Outside B2B Sales Executive (Commercial Facilities)

City 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 outcomesWho 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

👉 You bring the effort. We provide the framework

Benefits

What's In It For You?

• $55,000 to $65,000  base salary + unlimited commission and desired performance-based incentives (primary earnings driver). 👉 High performers will significantly outperform base salary
• Merit-based Growth and leadership Opportunities in a target rich environment
• A trusted, supportive environment that values honesty and self‑management.
• Exceptional training, mentorship, and a defined career path toward leadership or senior sales roles.
• A balanced hybrid work schedule, structure for year‑round productivity and well‑being.
• Comprehensive benefits, Industry Leading Sales Training and LMS,
• Generous monthly Vehicle Stipend, 401(k) match, and customizable QSEHRA health reimbursement.
• Company assigned iPhone & other devices

Why City Wide

• 100+ locations across the U.S. and Canada
• Largest management company in the building maintenance industry
• Proven, scalable sales model
• Clear path for growth and advancement

We reward:

• Discipline
• Execution

Important – Read Carefully

• To confirm you’ve read and understand the expectations of this role:
• 👉 Include the phrase:“I control the controllables” at the top of your application or cover message.
• Applications without this will not be considered.

Next Step

If you’re ready to:

• Own a territory
• Execute daily
• Build something meaningful

Apply now.City Wide Facility Solutions.

We don’t chase results. We build them.