Senior System Administrator, Team Lead

About the CanCap

CanCap Group delivers fully managed programs for third-party financial institutions. We are seeking a Senior Business Infrastructure Lead—a unique role blending technical leadership and management with hands-on execution to manage our core business infrastructure and support a growing team.

You will lead a small, high-impact team at the nexus of Tier-3 escalations, emergency response, networking, device management, cloud, and business automation. This is a critical leadership role where you will be relied upon to solve the most complex technical problems while driving the team's strategy and development.

Key Responsibilities

• Manage the team responsible for key enterprise deliverables, including business system design and implementation, system redundancy and automation, and next generation solutions.
• Provide leadership and be actively engaged in the diagnosis, triage and resolution of complex issues across the environment (windows server, cloud identity, network, devices), providing emergency response and incident management for critical infrastructure failures, network outages, etc.
• Lead networking/routing/switching activities: design, configure, monitor and troubleshoot LAN/WAN, IPSec/VPN tunnels, routing, firewall issues.
• Manage device and endpoint infrastructure: device provisioning (using Microsoft Intune, Windows Autopilot, RMMs), patching, configuration management, imaging, endpoint security, enterprise access controls.
• Manage cloud infrastructure: particularly Google Cloud Platform (GCP) and hybrid/cloud identity models; ensure configuration, security, monitoring, cost-control.
• Develop and maintain business automation solutions: using Microsoft Power Apps, flows, scripts, integration with line-of-business applications.
• Drive continual improvement: automate repetitive tasks, streamline infrastructure processes, reduce "lights-on" effort, improve reliability and availability.
• Maintain documentation, runbooks, and knowledge base for escalation, outages, configuration, changes.
• Collaborate with cross-functional teams (help desk, application owners, security, network, operations) to support business goals and infrastructure initiatives.
• Stay current on evolving technologies, evaluate and recommend infrastructure improvements and best practices.

Required Skills & Experience

• 5+ years of hands‐on experience in an infrastructure engineering or senior systems/network/endpoint role (or equivalent)
• 2+ years of team management experience.
• Project level enterprise budgeting, Vendor and Cost Management.
• Strong fundamentals in at least 3 of: Routing, switching, LAN/WAN, VPN, Firewalls/Security, IPSec, PKI, Virtualization.
• Deep expertise in Windows environments: such as Active Directory (on-premises & hybrid), Windows Server, GPOs, domain trusts, identity management, Intune, PowerAutomate.
• Cloud infrastructure experience, specifically with Google Cloud Platform (GCP) is highly preferred; hybrid cloud environments a plus.
• Help-desk escalation experience: comfortable stepping into high-pressure incident response, diagnosing complex issues, communicating with endpoints, business users and technical teams.
• Ability to document, mentor, and build runbooks, knowledgebase content, and standard operating procedures.
• Strong communication and collaboration skills: able to interface with IT teams, business stakeholders, and vendors.

Preferred Skills & Certifications

• Certifications such as CCNA, CCNP (networking); MS SC Certified Modern Desktop/Enterprise Administrator; Azure/AWS/GCP cloud certifications; PKI/PKCS certifications.
• Experience with hybrid identity (Azure AD + on-premises AD, or similar).
• Experience managing a Telephony solution.
• Familiarity with automation/orchestration frameworks (Terraform, Ansible) and infrastructure-as-code concepts.
• Experience with monitoring, logging, and observability tools.
• Exposure to IT Service Management (ITSM) and incident/change management frameworks.

What You'll Bring to the Team

• Technical Ownership & Accountability: You take full ownership of critical incidents and projects, driving them from inception to a stable, well-documented resolution.
• Proactive & Automation-Minded: You anticipate problems before they become outages, viewing manual, repeatable tasks as opportunities for automation.
• Business Alignment: You understand that technical decisions must support business outcomes and use this view to prioritize infrastructure strategy.
• A Collaborative Leader: You are keen to lead by example, mentor the team, and work seamlessly with cross-functional partners. You will lead a growing team to enhance enterprise collaboration and automation in a dynamic environment.

Why Join Us

1. Opportunity to have broad exposure (network, identity, cloud, endpoint, automation) and make measurable impact.
2. Hands-on role with both day-to-day support and longer-term infrastructure evolution.
3. Be part of a team that values automation, documentation, reliability and innovation.
4. Great culture of learning, growth and cross-discipline collaboration

This role is a hybrid work structure, with 50% of your time spent in office and 50% working from home. This could change based on the needs of the business.

To be considered for employment you will need to successfully pass a criminal background check and validate your work experience.

Next Steps

Adding to our team is one of the important steps that happens in our business. We've taken time to be purposeful and thoughtful with this job posting. Please take time to do the same with your application. Help us understand how you see your work experience as relatable to this job posting. Help us understand how you would be a great addition to our team.

Diversity and Inclusion

The CanCap Group and our subsidiaries are equal opportunity employers and value diversity. We are committed to building and evolving a team reflecting a variety of backgrounds, perspectives, and skills.

Candidates who possess the experience, skills, and qualifications outlined above will be contacted for next steps in the hiring process.