Short Term Rental Property Manager Jobs in Wheeling, IL

Property Management Sales Representative

Company Description

Hearth Property is an AI-first, full-service property management company serving rental property owners throughout the San Francisco Bay Area.

We manage short-term, mid-term, and long-term rental properties from end to end, including pricing, marketing, leasing, guest and tenant communication, turnovers, maintenance coordination, compliance, and owner reporting.

Our clients are rental property owners who want the income from their properties without the operational burden. Hearth combines local expertise, modern technology, and hands-on service to deliver a simpler and more profitable ownership experience.

We are building a high-performance sales team to help more property owners discover and sign with Hearth.

Role Description

This is a full-time, performance-driven sales role focused on acquiring new properties for Hearth to manage.

The Property Management Sales Representative will prospect rental property owners, identify qualified opportunities, conduct discovery calls, explain Hearth’s management services, follow up consistently, and help property owners execute management agreements.

This is not a traditional residential real estate role focused on representing buyers or sellers. Your primary objective is to sign qualified rental properties under management.

The position is hybrid and based in the San Francisco Bay Area, with a combination of remote prospecting, phone and video sales calls, local meetings, and occasional property walkthroughs.

Responsibilities

• Prospect rental property owners through outbound calls, email, text, social media, referrals, networking, and local outreach.
• Respond quickly to inbound leads and maintain consistent follow-up until a clear decision is reached.
• Conduct discovery calls to understand each owner’s property, current management situation, goals, and operational challenges.
• Present Hearth’s short-term, mid-term, and long-term property management services.
• Build trust with property owners and clearly communicate Hearth’s value, fees, process, and expectations.
• Overcome objections and guide qualified owners through the decision-making process.
• Secure signed property management agreements and completed onboarding information.
• Maintain accurate lead, activity, follow-up, and pipeline records in Hearth’s CRM.
• Develop referral relationships with real estate agents, lenders, contractors, investors, and other professionals who work with rental property owners.
• Coordinate with Hearth’s operations team to ensure a clean handoff after a property is signed.
• Meet defined daily activity, appointment, pipeline, and signed-door targets.

Qualifications

• Proven ability to generate leads, conduct outbound prospecting, and close sales.
• Strong phone presence and confidence speaking with property owners and real estate investors.
• Persistent and disciplined follow-up habits.
• Ability to build trust quickly and communicate complex services clearly.
• Comfortable discussing pricing, contracts, property performance, and operational challenges.
• Self-directed, competitive, accountable, and motivated by measurable results.
• Strong organizational and time-management skills.
• Comfortable using CRM systems, dialers, email, text, video conferencing, and other sales technology.
• Reliable transportation and willingness to travel locally for qualified opportunities.
• Previous experience in property management, real estate, home services, insurance, SaaS, financial services, or another consultative sales environment is beneficial.
• A California real estate license is helpful but not required for this sales position.

What Success Looks Like

Success in this role is measured by qualified owner conversations, appointments held, management agreements signed, and total rental doors added to Hearth’s portfolio.

The strongest candidates will be proactive salespeople who create opportunities rather than wait for leads, follow up longer than competitors, and are comfortable being paid based on performance.

Compensation

Competitive performance-based commission with substantial earning potential tied to qualified properties signed under management. This is a commission only role.

Specific compensation structure will be discussed during the interview process.

Ideal Candidate

You may be a strong fit if you are:

• A salesperson who wants direct control over your income.
• A real estate professional looking for a more repeatable sales opportunity.
• A business development representative who is comfortable with outbound prospecting.
• An investor or property management professional who understands rental owners.
• An ambitious closer who wants to help build an early-stage sales organization rather than inherit a mature corporate process.