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Iterable

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

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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!

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.

Recruitment Disclaimer:

Please be aware that Iterable, Inc. (“Iterable”) and our official professional recruiting agencies and platforms do not:

  • Send job offers from free email services like Gmail, Yahoo mail, Hotmail, etc.
  • Request money, fees, or payment of any kind from prospective candidates to apply to Iterable, for employment, or for the recruitment process (e.g. for home office supplies, or training, etc.).
  • Request or require personal documents like bank account details, tax forms, or credit card information as part of the recruitment process prior to the candidate signing an engagement letter or an employment contract with Iterable.

You may see all job vacancies on our official Iterable channels:

Iterable is not affiliated in any way to these impostors and we hereby confirm that such individuals/entities are not authorized, encouraged, or sponsored to act on behalf of Iterable. Such job opportunities are entirely fake and not valid. Therefore, please disregard any written or oral request for a job offer or an interview that you believe is or might be fraudulent or suspicious and immediately reach out to us via email at talent-ops@iterable.com upon receiving a suspicious job offer.

Criminal and/or civil liabilities may arise from such actions, and Iterable expressly reserves the right to take legal action, including criminal action, against such individuals/entities whenever such phenomena occur. In any case, please note that under no circumstances shall Iterable and any of its affiliates be held liable or responsible for any claims, losses, damages, expenses or other inconvenience resulting from or in any way connected to the actions of these impostors.

Iterable is an Equal Employment Opportunity employer that proudly pursues and hires a diverse workforce. Iterable does not make hiring or employment decisions on the basis of race, color, religion or religious belief, ethnic or national origin, nationality, sex, gender, gender-identity, sexual orientation, disability, age, military or veteran status, or any other basis protected by applicable local, state, or federal laws or prohibited by Company policy. Iterable also strives for a healthy and safe workplace and strictly prohibits harassment of any kind. Pursuant to the San Francisco Fair Chance Ordinance and other similar state laws and local ordinances, and its internal policy, Iterable will also consider for employment qualified applicants with arrest and conviction records.