Outside Sales Executive

About BrackenBox

BrackenBox is a locally owned roll-off dumpster service based in Chicago, providing reliable and sustainable waste solutions for general contractors and construction firms across the city. We pride ourselves on fast response, personalized service, and community-driven values.

What You'll Do

• Prospect & Generate Leads
  
  • Target general contractors, construction companies, and demolition firms across Chicago and downtown.
  • Conduct street-level solicitation, cold calls, site visits, networking, and referrals.‍
• Manage Full Sales Cycle
  
  • Prepare and deliver professional proposals, bids, and pricing tailored to C&D waste services.
  • Negotiate and close contracts for roll-off dumpsters and potentially compactor or portable restroom services.‍
• Territory & Account Management
  
  • Build and maintain a strong pipeline of new business while nurturing relationships with existing clients.
    
  • Meet or exceed monthly/quarterly sales targets.
  • Maintain timely and accurate activity logs in CRM systems (calls, meetings, proposals).‍
• ‍Cross-functional Collaboration
  
  • Partner with operations, dispatch, and customer service teams to ensure on-time delivery, pick-up, and client satisfaction.
  • Provide feedback on market trends, competitive positioning, and customer needs.‍
• Represent BrackenBox
  
  • Act as the face of BrackenBox at construction job sites and industry/network events.
    
  • Uphold the company's reputation for integrity, safety, and great customer service.

What We are Looking For

• 2+ years of relevant experience
• Strong prospecting skills: cold calling, field visits, networking.
• Proven track record meeting/exceeding sales goals.
• Familiarity with roll-off containers, compactor equipment, and construction site waste flows is a strong plus.
• Excellent verbal and written communication; consultative selling ability.
• Strong negotiation and closing skills.
• CRM proficiency (Salesforce, HubSpot, etc.) for pipeline management and activity tracking.
• Valid driver's license and reliable transportation for site visits throughout Chicago.
• Self-motivated and resilient with entrepreneurial drive; able to work independently in the field.
• Customer-focused, professional demeanor.

Why BrackenBox?

• Highly competitive base salary + uncapped commission.
• Comprehensive benefits: Health, Dental, Vision, 401(k) match, Paid Time Off.
• Company-funded safety training and certifications.
• Growth-oriented: Path to leadership or account management roles.
• Join a values-first, safety-conscious, community-rooted team not a faceless corporation.

How to Apply

Send your resume and a brief cover letter to careers@brackenbox.com with the subject line: Outside Sales Executive [Your Name].

We'll review your application and reach out to top candidates for phone screenings and on-site interviews.

Equal Opportunity Statement

BrackenBox is an equal opportunity employer. We celebrate diversity and are committed to crafting an inclusive environment for all employees