Regional Account Executive - Facility Services, Security & Staffing

Sizemore•Chicago, IL

1d•Remote

About The Position

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. Sizemore provides outsourced workforce and facility support solutions for commercial and industrial environments, including janitorial and facility services, security services, and 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.

Requirements

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

Nice To Haves

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

Responsibilities

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