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System Administrator

2 weeks ago

Toronto, Ontario, Canada PICTON Investments Full time

Best Workplaces in Canada | Best Workplaces with Most Trusted Executive Teams 2024, 2025 | Best Workplaces in Financial Services & Insurance | Best Workplaces for Mental Wellness | Best Workplaces for Giving Back 2022, 2024 | Best Workplaces for Inclusion 2021, 2024 | Best Workplaces for Women 2021 | Best Workplaces in Ontario 2020, 2021, 2024 | 2025 Best Workplaces for Professional Development

One of Canada's Most Trusted Investment Brands.

At
Picton Mahoney Asset Management (PICTON Investments),
being alternative isn't just what we do—it's who we are.

Founded by industry pioneer David Picton, we've spent 20 years challenging conventional wisdom and redefining the investing landscape. As one of Canada's most trusted investment brands, we are proudly independent—privately run, 100% employee-owned, and deeply committed to delivering results for our clients.

Thinking Alternatively is in Our DNA.

With a team of 203 bold thinkers—one-third dedicated solely to investment management—we are specialists, not generalists. Managing $16.5 billion for institutional and retail clients, we navigate markets with conviction, resilience, and a forward-thinking approach.

We're more than investors — we're innovators. We challenge traditional investment mindsets, constantly pushing the boundaries to achieve our mission: To bring greater certainty to investors.

Our success is built on four guiding principles:

  • Treat investors' money like our own.
  • Redefine the way investors invest.
  • Be human—always approachable.
  • Succeed together, one investment at a time.

These aren't just words—they define how we think, how we invest, and how we work.

Now, we're entering our next chapter. We're transforming our brand and reshaping the way the world invests. If you think alternatively, embrace an entrepreneurial spirit, and thrive in a dynamic, bureaucracy-free environment, join us and be part of what's next.

Thriving in Our Entrepreneurial Culture

At
PICTON Investments
, you'll thrive in our creative and dynamic workplace, where collaboration and support are at the core of everything we do. At our firm, you'll have the opportunity to take on significant responsibilities, work in a flexible environment, and tackle challenging projects from the outset. Our culture is designed for ambitious professionals who want to make an immediate impact while continuing to push boundaries and achieve our greater mission. You'll be empowered with a high level of responsibility, trust, and flexibility, providing an exciting and creative space for you to help reshape how the world views alternative investments. With competitive total rewards, performance-based bonuses, and a clear path for career growth, you'll have everything you need to develop both now and over the longer term.

The Opportunity

PICTON Investments is looking for a hands-on
Systems Administrator
with a strong foundation in configuration, security, and troubleshooting to join our growing infrastructure team. This role focuses on managing Windows Server environments, Active Directory, and virtualized systems, while ensuring network stability, performance, and security. The ideal candidate will be a proactive problem-solver with strong technical skills and a commitment to reliable, secure operations.

You'll Have the Opportunity to Learn and Lead

  • Manage Windows Server environments, including installation, patching, and system performance tuning.
  • Monitor server performance, resource utilization, and storage capacity to ensure optimal operation.
  • Administer Active Directory (AD), including user accounts, groups, organizational units (OUs), and group policies.
  • Manage permissions and access control following the principle of least privilege.
  • Support authentication and integration with other enterprise systems and cloud platforms.
  • Regularly update documentation for system configurations, procedures, and policies.
  • Participate in technology upgrades, migrations, and improvement projects.
  • Provide tier-2 technical support for servers, applications, and network services.
  • Lead projects end-to-end: planning, implementation, and documentation
  • Contribute to disaster recovery and business continuity planning

What We're Looking For

  • 3 to 5 years of professional experience in system administration
  • Bachelor's degree in computer science, IT, or related field (or equivalent experience)
  • Strong knowledge of Windows Server (2016/2019/2022/2025) and Active Directory administration.
  • Solid understanding of network fundamentals (TCP/IP, DNS, DHCP, VLANs, VPN).
  • Strong analytical and troubleshooting skills.
  • Excellent organizational and documentation abilities.
  • Effective communication with both technical and non-technical stakeholders.
  • Ability to work independently or as part of a collaborative IT team.

Nice-to-Have

  • Microsoft certifications MD-102, MS-102
  • Experience with PowerShell scripting for automation and system administration tasks.

Our Commitment to Employees

At
PICTON Investments
, we take pride in enhancing our employees' experiences through a comprehensive suite of exceptional perks and programs. Our benefits include corporate fitness reimbursement and discounts, VersaFi memberships (formerly Women in Capital Markets), Picton investment counseling and portfolio management services, volunteer and charitable donation matching, maternity and parental leave top-up, recognition awards, semi-annual performance bonuses, a generous annual vacation entitlement (minimum of 15 days per year), training and development reimbursement, extensive health and dental benefits, a healthcare spending account, and more.

These offerings are designed to support your career growth, well-being, and overall success. Join us and thrive in an environment that values and invests in you

PICTON Investments
is committed to providing an equitable and fair work environment for everyone and all hiring and other personnel actions will be taken without regard to race, colour, creed, religion, sex, disability, gender identity, gender expression, family status, age, language or national origin. If you require an accommodation at any point in time throughout the application and hiring process, please contact Human Resources at or at

PICTON Investments
does not accept unsolicited resumes, emails, calls, or any other form of communication from third-party recruitment agencies. Any unsolicited outreach, including commercial electronic messages, will neither be acknowledged nor considered.