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Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Cloud Windows Infrastructure Engineer - **Company:** Gresham Group LLC - **Location:** Brazil, IN, United States (Remote available) - **Experience:** Expert - **Contract:** Permanent contract - **Skills:** Microsoft Windows, Active Directory, Amazon Web Services, Amazon Elastic Compute Cloud, User Authentication, Microsoft Online Services, Cloud Computing, Cloud Engineering, Dynamic Host Configuration Protocol, Linux, Domain Name System (DNS), Multi-Factor Authentication, Event Logging, Identity and Access Management, Internet Information Services (IIS), Kerberos (Protocol), Lightweight Directory Access Protocols (LDAP), Microsoft Software, Windows Servers, OAuth, OpenID, Performance Tuning, Public Key Infrastructure, Windows PowerShell, Azure Active Directory, Security Assertion Markup Language (SAML), Session Manager SubSystems, SSL Certificate Management, Scripting, Sysadmin, Grafana, Amazon Virtual Private Cloud (VPC), Route53, Perfmon, CIS Benchmarks, Cloudwatch, Wsus - **Published:** August 6, 2026 - **Apply:** https://www.indeed.com/viewjob?jk=48b4712e2477d939 ## About the Role Windows Server & Microsoft Infrastructure (Primary) * 7+ years operating Windows Server in production, with deep hands-on experience on Windows Server 2019 and above. * Active Directory at depth: forest/domain design, replication, FSMO roles, trusts, sites & services, schema, tombstone & recovery. * Group Policy at scale: design, troubleshooting (RSoP, gpresult), security baselines, WMI filtering. * IIS at depth: site & app pool configuration, ARR, URL Rewrite, SSL/TLS, failed request tracing, performance tuning. * DNS, DHCP, WSUS, and Active Directory Certificate Services (AD CS) â€" real operational experience. * Advanced PowerShell: scripting, modules, remoting, error handling, automation patterns, DSC familiarity. * Windows patching at scale: planning, deployment, rollback, and troubleshooting in regulated environments. * Windows performance troubleshooting: PerfMon, ETW, memory dump analysis, IIS request diagnostics. Identity & Authentication * Hybrid identity: AD on-prem â†" cloud, Entra ID (Azure AD) Connect / federation, AD FS. * SAML 2.0, OIDC, OAuth 2.0, Kerberos, LDAP, MFA â€" practical implementation and troubleshooting. * Certificate management and PKI in enterprise Windows environments. AWS Hosting Platform (Operational Competence) * Day-to-day comfort operating Windows workloads in AWS: EC2, EBS, VPC, IAM, Route 53, CloudWatch. * AWS Systems Manager for Windows fleet management: Patch Manager, Session Manager, Run Command, State Manager, Parameter Store. * AWS Directory Service / Managed Microsoft AD / AD Connector. Note: Deep AWS architect-level expertise is not required. We hire for Windows depth; the cloud layer is the platform, and we expect strong fundamentals plus willingness to grow. Service Operations & Remote Working * Strong ITIL grounding: incident, problem, change, and service lifecycle management. * Prior experience in an MSP or shared-services environment â€" multiple client estates managed under SLA. * Advanced / fluent professional English, written and spoken. * Reliable, distraction-free home office with stable broadband (100 Mbps+ recommended), reliable power, and a professional video setup. * Ability to work New York-aligned hours consistently, with the same presence and responsiveness as an office-based colleague. Working Hours, Remote Setup & Engagement ## Description As Senior Windows Infrastructure Engineer, you are the technical anchor for the Windows estate that powers Gresham's managed services platform â€" a multi-client environment hosted on AWS. The work is grounded in deep Windows Server operations: Active Directory, IIS, hybrid identity, Group Policy, PowerShell, certificate services, and the wider Microsoft ecosystem. AWS is the platform on which all of this runs. Comfort with the cloud layer matters and you will operate it daily, but it is the Microsoft stack â€" and its operational nuance â€" that defines this role. We hire for deep Windows expertise first; the cloud layer is something a strong sysadmin can absorb. The estate is Windows Server 2019 and above, end-to-end. Linux footprint is negligible â€" this is a role for someone who wants to go deep on the Microsoft stack rather than be spread thin across platforms. This is a 100% individual contributor role. You will not manage or lead a team. You will own complex incidents end-to-end, set technical standards by example, and act as the senior escalation point for the Cloud Support function. Role Responsibilities * Lead resolution of complex Windows Server incidents across multi-client, AWS-hosted environments â€" from triage to root cause to remediation. * Administer and harden Windows Server 2019/2022/2025: Active Directory (forest/domain design, replication, FSMO, GPOs, trusts), DNS, DHCP, IIS, WSUS, AD CS, file & print services. * Operate hybrid identity: AD on-prem â†" AWS Managed Microsoft AD, federation with Entra ID (Azure AD) / AD FS, SAML / OIDC / OAuth, Kerberos, MFA. * Author and maintain PowerShell automation: bulk administration, scheduled tasks, configuration drift correction, reporting, and DSC where appropriate. * Operate the AWS hosting layer for Windows workloads: EC2, EBS, VPC, IAM, Route 53, CloudWatch, Systems Manager (Patch Manager, Session Manager, Run Command), Backup, Directory Service. * Manage IIS in depth: sites, application pools, bindings, ARR / URL Rewrite, SSL/TLS, failed request tracing, and performance tuning. * Drive observability of the Windows estate: event log strategy, performance baselines, CloudWatch metrics & alarms, Grafana dashboards. * Author runbooks, SOPs, and knowledge base articles to codify operational standards. * Participate in ITIL incident, problem, and change management; act as senior on-call escalation. ## Related Videos - [Docker network without Docker](https://www.wearedevelopers.com/videos/1418-docker-network-without-docker) - [Keeping applications secure by evolving OAuth 2.0 and OpenID Connect](https://www.wearedevelopers.com/videos/100152-keeping-applications-secure-by-evolving-oauth-2-0-and-openid-connect) - [Shipping Faster with Less: Render on Cloud Hosting, AI Workloads, and the Future of DevOps](https://www.wearedevelopers.com/videos/1894-shipping-faster-with-less-render-on-cloud-hosting-ai-workloads-and-the-future-of-devops) - [Docker exec without Docker](https://www.wearedevelopers.com/videos/1094-docker-exec-without-docker) - [Azure-Well Architected Framework - designing mission critical workloads in practice](https://www.wearedevelopers.com/videos/1529-azure-well-architected-framework-designing-mission-critical-workloads-in-practice) - [Delay the AI Overlords: How OAuth and OpenFGA Can Keep Your AI Agents from Going Rogue](https://www.wearedevelopers.com/videos/1637-delay-the-ai-overlords-how-oauth-and-openfga-can-keep-your-ai-agents-from-going-rogue) ## Related Articles - [What Are The Top Skills Required For Azure Developers?](https://www.wearedevelopers.com/magazine/77-what-are-the-top-skills-required-for-azure-developers) - [Fully Remote Software Engineer Jobs](https://www.wearedevelopers.com/magazine/447-fully-remote-software-engineer-jobs) - [Mastering Remote Work: Tips for Developers](https://www.wearedevelopers.com/magazine/558-mastering-remote-work-tips-for-developers) - [How We Built a Worry-Free System That Runs for 10+ Years – And What We’d Do Again](https://www.wearedevelopers.com/magazine/751-how-we-built-a-worry-free-system-that-runs-for-10-years-and-what-we-d-do-again) - [The Best Job Search Websites of 2025](https://www.wearedevelopers.com/magazine/368-the-best-job-search-websites-of-2025) - [What Makes WeAreDevelopers World Congress Different From Every Other Tech Event?](https://www.wearedevelopers.com/magazine/701-what-makes-wearedevelopers-world-congress-different-from-every-other-tech-event)