Senior Systems Engineer

Skyline Construction • Chicago, IL

16d • $102,584 - $133,057 • Hybrid

About The Position

The Senior Systems Engineer can be based out of Skyline Construction's office location in Bellevue, Washington, Chicago, Illinios or Phoenix, Arizona. This person is responsible for the design, implementation, security, and ongoing operation of Skyline's enterprise systems, cloud platforms, identity services, server infrastructure, storage, backup, and disaster recovery capabilities across multiple offices and data center environments. This role serves as a senior technical leader, owning complex infrastructure, leading modernization initiatives, mentoring technical staff, and partnering with the IT Service Delivery, Cybersecurity, and business stakeholders to deliver secure, resilient, and reliable services. The role also has responsibility for overseeing and managing an offshore Systems Engineering team.

Requirements

• 8+ years of progressive systems engineering or infrastructure experience in a multi-site enterprise environment, including senior-level ownership of production services.
• Bachelor's degree in information technology, computer science, engineering, or a related field preferred, or equivalent practical experience.
• Relevant Microsoft, Azure, VMware, Linux, backup, or security certifications are preferred.
• Deep hands-on experience with Windows Server, Active Directory, Group Policy, DNS, DHCP, identity, access management, and core infrastructure services.
• Experience administering Azure and Microsoft 365 in hybrid environments, including Entra ID and modern authentication.
• Experience with virtualization, enterprise storage, backup and recovery, monitoring, patch management, and disaster recovery.
• 3–5+ years in IAM, security engineering, or systems administration
• Hands-on experience with a major IdP (Okta, Entra ID, OneLogin) and Active Directory / LDAP
• Working knowledge of SAML, OIDC, OAuth 2.0, SCIM, and Kerberos
• Scripting/automation experience (PowerShell, Python) and familiarity with REST APIs
• Understanding of Zero Trust principles, least privilege, and segregation of duties
• Working knowledge of networking, firewalls, certificates, public key infrastructure, endpoint security, and security operations.
• Proficiency with PowerShell; experience with Python, configuration management, or infrastructure-as-code tools is a plus.
• Experience leading infrastructure projects, coordinating vendors, and supporting geographically distributed offices.
• Strong systems thinking, analytical judgment, and structured problem-solving under pressure.
• Excellent written and verbal communication with technical teams, business partners, vendors, and leadership.
• Ability to lead complex work independently, manage competing priorities, and follow through on commitments.
• Customer-focused mindset with strong ownership, collaboration, and continuous-improvement habits.
• Sound judgment when working with privileged access, sensitive information, and business-critical services.

Nice To Haves

• Proficiency with PowerShell; experience with Python, configuration management, or infrastructure-as-code tools is a plus.

Responsibilities

• Design, implement, and maintain scalable, secure, and highly available systems across on-premises, cloud, and hybrid environments.
• Define infrastructure standards, reference architectures, configuration baselines, and lifecycle roadmaps.
• Evaluate emerging technologies and recommend solutions that improve reliability, security, performance, and cost efficiency.
• Administer and optimize Windows and Linux server environments, virtualization platforms, and supporting infrastructure.
• Manage compute, storage, and related capacity to meet business performance, availability, and growth requirements.
• Plan and execute server upgrades, migrations, consolidations, and technology refresh initiatives with minimal disruption.
• Engineer and support Azure and Microsoft 365 services within a secure hybrid operating model.
• Administer Entra ID, Active Directory, Group Policy, domain services, authentication, and role-based access controls.
• Partner with application owners and service providers to improve platform integration, availability, and supportability.
• Administer and maintain identity providers (Okta, Entra ID/Azure AD, Active Directory), including SSO, MFA, and conditional access policies
• Design and manage role-based access control (RBAC) models, entitlements, and least-privilege access across enterprise systems
• Build and maintain automated user lifecycle workflows — onboarding, role changes, and offboarding — with SCIM/API-based provisioning
• Integrate SaaS and internal applications with SSO using SAML, OAuth 2.0, and OIDC
• Manage privileged access (PAM), including admin account governance, credential vaulting, and just-in-time elevation
• Conduct periodic access reviews and user access certifications to support audit and compliance requirements (SOC 2, ISO 27001, NIST)
• Monitor identity-related events and support incident response for account compromise, privilege misuse, and anomalous authentication activity
• Document IAM standards, procedures, and administrator policies; partner with Security, HR, and Legal on access governance
• Serve as escalation point for complex authentication and authorization issues
• Implement secure configuration standards and user provisioning, least-privilege access, multifactor authentication, system hardening, and vulnerability remediation.
• Own operating system and infrastructure patch management, including testing, deployment, exception tracking, and reporting.
• Collaborate with Cybersecurity to support audits, incident response, security investigations, and remediation activities.
• Engineer and manage backup, replication, retention, and recovery solutions for critical systems and data.
• Develop, maintain, and test recovery procedures and runbooks in alignment with defined recovery objectives.
• Identify resilience gaps and implement improvements that reduce operational risk and support business continuity.
• Implement proactive health, performance, capacity, and availability monitoring with actionable alerting and reporting.
• Lead troubleshooting and root-cause analysis for complex systems incidents, recurring problems, and service degradation.
• Participate in escalation and after-hours support for critical infrastructure incidents and planned maintenance when required.
• Automate provisioning, configuration, reporting, and routine administrative tasks using PowerShell, Python, or infrastructure automation tools.
• Reduce technical debt through standardization, simplification, documentation, and measurable operational improvements.
• Identify opportunities to improve service quality, operational efficiency, and the employee technology experience.
• Lead infrastructure change planning, testing, implementation, validation, and rollback preparation through established change-management processes.
• Maintain accurate architecture diagrams, system inventories, configuration records, standard operating procedures, and support runbooks.
• Ensure systems are operated consistently with IT policies, approved standards, licensing requirements, and vendor support models.
• Lead systems workstreams for office openings, relocations, acquisitions, cloud migrations, application deployments, and infrastructure modernization.
• Manage technical relationships with vendors and service providers, including solution evaluation, implementation coordination, and escalation.
• Collaborate across Network Operations, Cybersecurity, Service Desk, application teams, and business stakeholders to deliver reliable outcomes.
• Serve as a senior escalation point and trusted technical advisor for infrastructure and cloud services.
• Mentor engineers, administrators, contractors, and support staff through documentation, knowledge transfer, and hands-on guidance.
• Communicate technical risks, options, recommendations, and project status clearly to both technical and non-technical audiences.

Benefits

• Employee Stock Ownership Plan (ESOP)
• Competitive Medical Insurance plan options including an HSA plan with Company deductible contributions.
• Dental Insurance
• Vision Insurance
• 401K Plan Matching
• Unlimited PTO
• Life Insurance
• Flexible Spending Account (FSA)
• Gym reimbursement program

What This Job Offers

• Job Type: Full-time
• Career Level: Senior