Senior Security Engineer — Chicago, IL

About the Role

Most security roles end at the finding; this one starts there. We are looking for a Senior Security Engineer who would rather close a gap than write a memo about it: someone who spots a misconfiguration, works out the right fix, and addresses it.

You will own hands-on security engineering across our hybrid environment: our AWS hosting platform, Microsoft 365 and Entra ID, and Windows Server infrastructure. Your responsibilities also include running vulnerability and patch management and helping manage third-party risk. Reporting to the Vice President of Information Technology Operations, you will work across the organization, from the help desk to senior leadership.

What You Will Do

• Find and fix real security issues across AWS, Microsoft 365, Entra ID, Active Directory, and Windows Server, not just report on them

• Harden identity and access: Conditional Access, MFA, privileged access, and Microsoft 365 data governance, including how Copilot and shared content are exposed

• Secure our AWS environment, from IAM and network controls to logging, encryption, and backup

• Run vulnerability and patch management with a risk-based approach, and drive remediation to closure

• Work with our managed detection and response partner to investigate alerts and respond to incidents

• Work with a security vendor and a risk management program to address security findings and risk items: decide what matters most, then fix it

• Automate repeatable work with PowerShell, Python, and infrastructure-as-code

• Turn governance requirements and audit expectations into technical controls with evidence behind them

• Assess and monitor third-party vendors, and help decide where the real risk is

• Partner with staff across the organization to find secure ways to get their work done, offering practical solutions instead of just saying no

What Makes This Role Different

• Ownership. You decide what to fix first, and you get to fix it.

• Breadth. AWS, Microsoft 365, Windows infrastructure, vulnerability management, and third-party risk in one role, so no two weeks look the same.

• Visibility. You work directly with technology leadership to reduce risk and demonstrate the results. Documentation supports that work; it is not the end goal.

• A real mandate. Governance here means controls that are implemented and provable, not shelfware.

Required Skills:

• Bachelor’s Degree in an IT or cybersecurity-related discipline, or 7 years of relevant experience or equivalent

• 5+ years of hands-on experience in security or infrastructure engineering

• Practical experience securing Microsoft 365 and Entra ID

• Practical experience securing AWS environments

• Strong grounding in Windows Server, Active Directory, and Group Policy, with SQL Server and IIS exposure

• Experience running vulnerability management and patching programs

• Scripting ability in PowerShell and at least one of Python, AWS CLI, or infrastructure-as-code

• Clear written and verbal communication, and the judgment to explain risk to non-technical audiences

Nice to Have

• Security certifications such as AWS Security Specialty, SC-300 or SC-200, CISSP, CISM, or CISA

• Familiarity with frameworks such as NIST CSF, CIS Controls, or ISO 27001

• Experience with third-party risk management

• Insurance industry experience