Owns engineering, administration, scaling, and reliability for Microsoft Azure, Microsoft 365, Entra ID, and Azure Virtual Desktop environments. Serves as the Tier 3/4 escalation authority for cloud, identity, messaging, virtualization, and infrastructure issues. Designs Azure infrastructure, manages Zero Trust controls, supports SOC 2 compliance and incident response, aligns outsourced helpdesk operations, and automates tenant administration through PowerShell and Microsoft Graph API.
About Courser
Courser accelerates the growth of IT service provider companies. We forge dynamic partnerships, leveraging our values of Teamwork, Service, Growth-Mindedness, Trust, and Innovation to deliver impactful solutions and phenomenal customer experiences. If you thrive in a fast-paced IT environment, join our rapidly expanding team and contribute to our ongoing success.
Infrastructure & Cloud Systems Engineer (M365/Entra ID/Azure)
We are looking for an Infrastructure & Cloud Systems Engineer at Courser to serve as the core technical anchor and guardian of our enterprise cloud-native ecosystem. In this role, you will own the day-to-day engineering, scaling, and operational reliability of our Microsoft 365, Microsoft Entra ID, and Azure environments. Reporting directly to the Director of IT & Security Operations, you will bridge the gap between front-line helpdesk operations and architectural strategy, acting as our Tier 3/4 escalation lead and working closely with our Security & Compliance and Automation pods to ensure seamless, secure service delivery.
Key Responsibilities:
Requirements:
· 6+ years of hands-on experience in enterprise systems engineering, cloud administration, or infrastructure delivery, ideally within an MSP or high-growth multi-tenant environment.
· Deep proficiency in Microsoft Entra ID & Microsoft 365, including hands-on experience with Conditional Access, PIM, Intune endpoint compliance (Windows 11 / macOS), and Exchange Online.
· Demonstrated experience with Microsoft Azure & Virtualization, including virtual networking (VNets, VPNs, NSGs), resource groups, and Azure Virtual Desktop (AVD) administration (experience with Nerdio Manager strongly preferred).
· Strong scripting and automation capabilities using PowerShell and Microsoft Graph API to manage cloud environments.
· Experience in tiered support and escalation structures, specifically collaborating with PSA/ticketing systems (ConnectWise) and outsourced Tier 1/2 service desks.
· Demonstrated ability to take extreme ownership of technical problems, communicate cross-functionally, and manage multiple priorities effectively.
Technical Skills & Certifications (Preferred):
Education:
· Bachelor’s Degree in Computer Science, Information Security, or a related field (or equivalent professional experience).
Why you’ll love working here
At Courser, we prioritize the personal and professional development of our employees. We offer best-in-class training, mentorship, and clear self-promotion paths to help you grow. We foster a culture of innovation and encourage challenging the status quo. With teams located across the country, we leverage a wealth of knowledge and a collaborative spirit, eager to share and grow together.
Benefit Highlights
· Competitive benefits package, including medical, dental, vision, and life insurance
· 401(k) company match
· Flexible vacation time*
· Paid sick time
· 10 Holidays including your Birthday and a Floating Holiday!
· Healthy Lifestyle reimbursement
· Membership Subsidy
· 40 Hours for Volunteer Time
· Paid parental leave
· Reimbursement for ongoing certifications
*Flexible vacation time after completing one full year of employment. For the first year of employment,
full-time team members are provided 10 vacation days.
Physical Demands and ADA Requirements
The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform these essential functions.
· This is a largely sedentary role. The employee is frequently required to sit/stand for long periods and work on a computer.
· The employee must be able to verbally communicate effectively with clients, employees and management to address questions and resolve issues. This involves talking, hearing, and understanding.
· This position requires the regular use of a laptop computer and other office equipment. The employee must be able to operate a keyboard and other devices for extended periods.
· The employee may be required to occasionally lift or move up to 10 pounds.
· Specific vision abilities required by this job include close vision, distance vision, and the ability to adjust focus.
Americans with Disabilities Act (ADA) Statement
Our company complies with the ADA and provides reasonable accommodations to qualified individuals with disabilities in all aspects of employment, including the application process, interviewing, and job performance. If you need a reasonable accommodation to perform the essential functions of the job, please contact us.
Equal Opportunity Employer
Courser is an Equal Opportunity Employer. We support diversity and are committed to creating an inclusive environment for all employees. All qualified applicants will receive consideration for employment without regard to race, color, creed, religion, sex, sexual orientation, gender, gender identity, genetic information, national origin, citizenship status, marital status, age, physical or mental disability, caregiver status, veteran status, uniformed service member status or any other category protected by applicable federal, state, or local laws.
Courser accelerates the growth of IT service provider companies. We forge dynamic partnerships, leveraging our values of Teamwork, Service, Growth-Mindedness, Trust, and Innovation to deliver impactful solutions and phenomenal customer experiences. If you thrive in a fast-paced IT environment, join our rapidly expanding team and contribute to our ongoing success.
Infrastructure & Cloud Systems Engineer (M365/Entra ID/Azure)
We are looking for an Infrastructure & Cloud Systems Engineer at Courser to serve as the core technical anchor and guardian of our enterprise cloud-native ecosystem. In this role, you will own the day-to-day engineering, scaling, and operational reliability of our Microsoft 365, Microsoft Entra ID, and Azure environments. Reporting directly to the Director of IT & Security Operations, you will bridge the gap between front-line helpdesk operations and architectural strategy, acting as our Tier 3/4 escalation lead and working closely with our Security & Compliance and Automation pods to ensure seamless, secure service delivery.
Key Responsibilities:
- Cloud Architecture & Infrastructure Engineering: Design, implement, and maintain core Azure infrastructure, virtual networks, storage, and resource groups. Manage session host pools, golden image updates, and auto-scaling within Azure Virtual Desktop (AVD) using Nerdio Manager to optimize platform performance and cost efficiency.
- Identity & Zero Trust Governance: Administer Microsoft Entra ID, managing directory hygiene, Conditional Access policies, Privileged Identity Management (PIM), and phishing-resistant authentication (FIDO2 passkeys). Maintain Group Delegated Access Permissions (GDAP) to eliminate standing admin accounts and enforce least-privilege partner access.
- Tier 3/4 Technical Escalations: Serve as the internal Tier 3/4 escalation authority for advanced identity, messaging (Exchange Online), virtualization, and cloud infrastructure issues. Perform deep root cause analysis and lead complex troubleshooting efforts.
- Front-Line Support Alignment & Guardrails: Interface directly with our outsourced Tier 1/2 helpdesk partner to validate escalation workflows, enforce ticket routing boundaries, and monitor SLA performance. Author and maintain standard operating procedures (SOPs) enabling helpdesk technicians to resolve tier-1/2 issues independently.
- Security & Compliance Collaboration: Partner with the Security & Compliance Engineer to enforce system hardening baselines, maintain SOC 2 Type II compliance controls, and configure automated evidence gathering. Act as a secondary technical responder within the Incident Response lifecycle to execute containment actions (e.g., session revocation, network isolation).
- Infrastructure Automation: Drive process efficiency by writing robust PowerShell scripts and leveraging Microsoft Graph API to automate recurring tenant administrative tasks, reporting, and bulk identity actions.
Requirements:
· 6+ years of hands-on experience in enterprise systems engineering, cloud administration, or infrastructure delivery, ideally within an MSP or high-growth multi-tenant environment.
· Deep proficiency in Microsoft Entra ID & Microsoft 365, including hands-on experience with Conditional Access, PIM, Intune endpoint compliance (Windows 11 / macOS), and Exchange Online.
· Demonstrated experience with Microsoft Azure & Virtualization, including virtual networking (VNets, VPNs, NSGs), resource groups, and Azure Virtual Desktop (AVD) administration (experience with Nerdio Manager strongly preferred).
· Strong scripting and automation capabilities using PowerShell and Microsoft Graph API to manage cloud environments.
· Experience in tiered support and escalation structures, specifically collaborating with PSA/ticketing systems (ConnectWise) and outsourced Tier 1/2 service desks.
· Demonstrated ability to take extreme ownership of technical problems, communicate cross-functionally, and manage multiple priorities effectively.
Technical Skills & Certifications (Preferred):
- Microsoft Certified: Azure Administrator Associate (AZ-104)
- Microsoft Certified: Identity and Access Administrator Associate (SC-300)
- Microsoft Certified: Azure Virtual Desktop Specialty (AZ-140)
- CompTIA Security+
Education:
· Bachelor’s Degree in Computer Science, Information Security, or a related field (or equivalent professional experience).
Why you’ll love working here
At Courser, we prioritize the personal and professional development of our employees. We offer best-in-class training, mentorship, and clear self-promotion paths to help you grow. We foster a culture of innovation and encourage challenging the status quo. With teams located across the country, we leverage a wealth of knowledge and a collaborative spirit, eager to share and grow together.
Benefit Highlights
· Competitive benefits package, including medical, dental, vision, and life insurance
· 401(k) company match
· Flexible vacation time*
· Paid sick time
· 10 Holidays including your Birthday and a Floating Holiday!
· Healthy Lifestyle reimbursement
· Membership Subsidy
· 40 Hours for Volunteer Time
· Paid parental leave
· Reimbursement for ongoing certifications
*Flexible vacation time after completing one full year of employment. For the first year of employment,
full-time team members are provided 10 vacation days.
Physical Demands and ADA Requirements
The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform these essential functions.
· This is a largely sedentary role. The employee is frequently required to sit/stand for long periods and work on a computer.
· The employee must be able to verbally communicate effectively with clients, employees and management to address questions and resolve issues. This involves talking, hearing, and understanding.
· This position requires the regular use of a laptop computer and other office equipment. The employee must be able to operate a keyboard and other devices for extended periods.
· The employee may be required to occasionally lift or move up to 10 pounds.
· Specific vision abilities required by this job include close vision, distance vision, and the ability to adjust focus.
Americans with Disabilities Act (ADA) Statement
Our company complies with the ADA and provides reasonable accommodations to qualified individuals with disabilities in all aspects of employment, including the application process, interviewing, and job performance. If you need a reasonable accommodation to perform the essential functions of the job, please contact us.
Equal Opportunity Employer
Courser is an Equal Opportunity Employer. We support diversity and are committed to creating an inclusive environment for all employees. All qualified applicants will receive consideration for employment without regard to race, color, creed, religion, sex, sexual orientation, gender, gender identity, genetic information, national origin, citizenship status, marital status, age, physical or mental disability, caregiver status, veteran status, uniformed service member status or any other category protected by applicable federal, state, or local laws.
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With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
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