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Enterprise Sales Director - TOLA

Join us in bringing joy to customer experience.  Five9 is a leading provider of cloud contact center software, bringing the power of cloud innovation to customers worldwide.   

Living our values everyday results in our team-first culture and enables us to innovate, grow, and thrive while enjoying the journey together. We celebrate diversity and foster an inclusive environment, empowering our employees to be their authentic selves. 

The Enterprise Sales Director creates, identifies, and closes sales within North America or a set of named accounts. The Sales Director's primary responsibility is to acquire new customers and drive revenue. A successful Sales Director is a self-starting closer who can create a large pipeline of business within a short period of time. Based in Houston, Austin, Dallas or Oklahoma City preferred. We look for business athletes who are aggressive team players - hungry, nimble and intelligent - with the ability and willingness to close a mix of complex enterprise and more transactional deals.
 
Key Responsibilities:
  • Create and drive revenue within a specified region or list of named accounts
  • Generate business opportunities through professional networking and cold-calling
  • Drive brand awareness, campaigns, and lead generation via networking, associations, etc.
  • Meet and exceed all quarterly and annual sales quotas
  • Own the sales cycle from lead generation to closure
  • Develop business plan and present the business plan during quarterly review sessions
  • Maintain account and opportunity forecasting within our internal forecasting system (SFDC)
  • Self-generate leads from a personal connections, referral partners, and regional networking events
  • Ensure 100% customer satisfaction and retention throughout the Implementation and Support experience
Key Qualifications:
  • 5+ years of outside enterprise software sales experience
  • Be able to work independently and as part of a team in a fast pace, rapid change environment
  • Experience selling at the C-level
  • Proven track record of sales excellence
  • A proven sales hunter and closer
  • Superior professional presence and business acumen
Preferred Qualifications:
  • Contact Center Software Sales in less than 1,000-seat space
  • Experience selling to COO/CFO
  • Knowledge of territory or accounts assigned

Work Location: This role is fully remote for candidates who reside outside the 50 mile radius of our San Ramon office.  For candidates who reside within 50 miles of our San Ramon location, this role is Hybrid and would require 3 days a week (M, W, TH) in our San Ramon office. 


As part of our continued commitment to diversity, equity, and inclusion, Five9 supports pay transparency during the entire recruitment process.  Actual compensation packages are based on several factors that are unique to each candidate including, but not limited to: skill set, depth of experience, certifications, and specific work location. The range displayed reflects the minimum and maximum target for new hire salaries for the job across the United States. Your recruiter can share more about the specific compensation package during your hiring process.

Additionally, the total compensation package for this position may also include an annual performance bonus, stock, and/or other applicable incentive compensation plans.

Our total reward package also includes:

  • Health, dental, and vision coverage, beginning on the first day of employment. Five9 covers 100% of the employee portion of the health, dental and vision coverage and shares a high portion of the dependent cost. We also offer Short & Long-Term Disability, Basic Life Insurance, and a 401k saving plan with employer matching.
  • Access to an innovative mental health support platform that offers personalized care and resources in areas such as: therapy, coaching and self-guided mindfulness exercises for all covered employees and their covered dependents.
  • Generous employee stock purchase plan.
  • Paid Time Off, Company paid holidays, paid volunteer hours and 12 weeks paid parental leave.

All compensation and benefits are subject to the requirements and restrictions set forth in the applicable plan documents and any written agreements between the parties.

The US base salary range for this role is below.
$80,100$124,100 USD

Five9 embraces diversity and is committed to building a team that represents a variety of backgrounds, perspectives, and skills.  The more inclusive we are, the better we are.  Five9 is an equal opportunity employer. 


View our privacy policy, including our privacy notice to California residents here: https://www.five9.com/pt-pt/legal.  

Note: Five9 will never request that an applicant send money as a prerequisite for commencing employment with Five9.

Average salary estimate

$102100 / YEARLY (est.)
min
max
$80100K
$124100K

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What You Should Know About Enterprise Sales Director - TOLA, Five9

If you're looking to make a significant impact in the cloud contact center world, then the role of Enterprise Sales Director at Five9 might just be the perfect fit for you! Based in the United States, this exciting position involves creating, identifying, and closing sales within North America and a select group of named accounts. As the Enterprise Sales Director, your primary goal will be to acquire new customers and drive revenue in a fast-paced, dynamic environment. You'll be appreciated for your ability to create a large pipeline of business in no time, and we value self-starting closers who can successfully navigate both complex enterprise deals and more transactional opportunities. Your responsibilities will include generating business through networking and cold calls, driving brand awareness, and ensuring customer satisfaction throughout the sales cycle. With a focus on meeting and exceeding quarterly and annual sales quotas, you'll also be tasked with developing business plans and maintaining opportunity forecasting. Five9 prides itself on an inclusive, team-first culture where diversity is celebrated, and being yourself is encouraged. If you have a proven track record in software sales, strong professional presence, and are ready to thrive in an innovative environment, bring your talent to Five9 as we revolutionize customer experiences together!

Frequently Asked Questions (FAQs) for Enterprise Sales Director - TOLA Role at Five9
What are the key responsibilities of an Enterprise Sales Director at Five9?

The Enterprise Sales Director at Five9 is responsible for creating and driving revenue within a specified region or list of named accounts. This includes generating business opportunities through professional networking and cold-calling, driving brand awareness and lead generation, meeting and exceeding sales quotas, and maintaining account forecasting within our internal systems. You'll own the entire sales cycle from lead generation to closure while ensuring 100% customer satisfaction throughout the implementation process.

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What qualifications are needed to become an Enterprise Sales Director at Five9?

To become an Enterprise Sales Director at Five9, candidates should have a minimum of 5 years of experience in outside enterprise software sales. Strong qualifications include a proven track record of sales excellence, experience selling at the C-level, and the ability to work both independently and as part of a team in a fast-paced environment. Familiarity with contact center software sales and knowledge of the assigned territory are also preferred qualifications.

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What is the company culture like at Five9 for an Enterprise Sales Director?

At Five9, we prioritize a team-first culture that celebrates diversity and encourages employees to be their authentic selves. As an Enterprise Sales Director, you can expect a supportive, inclusive environment where innovation is fostered, and collaboration is key. We believe that the more inclusive we are, the better we perform, and you’ll be part of a team that thrives on growth and creativity.

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Can the Enterprise Sales Director work remotely at Five9?

Yes, the Enterprise Sales Director position at Five9 is remote for candidates residing outside the 50-mile radius of our San Ramon office. For those within this radius, a hybrid model requires three days a week on-site in San Ramon. This flexibility is designed to resonate with our commitment to work-life balance while retaining collaboration in the workplace.

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What potential compensation can the Enterprise Sales Director expect at Five9?

The salary range for the Enterprise Sales Director at Five9 ranges from $80,100 to $124,100 USD, based on various factors unique to each candidate. In addition to this base salary, candidates can expect potential annual performance bonuses, stock options, and other incentives. Five9 also offers comprehensive health benefits, a 401k savings plan with employer matching, and generous paid time off, ensuring a competitive total rewards package.

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Common Interview Questions for Enterprise Sales Director - TOLA
How do you approach lead generation for enterprise accounts?

When asked this question, highlight your proactive strategies for lead generation, such as leveraging your professional network, utilizing cold-calling techniques, and attending relevant networking events. Explain how you balance personal connections with structured lead generation processes to maximize opportunities.

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Can you describe your experience selling to C-level executives?

To answer effectively, discuss your approach to engaging C-level executives, focusing on relationship-building and understanding their specific pain points. Share examples showcasing your ability to craft tailored pitches that resonate with top executives' business goals.

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What techniques do you use to exceed sales quotas?

Discuss how you set personal benchmarks in addition to team quotas, along with effective time management and pipeline management strategies. Providing examples of past successes can demonstrate your commitment and effectiveness in exceeding goals.

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How do you maintain customer satisfaction throughout the sales process?

It's important to portray your understanding of customer success management. Talk about your methods for maintaining open communication, setting expectations, and following up post-sale to ensure clients feel valued and supported throughout their experience with the company.

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What is your strategy for closing complex deals?

Provide insight into your approach to identifying key stakeholders, understanding customer needs, and devising cost-benefit analyses that present a strong value proposition. Share specific instances where these strategies led to successful closures.

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How do you forecast sales opportunities?

Be clear about the tools or methodologies you employ to accurately forecast sales. Emphasize your experience using CRM systems, like SFDC, to track leads and opportunities, analyze market trends, and adjust forecasts based on data-driven insights.

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What steps do you take in developing a business plan?

Convey your methodical approach, detailing how you assess market conditions, identify potential customers, craft clear objectives, and outline actionable strategies. Support your answer with examples of successful business plans you've implemented in the past.

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How would you drive brand awareness for Five9?

Discuss the various channels available for driving awareness, emphasizing the importance of strategic networking, social media engagement, and participation in industry events. Show your understanding of Five9’s unique value proposition to effectively communicate this to potential clients.

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Describe a challenging sales situation you encountered and how you resolved it.

This is an opportunity to showcase your problem-solving skills. Share a specific challenge you faced, the steps you took to address it, and the result. Focus on not just resolving the issue but how it influenced your sales strategy moving forward.

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Why do you want to work for Five9 as an Enterprise Sales Director?

Prepare to express your enthusiasm for the company, highlighting Five9's innovative technology and commitment to customer experience. Discuss how your values align with theirs and how you see yourself contributing to the team’s success.

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DATE POSTED
April 2, 2025

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