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.

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 Salesforce, Gong, Clari, and modern sales technology platforms.
• Excellent communication, coaching, and leadership skills.

Qualifications

• Bachelor’s degree preferred.

Skills

• Leadership
• Team Management
• Forecasting
• Coaching
• Consultation
• Strategic Planning
• Customer Relationship Management
• Product Knowledge
• Sales Techniques
• Technology Integration

Benefits

• Paid parental leave
• Competitive salaries, meaningful equity, & 401(k) plan
• Medical, dental, vision, & life insurance
• Balance Day (First Friday off every quarter)
• Fertility & Adoption Assistance
• Paid Sabbatical
• Flexible PTO
• Monthly Employee Wellness allowance
• Monthly Professional Development allowance
• Pre-tax commuter benefits
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Pay

The annual cash compensation for this role is $336,000 - $456,000 and includes annual base salary and target variable pay (actual payout is subject to the percentage attainment of specific sales goals). The total compensation package also includes equity, plus a range of benefits, including medical, dental, vision, and financial. In addition, we offer perks such as generous stipends for health & fitness and learning & development, among others.

Schedule

Not specified.