Regional Account Executive

Job Description

Regional Account Executive.

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Chicago, Illinois (Remote/Field Based | $100k - $120K 1st year OTE (Base + Uncapped Commission) | Territory Sales | Commercial Growth | Relationship-Driven.

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Quick Role Snapshot.

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

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Business Development & Pipeline growth.

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• Proactively identify, pursue, and develop new commercial business opportunities through prospecting, networking, referrals, industry events, and outbound outreach.
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• Build and maintain a robust pipeline of commercial prospects and active opportunities throughout the territory.
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• Target the market segments, including multi-family residential communities, senior living facilities, managed property portfolios, and related commercial properties.
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• Develop referral relationships with contractors, service providers, and industry partners that can generate new business opportunities.
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• represent the organization at industry events, associate meetings, and networking functions to increase market visibility and expand referral channels.
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Client Engagement & Relationship Building.

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• Conduct site visits and assessments to understand client needs and identify service opportunities.
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• Develop customized proposals and solution recommendations tailored to individual property requirements.
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• Deliver presentations and recommendations to property managers, facilities leaders, and other decision-makers.
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• Negotiate agreements and secure long-term recurring service contracts.
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• Consistently generate new revenue through effective prospecting, relationship building, and account development.
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Consultative Sales.

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• Serve as a trusted advisor and primary point of contact for commercial clients.
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• Build long-term customer relationships that support retention, renewals, and account growth.
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• Identify opportunities to expand services within existing client portfolios.
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• Collaborate with operations and customer-facing teams to ensure successful onboarding and service delivery.
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Territory & Market Management.

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• Maintain accurate pipeline activity, customer interactions, proposals, and sales metrics within crms systems.
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• Track performance against individual sales goals and territory objectives.
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• Provide regular forecasting, pipeline updates, and business development reporting.
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• Monitor market activity, competitive trends, and opportunities for growth within the region.
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What We're Looking For.

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Required

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• 3+ years of B2B sales experience with a demonstrated ability to prospect, present, negotiate, and close business.
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• Experience in building and managing a territory with minimal supervision.
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• Strong prospecting, networking, and relationship-building skills
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• Excellent verbal and written communication abilities.
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• Comfortable meeting with property managers, facilities leaders, operations teams, and senior decision-makers.
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• Experience using CRM platforms to manage sales activities and pipeline development
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• Valid driver's licence and ability to travel throughout the assigned territory.
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Helpful but not required.

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

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

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

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