We are looking for a proven hunter , discipline prospector and closer - not an order taker.
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
THE OPPORTUNITY
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.
WHAT YOU WILL SELL
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
WHO YOU WILL SELL TO
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
WHAT YOU WILL OWN
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, ZoomInfo, Apollo, LinkedIn, Copilot, ChatGPT, and other approved resources.
WHO WE ARE LOOKING FOR
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.
LEARNS + APPLIES QUICKLY
You have the "aha" moment quickly. You absorb coaching, understand the why, and visibly apply what you learned in the next sales cycle.
THINKS LIKE A BUSINESSPERSON
You understand a prospect's operation, identify problems, connect them to business outcomes, and add useful insight to the conversation.
ENJOYS SELLING + CLOSING
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.
PROSPECTS WITHOUT BEING CHASED
You are willing and able to cold call, email, walk into facilities, network, ask for introductions, and find creative paths to the right decision-maker
COMMUNICATES WITH EXECUTIVE PRESENCE
You write clearly, speak confidently, present well, ask strong questions, listen carefully, and represent CWCS exceptionally with clients and stakeholders.
ORGANIZED + DISCIPLINED
You plan your week, manage priorities, keep CRM accurate, prepare before meetings, honor commitments, and close loops without repeated reminders.
HIGH INTEGRITY + WORK ETHIC
You are dependable, truthful, accountable, loyal to the team, and willing to do the consistent work required to build pipeline and produce results
SCALABLE TALENT
You want to grow with a business, increase responsibility, improve your commercial judgment, and become part of a high-performance sales organization.
Requirements
Bachelor's degree required.
4+ years of professional B2B sales experience preferred; recent, demonstrable success prospecting and closing new business is strongly preferred.
Experience selling janitorial, facility services, building maintenance, outsourced commercial services, route-based services, business services, or another closely related B2B service to facility/operations/property decision-makers is highly preferred.
Demonstrated ability to prospect both inside and outside: cold calling, email outreach, field prospecting, networking, and decision-maker access.
Demonstrated ability to manage a full sales cycle from lead generation through qualification, discovery, proposal, negotiation, and close.
Comfort working in a professional office environment and proficiency with Microsoft Office / Microsoft 365, CRM systems, email, spreadsheets, presentations, and modern sales/research tools.
Valid driver's license, reliable transportation, and willingness to prospect throughout the assigned Chicago Southland / Northwest Indiana territory.
Eligible to work in the United States.
If you are a smart, resilient B2B hunter who enjoys creating opportunities, solving business problems, and winning new clients, we want to meet you.
Benefits
$75,000 + USD/year, based on experience and the applicable sales compensation structure.
Competitive benefits package including QSEHRA medical, dental and vision benefits; 401(k) with match; PTO; paid holidays; and other Company-provided benefits as applicable.
