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Strategic Sales Director - Midwest / Southeast

Five9 Open · verified Sep 10, 2026
Remote US Director Sales Leadership

Leadership Sales Leadership role at Five9. Remote, United States · $125,900–$321,100 base.

SalaryStated by Five9
$125,900 – $321,100
Base salary for this role, in USD per year, as published in the posting.
Role brief

Growth Roles summary, based on the employer's posting.

What you'll do

  • Build and close revenue across assigned named accounts or a defined region
  • Find opportunities through cold calls, referrals, networking, and industry associations
  • Run the full sales cycle from lead creation through closure while meeting sales quotas
  • Create customer-focused business cases and turn strategic discussions into practical implementations
  • Track opportunity forecasts in SFDC and support satisfaction and retention through implementation

What you bring

  • At least ten years of outside enterprise software sales in the contact center field
  • Experience selling to C-level buyers with a record of strong sales performance
  • Active listening, objection handling, negotiation, communication, and collaboration skills
  • A self-directed, organized, persuasive approach in a fast-changing environment

Who this fits

You'll fit this role if you are customer-focused, strategic, persuasive, and resourceful while managing multiple accounts. You should be comfortable working independently and with a team, building trusted-advisor relationships, and pursuing new business. The role is fully remote outside a thirty-mile radius of a Five9 office; within that radius, you will work onsite three days each week from Tuesday through Thursday

From the employer

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.

As a consultative sales professional, the Strategic Sales Director creates, identifies, and closes sales within a set of named accounts. The Strategic Sales Director helps solve the business needs of prospects and customers by aligning those needs and objectives with Five9’s offerings. Once an opportunity has been closed, the Strategic Sales Director’s job is to help manage the initial phases of post-sales support and ensure implementation is set up accordingly. This is achieved through the support of additional resources such as Technical Pre-Sales Support and Professional Services, whose goal is to help you close and delivery the Five9 solution.

  • How does the Strategic Sales Director role generate value for customers?
    • Gain a deep understanding of the prospect or customer’s processes and problems
    • Ensure the right questions are being asked and answered
    • Obtain qualitative and quantitative data which can be leveraged by the sales support team to identify the right solution(s)
    • Justify all investments through compelling and customer-focused business cases
    • Determine next steps and turn strategic discussions into tactical implementations
  • What makes a great Strategic Sales Director?
    • Customer Focused: Approaching all opportunities through the lenses of the prospect or customer
    • Strategic: Able to prioritize and manage multiple accounts within territory
    • Persuasive: Achieves ‘win-win’ positioning and guides others to change status quo
    • Resourceful: Able to overcome obstacles and barriers to find appropriate sales solutions

Why consider this role?

  • Work for a successful technology frontrunner within the contact center industry with a positive track record of product innovation and market leadership.
  • Five9 is a high growth software leader with exceptional future upside.
  • Benefit from a customized B2B selling process that includes Sales Aids, guidance, a proven sales methodology, and using Salesforce in tracking opportunities.

We only hire professionals who have a minimum of 10 years operating, selling, or servicing customer contact/engagement centers for Sales or Service. Your relevant experience is paramount to being considered. Candidates should possess a high level of professionalism, persistence, focus, and ability to execute while selling or serving our customers.

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
  • Collaborate with peers and management around ways to continually improve the sales organization
  • Own the sales cycle from lead generation to closure
  • Provide expertise around particular areas of interest to discuss industry best practices and development of high level strategies
  • Develop business plan and present the business plan during quarterly review sessions
  • Be proactive in all aspects of opportunity development
  • Establish yourself as a ‘Trusted Advisor’ to the prospect or customer
  • Bring net new and innovative ideas to both internal teams and the customer
  • 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:

  • 10+ years of outside enterprise software sales experience in the contact center space
  • Superior active listening skills
  • Excellent objection handling and negotiating abilities
  • Strong collaboration skills and ability to work alongside multiple team members
  • Strong time-management and organization skills
  • Excellent written and verbal communication skills
  • 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
  • Highly persuasive
  • Superior professional presence and business acumen

Work Location: This role is fully remote for candidates who reside outside the 30 mile radius of one of our offices. For candidates who reside within a 30 mile radius of one of our offices, this role is Hybrid and would require 3 days a week (T, W, TH) in 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. $125,900—$321,100 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.

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