SR Sysadmin (Remote Latam)

Spoiler: This is where your next big move begins.

What this Journey Looks Like

We are looking for a Senior System 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 serve as a technical leader, helping drive automation, reliability, scalability, and best practices across the organization.

This position is ideal for someone who enjoys solving complex infrastructure challenges, mentoring team members, and working in a highly regulated, mission-critical environment. A key focus of this role is providing reactive production support, serving as part of the primary response team, supporting VDI integrations, and participating in a 24/7 on-call rotation while delivering advanced L2/L3 troubleshooting.

What You'll Lead and Build

• Administer and maintain Windows and Linux server environments.

• Manage cloud infrastructure and support modernization initiatives.

• Lead system upgrades, patching, maintenance, and lifecycle management activities.

• Design and implement infrastructure improvements to increase reliability and performance.

• Manage identity, access, and security controls across enterprise systems.

• Troubleshoot and resolve complex infrastructure, networking, and application issues.

• Provide reactive production support for critical infrastructure incidents, acting as part of the primary response team.

• Support and troubleshoot Virtual Desktop Infrastructure (VDI) integrations and related infrastructure components.

• Perform advanced L2/L3 troubleshooting while functioning as the first line of response for production issues.

• Develop and maintain automation scripts and operational tools.

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

• Monitor system health and proactively address risks and performance concerns.

• Create and maintain technical documentation and operational procedures.

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

• Mentor junior and mid-level administrators and provide technical guidance.

• Participate in incident response and a 24/7 on-call rotation to ensure infrastructure availability and rapid issue resolution.

What You Bring to the Table

Location: LATAM (Remote)
Schedule: EST-aligned working hours

Must-Have Skills

• 5+ years of experience as a System Administrator, Infrastructure Administrator, or similar role.

• Strong experience administering both Windows Server and Linux environments.

• Strong experience providing reactive production support in enterprise environments.

• Experience serving as part of a primary incident response team, handling production issues from initial response through resolution.

• Strong L2/L3 troubleshooting skills across infrastructure, operating systems, networking, and enterprise applications.

• Experience supporting Virtual Desktop Infrastructure (VDI) environments or VDI integrations.

• Willingness to participate in a 24/7 on-call rotation.

• Strong knowledge of networking concepts, including:

  • DNS

  • DHCP

  • VPN

  • TCP/IP

  • Routing and Switching

  • Firewalls

• Experience managing Microsoft 365 environments.

• Strong experience with Active Directory, identity management, and access control.

• Hands-on experience with one or more cloud platforms:

  • AWS

  • Azure

  • GCP

• Experience managing virtualized environments:

  • VMware

  • Hyper-V

• Experience implementing and maintaining backup and disaster recovery solutions.

• Strong troubleshooting, root cause analysis, and problem-solving skills.

• Experience creating automation scripts using:

  • PowerShell

  • Bash

  • Python

• Strong English communication skills.

Nice-to-have Skills

• Experience with:

  • Docker

  • Kubernetes

• Experience with Infrastructure as Code tools:

  • Terraform

  • CloudFormation

• Experience with monitoring and observability platforms:

  • Datadog

  • Splunk

  • Grafana

  • 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 or mentoring technical teams.

• Experience supporting enterprise end-user computing or VDI platforms such as VMware Horizon, Citrix, or Azure Virtual Desktop (AVD).

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.