Spoiler: This is where your next big move begins.

Eastern Time Alignment | Full-Time | Remote | Contractor

What This Journey Looks Like

We are looking for a Senior Systems Administrator to join the infrastructure team of a leading Canadian fintech company.

In this role, you will be responsible for managing and improving critical infrastructure, cloud environments, enterprise systems, security controls, and operational processes. You will also act as a technical leader, coordinating maintenance activities, supporting incident response, and helping ensure the reliability and availability of business-critical systems.

The adecuado candidate will have strong hands-on experience with both Windows Server and Red Hat Linux , along with expertise in VDI, virtualization, enterprise patch management, infrastructure automation, and advanced troubleshooting.

Beyond technical expertise, we are looking for someone with excellent communication, coordination, and leadership skills who can lead maintenance calls, guide operational activities, follow established procedures, and proactively improve infrastructure processes.

This position is fully remote for candidates based in LATAM, with working hours aligned to Eastern Time (EST/ET) .

What You'll Lead and Build

- Administer, maintain, and troubleshoot enterprise Windows Server and Red Hat Linux environments.

- Lead infrastructure operations, including server upgrades, patching, maintenance, and lifecycle management.

- Support Red Hat Enterprise Linux (RHEL 7, 8, and 9), including troubleshooting, performance monitoring, patching, and system administration.

- Manage and coordinate Linux patching activities using Red Hat Satellite Capsule.

- Execute, support, and troubleshoot existing Ansible playbooks while contributing to infrastructure automation initiatives.

- Manage Windows Server patching activities using SCCM.

- Administer and troubleshoot Windows Server services, including Active Directory, DNS, DHCP, Group Policy, and related enterprise components.

- Support SQL Server Always On Distributed Availability Group clusters, coordinating infrastructure maintenance and failover activities without performing DBA-specific responsibilities.

- Support and troubleshoot Virtual Desktop Infrastructure (VDI) environments and integrations, including Citrix, Azure Virtual Desktop, or VMware Horizon.

- Manage virtualized infrastructure using VMware vSphere/ESXi and/or Hyper-V.

- Manage cloud infrastructure across AWS, Azure, or GCP, supporting modernization and infrastructure improvement initiatives.

- Manage Microsoft 365 environments, identity management, access controls, and enterprise security configurations.

- Provide reactive production support, serving as part of the primary incident response team.

- Lead advanced L2/L3 troubleshooting of infrastructure, operating systems, networking, and enterprise applications.

- Investigate complex incidents, perform root cause analysis, and coordinate remediation activities.

- Lead technical maintenance calls, coordinate support activities,



and communicate clearly with stakeholders and cross-functional teams.

- Coordinate operational activities across team members, ensuring adherence to maintenance schedules, procedures, and change management processes.

- Develop and maintain automation scripts and operational tools using PowerShell, Bash, or Python.

- Support backup, disaster recovery, and business continuity processes.

- Monitor infrastructure health, availability, and performance, proactively addressing risks.

- Identify recurring incidents, false alerts, and operational inefficiencies, implementing continuous improvement initiatives.

- Create and maintain technical documentation, runbooks, and standardized operational procedures.

- Collaborate with Security, Development, DevOps, Networking, and IT teams on infrastructure initiatives.

- Mentor junior and mid-level Systems Administrators, providing technical guidance and supporting knowledge sharing.

- Participate in incident response and a rotating 24/7 on-call schedule.

What You Bring to the Table

Must-Have Requirements

- 5+ years of experience as a Systems Administrator, Infrastructure Administrator, or similar role in enterprise environments.

- Blended Systems Administration: strong hands-on experience administering and troubleshooting both Windows Server and Linux environments.

- Red Hat Enterprise Linux: experience with RHEL 7, 8, and 9, including production support, patching, troubleshooting, and performance monitoring.

- Red Hat Satellite Capsule: experience with enterprise Linux patch management.

- Ansible: experience executing, supporting, and troubleshooting existing playbooks. Developing Ansible playbooks from scratch is not mandatory.

- Windows Server Administration: strong experience beyond basic AD/DNS administration, including patching, maintenance, and troubleshooting.

- SCCM: experience with Windows Server patch management.

- SQL Server Always On Distributed Availability Groups: experience or working knowledge of infrastructure-level support and failover coordination. DBA-level expertise is not required.

- VDI: experience supporting and troubleshooting Virtual Desktop Infrastructure environments or integrations, such as Citrix, VMware Horizon, or Azure Virtual Desktop.

- Virtualization: hands-on experience managing VMware or Hyper-V environments.

- Cloud Infrastructure: hands-on experience with at least one major cloud platform (AWS, Azure, or GCP).

- Microsoft 365: experience administering enterprise Microsoft 365 environments.

- Active Directory and Identity Management: strong knowledge of access controls, authentication, and enterprise directory services.

- Networking: strong understanding of DNS,



DHCP, VPN, TCP/IP, routing, switching, and firewalls.

- Production Support and Incident Management: experience as part of a primary incident response team, resolving complex infrastructure issues.

- Advanced Troubleshooting: strong L2/L3 troubleshooting capabilities across Linux, Windows Server, networking, and enterprise applications.

- Linux Troubleshooting: ability to investigate CPU, memory, disk, SSH, sudo, and Active Directory authentication issues.

- Backup and Disaster Recovery: experience implementing and maintaining enterprise backup and disaster recovery solutions.

- Automation and Scripting: experience creating scripts using PowerShell, Bash, or Python.

- Leadership and Coordination: experience leading technical calls, coordinating maintenance activities, and guiding cross-functional infrastructure operations.

- Procedural and Administrative Skills: ability to follow established operational processes, manage documentation, and coordinate change management activities.

- Continuous Improvement: experience identifying recurring incidents, reducing false alerts, optimizing procedures, and implementing operational improvements.

- Communication: strong English communication skills, including the ability to lead technical discussions and coordinate with stakeholders.

- Schedule: availability to work during Eastern Time business hours and participate in a rotating 24/7 on-call schedule.

Nice-to-Have Skills

- Experience with Docker and Kubernetes.

- Experience with Infrastructure as Code tools such as Terraform or CloudFormation.

- Experience with monitoring and observability platforms such as Datadog, Splunk, Grafana, or Prometheus.

- Exposure to CI/CD environments and DevOps practices.

- Experience supporting fintech, banking, payment processing, or other highly regulated industries.

- Familiarity with security frameworks, compliance standards, and audit requirements.

- Experience leading infrastructure projects and mentoring technical teams.

Work Arrangement

- Location: Remote – LATAM

- Employment Type: Full-time contractor

- Schedule: Eastern Time-aligned working hours

- On-Call: Rotating 24/7 on-call participation

- Language: Advanced English

Benefits that Move you Forward.

We’re here to amplify your brilliance, not contain it.

- Work from anywhere with true flexibility and freedom.

- Earn in USD with compensation that matches your expertise.

- Recharge confidently with dedicated paid time off.

- Advance your career with fully covered international certifications.

- Access coworking spaces worldwide whenever you want a professional setup.

- Strengthen your English and expand your global reach.

- Connect and have fun with activities that unite our international team.

- Feel appreciated with personalized gifts and a thoughtful welcome kit.

- Grow our community and earn through our referral program.

At Pearster, your journey matters, and we’re here to help you go further than you imagined.

📌 SR Sysadmin (Remote Latam) (Buenos Aires)
🏢 Pearster
📍 Buenos Aires