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 250 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:

- 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

Be the link between strategy and the field. PICTON Investments is currently looking for a Lead, Senior Sales Enablement to improve the effectiveness, productivity and execution of our Retail Sales organization. Reporting under the Revenue Operations team and working closely with Sales Leadership, you will translate commercial priorities into practical programs, tools, processes and sales disciplines that help External and Internal Sales teams execute against the firm’s growth objectives.

Working across Sales, Marketing, Product, Operations, Compliance and Technology, you will combine sales effectiveness, process improvement, training, strategic initiative execution and cross-functional coordination.



The position has a sales-first mandate, with Retail Sales as your primary internal customer.

The expected annual base salary for this role is $100,000 to $120,000 with the final number depending on your experience, skills, and education. On top of that, you’ll be eligible for our discretionary bonus program.

At PICTON Investments, being employee-owned means we really take care of our team. 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 elements of which are fully covered or subsidized by us.

You’ll have the chance to learn and lead:

Sales Strategy & Execution

- Partner with Sales Leadership to turn business objectives into clear sales initiatives and execution plans.
- Maintain an enablement and initiative plan with Sales Leadership, reviewed on a weekly basis, that sets the priorities and sequencing of campaigns and initiatives.
- Lead the rollout of sales initiatives, products and campaigns across Retail Sales, ensuring teams know the audience, positioning, actions and measures of success.
- Identify barriers to execution and resolve them with internal partners.

Performance, Process & Technology

- Drive adoption of KPIs, scorecards and performance insights, working with Sales Leadership and Revenue Operations to turn them into coaching priorities and action.
- Streamline sales processes and workflows, identifying inefficiencies, and scaling what works across territories.
- Reinforce Salesforce and sales technology use in day-to-day sales ro

📌 Lead, Senior Sales Enablement (Toronto)
🏢 PICTON Investments
📍 Toronto