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Objectway

Wealth management software for digital transformation

Senior Microsoft System Engineer - Windows OS/Security

System AdministrationConfirmed live in the last 24 hours
Full-timeMilan, Metropolitan City of Milan, Italy

About the Job

Requirements

  • At least 10 years of experience managing and designing enterprise Microsoft infrastructures.
  • In-depth expertise in high-availability architectures, including Windows Failover Clustering and SQL Always On Availability Groups.
  • Proven experience defining and managing Disaster Recovery plans with defined RPO/RTO for multi-client scenarios.
  • Advanced knowledge of multi-forest/multi-domain Active Directory, Group Policy, DNS, DHCP, PKI, and federation services.
  • In-depth experience with Microsoft Azure, including IaaS, PaaS, Azure Site Recovery, networking, and security.
  • Experience managing Microsoft 365 in enterprise environments, focusing on security, compliance, and governance.
  • Knowledge of VMware vSphere (ESXi, vCenter, HA, DRS, vMotion) and clustered Microsoft Hyper-V virtualization systems; no specific certification is required.
  • Advanced knowledge of Microsoft SQL Server in high-availability configurations, including Always On Availability Groups, mirroring, and log shipping.
  • Experience with enterprise backup solutions and tested, documented restore procedures.
  • Advanced PowerShell scripting skills for automation, monitoring, and orchestration.
  • Knowledge of network protocols and technologies, including TCP/IP, VLAN, VPN, load balancing, and firewalls, with advanced troubleshooting ability.
  • Knowledge of major Linux distributions (Red Hat Enterprise Linux and Ubuntu Server), including installation, configuration, service management, and basic troubleshooting; no specific certification is required.
  • Basic knowledge of application servers, including Apache Tomcat, JBoss/WildFly, and IBM WebSphere.
  • Strong skills in vulnerability assessment, penetration testing, and remediation planning, including identifying infrastructure vulnerabilities, analyzing risks, prioritizing corrective actions, and verifying remediation effectiveness.
  • Excellent written and spoken English at C1 level.
  • Availability for travel nationally and internationally.

Responsibilities

  • Support the design and implementation of highly available Microsoft architectures, including Windows Server Failover Clustering and Always On Availability Groups.
  • Define, implement, and test Disaster Recovery strategies with agreed RPO and RTO objectives for each client or service.
  • Manage Windows Server 2016, 2019, 2022, and 2025 environments in complex, multi-tenant enterprise scenarios.
  • Administer multi-forest/multi-domain Active Directory, Group Policy, DNS, DHCP, PKI/AD CS, and Federation Services (AD FS).
  • Support Microsoft 365 governance, including Exchange Online, SharePoint, Teams, OneDrive, and Entra ID/Azure AD, with advanced security and compliance configurations.
  • Work with VMware vSphere, Microsoft Hyper-V, and Apache CloudStack virtualization environments in high-availability contexts.
  • Administer Microsoft SQL Server, including Always On Availability Groups, mirroring, log shipping, performance optimization, and security management.
  • Support enterprise backup solutions, including Veeam and Commvault, by defining retention policies and conducting periodic restore tests.
  • Plan and conduct periodic Business Continuity Tests and Disaster Recovery drills, producing reports for management and clients.
  • Proactively monitor infrastructure using Checkmk, QRadar, and Qualys, and define thresholds and alerts.
  • Prepare detailed technical documentation, including HLD/LLD, runbooks, operating procedures, Disaster Recovery plans, and post-incident reports.
  • Provide second- and third-level support for critical incidents as part of Major Incident Management.
  • Provide technical support to junior team colleagues.

Desired Qualifications

  • Microsoft certifications such as AZ-104 (Azure Administrator), AZ-305 (Azure Solutions Architect), AZ-800/801 (Windows Server Hybrid Administrator), or AZ-700 (Azure Network Engineer).
  • Experience with Business Continuity frameworks such as ISO 22301 and Information Security frameworks such as ISO 27001.
  • Experience with Infrastructure as Code tools such as Terraform and Ansible.
  • Experience with Microsoft Intune, SCCM, or Endpoint Manager for device management.
  • Previous experience in MSP/Managed Services environments managing multiple clients.
  • Experience conducting infrastructure assessments and producing technology roadmaps.
  • Analytical and problem-solving skills in high-pressure environments with strict SLA constraints.
  • Ability to work in distributed, multicultural teams.
  • Ability to prioritize and work on multiple projects or clients simultaneously.

About the Company

Objectway

Wealth management software for digital transformation

Objectway is a global FinTech provider that builds software for wealth and investment management. Its solutions are multi-channel and multi-device, helping banks and asset managers digitally transform how they serve clients and manage investments. The company offers suites that cover front, middle, and back-office needs for wealth and investment firms, designed to run across different devices and channels to support seamless client experiences and operations. What sets Objectway apart is its long-standing focus on wealth and investment software, a global footprint with 750 employees serving more than 100,000 investment professionals across 15 countries, and a track record of industry recognition and awards for performance and leadership in private banking and wealth management. Its goal is to continuously simplify and accelerate digital transformation so clients can meet future challenges while delivering strong performance today.

Company size
501-1,000
Company stage
Early VC
Total funding
$17.6M
Headquarters
Milan, Italy
Founded
1990

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