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Director of Residential Sales

Pioneer Realty Group | Chicago, IL

Help Build the Future of an Independent Chicago Brokerage

Pioneer Realty Group is looking for an experienced, motivated real estate professional to become our Director of Residential Sales.

This is a rare opportunity to partner directly with ownership and help build the next chapter of one of Chicago's fastest-growing independent brokerages.

Working alongside Helen Bailey, Managing Broker, Co-Owner, and active member of the Lakeview Chamber of Commerce, you'll help recruit, mentor, and develop our growing residential sales team while continuing to build your own successful real estate business.

We're looking for someone with ideas, leadership, and the drive to build something that lasts.

About Pioneer Realty Group

Since 2017, Pioneer Realty Group has grown into one of Chicago's leading rental-focused brokerages with a rapidly expanding residential sales division.

Each year we help hundreds of clients rent, buy, sell, and invest in Chicago real estate while managing a growing portfolio of investment properties throughout the city.

Over the years, we've built something incredibly valuable:

• A database of 100,000+ past clients and prospects
• Strong relationships with some of Chicago's largest property owners and investors
• A steady stream of buyer and seller opportunities generated through our rental business
• Proven systems, technology, and marketing that allow agents to focus on what they do best—serving clients and closing deals

Now we're ready to take our residential sales division to the next level.

Why Now?

Over the past several years, we've intentionally invested in building the foundation of our company.

We've developed the systems, technology, marketing infrastructure, operations, and client database that many brokerages spend years trying to create.

Now it's time to invest in leadership.

Rather than simply hiring another salesperson, we're looking for someone who wants to help build the future of Pioneer Realty Group alongside ownership. You'll have a seat at the table, the ability to influence company strategy, and the opportunity to create something that will have a lasting impact on our agents, clients, and company.

If you've ever wanted the opportunity to help shape a brokerage—not just work for one—this is it.

What You'll Do

As Director of Residential Sales, you'll work directly with ownership to:

• Recruit, coach, and mentor residential sales agents
• Grow and lead Pioneer Realty Group's residential sales division
• Develop training programs, accountability systems, and sales processes
• Create recruiting and retention strategies
• Collaborate on marketing campaigns and business development initiatives
• Continue building your own personal sales business
• Help shape the long-term vision of Pioneer Realty Group

This isn't a middle-management position.

It's an opportunity to help build a brokerage.

What We Provide

You'll have the resources to succeed from day one, including:

• No desk fees. No monthly brokerage fees. No franchise fees.
• A highly competitive commission split on your own production
• Leadership compensation tied to the success and growth of the team you help develop
• Priority access to incoming company sales leads
• A monthly marketing budget that you help direct and control
• Follow Up Boss CRM
• Branded Canva Pro account
• ChatGPT Team account and AI marketing tools
• Professionally designed marketing and print materials
• Access to our proprietary rental listing database
• Administrative and operational support
• The opportunity to market directly to our database of 100,000+ past rental and sales clients

Instead of spending your time building systems from scratch, you'll have the freedom to focus on growing people, generating business, and closing transactions.

Who We're Looking For

The ideal candidate:

• Has a proven track record in residential real estate sales
• Is passionate about coaching and developing other agents
• Has leadership, recruiting, or mentoring experience
• Brings fresh ideas for marketing and business development
• Wants to build a team—not simply manage one
• Is excited to help shape the future of an independent brokerage

Why Pioneer?

We're intentionally independent.

That means decisions happen quickly, great ideas get implemented, and leadership has a direct impact on the future of the company.

You'll work side-by-side with ownership—not layers of corporate management.

You'll help determine how marketing dollars are invested, influence recruiting strategy, build company culture, and develop the next generation of successful agents.

Your success won't just be measured by your own production, but by the team and business you help build.

Ready to Build Something Great?

If you're looking for another brokerage to hang your license, this probably isn't the right opportunity.

If you're looking for the chance to help build one of Chicago's premier independent brokerages while growing your own business and creating long-term leadership opportunities, we'd love to have a confidential conversation.

Pioneer Realty Group

Chicago, Illinois

• Apply today or reach out confidentially to learn more.

Pioneer Realty Group is a family owned full-service community-based brokerage. What does that mean? A full-service brokerage means we can help you with pretty much any real estate transaction or contract. We handle rentals, sales, investments, condo deconversions, gut rehabs, and property management to name a few. A community-based brokerage means we are here to serve the people of this community.

The owners of the company live and invest in the community and we routinely participate in volunteer events. We are not a profit driven company just trying to make the next deal. Instead we want to provide the community with a trustworthy local Realtor that can service all their real estate needs and that they will continue to use and recommend. We pride ourselves in being a small, smart brokerage that offers superior services to our clients. Our agents are dedicated, hard working, and extremely knowledgeable of the local Chicago real estate market. Our office is very open with shared space for agents and dedicated work space for admins.

Take a look at our growing you tube channel to get a better idea of who PRG is and if you may be a good fit! You can find it here;
https://www.youtube.com/channel/UCmLx4fiebHvaf1ZWtBDWhTg
Here you can find several videos of construction projects managed by Pioneer
https://www.youtube.com/playlist?list=PLSL-0nxGFraCWe7krF1THdmb0cEyVTsUD
Here you can find several funny short videos starring our amazing agents
https://www.youtube.com/playlist?list=PLSL-0nxGFraAyh1SUvUSSIkRQ9WP96E0H
Want to hear what it is like to work at Pioneer Realty Group from a current agent? Check out our agent testimonials here.
https://www.youtube.com/playlist?list=PLSL-0nxGFraDiGCdbjZYKw9BlgWZC3qk0