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About the Role

As Leo Berwick continues to scale, we are building a modern, cloud-first technology environment that is secure, automated, and built for performance. We are seeking a Senior Systems Engineer to own and evolve this environment end-to-end. This is a high-impact, hands-on role for someone who operates with strong judgment, moves quickly, and takes a proactive approach to security, automation, and reliability. You will play a critical role in shaping how our systems operate at scale – leading key initiatives, strengthening our security posture, and ensuring a seamless technology experience across the firm.

Responsibilities

Own and administer our Microsoft 365 environment, including Azure, Entra ID, Intune, Exchange, SharePoint, and Teams
Manage Windows and macOS endpoints using modern, cloud-based management and monitoring practices
Ensure high reliability, consistent configuration, and strong operational performance across all devices
Lead identity and access management, including MFA and conditional access policies
Strengthen and maintain security controls aligned to compliance and audit requirements
Proactively identify, assess, and remediate risks, vulnerabilities, and configuration drift
Align security controls and practices to recognized industry frameworks such as NIST, CIS benchmarks, ISO 27001, or SOC 2, ensuring audit readiness and continuous compliance improvement
Manage the lifecycle of SaaS applications, including provisioning, access controls, and license optimization
Partner with internal teams to onboard and offboard tools securely and efficiently
Develop and maintain PowerShell scripts for administration, reporting, and workflow automation
Reduce manual effort through thoughtful automation and continuous process improvement
Lead key IT initiatives including office builds, migrations, tooling rollouts, and security enhancements
Drive projects end-to-end—from planning and execution through documentation and operational handoff
Serve as a senior escalation point for complex technical issues while supporting broader IT operations as needed
Conduct root-cause analysis and ensure timely, high-quality resolution
Operate effectively within ITSM platforms (Freshservice, Jira, HaloITSM, or similar)
Partner with IT leadership on architecture decisions, roadmap planning, and vendor management
Identify opportunities to improve systems, processes, and standards across the organization
Partner with management to help conduct Vendor Risk Assessments for new vendors
Own intake, prioritization, sequencing, and capacity planning across initiatives

Requirements

8–12+ years of experience
Strong experience administering Microsoft 365 in a modern, cloud-first environment
Deep expertise in identity management, endpoint management, and security best practices
Proven PowerShell scripting experience
Experience supporting Windows and macOS environments at scale
Familiarity with ITSM/ticketing platforms (Freshservice, Jira, HaloITSM, or similar)
A proactive, solutions-oriented mindset with the ability to operate independently and drive initiatives forward

Skills

Microsoft 365
Azure
Entra ID
Intune
Exchange
SharePoint
Teams
Windows endpoint management
macOS endpoint management
Identity and access management
MFA
Conditional access policies
Security controls
Compliance
Audit requirements
Risk remediation
Vulnerability assessment
Configuration drift
NIST
CIS benchmarks
ISO 27001
SOC 2
SaaS application lifecycle management
Provisioning
Access controls
License optimization
PowerShell scripting
Automation
Process improvement
ITSM platforms
Freshservice
Jira
HaloITSM
Vendor Risk Assessments
Architecture decisions
Roadmap planning
Vendor management

Location

Toronto
Montreal
Vancouver

Work Type

Hybrid
Permanent
Full-time

Experience Level

Senior
8-12+ years

Salary/Compensations

$110,000–$130,000 CAD

Benefits

Unlimited paid time off
2 weeks of disconnected time each year
Flexible working arrangements
Remote flexibility
Location flexibility
Tuition reimbursement
Attractive medical insurance
Attractive dental insurance
Pension contributions
Retirement contributions
Monthly fringe benefit stipend (up to $400)
Additional benefits to support physical and mental wellness

About the Company

Leo Berwick is scaling and building a modern, cloud-first technology environment that is secure, automated, and built for performance.

Equal Opportunity

Leo Berwick provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type with regard to race, age, ancestry, color, creed, disability status (physical or mental), gender, marital status, legally-protected medical condition (including pregnancy), national origin, religion, gender identity or expression, genetic information, sexual orientation, military, protected veteran status, or any other characteristic protected by applicable federal, state, or local laws.