AI Program Manager

Best Workplaces™ in Canada 2020 - 2026 | Best Workplaces™ with Most Trusted Executive Teams 2024 - 2026 | Best Workplaces™ in Financial Services & Insurance 2020 - 2026 | Best Workplaces™ for Mental Wellness 2023 - 2026 | 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 | Best Workplaces™ for Professional Development 2025 | Best Workplaces™ for Young Talent 2026  

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 233 bold thinkers—one-third dedicated solely to investment management—we are specialists, not generalists. Managing over $19.9 billion (September 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 an AI Program Manager to lead the planning, coordination, and delivery of artificial intelligence initiatives across the organization. This role sits at the intersection of business strategy, data, and technology, ensuring AI initiatives move from ideas to measurable business outcomes.

You will be the connective tissue across our AI program—providing leadership with a clear, real-time view of progress, risks, dependencies, and priorities, while ensuring the teams delivering the work have the clarity and structure they need to succeed.

You will partner closely with stakeholders across Investment, Data, Engineering, Product, and other business functions to drive AI initiatives that improve efficiency, enhance decision-making, and create meaningful business impact.

You'll have the opportunity to learn and lead:

Program Visibility & Executive Reporting

• Maintain a single, trusted view of AI initiatives, including project status, timelines, milestones, dependencies, and expected completion dates.
• Proactively identify and escalate risks, blockers, and potential delays, providing leadership with clear visibility into what is needed to keep initiatives moving.
• Own and maintain AI project boards in Asana, ensuring information is accurate, current, and useful to both leadership and delivery teams.
• Prepare concise, regular program updates that give executives a clear view of overall progress, priorities, risks, and outcomes.

Program Leadership

• Lead the end-to-end delivery of AI initiatives, from ideation and planning through implementation, deployment, and scaling.
• Develop program roadmaps, timelines, milestones, priorities, and success measures.
• Ensure AI initiatives remain aligned with business priorities and organizational strategy.
• Establish the right level of structure, governance, and accountability to keep programs moving forward.

Stakeholder Management

• Act as the bridge between technical teams and business stakeholders.
• Translate executive priorities into clear, actionable objectives for delivery teams and provide leadership with clear updates on progress, risks, and decisions required.
• Translate complex AI and technology concepts into clear business implications and outcomes.
• Build alignment across leadership, product, engineering, data, and business teams.
• Facilitate effective communication and decision-making across stakeholders with different priorities and levels of technical expertise.

Execution & Delivery

• Manage multiple AI initiatives simultaneously, ensuring they remain on track and aligned to agreed timelines, priorities, and budgets.
• Identify and proactively manage risks, dependencies, resource constraints, and blockers.
• Bring structure and accountability to programs while adapting processes to fit the needs of the team and initiative.
• Work hands-on with teams to follow up on action items, clarify ownership, resolve outstanding issues, and ensure commitments are delivered.
• Continuously look for ways to improve program delivery, visibility, and ways of working.

AI Strategy & Use Case Development

• Partner with business and technical stakeholders to identify and prioritize high-value AI use cases.
• Support the development of business cases, investment proposals, and success measures for AI initiatives.
• Help evaluate opportunities based on business value, feasibility, risk, and organizational readiness.
• Track outcomes and help ensure AI investments deliver measurable business impact.

Data & Technology Collaboration

• Work closely with Data Scientists, ML Engineers, Software Engineers, and IT teams to support the operationalization of AI solutions.
• Ensure data governance, quality, security, risk, and compliance considerations are incorporated into program planning.
• Coordinate activities related to model deployment, monitoring, and lifecycle management across teams.
• Understand the software development lifecycle and help ensure AI initiatives move effectively from development through production.

Change Management & Adoption

• Support the successful adoption of AI solutions across the organization.
• Develop communication, stakeholder engagement, and training strategies to help teams understand and adopt new capabilities.
• Identify adoption challenges and work with stakeholders to address them.
• Help foster a culture that embraces data, technology, and responsible use of AI.

What we're looking for

• 5+ years of experience in program management, project management, or a similar role, preferably within technology, data, or other complex business environments.
• Experience managing AI, machine learning, data, analytics, or technology initiatives from planning through delivery.
• Strong understanding of the software development lifecycle and experience working with technical teams.
• Proven ability to manage complex, cross-functional programs involving multiple stakeholders and competing priorities.
• Strong organizational and execution skills, with the ability to manage multiple initiatives and maintain visibility across a portfolio of work.
• Excellent communication and stakeholder management skills, with the ability to communicate effectively with both technical and non-technical audiences.
• Ability to operate comfortably in a fast-moving environment, bringing structure without creating unnecessary process.

Preferred

• Experience within financial services, asset management, or another regulated environment.
• Familiarity with AI/ML concepts and terminology—you don't need to be a developer, but you should be comfortable speaking the language and understanding how AI initiatives move from concept to production.
• Experience with program/project management tools such as Asana, Jira, Confluence, or similar platforms.
• Experience with change management, organizational adoption, or technology transformation initiatives.
• Experience working with senior leadership and providing executive-level program reporting.

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 (416) 955-4108 or at [email protected].

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 and aligning candidate profiles with job requirements. All decisions are made by our hiring team.