Regional Account Executive - Chicago

Regional Account Executive

Chicago, Illinois (Remote/Field Based | $100k - $120k+ Base + Uncapped Commission | Territory Sales | Commercial Growth | Relationship-Driven.

Quick Role Snapshot

• What you'll do: Drive new business growth and develop strategic relationships across a commercial property portfolio market.
• Industry: Commercial property services, facilities, and recurring maintenance solutions.
• Territory: Chicago, Illinois
• Compensation: $100k - 120k 1st Year OTE (Base + Uncapped Commission)
• Experience Level: 3+ Years of sales or client-facing experience.
• Travel: Regular Territory travel throughout the Boston market and the surrounding region.

Why This Role Exists (Why Now)

Business Development & Pipeline Growth

• 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 the 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.

Client Engagement & Relationship Building

• 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.

Consultative Sales

• 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.

Territory & Market Management

• 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.

What We're Looking For

Required

• 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 licence and ability to travel throughout the assigned territory.

Helpful but not required.

• 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.

Ideal Candidate Profile

• True hunter mentality with a passion for developing new opportunities.
• Highly motivated, independent, and field-oriented.
• Strong business development mindset with a consultative sales approach.
• Skilled at building trust and credibility with clients over long sales cycles.
• Driven by performance, growth, and uncapped earning potential.

Compensation & Benefits

• Base Salary: $70 000 - $80 000
• Ramp -up Bonus: Up to $15 000 during the first six months based on activity and performance milestones.
• Commission: Uncapped earning potential on closed revenue
• First-Year On target Earnings: $100 000 - $120 000+
• Medical, Dental & Vision Insurance.
• 401(k) with Company Match
• Paid time off.

Why This Role is Worth Your Time

• Join a stable, growth-oriented organization with strong market positioning.
• High-autonomy territory ownership with significant earning potential.
• Opportunity to build long-term client partnerships and recurring revenue streams.
• Strong support structure from operations and leadership teams.
• Uncapped commission plan with clear performance expectations.
• Direct impact on regional growth and market expansion.