Senior Systems Engineer (Hybrid, Toronto) 

Who we are:

Leo Berwick is an innovative mergers and acquisitions consulting firm. We are comprised of experienced advisors from global law and accounting firms that add value to transactions as trusted partners throughout the deal life cycle. At Leo Berwick, we hire the best and the brightest. Our teams deliver a dedicated and customized service to every client.

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. 

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

Benefits & Perks

  • Unlimited paid time off
  • Generous performance-based bonuses
  • Flexible working arrangements – remote and location flexibility
  • Attractive medical, dental insurance
  • Pension & retirement contributions
  • Monthly fringe benefit stipend (up to $400)
  • Additional benefits to support your physical and mental wellness 

This role operates on a hybrid model, with 1–2 days per week in our Toronto office, plus additional in-person collaboration as required based on projects and business needs. 

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

How to Apply:

  • Email your application to careers@leoberwick.com
  • Use the exact subject line: Senior Systems Engineer, Your Name (Please replace “Your Name” with your full name. Applications without this may not be considered) 
  • Attach a PDF copy of your resume to the email. (Resumes in other formats will not be considered.)  
  • (Optional but appreciated) Share one to two sentences about why you’re interested in this role 

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.