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 wit