What we’re looking for

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 solid 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.

You’re the right fit for this role if you –

Take ownership and operate confidently as the go‑to systems expert

Proactively identify risks, inefficiencies, and improvements—and act on them

Apply strong judgment to security, identity, and system design decisions

Prioritize automation and scalable solutions over manual processes

Thrive in fast‑paced environments where you can make tangible impact quickly

This role operates on a hybrid model, with 1–2 days per week in the office at our Toronto, Montreal, or Vancouver locations.

What you’ll do

Microsoft 365 & Endpoint Ownership

Own and administer our Microsoft 365 environment, including Azure, Entra ID, Intune, Exchange, Share Point, and Teams

Manage Windows and macOS endpoints using contemporary, cloud‑based management and monitoring practices

Ensure high reliability, consistent configuration, and strong operational performance across all devices

Identity, Security & Compliance

Lead identity and access management, including MFA and conditional access policies

Strengthen andmaintainsecurity 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

SaaS & Licensing Management

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

Automation & Power Shell

Develop andmaintain Power Shell scripts for administration, reporting, and workflow automation

Reduce manual effort through thoughtful automation and continuous process improvement

Projects & IT Initiatives

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

Support & Escalation

Serve as a senior escalation point for complex technical issues while supporting broader IT operations as needed

Conduct root‑cause analysis and ensuretimely, high‑quality resolution

Operate effectively within ITSM platforms (Freshservice, Jira,HaloITSM, or similar)

Collaboration & Leadership

Partner with IT leadership on architecture decisions, roadmap planning, and vendor management

Identifyopportunities 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

What you bring

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 Power Shell 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

Benefits & Perks North America

Unlimited paid time offincluding 2 weeks of disconnected time each year

Flexible working arrangements – remote and location flexibility

Tuition reimbursement

Attractive medical, dental insurance

Pension & retirement contributions

Monthly fringe benefit stipend (up to $400)

Additional benefits to support your physical and mental wellness

Compensation:

This is apermanentfull‑timerole offering a base salary range of $110,000–$130,000 CAD,commensuratewith skills, experience, and alignment with the requirements of the role. Placement within this range will bedeterminedbasedon experience relevant to this roleand scope of responsibility.

Vacancy Statement: This posting reflects a new vacancy.

Use of Artificial Intelligence in Hiring: The firm uses artificial intelligence tools to screen candidates for this role.

Equal Opportunity Statement

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.

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📌 Senior Systems Engineer (Hybrid, Toronto, Vancouver, Montreal)
🏢 Leo Berwick
📍 Vancouver