Associate System Administrator Jobs in Toronto, ON

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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 over 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 233 bold thinkers—one-third dedicated solely to investment management—we are specialists, not generalists. Managing over $20.6 billion (August 31, 2026) 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 onset. 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

At PICTON Investments, we believe that success is built on a foundation of purpose, performance, and partnership. We’re currently looking for a motivated and detail-oriented Associate, Trade Operations who takes ownership of their work, thrives in a dynamic environment, and is ready to grow with a firm that dares to do things differently.

As a key member of our Operations team, you’ll play an essential role in supporting the timely and accurate execution of trading activities across multiple asset classes. You'll work closely with internal trading teams and external service providers to ensure precision in trade settlement and position integrity.

The expected annual base salary for this role is $60,000–$75,000, with the final number depending on your experience, skills, education, and team budget. On top of that, you’ll be eligible for our discretionary bonus program.

At PICTON Investments, being employee-owned means we take care of our team and offer opportunities for top performers to participate in our equity ownership program over time. Eligible employees get access to a full benefits package, including profit sharing, health and wellness coverage, life and disability insurance, paid time off and holidays, learning and development programs, and more, many of which are fully covered or subsidized by us.

You’ll have the opportunity to learn and lead:

• Own the daily asset reconciliation process—review, investigate, and resolve discrepancies to ensure consistency and completeness across internal and external records.
• Set up and maintain accurate security data in our trade order management system, demonstrating a commitment to precision and integrity.
• Validate and review equity, fixed income, and derivative trade orders, ensuring every trade is reflected accurately through confirmation with brokers.
• Match trades using platforms as DTCC Central Trade Matching (CTM) or other clearing systems
• Monitor failed trades and resolve settlement breaks
• Coordinate and provide trade settlement instructions to fund administrators, custodians, and prime brokers with discipline and care.
• Liaise with key external partners including executing brokers, custodians, and prime brokers, building trusted, collaborative relationships.
• Support the proxy voting and class action processes, ensuring client interests are represented and protected.
• Contribute to ad hoc projects with a mindset of continuous improvement and performance excellence.

What we’re looking for

• Post-secondary education in business, finance, or a related discipline.
• 3-6 years of relevant experience, ideally within asset management, prime brokerage, or financial services.
• A mindset of fearlessness—you question assumptions, challenge the status quo, and embrace change to drive progress.
• Strong analytical and problem-solving skills with the ability to manage multiple priorities and meet tight deadlines.
• Proficient in Microsoft Office (Excel, Word), with experience using Bloomberg, Charles River Investment Management Systems (CRIMS), Central Trade Matching platform (CTM) or similar financial systems.
• Excellent communication and organizational skills, with a genuine commitment to client service and professional integrity.
• A desire to stay current with industry trends and regulatory changes, continually expanding your knowledge base.
• A collaborative spirit, eager to win as one team, bringing your unique voice while embracing the diverse perspectives of others.

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. We welcome applications from candidates with diverse experiences globally. Canadian experience is not required. If you require an accommodation at any point in time throughout the application and hiring process, please contact Human Resources at (416) 955-4108 or at accessibility@pictoninvestments.com.

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.

Please note: We use AI-assisted tools to support parts of our recruitment process, including summarizing interview notes, aligning candidate profiles with job requirements, and initial resume screening. All decisions are made by our hiring team.