YJ Maintenance - Senior Account Executive

HOA Talent; Chicago (IL); On-site; USD 60,000 - 110,000; Full time

Benefits offered by this job

Medical, dental, vision insurance

Front-loaded PTO

401(k) with company match up to 4%

Short-term and long-term disability

Job summary

YJ Maintenance is hiring a Senior Account Executive to lead outbound prospecting and close new commercial service contracts in the local market. You will target property managers, facility managers, and business owners to uncover needs and win opportunities, coordinating pricing and proposals.

The role requires a self-starter with persistence, strong communication, and the ability to travel within the local territory to build a robust pipeline and deliver recurring revenue.

Qualifications

• 3+ years of sales, customer-facing, field, or business development experience.
• Experience selling to property managers, HOAs, multifamily properties, or similar commercial buyers is a plus.
• CRM, spreadsheets, email, and standard business software proficiency.
• High school diploma required; college degree helpful but not required.

Responsibilities

• Prospect daily and build targeted lead lists for outbound outreach.
• Connect with property managers and other commercial buyers to uncover service needs.
• Qualify prospects, schedule site visits, coordinate pricing, and prepare proposals.
• Sell multiple service lines and cross-sell to drive new business.
• Maintain CRM records of activity, leads, opportunities, and next steps.

Skills

Self-starter

Cold calling

Communication skills

Organization

Travel willingness

Education

High school diploma

College degree helpful

Tools

CRM

Spreadsheets

Job description

YJ Maintenance - Senior Account Executive (Outbound Commercial Services Sales)

The Opportunity

YJM and Elevation Exterminating are looking for a high-energy, early-career sales professional who likes opening doors, creating conversations, and winning new business. This is a true hunter role focused on outbound prospecting and closing new commercial service customers—not managing an existing book of accounts. The right person is resourceful, competitive, comfortable hearing "no," and willing to do the consistent daily work required to build a pipeline.

What You Will Sell

You will introduce commercial clients to services provided by YJM and Elevation Exterminating, including:

• Facility and property maintenance services
• Janitorial and commercial cleaning services
• Sewer and drain services
• Preventative and recurring pest control services
• Additional commercial property services as the businesses expand

What You Will Do

• Prospect every day. Build targeted lead lists and conduct high-volume outreach through phone calls, email, LinkedIn, direct mail, walk-ins, networking, and local market visits.
• Create new opportunities. Connect with property managers, facility managers, business owners, HOA decision-makers, and other commercial buyers to uncover service needs and upcoming contract opportunities.
• Run the sales process. Qualify prospects, schedule site visits, understand needs, coordinate pricing, prepare straightforward proposals, follow up persistently, negotiate within approved guidelines, and ask for the business.
• Sell multiple service lines. Identify the best entry point for each prospect and cross-sell relevant YJ Maintenance division services (Janitorial & Commercial Cleaning, Sewer & Drain, Pest Control, and Facility Maintenance).
• Work the territory. Develop a focused local market and build route density by targeting clusters of commercial properties and businesses.
• Keep the pipeline clean. Record activity, contacts, opportunities, next steps, and expected close dates in the CRM; maintain a consistent follow-up cadence.
• Handoff new customers well. Coordinate a clean transition to operations after the sale, including scope, pricing, contacts, timing, and customer expectations.
• Learn from the market. Share customer feedback, competitor information, pricing observations, and common objections with leadership and operations.

How Success Will Be Measured

• Outbound activity: calls, emails, social outreach, in-person visits, and new contacts added
• Qualified meetings and site walks scheduled
• New opportunities and proposal value created
• Proposal follow-up speed and pipeline progression
• New customers won and new recurring revenue sold
• Close rate, average deal size, and sales cycle
• Pipeline accuracy and CRM discipline
• Territory penetration and route density

What We Are Looking For

• A self-starter with urgency, persistence, and a strong work ethic
• Comfort with cold calling, walking into businesses, and starting conversations with strangers
• A competitive, goal-oriented mindset and the resilience to handle rejection
• Clear, professional communication in person, by phone, and in writing
• Strong organization and follow-through; able to manage many prospects without losing momentum
• Coachability and willingness to follow a sales process while continuously improving
• Good judgment and a practical, customer-focused approach to solving problems
• Reliable transportation and willingness to travel throughout the local territory

Role Boundaries

This position owns new business development through signed agreement and successful operational handoff. Ongoing account management, routine service coordination, and day-to-day customer support will primarily sit with the operating teams. The Business Development Manager may help protect a new relationship during transition, but the role's core responsibility is to return to prospecting and winning the next customer.

Why This Role

• Opportunity to sell practical, recurring services that commercial properties need
• Direct exposure to business leaders and multiple growing service lines
• Clear activity and revenue goals with meaningful performance-based upside
• Room to grow as the sales organization and service platform expand

Experience & Qualifications

• 3+ years of sales, customer-facing, field, or business development experience; strong entry-level candidates are encouraged to apply
• Commercial services experience is preferred- especially facility services, janitorial, pest control, landscaping, HVAC, plumbing, restoration, security, waste, or property maintenance
• Experience selling to property managers, facility managers, HOAs, multifamily properties, retail, restaurants, offices, local government, or similar commercial buyers is a plus
• Comfort using a CRM, spreadsheets, email, and standard business software
• High school diploma required; college degree is helpful but not required

Compensation & Benefits

• Medical, dental, and vision insurance
• Front-loaded PTO (paid time off)
• 401(k) with company match up to 4%
• Company-paid short-term and long-term disability