Job Description
Job Description
Launch or Level-Up Your Real Estate Career with Pioneer Realty Group
Location: Lakeview | Chicago, IL
Status: Full-Time or Part-Time | Commission-Based
Are you just getting started in real estate—or feeling stuck at a brokerage that’s not investing in you?
At Pioneer Realty Group, we believe in building careers, not just closing deals. Whether you’re a newly licensed agent or ready to take your business to the next level, our community-rooted brokerage offers the tools, mentorship, and opportunity to help you grow into the professional you want to be.
We're not a corporate machine—we're a passionate, family-owned brokerage founded by a husband-and-wife team who understand what it means to hustle. Our leadership team brings decades of combined experience in property management, investment, and residential real estate, and they're ready to guide you from day one.
Why Join Pioneer?
-
Mentorship That Moves the Needle
Learn directly from experienced leaders like Helen Bailey (MBA, Real Estate Finance) and Sean Flynt (12+ years in property management), plus hands-on coaching from active leasing and sales professionals who started where you are now. -
Close Deals Fast – Even as a New Agent
Gain immediate access to our exclusive rental unit database, giving you a competitive edge in Chicago’s fast-paced market. -
From Leasing to Lifetime Clients
We don’t just teach you how to lease—we show you how to build a book of business that converts to buyers, sellers, and investors over time. -
Real Estate with Purpose
We're deeply involved in the neighborhoods we serve. From Sean’s tenant-first management philosophy to Helen’s work on the Lakeview SSA, we believe in doing well by doing good. -
Multiple Paths for Growth
Look at Savannah Whittington, who started with rentals and has since grown into a top-producing sales agent, thanks to mentoring and support that helped her build a client base from the ground up.
Meet the Management & Mentor Team
At Pioneer, you won’t be left figuring it out alone. Get to know the people who will actually help shape your journey:
-
Helen Bailey – Managing Broker
www.chicagoprg.com/helen-bailey
Strategic thinker, community advocate, and the brains behind our growth-oriented approach to real estate. -
Sean Flynt – Co-Founder & Property Manager
www.chicagoprg.com/sean-flynt
12+ years of boots-on-the-ground experience in leasing and investment—he’s walked the talk. -
Jon Hamilton – Property Manager
www.chicagoprg.com/jon-hamilton
Operational wizard and expert in keeping client satisfaction and building performance aligned. -
Ryan Anguilm – Leasing Director
www.chicagoprg.com/ryan-anguilm
Mentor and motivator who helps new agents hit the ground running and build confidence fast. -
Savannah Whittington – Director of Sales
www.chicagoprg.com/savannah-whittington
A top closer who started where you are—now mentoring others to build high-trust, high-volume businesses. -
Matt Byrne – Leasing Manager
www.chicagoprg.com/matthew-byrne
Chicago native with serious hustle and a heart for helping people find home.
Pro Tip: Check out their bios and social media to get a feel for their vibe—these are the people you’ll actually be learning from and working with every day.
What You’ll Do
-
Help clients find and lease apartments across Chicago
-
Learn how to nurture long-term buyer/seller relationships
-
Conduct showings, write contracts, and negotiate deals
-
Build your network and reputation with our support
-
Work from our Lakeview office or in the field
What You Need
-
Illinois Real Estate License (or a plan to get one—we’ll guide you)
-
A desire to grow your business and learn the industry inside-out
-
Great communication skills and a commitment to follow through
-
A car, smartphone, and laptop—and the motivation to use them daily
Perks & Support
-
Competitive commissions (earn what you put in)
-
Real, daily mentorship and one-on-one coaching
-
Access to exclusive property listings and a proprietary lead database
-
Supportive, collaborative culture that celebrates your wins
-
Flexible scheduling—run your day, your way
-
Marketing and tech tools to help you stand out
Ready to Start—or Restart—Your Real Estate Career?
Let’s talk about your future with Pioneer Realty Group.
Apply now by visiting:
www.chicagoprg.com/work-with-us
or email your resume to: Careers@ChicagoPRG.com
Want to learn more about us?
Follow us on social to get a behind-the-scenes look:
LinkedIn: www.linkedin.com/company/pioneer-realty-group
Facebook: www.facebook.com/ChicagoPRG
YouTube: www.youtube.com/@pioneerrealtygroup2504/videos
Company DescriptionPioneer 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
Company Description
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. \r\n\r\nThe 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. \r\n\r\nTake 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;\r\nhttps://www.youtube.com/channel/UCmLx4fiebHvaf1ZWtBDWhTg\r\nHere you can find several videos of construction projects managed by Pioneer\r\nhttps://www.youtube.com/playlist?list=PLSL-0nxGFraCWe7krF1THdmb0cEyVTsUD\r\nHere you can find several funny short videos starring our amazing agents\r\nhttps://www.youtube.com/playlist?list=PLSL-0nxGFraAyh1SUvUSSIkRQ9WP96E0H\r\nWant to hear what it is like to work at Pioneer Realty Group from a current agent? Check out our agent testimonials here.\r\nhttps://www.youtube.com/playlist?list=PLSL-0nxGFraDiGCdbjZYKw9BlgWZC3qk0