Regional Account Executive - Facility Services, Security & Staffing

Base Salary: $70,000-$90,000  |  Total Target Compensation: $160,000 OTE

Location: Home-office based  |  Markets: Chicago - Upper Midwest (Indy, Detroit, Minneapolis, Milwaukee)  |  Travel: Approximately 50%

Sizemore is hiring a driven Regional Account Executive to open new business in Chicago. This is a true hunter sales role for someone who knows how to build a territory, create pipeline, get in front of decision-makers, and close profitable B2B service contracts.

As a Sizemore Regional Account Executive, you will sell across Sizemore's three core service lines: facility services, security, and staffing solutions. The role offers a strong base salary, meaningful upside, multi-state territory potential, and the ability to sell multiple recurring-revenue service lines.

What You'll Sell

Sizemore provides outsourced workforce and facility support solutions for commercial and industrial environments, including:

• Janitorial and facility services

• Security services

• Staffing and workforce support

Target customers include distribution centers, manufacturing facilities, logistics operations, healthcare facilities, corporate campuses, property management groups, and other large commercial sites.

Most opportunities will focus on SMB and lower mid-market accounts, typically locations with 500+ employees, with potential for larger multi-site opportunities.

What You'll Do

You will own the new-business sales process from prospecting through close with support from the VP of Sales. Responsibilities include:

• Build a territory plan and identify high-potential target accounts

• Prospect through cold calling, email, referrals, networking, events, and local market outreach

• Meet with Facilities, Operations, HR, Procurement, Safety, Property Management, and site leadership contacts

• Conduct discovery to understand service needs, decision process, timeline, budget, and fit

• Coordinate site walks, scope reviews, and solution development with internal operations leaders

• Prepare and present proposals for facility services, security, staffing, or bundled solutions

• Negotiate terms and close new contracts

• Maintain accurate pipeline, activity, and forecast information in HubSpot

• Partner with operations after close to support a clean handoff and successful startup

This role is primarily focused on new-logo acquisition. There will be limited involvement in rebids or account support; the core expectation is to hunt, develop, and close new business.

What Makes This Role Attractive

• $70K-$90K base salary

• $160K OTE

• Multiple service lines to sell

• Recurring-revenue B2B contract model

• Large target account base across commercial and industrial markets

• Home-office based with field sales flexibility

• Multi-state territory opportunity

• No degree required

• Opportunity to help build Sizemore's presence in a growth market

What We're Looking For

The ideal candidate has:

• 2+ years of B2B sales experience

• Strong prospecting and pipeline-building ability

• Experience selling services, solutions, staffing, facility services, security, janitorial, logistics services, outsourced labor, or another recurring B2B service

• A track record of quota attainment or measurable sales success

• Comfort selling to multiple stakeholders

• Strong discovery, presentation, negotiation, and closing skills

• Experience using a CRM; HubSpot experience is a plus

• Ability to work independently from a home office

• Valid driver's license and ability to travel approximately 50% within the assigned territory

No degree is required. We care more about sales performance, discipline, and the ability to open doors and close business.

Preferred Experience

Experience in any of the following is helpful but not required:

• Facility services, janitorial services, security services, staffing, or workforce solutions

• Logistics, manufacturing, industrial, or commercial services

• Multi-site or territory-based B2B sales

• Selling to facilities, operations, HR, procurement, or property management leaders

Work Environment

This is a home-office-based field sales role. You will spend time prospecting, meeting with prospective customers, conducting site visits, networking locally, and working with internal teams to build solutions.

You must be comfortable visiting operating environments such as warehouses, distribution centers, manufacturing facilities, healthcare facilities, and corporate sites.

About Sizemore

Sizemore provides integrated facility service solutions, including facility services, security, staffing, and workforce support for commercial, industrial, logistics, healthcare, and corporate environments.

We value Flexibility, Improvement, Reliability, Safety, and Teamwork.

Equal Opportunity Employer

Sizemore provides equal employment opportunities to all associates and applicants for employment and prohibits discrimination or harassment based on any characteristic protected by federal, state, or local law.