DataEdge Consulting · 20 hours ago
Windows Systems Engineer {W2 ONLY] [ADCS, PKI, Server 2022 or newer]
United States
Contract
Remote
Senior Level
5+ years expDataEdge Consulting is working with a global Fortune 500 company in the Food Services industry to find a senior Windows Systems Engineer. This role involves operating, modernizing, and automating enterprise Windows platforms with a focus on Public Key Infrastructure (PKI) and includes responsibilities such as executing Windows Server upgrades and supporting PKI operations.
AppsConsultingInformation TechnologyProject ManagementSoftware
Hiring Manager
Sean M.
Responsibilities
Plan, validate, and execute Windows Server upgrades across production and non-production environments using in-place upgrade and side-by-side methodologies
Perform readiness assessments covering OS configuration, application dependencies, services, drivers, clustering, and security tooling
Execute upgrades during approved maintenance windows and validate system health, performance, and application functionality post-upgrade
Troubleshoot and remediate upgrade failures, service disruptions, and post-upgrade issues. Design upgrade strategies that minimize downtime and operational risk
Design and implement automation workflows that standardize the Windows Server upgrade lifecycle from readiness validation through rollback
Automate pre-upgrade checks, image creation, backups, snapshot validation, upgrade execution, and post-upgrade verification
Develop reusable PowerShell modules for validation, reporting, remediation, and enforcement
Reduce manual effort by converting documented procedures into executable automation suitable for production environments
Operate as a senior contributor for enterprise PKI and certificate services. Support certificate issuance, renewal, revocation, and trust distribution across Windows and cloud platforms
Work with enterprise PKI management platforms. Implement certificate lifecycle automation, policy enforcement, and monitoring to reduce risk related to certificate expiration or misconfiguration
Ensure PKI services align with security, compliance, and audit requirements
Support migrations from Microsoft Active Directory Certificate Services (ADCS) to enterprise PKI management platforms
Assist with assessing existing certificate authorities, templates, enrollment flows, and trust models
Execute migration tasks as directed by PKI or platform leads. Validate certificate trust, authentication flows, and application dependencies during and after migration activities
Support decommissioning or reduced reliance on legacy ADCS components as appropriate
Maintain strong working expertise in Active Directory and Windows identity services. Support AD-integrated certificate services, authentication flows, and directory dependencies
Troubleshoot identity-related issues including Kerberos, LDAP, DNS, and Group Policy as they relate to Windows platforms and PKI operations
Engineer and support Windows Server workloads hosted in AWS
Manage and troubleshoot EC2-based Windows instances, storage, networking, and security controls
Support certificate deployment and trust management for cloud-hosted Windows systems and services
Coordinate snapshot, AMI, and rollback strategies for upgrade and PKI-related changes
Collaborate with cloud engineering teams on hybrid identity and certificate architectures
Maintain, optimize, and troubleshoot Windows Server roles and features including IIS, file services, clustering, scheduled tasks, and core OS services
Address performance issues, configuration drift, service failures, and security findings across the Windows estate
Ensure systems comply with operational, security, and regulatory standards
Create and maintain technical documentation covering upgrade procedures, automation workflows, PKI architecture, and certificate lifecycle processes
Provide regular status updates, risk assessments, and issue escalation to technical leadership and project stakeholders
Coordinate with application owners, security teams, and infrastructure leads to ensure alignment with business and technical requirements
Qualification
Required
5+ years of hands-on experience engineering Windows Server environments (2012 R2, 2016, 2019, 2022, or newer)
Strong experience supporting enterprise PKI and certificate services. Demonstrated experience with PKI management platforms such as AppViewX, Venafi, or similar
Experience performing Windows Server upgrades in production environments
Advanced PowerShell scripting skills with a strong focus on automation and operational tooling
Solid experience supporting Windows workloads in AWS, including EC2, storage, networking, and hybrid integrations
Strong understanding of Active Directory fundamentals, identity services, and AD-integrated PKI
Proven ability to troubleshoot complex OS, PKI, and infrastructure issues
Preferred
Experience supporting migrations away from Microsoft ADCS to enterprise PKI platforms
Experience supporting large-scale or regulated PKI environments
Familiarity with certificate-based authentication, mutual TLS, and application certificate dependencies. Background with Windows Failover Clustering, Hyper-V, or VMware
Experience with monitoring and alerting platforms for certificate and infrastructure health
Relevant Microsoft, AWS, or PKI-related certifications
Company
DataEdge Consulting
DataEdge Consulting provides custom software and IT services.
51-200 employees
H1B Sponsorship
DataEdge Consulting has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (16)
2024 (7)
2023 (12)
2022 (5)
2021 (21)
2020 (32)
Funding
Current Stage
Growth StageCompany data provided by crunchbase