Account Executive – Chicago, IL

About This Opportunity

We are representing a confidential shared housing technology company seeking an Account Executive in Chicago, Illinois. Our client operates an innovative marketplace model that helps property owners generate enhanced rental income while addressing housing affordability challenges. This role focuses on engaging traditional property owners and real estate investors to participate in the platform.

As the Account Executive, you'll prospect property owners in the Chicago market, demonstrate how our client's platform consistently outperforms traditional single-family rental models, and guide owners through the onboarding process. This is a remote position requiring someone who thrives independently while making a tangible impact on housing accessibility.

Responsibilities

• Research and qualify property owners and real estate investors who would benefit from our client's platform model
• Execute multi-channel outreach strategies including cold calling, email campaigns, and networking to connect with property owners
• Conduct discovery calls and meetings to understand owner goals, financial objectives, and potential concerns
• Present customized value propositions demonstrating increased revenue potential and simplified property management
• Build trust-based, long-term relationships with property owners as a consultative advisor
• Develop tailored hosting solutions including financial modeling and property suitability assessments
• Guide prospects through decision-making, negotiate terms, and close agreements to onboard new participants
• Coordinate with internal onboarding teams to ensure smooth transitions for new property listings
• Maintain detailed CRM records tracking outreach activities, conversion metrics, and pipeline development
• Monitor Chicago real estate market trends and competitive landscape to refine positioning
• Organize educational webinars or sessions to address common questions and misconceptions

What We're Looking For

• Proven B2B or B2C sales experience, particularly in real estate or property management sectors
• Consistent track record of meeting or exceeding sales targets and quotas
• Strong relationship-building and communication skills with property owners and investors
• High level of self-motivation and discipline to excel in a remote startup environment
• Adaptability and problem-solving abilities to overcome objections and customize solutions
• Knowledge of real estate investing dynamics, rental markets, and property management principles
• Proficiency with CRM platforms (Salesforce and HubSpot experience preferred)
• Confident presentation skills for virtual meetings and live demonstrations
• Analytical capabilities to interpret market data and calculate ROI for prospects
• Collaborative approach when working with cross-functional teams including marketing and operations
• Entrepreneurial mindset with resilience to navigate a fast-paced, evolving environment
• Authorization to work in the United States (E-Verify participation required)

How We Work With You

Candidates apply directly through Get A Job.ai. Our talent team will conduct an initial screening to assess fit and answer your questions about the role. Qualified candidates are then submitted to our client for consideration. The client's interview process includes a phone screen with their PeopleOps team, video interviews with the Head of Sales and a stakeholder panel (including a case study presentation), and a final in-person meeting at a company event.

Please do not contact the client directly. All communication and coordination will be managed through Get A Job.ai to ensure a professional experience for all parties.

Pay

Pay via Get A Job.ai: The base salary for this position is $70,000 per year with an attainable commission structure. The annual commission target is set at $180,000, achieved by onboarding approximately 80 new hosts annually with specific performance milestones. Total on-target earnings potential is $250,000.

The client offers a competitive benefits package including national medical, dental, and vision coverage, company-provided life insurance, unlimited PTO with eleven observed holidays, 401(k), twelve weeks of paid parental leave, equity incentive plan, and optional FSA/DCFSA benefits.

Get A Job.ai is an equal opportunity recruiter. We welcome applicants of all backgrounds and do not discriminate based on race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status.