Outside Sales Representative
Remote / Online - Candidates ideally in
Chicago, Cook County, Illinois, 60623, USA
Listed on 2026-01-13
Chicago, Cook County, Illinois, 60623, USA
Listing for:
ThinkingAhead
Full Time, Remote/Work from Home
position Listed on 2026-01-13
Job specializations:
-
Sales
Outside Sales, Sales Representative, Business Development
Job Description & How to Apply Below
What You’ll Be Doing
• Canvass assigned neighborhoods and initiate face-to-face conversations with homeowners
• Educate homeowners on storm-related roof damage and insurance coverage
• Schedule property inspections (performed by internal inspection specialists)
• Guide customers through the insurance claim and approval process
• Secure signed contracts, scopes of work, and customer deposits
• Track activity and performance using company CRM and sales tools
• Earn bonuses daily through measurable sales behaviors Compensation & Earnings Base Pay • $48,100 annual base salary
• Approximately $925 per week in guaranteed pay Vehicle & Fuel (Added Take-Home Value)
• Company vehicle provided through a $75/week program
• Vehicle available for work and personal use
• Gas card provided with all fuel fully covered
• Gas card is non-taxable, increasing net take-home pay Performance-Based Bonus Structure There is no traditional commission plan. Earnings above base are driven by a behavior-based bonus system that rewards production immediately rather than waiting months for commission payouts. Bonuses are earned through key sales activities, including:
• Signed customer contracts
• Approved scopes of work
• Customer deposits collected
• Insurance claims filed and approved
• Confirmed inspections Each completed KPI earns points, and each point equals $1. Bonuses are paid monthly, quarterly, and annually, allowing top performers to stack earnings quickly. Earnings Potential
• Most representatives exceed base pay within 6 months
• High performers consistently reach six-figure annual earnings by year one Benefits
• Full medical, dental, and vision insurance
• 401(k) eligibility after 90 days
• Paid training with structured performance tracking
• Cell phone reimbursement
• Mileage and travel reimbursement
• Work-from-home flexibility for administrative tasks Schedule
• Monday through Friday, 10:00 AM – 8:00 PM
• Core sales hours: 2:00 PM – 8:00 PM
• Some Saturdays may be required based on territory demand Advancement Opportunities High performers have a clearly defined path into leadership, including:
• Senior Sales Representative
• Field Supervisor
• Sales Manager
• Territory Lead Advancement is performance-based. Production drives promotion. Ideal Candidate Profile
• Prior experience in door-to-door sales, roofing, solar, pest control, alarms, security, telecom, home services, or automotive sales is helpful but not required
• Comfortable initiating conversations with homeowners
• Resilient, competitive, and self-motivated
• Thrives in a performance-based pay environment
• Prefers field sales over a traditional desk role Markets Hiring Now
• Chicago, IL
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• Milwaukee, WI
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• Kansas City, MO
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