OutsideSales Representative in Chicago + Drive Revenue & Grow Your Career

Join our dynamic team in Chicago as an Outside Sales Representative and become the engine driving our client acquisition and market expansion. We’re seeking a proactive, relationship-focused sales professional ready to leverage their skills to generate significant new business and build lasting partnerships. This is your opportunity to thrive in a fast-paced environment, make a tangible impact, and accelerate your sales career with a leading organization.

About the Role

As an Outside Sales Representative, you will be the face of our company, actively prospecting and cultivating relationships with potential clients across the Chicago metropolitan area. Your core responsibility will be to identify new business opportunities, understand client needs, and effectively present our solutions to convert prospects into loyal customers. You’ll utilize a strategic mix of outbound calling, targeted outreach, and personalized in-person meetings to build a robust pipeline and consistently meet/exceed ambitious sales targets. This role demands initiative, resilience, and a genuine passion for driving revenue growth from scratch.

Drive Revenue & Build Relationships

• Proactively identify and qualify new business opportunities within the Chicago market.
• Develop and maintain a deep understanding of client industries, challenges, and decision-making processes.
• Deliver compelling product/service presentations and demonstrations to secure sales agreements.
• Build and nurture long-term relationships with key clients, ensuring satisfaction and fostering repeat business.
• Collaborate effectively with internal teams (Marketing, Product) to refine sales strategies and support client needs.

Requirements

We’re looking for a candidate with a proven track record in outside sales and a genuine desire to excel. The ideal Outside Sales Representative possesses:

Essential Qualifications

• 2+ years of verifiable experience in outside sales, specifically within a B2B environment.
• Demonstrated success in consistently meeting and exceeding individual sales quotas.
• Exceptional communication, presentation, and negotiation skills.
• Proven ability to prospect effectively using a variety of channels (phone, email, in-person).
• Strong organizational skills, self-motivation, and the ability to work independently with minimal supervision.
• Ability to travel locally within the Chicago area as required.
• Bachelor’s degree preferred.

Benefits

We offer a competitive compensation package designed to reward your hard work and support your well-being, including:

Competitive Compensation

• Base salary plus a highly competitive commission structure (target: $45,000 – $65,000 USD/year based on experience and performance).
• Comprehensive health, dental, and vision insurance plans.
• Retirement savings plan with company match.
• Generous paid time off and company holidays.
• Professional development opportunities and training programs.
• Company vehicle or substantial vehicle allowance.
• Performance-based bonuses and incentives.

Career Growth

We are committed to your long-term success. This role provides a clear path for advancement into senior sales positions, sales management, or specialized roles within our organization, fueled by your performance and potential.

If you are a driven, results-oriented Outside Sales Representative ready to make a significant impact in Chicago and grow your career with a dynamic company, we want to hear from you. Submit your resume and a compelling cover letter outlining your sales achievements today.