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 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.

What We're Looking For

• 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.
• Bachelor's degree preferred.

What Success Looks Like

During your first year, you will:

• Build and develop a high-performing, engaged Mid-Market Sales team.
• Deliver consistent forecast accuracy and operational rigor.
• Improve rep productivity through coaching, inspection, and effective deal strategy.
• Recruit and develop exceptional talent while building future sales leaders.
• Drive predictable revenue growth through disciplined execution and cross-functional partnership.
• Help shape the evolution of Iterable's go-to-market strategy as we continue to scale.

Why Iterable

Iterable is the AI-powered customer communication platform that helps the world's leading brands deliver joyful, individualized experiences at scale. We partner with innovative companies across industries to help them create seamless, cross-channel customer journeys powered by data, experimentation, and intelligence.

Joining Iterable means working alongside talented, ambitious people who care deeply about our customers, our teammates, and building a category-defining company. If you're energized by coaching people, solving complex business challenges, and helping build a world-class sales organization, we'd love to meet you.

Perks & 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
• Complete laptop workstation

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.