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.

Responsibilities

• 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 and best practices that improve seller effectiveness and customer engagement.
• Foster a culture of curiosity, ownership, and continuous learning while developing future leaders within the organization.

Requirements

• 3+ years leading high-performing quota-carrying SaaS sales teams in a fast-paced technology company.
• 5+ years of successful enterprise software sales experience prior to moving into leadership.
• Demonstrated success personally closing complex software opportunities ranging from approximately $100K to $500K+ ARR involving multiple stakeholders and executive decision-makers.
• Experience coaching teams using MEDDPICC (or a comparable enterprise qualification methodology).
• Experience developing consultative sellers through Challenger Sale or other value-based sales methodologies.
• Consistent track record of building teams that exceed quota and improve performance over time.
• Strong forecasting discipline with a history of delivering predictable revenue outcomes.
• Excellent executive presence with the ability to influence customers, internal stakeholders, and senior leadership.
• Strong analytical mindset with the ability to diagnose pipeline risk, identify trends, and drive measurable improvements.
• Experience working within

Benefits

Additional Information

Iterable is the leading AI-powered customer engagement platform that helps leading brands like Redfin, SeatGeek, Priceline, Calm, and Box create dynamic, individualized experiences at scale. Our platform empowers organizations to activate customer data, design seamless cross-channel interactions, and optimize engagement-all with enterprise-grade security and compliance. Today, nearly 1,200 brands across 50+ countries rely on Iterable to drive growth, deepen customer relationships, and deliver joyful customer experiences. Our success is powered by extraordinary people who bring our core values-Be an Owner, Growth Mindset, Run as One, Transparency -to life. We foster a culture of innovation, collaboration, and inclusion, where ideas are valued and individuals are empowered to do their best work. That's why we've been recognized as one of Inc's Best Workplaces and Fastest Growing Companies , and were recognized on Forbes' list of America's Best Startup Employers in 2022. Notably, Iterable has also been listed on Wealthfront's Career Launching Companies List and has held a top 10 ranking on the Top 25 Companies Where Women Want to Work . With a global presence-including offices in San Francisco, New York, Denver, London, and Lisbon, plus remote employees worldwide-we are committed to building a diverse and inclusive workplace. We welcome candidates from all backgrounds and encourage you to apply. Learn more about our story and mission on our Culture and About Us pages. Let's shape the future of customer engagement together!

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