Entry-Level Outside Sales Representative
About The Position
The Outside Sales Representative works directly with local business owners throughout Chicago and the surrounding Chicagoland area. The representative visits businesses such as convenience stores, gas stations, laundromats, restaurants, and bars to introduce vending and coin-operated equipment partnership opportunities, explain their potential benefits, and secure new equipment locations. This is an active, face-to-face field position rather than a call-center, desk, or remote job. The role involves frequent travel between businesses and developing new relationships. Compensation includes a $40,000–$60,000 annual base salary, depending on qualifications and relevant experience, uncapped commissions for qualifying new business, performance-based bonus opportunities, and a $1,000 sign-on bonus after successful completion of the probationary period. Gas, toll, and parking are reimbursed under company policy. Health-related benefits and paid time off are provided under company policy. Commission earnings depend on results and are not guaranteed.
Requirements
- Valid driver's license.
- Reliable personal vehicle for daily business travel.
- Ability to travel throughout the assigned Chicago-area territory.
- Comfort approaching businesses without scheduled appointments.
- Ability to communicate professionally with business owners.
- Basic smartphone and computer skills for tracking daily activity.
- Willingness to learn and meet performance expectations.
- Ability to complete the required background check.
- Dependable, organized, and comfortable working independently.
- Willingness to accept coaching.
- Previous sales experience is not required; customer-facing experience may be valuable.
Nice To Haves
- Experience working with customers, guests, or the public, including in retail, restaurants, hospitality, customer service, automotive services, or other public-facing roles.
- Previous sales experience.
Responsibilities
- Visit approximately 20 or more local businesses per day.
- Introduce yourself to business owners and managers.
- Explain equipment partnership opportunities.
- Ask questions to understand each business and identify potential opportunities.
- Build relationships and follow up with interested businesses.
- Learn to handle objections and confidently ask for the business.
- Plan daily driving routes and maintain records of activity.
- Work toward individual sales and activity goals.
Benefits
- Uncapped commissions for qualifying new business; earnings depend on results and are not guaranteed.
- Additional performance-based bonus opportunities.
- $1,000 sign-on bonus after successful completion of the probationary period.
- Gas, toll, and parking reimbursement under company policy.
- Health-related benefits under company policy.
- Paid time off under company policy.
- Opportunities to develop business development and territory management skills.
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What This Job Offers
Job Type
Full-time
Career Level
Entry Level
Education Level
No Education Listed
