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Director, Mid-Market Sales - West Region

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—Trust, Growth Mindset, Balance, and Humility—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!

Position Overview:  Director, MidMarket Sales, West Region

You will be responsible for achieving team quotas and report directly to the VP of Sales.  As a team-oriented management professional, you be working cross-functionally with critical members of the Customer Success, Marketing, and Sales Operations teams.

Responsibilities:

  • Provides directional leadership for a growing team of Mid-Market Account Executives
  • Oversee the daily activities, deal inspection, pipeline inspection and performance of each Mid-Market Account Executives
  • Consistently meets/exceeds the outlined metrics as a manager 
  • Continue to build and strengthen your team through recruiting, hiring, and development strategies
  • Drive operational excellence through constant process innovation and technology toolsets
  • Proactively identify and implement new strategies to improve sales cycle
  • Strong organization/prioritization skills; proven ability to consistently meet deadlines

Qualifications:

  • B.A./B.S. in Business Administration, Finance, Marketing,related fields, or equivalent experience
  • 2+ years of sales management experience in a high-tech startup environment
  • 5+ years of quota carrying B2B enterprise software sales experience, strong Saas Business Application sales experience
  • Previous experience with enterprise email marketing and/or marketing automation solutions preferred
  • Proven track record of consistently exceeding against quota and outlined metrics
  • Strong experience working with Salesforce.com and other CRM platforms
  • Team player who’s comfortable working with all department leaders in a startup environment
  • Excellent communication skills and the ability to be an inspirational leader

Perks & Benefits: 

  • Paid parental leave
  • Competitive salaries, meaningful equity, & 401(k) plan
  • Medical, dental, vision, & life insurance
  • Balance Days (additional paid holidays)
  • 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 $345,000 - $430,000 and includes annual base salary and target variable pay (actual payout is subject to the percentage attainment of specific sales goals) on target, NO CAP. 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.

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Average salary estimate

$387500 / YEARLY (est.)
min
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$345000K
$430000K

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What You Should Know About Director, Mid-Market Sales - West Region, Iterable

Join Iterable as the Director of Mid-Market Sales for the West Region, where you will play a pivotal role in shaping customer engagement for some of the world's most reputable brands like Redfin and SeatGeek. In this fully remote position, you will work directly with the VP of Sales, providing leadership to a growing team of Mid-Market Account Executives. Your responsibilities will encompass daily team oversight, performance measurement, and deal inspections, ensuring that your team always meets or exceeds their sales metrics. With Iterable’s dynamic work culture, you will have the chance to not just manage—but also recruit and develop your team, fostering an environment where collaboration and innovation thrive. You’ll be strategically identifying ways to improve the sales cycle, leveraging technology and process innovation to drive operational excellence. Ideal candidates will have a B.A./B.S. in relevant fields, along with significant experience in sales management in a fast-paced tech startup. Plus, this role offers competitive salaries, equity, and an enticing benefits package, including paid sabbaticals and wellness allowances. Come help us shape the future of customer engagement and make your mark in a company celebrated for its vibrant workplace culture!

Frequently Asked Questions (FAQs) for Director, Mid-Market Sales - West Region Role at Iterable
What are the primary responsibilities of the Director of Mid-Market Sales at Iterable?

The Director of Mid-Market Sales at Iterable is responsible for providing leadership to a team of Mid-Market Account Executives. This includes overseeing daily activities, conducting deal inspections, and ensuring that each executive meets and excels against their quotas. The role is also pivotal for developing team members through effective recruiting and training strategies, fostering a high-performance culture while constantly innovating processes to optimize the sales cycle.

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What qualifications are needed for the Director of Mid-Market Sales position at Iterable?

To be considered for the Director of Mid-Market Sales role at Iterable, candidates should have a B.A./B.S. in Business Administration, Finance, Marketing, or a related field. Additionally, a minimum of 2 years of sales management experience within a high-tech startup and at least 5 years of quota-carrying B2B enterprise software sales experience is required. Previous experience with enterprise email marketing or marketing automation solutions is a plus, along with proficiency in Salesforce.com or similar CRM platforms.

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What kind of work culture can I expect as a Director of Mid-Market Sales at Iterable?

Iterable is known for its inclusive, innovative, and collaborative work culture. As the Director of Mid-Market Sales, you will be part of a team that values ideas and empowers individuals to excel. The company's core values of Trust, Growth Mindset, Balance, and Humility guide everyday interactions, making it a great place to drive growth and customer engagement.

Join Rise to see the full answer
How does Iterable support professional development for the Director of Mid-Market Sales?

Iterable places high importance on professional development for all its employees, including the Director of Mid-Market Sales. The position comes with a monthly professional development allowance, encouraging continuous learning and skills enhancement, alongside various wellness programs to support a healthy work-life balance.

Join Rise to see the full answer
What is the compensation structure for the Director of Mid-Market Sales role at Iterable?

The compensation for the Director of Mid-Market Sales at Iterable varies based on experience and performance, with an annual cash compensation range between $345,000 and $430,000, which includes a base salary and target variable pay based on achieving specific sales goals. Additional benefits include equity options, comprehensive health coverage, and various perks such as paid parental leave and flexible PTO.

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Common Interview Questions for Director, Mid-Market Sales - West Region
Can you describe your leadership style as a Director of Mid-Market Sales?

When addressing your leadership style, it’s important to emphasize collaboration and empowerment. Discuss how you prioritize team development and engagement, using specific examples of how you've inspired your team to achieve exceptional results while maintaining a positive work environment.

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How do you ensure your sales team meets their quotas?

In your response, highlight the importance of setting clear expectations and regular check-ins. Talk about implementing performance metrics, coaching team members through challenges, and celebrating their successes as a way to keep motivation high and ensure quotas are met.

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What strategies have you implemented in the past to improve sales cycles?

Frame your answer around specific actions taken to streamline processes or integrate technology. Discuss any innovative techniques that reduced sales cycle times and how you gathered feedback from your team to refine these strategies continuously.

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How do you foster team collaboration across departments?

Discuss your approach to building strong interdepartmental relationships. Mention activities or systems you've put in place to facilitate communication and collaboration among sales, marketing, and customer success teams, ensuring everyone is aligned towards shared objectives.

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What experience do you have with SaaS and B2B enterprise software sales?

Highlight your relevant experience in SaaS and B2B sales, focusing on your role in driving growth and boundaries you pushed. Share successes, sales techniques that worked, and your understanding of the market to demonstrate you're well-versed in the dynamics of these industries.

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How do you handle underperforming team members?

When discussing this, emphasize a supportive approach. Talk about identifying root causes for underperformance, creating tailored development plans, and utilizing performance reviews to ensure team members are receiving the guidance they need to improve.

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Can you give an example of a time you exceeded your sales goals?

Prepare to share a specific achievement where your leadership directly impacted sales outcomes. Detail the strategies you employed and how you motivated your team to achieve and surpass expectations, illustrating the direct correlation between your leadership and the results.

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How do you prioritize tasks and manage your time effectively as a Director?

Discuss tools and techniques you use for your day-to-day task management and prioritization. Mention how you balance operational necessities with strategic planning while ensuring you allocate time for team development.

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What are your thoughts on using data to drive sales strategies?

Express your belief in leveraging analytics and metrics to inform decision-making. Provide an example of how data has guided your sales strategies in the past and how you've adapted them based on performance insights.

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Why do you want to work for Iterable as the Director of Mid-Market Sales?

Frame your answer around your admiration for Iterable’s commitment to innovation and inclusion. Discuss how your values align with the company’s mission and how this role presents an exciting opportunity to contribute to impactful customer engagement initiatives.

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Full-time, remote
DATE POSTED
April 18, 2025

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