Licensed Real Estate Sales Agent at Skyward Realty, LLC – Oak Park, Illinois

Real Estate Sales Agent – Community & Relationship Focused

Location: Oak Park, IL (serving Chicago's western suburbs)

Skyward Realty is seeking motivated real estate professionals who are passionate about helping people and want to grow their career within a structured, professional brokerage environment.

This opportunity is ideal for agents who enjoy building relationships in their community and want to focus on serving clients while operating within a well-organized system.

At Skyward Realty, we believe exceptional service should exist at every price point. Our agents represent clients with professionalism, clear communication, and thoughtful guidance throughout the entire home-buying and selling process.

We are intentionally building a boutique brokerage that prioritizes organization, client experience, and long-term relationships. Our agents benefit from a strong operational structure, professional marketing resources, and leadership support designed to help them build a sustainable real estate career.

This role is best suited for agents who appreciate structure, strong systems, and a collaborative brokerage environment designed for long-term professional growth.

The Opportunity

Skyward agents have the opportunity to:

• Build meaningful relationships with buyers and sellers in their community
• Work within a professional system that keeps transactions organized and efficient
• Focus on serving clients while operations and marketing systems support their success
• Participate in niche marketing initiatives designed to attract motivated buyers and sellers
• Collaborate with leadership to grow their business and reputation in the market

Our agents serve a wide range of clients — from first-time homebuyers to move-up buyers, relocations, and lifestyle properties — while delivering the same high level of service and care to every client.

What Makes Skyward Different

• Centralized CRM and systems — no need to build or manage your own tech stack
• Brokerage-led marketing, branding, and advertising support
• Non-selling owner leadership — no internal competition
• Clear expectations, structure, and accountability
• Multi-state growth opportunities
• A disciplined approach to building a luxury-positioned brand over time

Compensation & Earnings

This is a commission-based role.

Estimated earnings potential of $75,000+ annually at plan, based on production and market conditions. This figure represents potential earnings and is not a guaranteed salary.

$75,000+ at plan potential

• Guide buyers and sellers through the real estate process from consultation to closing
• Build relationships within the community and maintain a strong professional network
• Prospect and follow up with leads to generate new business opportunities
• Conduct buyer consultations and listing presentations
• Price, market, and negotiate real estate transactions on behalf of clients
• Coordinate showings, inspections, and transaction timelines
• Maintain organized client records within the brokerage CRM
• Represent the Skyward brand with professionalism, integrity, and excellent communication

• Active Illinois real estate license (or actively pursuing licensure)
• Strong interpersonal and relationship-building skills
• Self-motivated with a desire to grow a successful real estate career
• Professional, ethical, and service-oriented mindset
• Comfortable working within a structured brokerage environment and CRM system
• Coachable, collaborative, and growth-minded
• Interested in building a sustainable, long-term real estate career

Skyward Realty, LLC is a multi-state boutique real estate brokerage proudly serving Illinois, Indiana, and Florida. We specialize in helping clients buy and sell homes with confidence, offering concierge-level service, expert negotiation, and personalized marketing strategies. Led by an experienced Broker-Owner with nearly two decades in the industry, our team of Your Dream Home Specialists is dedicated to turning every client’s real estate goals into reality — with integrity, care, and precision.

Our Commitment

We are building a select, high-performing sales team, not a high-headcount brokerage. Our goal is to support agents at every stage of their growth while maintaining brand integrity, operational excellence, and a consistently elevated client experience.

If you are looking to grow within a structured, professional environment that values both production and standards, we invite you to apply.