Mid-Market Sales Director

    Five9

    🇺🇸 San Francisco, CA (Hybrid)
    SaaS
    Hybrid
    See your match score
    Posted Today
    Work Type

    On-site

    Vertical

    SaaS

    Source

    greenhouse

    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 Mid-Market Sales Director is an individual contributor role. In this position, the individual creates, identifies, and closes sales. 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 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. 

    Location: This role is hybrid. 3 days a week (M, W, TH) in our San Ramon, CA or San Francisco, CA office is required.

    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<

    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

    Bachelor's Degree·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

    Commercial 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
    Review the job description and map your experience to each requirement
    Role Insights

    This leadership position involves both strategic planning and hands-on coaching of the sales team.

    Top SaaS reps often earn significant upside through accelerators once quota is exceeded.

    The US market offers the highest OTE potential globally for sales professionals, with a highly competitive talent landscape.

    Are you a closer?

    Interested in SaaS? Build your profile to get matched with roles like this.

    Explore More Sales Jobs

    Similar Roles

    Browse More Jobs

    Powered by LemClosers

    Ready to land your next closing role?

    Build your free closer profile to get matched with high-ticket sales opportunities, track applications, and showcase your track record.

    Create a free profile to save sales jobs and track applications

    Get matched
    Create Free Profile