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    Enterprise Sales Director - Northeast

    Five9

    🇺🇸 USA
    Remote
    ["Full-Time"]
    SaaS
    Hybrid
    See your match score
    Posted Aug 25, 2026
    Job Type

    ["Full-Time"]

    Work Type

    Remote

    Vertical

    SaaS

    Source

    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

    Experience·10+ years required
    Lead Generation·Required skill

    Typical Day — Sales Rep

    Stakeholder meetings3–5/week
    Proposals & business cases1–2/week
    Pipeline managementDaily

    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

    ARR / MRRNet Revenue Retention (NRR)CAC Payback PeriodLogo Churn vs Revenue ChurnACV (Avg Contract Value)Magic Number

    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

    sales
    —

    How do you coach underperforming reps?

    Template question
    —

    Describe your forecasting methodology.

    Template question
    —

    How do you structure onboarding for new hires?

    Template question
    Research Five9's product, recent news, and key competitors
    Prepare metrics: quota attainment %, average deal size, win rate
    Practice a 2-minute product demo pitch for a mock discovery call
    Prepare to discuss your home office setup and self-management discipline
    Review the job description and map your experience to each requirement
    Role Insights

    Sales 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.

    Are you a closer?

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