["Full-Time"]
Remote
SaaS
jobicy
About this role
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 and Central 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. We 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. 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.
States include: Maine, New Hampshire, Vermont, Massachusetts, Rhode Island, New York, New Jersey, Pennsylvania and Connecticut.
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
Selling Motion
Sales Cycle
Enterprise
6–18 month cycles, complex multi-stakeholder deals
Buyer Persona
C-Suite
Selling to executive decision-makers
Territory
Named Accounts
Pre-assigned list of target companies
Requirements at a Glance
Typical Day — Sales Rep
Estimates based on role type and selling motion — actual may vary by company.
SaaS — Interview Intel
Typical Sales Cycle
30–90 days (SMB) · 3–9 months (Mid-Market) · 6–18 months (Enterprise)
Common Buyer Objections
- "We're locked into a contract with [competitor]"
- "We built something in-house already"
- "We don't have budget until next quarter"
- "Our team won't adopt another tool"
Key Industry Metrics
Hot Topics to Reference
- • AI-native product disruption
- • PLG vs sales-led motion debate
- • Vertical SaaS consolidation
- • Usage-based pricing models
Use these insights to speak the buyer's language in interviews.
Tags
How do you coach underperforming reps?
Template questionDescribe your forecasting methodology.
Template questionHow do you structure onboarding for new hires?
Template questionSales leadership roles require balancing individual contributor revenue with team performance management.
Top SaaS reps often earn significant upside through accelerators once quota is exceeded.
This remote-friendly role provides geographic flexibility while maintaining access to a SaaS market.
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