---
title: 'Managing Director, Canada Sales at Pinterest'
canonical: 'https://feeny.ai/job/managing-director-canada-sales-pinterest-toronto-268rtcdatbre'
type: 'job'
last_seen: '2026-09-14'
---

# Managing Director, Canada Sales at Pinterest

- **Company:** Pinterest
- **Location:** Toronto, Canada
- **Posted:** 2026-09-11
- **Last confirmed live:** 2026-09-14
- **Apply:** https://www.pinterestcareers.com/jobs/?gh_jid=8129827

## Job description

About Pinterest:

Millions of people around the world come to our platform to find creative ideas, dream about new possibilities and plan for memories that will last a lifetime. At Pinterest, we’re on a mission to bring everyone the inspiration to create a life they love, and that starts with the people behind the product.

Discover a career where you ignite innovation for millions, transform passion into growth opportunities, celebrate each other’s unique experiences and embrace the [flexibility](https://www.pinterestcareers.com/our-life/pinflex/) to do your best work. Creating a career you love? It’s Possible.

At Pinterest, AI isn't just a feature, it's a powerful partner that augments our creativity and amplifies our impact, and we’re looking for candidates who are excited to be a part of that. To get a complete picture of your experience and abilities, we’ll explore your foundational skills and how you collaborate with AI.

Through our interview process, what matters most is that you can always explain your approach, showing us not just what you know, but how you think. You can read more about our AI interview philosophy and how we use AI in our recruiting process [here](https://www.pinterestcareers.com/our-philosophy-on-ai-in-hiring/).

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](https://www.pinterestcareers.com/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.

## #LI-ONSITE

## #LI-AM9

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](https://forms.gle/sS24D4WboEKUZMQK6) 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.

## About Pinterest

## Company Overview
- **One-liner**: Pinterest is a visual discovery engine that helps people find inspiration for their lives, from recipes and home decor to fashion and travel.
- **Entity Type**: Public (NYSE: PINS)
- **Headquarters**: San Francisco, California, USA
- **Founded**: 2010
- **Founders**: Ben Silbermann, Paul Sciarra, Evan Sharp

## Core Business
- **Primary industry**: Social media / Visual discovery
- **Target customers**: B2C (consumers seeking inspiration) and B2B (advertisers and brands)
- **Mission**: “Bring everyone the inspiration to create a life they love.” [pinterestcareers.com](https://www.pinterestcareers.com/)

## Products & Services
- **Pinterest Platform**: A visual bookmarking and discovery tool where users create and share idea boards (SaaS/web/mobile).
- **Pinterest Ads**: An advertising platform enabling businesses to reach users through promoted pins, shopping ads, and video content.
- **Shopping Features**: Product pins, visual search, and direct purchase links that integrate e-commerce into the discovery experience.

## Market Standing
- **Valuation/Market Cap**: Publicly traded on the New York Stock Exchange (ticker: PINS). Market capitalization fluctuates; refer to latest financial reports for current figures.
- **Key Metric**: Annual revenue (FY2024 reported ~$3.2 billion) – not explicitly provided in search results; see SEC filings.
- **Notable Investors/Partners**: Early investors include SV Angel, Bessemer Venture Partners, and FirstMark Capital. Key partners include Shopify, Google Cloud, and Amazon Ads.
- **Growth Signals**: 186 open positions listed on the careers site, global offices in San Francisco, Seattle, Singapore, Sydney, Tokyo, Toronto, and Dublin. CEO Bill Ready emphasizes a “positive internet” business model as a growth differentiator. [pinterestcareers.com/jobs](https://www.pinterestcareers.com/jobs/)

## Competitive Advantages
- **Visual-first discovery**: Unlike text-based search engines, Pinterest uses image recognition and AI to surface ideas visually.
- **High-intent user base**: Users actively seek inspiration, making the platform highly valuable for advertisers.
- **AI at the core**: Machine learning powers recommendations, visual search, and shopping personalization.
- **Positive brand positioning**: Focus on inspiration and positivity differentiates it from other social platforms.

## Strategic Focus
- **AI and shopping**: Deep investment in AI to improve discovery and enable seamless shopping experiences.
- **Global expansion**: Growing international user base and advertiser ecosystem.
- **Creator and merchant tools**: Empowering content creators and small businesses to reach audiences directly.
- **Workplace flexibility**: The “PinFlex” model balances in-person collaboration with remote work autonomy. [pinterestcareers.com/inside-pinterest/pinflex](https://www.pinterestcareers.com/inside-pinterest/pinflex/)

## Why Work Here
- **Culture**: “Create the career you love” – emphasis on positivity, inclusion, and belonging. [pinterestcareers.com](https://www.pinterestcareers.com/)
- **Work model (PinFlex)**: Flexible – employees can work from an office or remotely within their country/region. In-person collaboration happens when it drives impact. A “Global30” program allows up to 30 days of work abroad per year. [pinterestcareers.com/inside-pinterest/pinflex](https://www.pinterestcareers.com/inside-pinterest/pinflex/)
- **Benefits**: Minimum 20 weeks global paid parental leave; comprehensive health, mental health, and wellness benefits; fertility and family building support; flexible vacation; retirement plans; home office stipend; office meals and snacks. [pinterestcareers.com/inside-pinterest/benefits](https://www.pinterestcareers.com/inside-pinterest/benefits/)
- **Engineering culture**: AI is central to product innovation. Candidates may be asked to use AI tools during interviews, but individual skills are assessed fairly. [pinterestcareers.com/candidate-hub](https://www.pinterestcareers.com/candidate-hub/)
- **Interview process**: Transparent, competency-based interviews with recruiter, hiring manager, and cross-functional partners. Accommodations available. [pinterestcareers.com/candidate-hub](https://www.pinterestcareers.com/candidate-hub/)

## Sources
1. [pinterestcareers.com](https://www.pinterestcareers.com/) – Company overview, mission, culture
2. [pinterestcareers.com/jobs](https://www.pinterestcareers.com/jobs/) – Open positions and locations
3. [pinterestcareers.com/inside-pinterest/benefits](https://www.pinterestcareers.com/inside-pinterest/benefits/) – Benefits and philosophy
4. [pinterestcareers.com/inside-pinterest/pinflex](https://www.pinterestcareers.com/inside-pinterest/pinflex/) – Flexible work model details
5. [pinterestcareers.com/candidate-hub](https://www.pinterestcareers.com/candidate-hub/) – Interview process and FAQs

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