Outside B2B Sales Executive (Commercial Facilities)

Job Description

Job DescriptionCity Wide Facility Solutions – Chicago Shores (Frankfort, IL)Territory: Chicago Southland & Northwest Indiana

The Opportunity

This is not a typical sales role.

This is a disciplined, full-cycle, outside B2B sales position built for individuals who want to control their outcomes through consistent execution.

At City Wide, we don’t rely on luck, inbound leads, or personality-driven selling.
We win by controlling the controllables - through disciplined, repeatable actions that build momentum, strengthen habits, and directly increase our chances of success. These include, but are not limited to:

• Daily activity discipline
• Territory ownership
• Process-driven execution
• Relentless follow-up

Requirements

What You’ll Be Doing

You will own a defined territory across Chicago Southland and NW Indiana, operating under a structured ring-fence strategy: Prospecting primarily within a 1 - 3 mile radius of existing clients

Daily Execution Includes:

• 40+ outbound calls per day
• Consistent email and LinkedIn outreach
• 10–15+ in-field prospect visits per week
• Building and managing your pipeline in CRM (Microsoft Dynamics)
• Setting and running qualified appointments
• Managing the full sales cycle from prospecting → close

Sales is a high-activity, high-accountability base role, therefore you will be measured on execution, not just outcomes

Who This Role Is For

• 3–5 years of B2B sales experience
• Comfortable with cold outreach and field prospecting
• Coachable and open to feedback
• Not stuck in old habits or ego-driven selling
• Highly disciplined and process-oriented
• Wants to learn, improve, and apply quickly

You take ownership of:

• Your numbers in the CRM
• Your activities in the CRM
• Your growth within the team and the company
  

Who This Role Is NOT For

• Individuals who need constant direction
• Those who avoid outbound activity
• Candidates looking for inbound-only or relationship-only sales

Anyone unwilling to be measured on daily execution

Territory & Work Style

• Based in Frankfort, IL
• Territory: Chicago Southland + NW Indiana
• Field-driven role (this is NOT remote sales)

Hybrid flexibility is earned through:

• Consistency
• Trust
• Execution

Support & Resources

You will not be left alone to figure it out.

We provide:

• Sales coaching and mentorship
• Structured playbooks and systems
• CRM tools and data resources
• A robust LMS with 60+ years of knowledge, training, and best practices