Director, Mid-Market Sales, North America - West Region

About the Role

Iterable is looking for an experienced sales leader to build, coach, and scale a high-performing Mid-Market Sales team. As Director of Mid-Market Sales, you will lead a team of Account Executives responsible for acquiring strategic customers across North America.

This role combines front-line coaching, operational excellence, executive deal strategy, and talent development. You’ll work closely with Sales Engineering, Marketing, Customer Success, Product, and Executive Leadership to build a predictable, scalable business while helping develop the next generation of sales leaders at Iterable.

We’re looking for someone who thrives in fast-paced environments, enjoys coaching as much as closing, and believes that developing people is the most scalable way to drive results.

What You’ll Do

• Lead, coach, and develop a high-performing team of Mid-Market Account Executives responsible for achieving and exceeding quarterly and annual revenue goals.
• Drive consistent forecast accuracy through rigorous pipeline inspection, opportunity coaching, and data-driven forecasting.
• Coach complex, multi-threaded sales cycles from discovery through negotiation, helping Account Executives navigate executive buying committees and competitive evaluations.
• Inspect opportunities using MEDDPICC (or a comparable enterprise sales methodology) to improve qualification, execution, and win rates.
• Develop consultative, Challenger-style sellers who create business value beyond product demonstrations.
• Recruit, hire, onboard, and develop exceptional sales talent while fostering a culture of accountability, continuous improvement, and collaboration.
• Partner cross-functionally with Marketing, Customer Success, Product, Sales Engineering, and Sales Operations to improve customer outcomes and influence go-to-market strategy.
• Act as an executive sponsor on strategic opportunities, helping teams navigate complex commercial negotiations and executive relationships.
• Drive operational excellence by leveraging Salesforce, Momentum, Outreach, and other sales technologies to improve productivity, inspection, and execution.
• Champion the adoption of AI-powered selling tools.