Outside Sales Representative

W3Global; Illinois City (IL); On-site; USD 55,000 - 75,000; Full time

Job summary

W3Global is seeking an experienced Outside Sales Representative to generate new business opportunities across Chicago and surrounding suburbs through proactive, in-person prospecting. You will visit prospective customers, connect with CFOs, Controllers, and accounting teams, identify needs, qualify opportunities, and schedule discovery meetings and product demonstrations.

The role focuses on prospecting and appointment setting, with potential growth into demonstrations, deal management, and

Qualifications

• At least 1 year of outside sales or field sales experience.
• Proven success in generating leads, securing appointments, or meeting targets.
• Comfort with cold outreach and in-person conversations.
• Strong communication, organization, and follow-up skills.
• Ability to manage a local territory and travel across Chicago and suburbs.

Responsibilities

• Develop a pipeline of prospective customers through in-person visits, referrals, and follow-ups.
• Conduct regular prospecting, including unannounced visits to offices.
• Identify finance decision-makers and present the company’s AI-powered accounting software.
• Qualify opportunities and schedule meetings with decision-makers.
• Coordinate meeting confirmations and provide clear notes for leadership.
• Plan efficient daily routes and prioritize accounts within the territory.
• Maintain accurate CRM records of activities and next steps.
• Meet activity targets and review results with sales leadership.

Skills

Outside sales

Lead generation

Prospecting

Communication

CRM experience

Tools

CRM software

Job description

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