Outside Sales Representative

Location: Chicago and surrounding suburbs - Field-Based

Job Type: Full-Time, W-2

Travel: Reliable personal vehicle required; mileage and business-related expenses covered

About The Role We are seeking an experienced Outside Sales Representative to generate new business opportunities across Chicago and the surrounding suburbs through proactive, in-person prospecting.

The company provides AI-powered accounting software to construction and manufacturing companies. In this role, you will visit prospective customers, connect with CFOs, Controllers, and accounting teams , identify their needs, qualify opportunities, and schedule discovery meetings and product demonstrations.

The initial focus will be on prospecting and appointment setting . Strong performance can lead to expanded responsibilities in demonstrations, deal management, closing, and potentially leading a regional sales team.

Responsibilities

• Develop a pipeline of prospective customers through business visits, cold outreach, referrals, and consistent follow-up.
• Conduct regular in-person prospecting, including unannounced visits to corporate offices.
• Identify finance decision-makers, introduce the company's solutions, and uncover relevant accounting challenges.
• Qualify opportunities and schedule meetings with appropriate decision-makers.
• Coordinate meeting confirmations and provide clear prospect notes for sales leadership.
• Organize efficient daily routes and prioritize accounts across the assigned territory.
• Maintain accurate contact information, activities, and next steps in the CRM.
• Meet agreed activity and qualified-meeting targets and review results with sales leadership.

Qualifications

• At least 1 year of experience in outside sales, field sales, business development, or another sales role involving proactive customer acquisition.
• Demonstrated success generating leads, securing appointments, or meeting sales targets.
• Confidence conducting cold outreach and initiating face-to-face business conversations.
• Strong communication, objection-handling, organization, and follow-up skills.
• Ability to manage a local territory and work independently.
• Experience using a CRM or similar system to track sales activity.
• Valid driver's license and reliable, insured personal vehicle.
• Ability to travel regularly throughout Chicago and surrounding suburbs during business hours.

Preferred Experience B2B field sales experience is preferred. Experience selling business services, payroll, staffing, merchant services, telecom, industrial products, software, or accounting solutions is relevant.

Prior software or accounting industry experience is helpful but not required.

How We'll Measure Success

Success Will Be Measured Through

• Qualified meetings that take place
• Relevant business relationships developed
• Consistent prospecting activity
• Strong follow-through
• Development of meaningful sales opportunities