B2B Sales Executive

You should enjoy prospecting, building relationships, learning a client’s operation, uncovering real facility needs, and confidently moving opportunities from first contact through building survey, proposal, negotiation, and Closed Won. You will own the full new-business sales cycle across South Chicagoland and Northwest Indiana

City Wide Facility Solutions Chicago Shores is scaling. We need a smart, disciplined B2B Sales Executive who can create net-new logos by selling recurring janitorial and facility-maintenance services to commercial facilities of many types. This is a field-oriented business development role for someone who is comfortable initiating conversations, earning access to decision-makers, understanding operational pain, presenting solutions, and asking for the business.

• Recurring janitorial services
• Day porter and recurring support services
• Floor care and specialty cleaning
• Window, pressure washing and related recurring services
• Other recurring facility-maintenance solutions as assigned

• Manufacturing and light industrial
• Distribution, logistics and warehousing
• Medical / clinical and professional offices
• Schools, private schools and day care
• Property-managed commercial buildings
• Other qualified commercial facilities

• Prospect aggressively and intelligently for new commercial clients through phone, email, field visits, referrals, networking, research, and other outbound channels.
• Build and maintain a high-quality territory plan and target-account list based on facility fit, pain, decision-maker access, timing, and buying triggers.
• Identify and qualify real opportunities - not just names - by understanding the facility, current service model, pain points, decision process, timing, budget path, and competitive situation.
• Schedule and conduct building surveys, discovery meetings, presentations, money calls, proposal reviews, and closing conversations.
• Advance opportunities with clear, dated next steps and disciplined follow-through until they are won, lost, or intentionally nurtured.
• Communicate City Wide’s value proposition with confidence and credibility; diagnose before recommending and sell business outcomes, not just cleaning tasks.
• Use CRM rigorously and accurately. Maintain current notes, contacts, opportunity stages, close dates, next actions, and forecast information.
• Coordinate effectively with operations, account management, pricing, and leadership so what is sold can be delivered well and profitably.
• Continuously improve through coaching, role play, self-study, market intelligence, and thoughtful use of Microsoft Dynamics 365 Cloud CRM, Zoom Info, Apollo, Linked In, Copilot, ChatGPT, and other approved resources.

This role is best suited to someone who has already learned how to sell in a professional B2B environment and wants to become an exceptional commercial hunter. We value judgment, curiosity, discipline, speed of learning, follow-through, and integrity as much as raw activity.

You have the “aha” moment quickly. You absorb coaching, understand the why, and visibly apply what you learned in the next sales cycle.

You understand a prospect’s operation, identify problems, connect them to business outcomes, and add useful insight to the conversation.

You are energized by winning new clients. You handle objections, ask for commitment, create urgency without pressure, and confidently move a buyer toward a decision.

You are willing and able to cold call, email, walk into facilities, network, ask for…