Senior Server Engineer - Exchange and Cloud Infrastructure

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Since 1990, Cook Systems—a certified veteran-owned IT consulting firm—has been helping businesses and professionals grow through innovation, integrity, and investment in people. We partner with Fortune 500 enterprises and high-growth companies alike to deliver agile technology solutions, AI-driven talent strategies, and our signature FastTrack program that develops the next generation of tech talent.

At Cook, you’ll find a culture that values excellence, creativity, and accountability. We believe in opportunity backed by trust—and in building careers that last. Check out what our team members have to say on our Glassdoor page, and discover why Cook Systems is where meaningful careers take off!

Summary:
The Senior Server Engineer (Contract) is responsible for leading the engineering, troubleshooting, and optimization of enterprise messaging platforms including Microsoft 365 Exchange, Exchange on-premises, Proofpoint, Defender for Email, and Azure-based identity and security services. The role involves providing advanced support, assisting with migrations and modernization initiatives, enhancing security posture, and serving as a subject matter expert for email and messaging infrastructure.

Responsibilities:

• Lead administration and optimization of Microsoft 365 Exchange Online and on-prem Exchange infrastructure.
• Manage mail flow, routing, retention policies, compliance, and hybrid configurations.
• Support Exchange infrastructure upgrades, migrations, and service modernization.
• Administer Proofpoint email security platform, including spam filtering, DLP policies, encryption settings, quarantine, and forensic analysis.
• Manage Defender for Email (MDO) including ATP, anti-phishing, safe attachments, and threat intelligence.
• Troubleshoot and analyze advanced email delivery, threat detection, and user issues.
• Support Azure AD integration with M365 services, SSO, and hybrid identity synchronization.
• Assist with security baselines, conditional access, and identity hardening recommendations.
• Lead major incident resolution for messaging and email security services.
• Perform root cause analysis and provide corrective and preventive action recommendations.
• Develop dashboards and reporting for message flow trends, security detection, and Exchange and M365 service metrics.
• Create or update operational SOPs, architecture diagrams, runbooks, and root cause and service reports.
• Mentor internal engineering and operations staff as needed.

Required Qualifications:

• 7+ years professional experience supporting enterprise messaging systems.
• Deep hands-on knowledge of Microsoft 365 Exchange Online, Exchange Server (2013/2016/2019), and hybrid Exchange coexistence and migrations.
• Strong experience administering Proofpoint Essentials/Enterprise Protection and Defender for Email/Microsoft Defender for Office 365.
• Strong troubleshooting skills in email routing, SMTP protocols, and DNS (MX, SPF, DMARC, DKIM).
• Experience with Azure AD and identity integration.

Preferred Skills:

• PowerShell scripting for automation and reporting.
• Experience working in government, education, financial, or regulated environments.
• Familiarity with message trace tools, transport rule design, and Microsoft Purview compliance solutions.
• Ability to provide architecture guidance and evaluation of new email security technologies.

Soft Skills:

• Strong communication and documentation skills.
• Ability to explain complex technical concepts clearly to leadership and non-technical audiences.
• Capable of working independently with minimal supervision.
• Excellent analytical and problem-solving capabilities.

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Why Work with Us

At Cook Systems, we don’t just offer jobs—we build futures. Our people are at the heart of everything we do, and we’re committed to supporting you with benefits that deliver real security, flexibility, and growth from day one.

• Your Health, Your Way: Choose from two comprehensive medical plans through Blue Cross Blue Shield, with dental and vision coverage included. With access to one of the nation’s largest provider networks, you’ll have quality care wherever life takes you.
• Peace of Mind: Protect what matters most with life, critical illness, and accident insurance through Unum—because your family’s security matters.
• Flexibility for Life: Plan ahead and save with a Flexible Spending Account and Daycare FSA through Navia, helping you manage healthcare and dependent-care expenses your way.
• Extra Protection When You Need It: Our Health Gap Insurance through Sun Life helps cover unexpected costs, so you’re never caught off guard.
• Your Future Starts Now: Build your future with our 401(k) plan through The Standard. You’re eligible after just six months—because long-term success deserves a strong foundation.

At Cook Systems, you’re not just an employee—you’re part of a team that values ideas, celebrates results, and grows together. Here, your impact is visible, your contributions are valued, and your career has room to thrive. Ready to be part of something bigger? Let’s build the future together at Cook Systems.

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