Strategic Sales Director - Midwest/Southeast

September 28, 2026

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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

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