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    Sales Director, Workers Compensation (Greater Midwest)

    Dane Street

    🇺🇸 United States
    Remote
    SaaS
    Hybrid
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    Posted Today
    Work Type

    Remote

    Vertical

    SaaS

    Source

    himalayas

    About this role

    Seeking a Sales Director!This position will cover:Greater Midwest regionDane Street is looking for highly motivated candidates to join our organization in the position of Sales Director. Dane Street offers an exciting work environment, competitive compensation, and strong growth potential.The Sales Director is in the center of our critical relationships with our clients and our operations teams.

    As a member of our team, you will be responsible for achieving your territory's revenue target by identifying and developing new accounts, and growing Dane Street's wallet share with existing national and local accounts.

    Individuals should possess the right balance of relationship-building skills and motivation to significantly impact Dane Street’s sales growth targets within the local market.Required Minimum Education/Experience: 4-year College degree (BA/BS) Auto OR Workers Compensation Claims experience (Preferred) IME sales experience is a plus

    Description of Key Tasks and Responsibilities:

    Initiates sales process by scheduling appointments, understanding account

    requirements and building personal relationships with adjusters, team leads and supervisors. Recommends new products and services by evaluating current product results and identifying needs to be filled. Increase referral volume and revenue by building rapport with potential accounts, explaining product and service capabilities and overcoming objections.

    Documenting related sales and account activities and results into our internal CRM platform. Updates job knowledge by participating in industry opportunities such as conferences and seminars. Other duties as assigned dependent on the needs of the business.

    Special Skills and Attributes:

    Business Development mindset

    Presentation Skills

    Proficiency in Microsoft Excel and PowerPoint is a must Excellent Communication Skills (both internal and external) Closing Skills Motivation For Sales Sales Planning Prospecting Skills Strong Follow-Up Ability to Meet Sales Goals

    Selling Motion

    Prospecting

    Outbound-Heavy

    Self-sourced pipeline via cold outreach

    Buyer Persona

    C-Suite

    Selling to executive decision-makers

    Requirements at a Glance

    Bachelor's Degree·Required
    Prospecting·Required skill

    Typical Day — Sales Rep

    Outreach calls30–50/day
    Email sequences20–40/day
    Client meetings3–5/week

    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-Director
    Regional-Sales-Director
    Territory-Sales-Director
    Insurance-Sales-Director
    Workers-Compensation-Sales
    —

    How do you coach underperforming reps?

    Template question
    —

    Describe your forecasting methodology.

    Template question
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    How do you structure onboarding for new hires?

    Template question
    Research Dane Street'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

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

    Expect to work with recurring revenue models where customer retention is as important as acquisition.

    This remote-friendly role provides geographic flexibility while maintaining access to a SaaS market.

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