Job Title: Director of Mid-Market Sales

About Iterable

Iterable is the premier AI-powered customer engagement platform, enabling leading brands like Redfin, SeatGeek, and Calm to create dynamic, individualized experiences at scale. Our platform empowers organizations to activate customer data, design seamless cross-channel interactions, and optimize engagement with enterprise-grade security. Nearly 1,200 brands globally rely on Iterable to drive growth and deepen customer relationships. Our success is driven by our core values—Be an Owner, Growth Mindset, Run as One, Transparency—fostering a culture of innovation, collaboration, and inclusion. We are recognized as a top workplace, including Inc's Best Workplaces and Forbes' Best Startup Employers.

About the Role

Iterable is looking for an experienced sales leader to build, coach, and scale a high-performing Mid-Market Sales team. As the Director of Mid-Market Sales, you will lead a team of Account Executives focused on acquiring strategic customers across North America. This role blends front-line coaching, operational excellence, executive deal strategy, and talent development. You will collaborate closely with Sales Engineering, Marketing, Customer Success, Product, and Executive Leadership to build a predictable, scalable business and develop the next generation of sales leaders at Iterable. We seek individuals who thrive in fast-paced settings, enjoy coaching and closing, and believe in developing people as the most scalable path to results.

What You’ll Do

• Lead, coach, and develop a high-performing team of Mid-Market Account Executives to achieve and exceed 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, assisting Account Executives in navigating executive buying committees and competitive evaluations.
• Inspect opportunities using MEDDPICC (or a comparable methodology) to enhance 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, guiding teams through 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 to enhance 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 of experience leading high-performing, quota-carrying SaaS sales teams in a fast-paced technology company.
• 5+ years of successful enterprise software sales experience prior to leadership roles.
• Demonstrated success closing complex software deals ($100K-$500K+ ARR) involving multiple stakeholders and executive decision-makers.
• Experience coaching teams using MEDDPICC or a similar enterprise qualification methodology.
• Proven experience developing consultative sellers through Challenger Sale or other value-based 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 for diagnosing pipeline risk, identifying trends, and driving measurable improvements.
• Experience with 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

Compensation

The annual cash compensation for this role is $336,000 - $456,000, including base salary and target variable pay. Total compensation includes equity and a comprehensive benefits package. Additional perks include generous stipends for health & fitness and learning & development.

Recruitment Disclaimer

Iterable, Inc. and its official recruiting agencies do not: send job offers from free email services (Gmail, Yahoo, etc.); request money or fees from candidates; or require personal banking/financial details before a formal contract. Please verify job vacancies on Iterable's official website or LinkedIn page. Report any suspicious offers to talent-ops@iterable.com. Iterable reserves the right to take legal action against fraudulent entities.