Now Hiring in Chicago, IL

What You'll Do: As a door-to-door canvasser in Chicago, you'll be the first point of contact with homeowners after storm events across the city's diverse neighborhoods. Your primary responsibility is to identify properties with potential storm damage and schedule free inspections with our sales team. You'll work in neighborhoods ranging from Lincoln Park and Lakeview to Albany Park and Pilsen, covering the varied property types that have recently experienced hail, wind, or other weather events that commonly cause roof and exterior damage.

Why This Role Works in Chicago: Chicago offers unparalleled canvassing opportunities due to its massive population density, diverse neighborhood character, and position as the heart of the Midwest storm corridor. The city's mix of single-family homes, multi-unit buildings, condominiums, and townhomes creates diverse revenue opportunities across different price points and demographic segments. Chicago's culturally diverse population provides opportunities to work with homeowners from all backgrounds who understand the value of professional restoration services. The city's location directly in major storm pathways ensures consistent weather-related opportunities throughout the season, while the urban density allows for efficient territory coverage and high appointment volume potential.

Requirements: Valid driver's license, reliable transportation, strong communication skills, and the ability to navigate diverse urban neighborhoods for several hours. We provide all training, materials, and leads. Success in Chicago requires adaptability to work with varied demographics, from young professionals in trendy neighborhoods to established families in residential areas. Bilingual skills (English/Spanish) are highly valued and can significantly increase your earning potential given Chicago's large Hispanic/Latino population. Cultural awareness and the ability to connect respectfully with diverse communities is essential for building trust and success across the city's many distinct neighborhoods.

Compensation: Earn $50-150 per confirmed appointment, with top performers setting 20-30 appointments per week in this target-rich metropolitan environment. Weekly pay with performance bonuses and vehicle allowance available. Chicago's diverse property mix and high population density provide exceptional earning opportunities for dedicated canvassers who understand neighborhood dynamics and can build relationships across cultural and economic boundaries while establishing territory presence in this dynamic urban market.

What You'll Do: Manage the complete sales process from initial inspection to project completion for residential and commercial properties throughout Chicago and surrounding Cook County areas. You'll work with diverse homeowners including young professionals, established families, and property investors to assess storm damage, prepare detailed estimates, and guide them through the insurance claim process. This role involves meeting with insurance adjusters, coordinating with our production teams, and ensuring customer satisfaction throughout the restoration process for varied property types across the metropolitan area.

The Chicago Advantage: Chicago represents our largest and most diverse market with exceptional opportunities due to its massive population base, varied property types, and strategic location in the Midwest storm belt. The city's demographic diversity creates multiple revenue streams, from high-end condominiums in downtown and North Side neighborhoods to family homes throughout the South and West sides. Chicago's position as a major metropolitan center means access to homeowners with stable employment, good insurance coverage, and understanding of quality restoration services. The city's strong neighborhood networks and community connections provide excellent referral opportunities for sales professionals who focus on building relationships and delivering exceptional service quality that meets the varied needs of urban homeowners.

Requirements: Previous experience in roofing, insurance, exterior sales, or related residential/commercial services preferred. Knowledge of storm damage assessment, insurance claim processes, and construction techniques is valuable but not required - we provide ongoing training. Must have excellent communication skills and professional appearance for meetings with diverse homeowners and adjusters across metropolitan markets. Ability to work effectively with varied demographics, adapt communication style to different cultural backgrounds, and navigate urban environments efficiently is essential for success in this complex, multi-neighborhood market environment. Bilingual abilities (English/Spanish) are highly preferred and can significantly boost earnings and advancement opportunities.

Compensation: Base salary plus commission structure with unlimited earning potential based on individual performance and territory development across diverse market segments. Company-provided leads, vehicle allowance, health insurance, and performance bonuses. Top performers in major metropolitan markets like Chicago typically earn $200,000-$350,000 annually due to high population density, diverse project types, varied property values, and strong referral networks that drive repeat and referral business opportunities throughout the greater Chicagoland area and surrounding communities.

What You'll Do: Work from home contacting potential customers throughout Chicago and surrounding metropolitan areas via phone, text, and email to schedule storm damage inspections. You'll use our CRM system to manage leads generated from digital marketing, referrals, and canvassing efforts across diverse urban neighborhoods. This role is perfect for someone who wants to contribute to our storm restoration success while maintaining work-life balance and flexible scheduling that accommodates the varied schedules and time zones of a major metropolitan market.

Why Remote Works for Chicago: Our appointment setters can effectively serve the massive Chicago market from anywhere while maintaining personal flexibility and eliminating commute time in this major metropolitan area with complex traffic patterns. You'll have access to warm leads from homeowners who have already expressed interest in our services, making conversations more productive and relationship-focused rather than cold calling. The city's diverse demographics and varying work schedules appreciate organized, professional appointment scheduling that accommodates different language preferences, cultural expectations, and time constraints across neighborhoods with different rhythms and lifestyles.

Requirements: Strong phone communication skills, basic computer proficiency, reliable internet connection, and quiet home office space suitable for professional conversations. Previous customer service or sales experience helpful but not required. Must be available during standard business hours with some evening flexibility for contacting busy professionals and families across different neighborhoods. Bilingual capabilities (English/Spanish) are highly preferred for effectively serving Chicago's diverse population and can significantly impact earning potential and advancement opportunities in this multicultural metropolitan market.

Compensation: Competitive hourly rate plus commission for confirmed appointments that convert to completed inspections and satisfied customers across diverse market segments. Performance bonuses available based on appointment confirmation rates, customer satisfaction scores, and conversion metrics in major metropolitan markets. Part-time and full-time positions available with flexible scheduling options to accommodate different lifestyle needs, family commitments, and career goals in this remote work-from-home environment that serves one of America's largest and most dynamic urban markets with exceptional growth potential.

What You'll Do: Lead and develop a team of sales representatives and canvassers covering Chicago and surrounding Cook County metropolitan markets. Responsibilities include recruiting qualified candidates from diverse backgrounds, training team members on effective approaches for multicultural urban environments, and mentoring them while maintaining your own book of business. You'll coordinate territory assignments across different neighborhoods, monitor performance metrics, and implement strategies to maximize market penetration in these diverse urban communities where cultural sensitivity and adaptability drive long-term success.

Territory Leadership Opportunity: The Chicago territory offers exceptional growth potential as our flagship metropolitan market with massive population density and strategic importance in the Midwest region. As Sales Manager, you'll oversee expansion throughout the greater Chicagoland area while building relationships with contractors, community organizations, and establishing our brand presence among homeowners who value quality restoration services. Your leadership directly impacts our success in America's third-largest city, with opportunities to develop innovative approaches for urban restoration challenges, multicultural market development, and high-density territory management that can be replicated in other major metropolitan markets nationwide.

Requirements: Proven track record in storm restoration, roofing, or related sales management with experience building and leading diverse teams in major metropolitan markets. Experience recruiting, training, and managing sales professionals who serve multicultural urban demographics and varied property types. Strong understanding of insurance processes, construction project management, and team development strategies for complex urban environments. Must be results-oriented with excellent leadership and communication skills suitable for managing teams serving diverse metropolitan markets where cultural competency, community engagement, and adaptive leadership drive sustainable business success and competitive advantages.

Compensation: Base salary plus override commissions on team production, personal sales commission from your own accounts, and performance bonuses tied to territory growth and team development success in major metropolitan markets. Company vehicle, expense account, comprehensive health benefits, and profit sharing opportunities. Career advancement to Regional Director level available for top performers who demonstrate ability to develop major urban markets, mentor diverse teams, and build sustainable business growth in complex metropolitan territories where leadership excellence, cultural competency, and strategic vision create long-term competitive advantages and exceptional earning potential throughout the greater Chicago metropolitan area and Midwest region.