Careers » The Southside Group

Careers at The Southside Group Real Estate

We’re building the most driven, community-focused real estate team in Southern Maryland.

About Our Culture

More Than a Brokerage — We’re a Family

At The Southside Group, we believe real success isn’t just measured in closings—it’s measured in trust, community impact, and the relationships we build. Our team lives by honesty, integrity, and a dedication to serving Southern Maryland homeowners with excellence.

Here, you’re not just joining a brokerage—you’re joining a network of professionals who support one another, grow together, and celebrate together.

From local events to community sponsorships and local partnerships, our commitment extends beyond the transaction—it’s about making a meaningful impact.

Why Join The Southside Group

Why Agents Choose Us

Discover the difference with The Southside Group Real Estate — where exceptional service, proven systems, and strong local roots make us the top choice for ambitious agents looking to build lasting success in Southern Maryland. Whether you’re launching your career or ready to take it to the next level, our team provides the training, tools, and culture to help you thrive.

What Sets Us Apart

Proven Lead Generation & Marketing Systems: Leverage powerful tools like Sierra CRM, ExploreMDHomes.com, and optimized Google Business strategies to generate high-quality leads and build your brand.
Robust Training & Mentorship: Access in-house coaching, mentorship, and weekly accountability programs designed to help you stay consistent and confident.
Full Operations & Marketing Support: Focus on clients while our dedicated marketing, transaction, and admin teams handle the rest.
Top-Notch Tools & Systems: Gain access to BoldTrail BackOffice, Canva templates, listing playbooks, and branded marketing materials that make you stand out.

Growth Opportunities: From leadership roles to expansion teams and joint ventures, your growth has no limits at Southside.

Proven Success You Can Trust

Award-Winning Performance: Consistently recognized as one of Southern Maryland’s top-producing teams, our results speak for themselves.
300+ Homes Sold (and Counting): Our experience and commitment deliver real results — and you’ll learn directly from top performers.
Local Market Mastery: With deep roots in Southern Maryland, our insights give you the competitive edge to serve clients better and close more deals.
Creative Marketing Excellence: Our in-house design and media team helps you showcase listings beautifully, attract attention, and stand out from the competition.
Personalized Support: From first contact to closing, we emphasize collaboration, communication, and client satisfaction — ensuring you and your clients feel supported every step of the way.

What We Offer

Training & Mentorship

Start strong with hands-on onboarding, one-on-one mentorship, and weekly growth sessions. Learn time-blocking, goal-setting, and business-building with personalized coaching every step of the way.

Marketing Support

Work like a top producer from day one. Get access to professional templates, ad campaigns, social strategies, and branding support — everything you need to stand out in today’s market.

Technology & Systems

Simplify your workflow with seamless transaction tools, CRM automation, and full admin support. Our tech stack — including BoldTrail BackOffice and Sierra CRM — keeps your business organized and efficient.

Culture & Collaboration

Join a team built on positivity, teamwork, and shared success. We celebrate wins, give back through community events, and connect through team gathering.