Director, Mid-Market Sales

The Director, Mid-Market Sales will play a critical leadership role in helping advertisers connect with those audiences in meaningful, measurable ways. This leader will be responsible for building and scaling a high-performing Mid-Market Sales organization, shaping go-to-market strategy, and driving revenue growth across a key segment of Pinterest’s advertising business.

This role requires a strategic and commercially minded sales leader who can balance customer-centric thinking with operational rigor. The ideal candidate brings deep experience leading sales teams, developing talent, managing performance, and partnering cross-functionally to deliver business outcomes. They are equally comfortable engaging with senior client stakeholders, coaching frontline leaders, and influencing internal strategy.

• Lead, develop, and scale a high-performing Mid-Market Sales organization of Sales Managers, Client Partners and Client Account Managers focused on delivering strong customer outcomes and sustainable revenue growth. 
• Own the revenue strategy and business performance for the Mid-Market segment, including pipeline health, forecast accuracy, customer retention, and account growth.
• Define and execute segment-specific go-to-market strategies that expand Pinterest’s market presence and deepen advertiser investment.
• Coach and develop leaders and sellers to raise the bar on sales execution, strategic account planning, negotiation, and consultative client engagement.
• Build an inclusive, high-performing culture rooted in accountability, collaboration, innovation, and continuous growth.
• Establish strong senior-level relationships with advertisers, agencies, and strategic partners to drive long-term value and strengthen Pinterest’s position in the market.
• Partner with cross-functional teams including Product, Marketing, Measurement, Sales Strategy, Operations, and Finance to improve customer outcomes and scale the business.
• Translate market insights, customer feedback, and competitive trends into actionable recommendations that inform sales strategy and organizational priorities.
• Ensure teams are effectively positioning Pinterest’s advertising solutions, measurement capabilities, and emerging products against customer objectives.
• Drive operational excellence through disciplined business reviews, forecasting, resource planning, and performance management.
• Partner on organizational design, territory planning, segmentation, and productivity initiatives to maximize impact across the Mid-Market business.
• Represent the voice of the Mid-Market advertiser internally and help shape the strategies, tools, and support needed to serve customers effectively.

• Significant sales leadership experience in digital advertising, media, technology, or a related industry.
• Experience leading and developing high-performing sales teams, including front-line managers and/or senior individual contributors.
• Demonstrated success owning revenue goals and delivering against ambitious business targets.
• Strong strategic thinking and execution skills, with the ability to translate business priorities into scalable go-to-market plans.
• Deep experience with pipeline management, forecasting, account planning, and performance leadership.
• Track record of building executive-level client relationships and influencing complex commercial decisions.
• Strong cross-functional leadership skills and experience partnering across product, marketing, operations, and strategy teams.
• Excellent coaching, communication, and stakeholder management skills.
• Analytical mindset with the ability to use data and insights to drive decisions and improve performance.
• Passion for developing talent and building inclusive, high-accountability team cultures.
• AI Enthusiast: Demonstrates a strong curiosity for and practical application of AI to improve productivity, streamline workflows, and elevate client communications, presentations, and recommendations. Uses AI thoughtfully across account strategy and sales motions to uncover insights, sharpen strategic narratives, and show up as a strong, trusted advisor while maintaining sound judgment and a high bar for quality.
• Bachelor’s degree in a relevant field such as business, management or a related field or equivalent experience.

Relocation Statement: 

• This position is not 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 requires the individual to be in person at least 3 days per week, either meeting with clients or collaborating with teammates in the Pinterest Chicago office. Therefore, the role requires a commutable distance from the Pinterest Chicago office. Regular domestic travel will also be necessary to meet with clients and teams.

Working Expectations:

• In-market focused sales team focused on velocity, expect to be traveling in market 50% of the time