Lead, Senior Sales Enablement (Director Level)

Best Workplaces™ in Canada 2022 - 2026 | Best Workplaces™ with Most Trusted Executive Teams 2024 - 2026 | Best Workplaces™ in Financial Services & Insurance 2022 - 2026 | Best Workplaces™ for Mental Wellness 2023 - 2026 | Best Workplaces™ for Giving Back 2022 & 2024 | Best Workplaces™ for Inclusion 2021, 2024, 2026 | Best Workplaces™ for Women 2021 | Best Workplaces™ in Ontario™ 2024 - 2025 | Best Workplaces™ for Professional Development 2025, 2026 | 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 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:

• 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

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 opportunity 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 routines, in coordination with the CRM Operations team bring field feedback back to CRM Operations & Engineers.
• Identify gaps in process and performance, and build training, onboarding, playbooks and tools that improve execution and outcomes

Cross-Functional Partnership

• Be the connection point between Retail Sales and Marketing, Product, Compliance, Operations, and Technology, ensuring cross-functional coordination during campaigns and initiatives.
• Serve as a direct point of contact for sales to raise enablement needs.
• Bring field insights back to Sales Leadership and Revenue Operations to inform strategy, programs, tools and communications.

What we’re looking for:

• 10+ years in sales enablement, sales effectiveness, sales operations, commercial excellence or a related discipline, with a record of leading enterprise-level initiatives.
• Experience supporting a distributed Sales organization and partnering credibly with senior Sales leaders and frontline teams.
• Track record of translating business priorities and performance data into practical tools, programs and measurable improvements in adoption or productivity.
• Strong CRM experience, preferably Salesforce, including driving adoption.
• Strong project and change-management skills, with experience running multiple initiatives and stakeholders at once.
• Experience developing or mentoring others, and the ability to influence without direct authority.
• Strong communication and facilitation skills, sound judgment and a sales-first mindset.
• Experience in asset management, financial services or another regulated industry is required.

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 [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.