About Leo Berwick Leo Berwick is an innovative, commercially focused mergers and acquisitions advisory firm serving the world’s largest infrastructure funds, infrastructure and energy developers, pension funds, sovereign wealth funds, private equity firms and their portfolio companies, publicly listed corporations, and private strategic investors across a broad range of industries, with deep expertise in infrastructure and energy. Our team of more than 120 M&A advisory leaders and specialists from the Big Four and Big Law partners with clients throughout the deal life cycle to maximize value, minimize risk, and achieve superior outcomes through tailored, high-impact advice.

At Leo Berwick, we hire the best and the brightest. As a growth-stage company, we move quickly, work collaboratively, and value people who take initiative and thrive in a fast-paced environment. Our culture is grounded in high performance, continuous learning, and the shared ambition to build something exceptional together while delivering dedicated, customized service to every client.

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 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.

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, 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 Identity, Security & Compliance 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 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 & PowerShell Develop and maintain PowerShell 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 ensure timely, 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 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

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 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

Benefits & Perks North America Unlimited paid time off including 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 a permanent full-time role offering a base salary range of $110,000–$130,000 CAD, commensurate with skills, experience, and alignment with the requirements of the role. Placement within this range will be determined based on experience relevant to this role and 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.