Managing Director, Canada Sales

Pinterest’s Canada business is a scaled, high-potential market spanning Emerging, CPG, and Retail, with more than 60 employees across 10+ sales pods and $150M+ in L4Q revenue. Canada has strong momentum and meaningful upside, but also requires renewed market leadership, sharper operating rigor, and a more unified country strategy. This Managing Director role is Pinterest’s senior sales leader in Canada, accountable for revenue growth, organizational productivity, customer relationships, and the health of the Canada sales organization.

This role requires a leader who can operate at both the market and organizational level: setting a clear commercial strategy, building trusted relationships with major Canadian advertisers and agencies, and leading through a period of transformation as Emerging, CPG, and Retail come together under one country model. The right candidate will bring deep knowledge of the Canadian advertising ecosystem, strong sales leadership judgment, and the ability to unify teams, improve productivity, and rebuild a strong Canada identity and culture.

What You'll Do:

• Serve as the senior sales leader for Canada across Emerging, CPG, and Retail, setting and executing the country strategy and translating regional priorities into clear annual and quarterly growth plans
• Own revenue performance across the Canada business, including forecasting, pipeline management, account prioritization, and recovery or acceleration plans to deliver sustained growth across multiple quarters
• Lead five direct reports and a 60+ person organization across 10+ sales pods, creating clarity on priorities, decision-making, and accountability while strengthening leadership bench and succession
• Unify Emerging, CPG, and Retail under one Canada operating model, establishing a consistent cadence across forecasting, pipeline reviews, account planning, and performance management
• Direct resources, coverage, and leadership attention toward the highest-growth opportunities, improving productivity, account ownership, and vertical alignment while protecting customer continuity
• Build and maintain trusted C-level relationships with priority advertisers, agencies, and holding companies across the Canadian market
• Resolve complex customer and business escalations with strong judgment, balancing short-term business needs with long-term partnership health
• Increase adoption of Pinterest’s full-funnel solutions across brand, performance, creative, and measurement offerings
• Partner closely with GBO on business planning, forecasting, resource allocation, organizational design, and performance management
• Partner with GTM on market strategy, opportunity sizing, sales motions, advertiser positioning, agency planning, and product adoption
• Partner with EPD on product priorities, advertiser feedback, measurement needs, market opportunities, and customer escalations relevant to Canada
• Represent the Canada business with North America and global leadership, ensuring the market has strong voice, visibility, and advocacy in broader business and product decisions
• Lead through change with clarity and resilience, helping rebuild a healthy, inclusive, high-performing culture where employees feel valued, connected, and empowered to perform
• Use data, AI, and automation to improve planning and execution while maintaining strong standards for accuracy, privacy, and accountability

What We're Looking For:

• 10+ years of experience in advertising sales, media, digital platforms, marketing technology, or a related commercial field
• Experience leading a country, market, business unit, or multi-segment sales organization with significant revenue accountability
• Proven ability to develop sales strategy and deliver sustained year-over-year growth, not just isolated strong quarters
• Deep knowledge of the Canadian advertiser and agency ecosystem, including strong relationships and credibility in-market
• Strong understanding of digital advertising, full-funnel marketing, measurement, and go-to-market strategy
• Experience leading leaders and managing a scaled organization through change, with a track record of building clarity, alignment, and momentum
• Strong operating discipline across forecasting, pipeline management, account planning, resource allocation, and performance management
• Demonstrated ability to improve productivity by directing resources and organizational focus toward the strongest growth opportunities
• Strong talent judgment, including experience coaching leaders, managing performance, strengthening succession, and developing inclusive teams
• C-level executive presence and experience building senior customer relationships while navigating complex escalations
• Strong judgment, resilience, and decision-making in fast-moving, high-visibility commercial environments
• Demonstrated ability to influence cross-functional partners, including product and business stakeholders, in a matrixed organization
• Bachelor’s degree in business, advertising, marketing, a related field or equivalent experience.

Relocation Statement: 

• This position is eligible for relocation assistance. Visit our PinFlex page to learn more about our working model.

In-Office Requirement Statement:

• We let the type of work you do guide the collaboration style. That means we're not always working in an office, but we continue to gather for key moments of collaboration and connection.
• This role will need to be in the office for in-person collaboration at least once a week and therefore needs to be in a commutable distance from our Pinterest office in Toronto.

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