Enterprise Sales Director - Great Plains at five9

This role is ideal for a high-energy "hunter" with at least 5 years of experience in enterprise software sales. Since the territory covers the Great Plains, candidates should ideally be based in Chicago, St. Louis, Kansas City, or Omaha. Experience selling to C-suite executives (specifically COOs/CFOs) and a background in high-velocity, complex cloud software environments are essential. The position offers a competitive salary range ($88k - $211k base) plus commissions, stock options, and a performance bonus. The benefits package is particularly strong, featuring 100% employer-paid healthcare premiums for employees and a generous 12-week parental leave policy. While the role is fully remote for most, it provides the stability of a leading cloud contact center provider. **You might be a good fit if you:** * Have a proven track record of exceeding quotas in the Contact Center (CCaaS) or SaaS space. * Are a self-starter comfortable with cold-calling and generating your own leads through networking. * Enjoy "business athlete" culture—being aggressive, nimble, and able to close both complex and transactional deals. * Reside in the Midwest and have an established network within the Great Plains territory.