Regional Account Executive - Chicago

DWS Professional Search Group • Chicago, IL

33d • Remote

About The Position

The Regional Account Executive will drive new business growth and develop strategic relationships across a commercial property portfolio market. This role is focused on commercial property services, facilities, and recurring maintenance solutions. The position involves regular territory travel throughout the Chicago market and surrounding regions. The primary goal is business development and pipeline growth through proactive identification and pursuit of new commercial business opportunities.

Requirements

• 3+ years of B2B sales experience with a demonstrated ability to prospect, present, negotiate, and close business.
• Experience building and managing a territory with minimal supervision.
• Strong prospecting, networking, and relationship-building skills.
• Excellent verbal and written communication abilities.
• Comfortable meeting with property managers, facilities leaders, operations teams, and senior decision-makers.
• Experience using CRM platforms to manage sales activities and pipeline development.
• Valid driver's license and ability to travel throughout the assigned territory.

Nice To Haves

• Experience selling into multi-family housing, property management groups, senior living communities, facilities management, or related commercial markets.
• Background in recurring service contracts, facilities services, maintenance solutions, or similar industries.
• Existing relationships within local property management and real estate networks.
• Experience participating in industry associations and networking organizations.
• Bachelor's degree or equivalent professional experience.

Responsibilities

• Drive new business growth and develop strategic relationships across a commercial property portfolio market.
• Proactively identify, pursue, and develop new commercial business opportunities through prospecting, networking, referrals, industry events, and outbound outreach.
• Build and maintain a robust pipeline of commercial prospects and active opportunities throughout the territory.
• Target market segments including multi-family residential communities, senior living facilities, managed property portfolios, and related commercial properties.
• Develop referral relationships with contractors, service providers, and industry partners that can generate new business opportunities.
• Represent the organization at industry events, associate meetings, and networking functions to increase market visibility and expand referral channels.
• Conduct site visits and assessments to understand client needs and identify service opportunities.
• Develop customized proposals and solution recommendations tailored to individual property requirements.
• Deliver presentations and recommendations to property managers, facilities leaders, and other decision-makers.
• Negotiate agreements and secure long-term recurring service contracts.
• Consistently generate new revenue through effective prospecting, relationship building, and account development.
• Serve as a trusted advisor and primary point of contact for commercial clients.
• Build long-term customer relationships that support retention, renewals and account growth.
• Identify opportunities to expand services within existing client portfolios.
• Collaborate with operations and customer-facing teams to ensure successful onboarding and service delivery.
• Maintain accurate pipeline activity, customer interactions, proposals, and sales metrics within CRM systems.
• Track performance against individual sales goals and territory objectives.
• Provide regular forecasting, pipeline updates, and business development reporting.
• Monitor market activity, competitive trends, and opportunities for growth within the region.

Benefits

• Medical, Dental & Vision Insurance
• 401(k) with Company Match
• Paid time off
• Ramp-up Bonus: Up to $15,000 during the first six months based on activity and performance milestones.
• Uncapped earning potential on closed revenue

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: Associate degree