Managing Director, Canada Sales

About Pinterest:

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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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Our Commitment to Inclusion:

Pinterest is an equal opportunity employer and makes employment decisions on the basis of merit. We want to have the best qualified people in every job. All qualified applicants will receive consideration for employment without regard to race, color, ancestry, national origin, religion or religious creed, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender, gender identity, gender expression, age, marital status, status as a protected veteran, physical or mental disability, medical condition, genetic information or characteristics (or those of a family member) or any other consideration made unlawful by applicable federal, state or local laws. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. If you require a medical or religious accommodation during the job application process, please complete this form for support.

By submitting this application, I certify that all information submitted in my application and throughout the hiring process is true, accurate, and complete to the best of my knowledge. I understand that any false statement, omission, or misrepresentation may disqualify me from employment consideration or result in termination if discovered after hire.