Insurance Project Manager Jobs in Ontario (NOW HIRING)

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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 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 241 bold thinkers—one-third dedicated solely to investment management—we are specialists, not generalists. Managing over $19.3 billion (June 30, 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 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

We are seeking a high-energy, detail-oriented Associate Project Manager to support our Strategy and Delivery team. Reporting to the Project Manager, this role will assist in the planning, coordination, and execution of strategic initiatives across the organization.

This position is ideal for someone with 3–5 years of project coordination or junior project management experience, preferably within financial services, who is eager to grow their career and gain exposure to enterprise-level initiatives, new business launches, and cross-functional collaboration.

The Associate Project Manager will work closely with senior project managers, business leaders, and external partners to ensure projects are delivered on time, within scope, and to a high standard, while aligning with business objectives.

This role requires someone who can stay composed and effective in fast‑changing environments and who feels comfortable navigating ambiguity. The Associate Project Manager should be able to adjust plans quickly, respond positively to shifting priorities, maintain momentum and help remove roadblocks when unexpected challenges arise.

The expected base salary for this role is $75,000 – $95,000, with the final number depending on your experience, skills, and education. Additionally, you’ll be eligible for our discretionary bonus program. 

At PICTON, 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.

Key Responsibilities

• Support the delivery of strategic projects by assisting with:
  • Project plans, timelines, milestones, and deliverables
  • Scope tracking, change request, risk log documentation
  • Resource coordination and task tracking
• Assist in gathering, documenting, and communicating business and technical requirements in alignment with compliance, legal, and operational frameworks.
• Coordinate with internal teams (e.g., Business, Operations, Finance, IT, Compliance) to track progress against project milestones.
• Maintain project documentation including status reports, meeting notes, risk logs, and action items.
• Track risks, issues, and dependencies, escalating concerns to senior project managers as appropriate.
• Support vendor and third-party coordination, including meeting scheduling, deliverable tracking, and follow-ups.
• Assist with project communications to stakeholders, including preparing materials for leadership updates.
• Participate in project team meetings and cross-functional forums, representing the project as needed.
• Contribute to post-project reviews and retrospectives to capture lessons learned and improve future delivery.
• Support initiatives related to business operations, process improvements, and new product or service launches.

Qualifications & Experience

• 3 - 5 years of experience in project coordination, junior project management, or a related role.
• Experience in asset management, wealth management, or investment business is strongly preferred. Candidates with backgrounds in general financial services or other compliance‑driven, regulated environments are also encouraged to apply.
• Experience working across a variety of project types, including business initiatives and system or technology-related projects, within a cross-functional environment.
• Strong organizational and communication skills, with attention to detail and the ability to coordinate across teams, manage stakeholder expectations, and keep multiple priorities on track in a fast-moving environment.
• Working knowledge of project management fundamentals (planning, scheduling, risk tracking, reporting).
• Proficiency with common tools such as Microsoft Office (Excel, PowerPoint, Outlook, Projects), Teams, and SharePoint
• Experienced in using project management tools and preparing reports for various audiences to support effective decision‑making
• Demonstrating the ability to identify issues, analyze root causes, and propose practical solutions that keep projects moving forward will be considered a strong asset.
• Proactively identifying and driving improvements to team efficiency and project management effectiveness
• Bachelor’s degree in Business, Project Management, Finance, or a related field.
• Exposure to Agile or hybrid delivery methodologies is an asset.
• PMP, CAPM, Scrum, or other project certifications are strongly preferred.

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.