Outside Sales Rep

This field-based role supports a new delivery program by recruiting local businesses to join a hub delivery partner network across targeted towns in Illinois. You will visit prospective businesses in person, present and pitch the program, qualify leads, guide them through the application process, and support community-based recruitment events. The position involves regular travel within a two-hour driving radius, close collaboration with a Field Manager and other local contractors, and active use of Salesforce to manage your pipeline.

This opportunity offers uncapped commission tied to partner conversion milestones and the chance to help shape a brand-new delivery initiative.

• Visit prospective businesses door to door in targeted towns within up to a two-hour driving distance to generate interest in the delivery partner program.
• Present and pitch the new delivery program opportunity to local businesses in a clear, compelling, and professional manner.
• Qualify prospective businesses based on program criteria and assess their fit for the delivery partner network.
• Guide qualified businesses through the full application process, providing support and answering questions to ensure accurate and timely completion.
• Lead and track all prospecting and follow-up activities in Salesforce, maintaining an organized and up-to-date pipeline.
• Collaborate closely with the Field Manager and other local contractors to plan, coordinate, and host recruitment events such as lunch-and-learn sessions and town hall meetings.
• Work with community organizations and local influencers, including chambers of commerce and economic development associations, to drive referrals and expand program awareness.
• Import and update Excel spreadsheets into Salesforce on a weekly basis to ensure accurate reporting and partner tracking.
• Provide exceptional customer service to prospective partners, addressing concerns, resolving issues, and ensuring a positive experience throughout the recruitment journey.
• Travel regularly within the assigned territory, managing daily routes efficiently to maximize business outreach and partner conversion.
• Demonstrate professionalism and a high sense of urgency in all interactions, representing the program positively in the local community.

• 12+ years of experience in sales and/or customer service.
• Proven outside/field sales experience.
• CRM experience required, with Salesforce strongly preferred.
• Strong customer service and communication skills, both in person and over the phone.
• Demonstrated ability to manage a sales pipeline and document activities in a CRM system.
• Ability to travel up to a four-hour round-trip distance on a daily basis.
• Comfort working independently in a field-based role while collaborating effectively with a remote team.
• Attention to detail and the ability to solve problems for applicants in the field.

• Prior experience in roles involving sales and/or negotiation with customers is a plus.
• Previous field sales experience is a plus.
• Professional demeanor with enthusiasm for working with others and a strong sense of urgency.
• Tech-savvy, with experience working across multiple systems and technologies.
• Strong organizational skills and the ability to manage multiple prospects and tasks simultaneously.
• Comfort hosting or supporting community events such as lunch-and-learn sessions and town hall meetings.

This is a primarily field-based position with significant time spent on the road visiting local businesses. You can expect to be on the road 45 days per week, with the remaining time spent working from home for follow-up, administrative tasks, and CRM updates. Travel is typically within a two-hour driving distance each way, up to a four-hour round trip daily. You will use Salesforce as the primary CRM platform and work regularly with Excel spreadsheets for data import and reporting.

The role includes a monthly phone stipend and mileage reimbursement. The territory includes at least one position based in North Chicago, IL and one in or near Springfield, IL. The work environment emphasizes professionalism, community engagement, and collaboration with a Field Manager and other contractors while maintaining flexibility and autonomy in managing your daily schedule.

This is a Contract position based out of Springfield, IL.

The pay range for this position is…