hours maintenance and on-call rotations

Skills

AWS cloud engineering

Networking

Automation & scripting

Cloud migration

Communication & collaboration

Education

Bachelor’s degree in IT/CS or equivalent

Tools

PowerShell

Terraform

Python

Ansible

VMware

Windows Server/Active Directory

Job description

Tokio Marine Highland is seeking a Senior Cloud & Infrastructure Engineer to help design, modernize, and support our cloud and on-premises 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, solid networking fundamentals, and the ability to troubleshoot complex issues across cloud and on-premises environments. The role will independently support AWS and enterprise networking, use automation to improve infrastructure operations, and serve as a senior escalation point for infrastructure-related issues.

The position also supports VMware and Windows Server/Active Directory environments. Experience with Azure, Microsoft 365, backup and disaster recovery, Snowflake, and related technologies is helpful, but these are supporting rather than primary areas of focus.

Key Responsibilities

• Design, implement, and optimize secure, scalable, and highly available AWS cloud infrastructure.
• Support and advance TMH’s integrated cloud and on-premises infrastructure environment, including VMware and Windows Server/Active Directory.
• Independently support and troubleshoot enterprise networking across AWS and on-premises environments, including routing and switching, VLANs, firewalls, VPNs, DNS/DHCP, VPC connectivity, and network resiliency; make appropriate configuration changes and own network-related infrastructure incidents through resolution.
• 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 an 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, implementing, supporting, securing, and optimizing AWS cloud environments.
• Solid hands-on networking experience, including the ability to independently troubleshoot routing, switching, firewalls, VPNs, DNS/DHCP, AWS VPC networking, and cloud-to-on-premises connectivity.
• Strong troubleshooting and analytical skills, with experience serving as a senior escalation point for complex cloud and infrastructure issues.
• Hands-on experience with infrastructure automation and scripting, particularly PowerShell; experience with Terraform, Python, Ansible, or similar tools is also valuable.
• Working proficiency supporting VMware and Windows Server/Active Directory environments.
• Experience leading or independently delivering cloud migrations, infrastructure implementations, upgrades, modernization initiatives, or other complex technical projects.
• Strong 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 Azure, Microsoft 365, backup and disaster recovery, Snowflake, or related infrastructure and data-platform technologies.
• Relevant AWS, networking, Microsoft, VMware, or infrastructure certifications.

Additional Job Details:

This hybrid position is based in Chicago, IL, with an expectation of 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.