Sales Development Representative-Real Estate

Ready to launch your sales career? We want to talk to you .

OSG is looking for hungry, coachable recent grads to join our Sales team. You don't need years of experience — you need curiosity, drive, and a genuine passion for building relationships and solving problems.

You'll sell print, mail, and communication solutions to property management companies, HOAs, and real estate organizations. We'll teach you the industry. You bring the energy!

You'll learn the full sales cycle — from finding new prospects to closing deals and growing accounts. Day to day, that means outbound outreach, attending industry events, running needs assessments, and presenting tailored solutions to real estate decision-makers. You'll be paired with experienced teammates and supported by our production and operations teams, so you're never figuring it out alone.

What We're Looking For

• Bachelor's degree (Business, Marketing, Communications, or related field)
• Genuine interest in sales — internships, part-time sales roles, or even side hustles count
• Strong communication skills and the confidence to pick up the phone
• Organized, self-motivated, and comfortable with CRM tools and Microsoft Office
• Coachable attitude and a competitive streak
  
  

Bonus Points

• Any exposure to real estate, property management, or B2B sales
• Familiarity with print, mail, or marketing services
• You actually like talking to people
  
  

What We Offer

• Structured training and mentorship — we invest in your development
• A real book of business with cross-sell and upsell opportunities
• Territory coverage in the Chicago, IL (Midwest) or Phoenix, AZ (Southwest) markets
• Local travel for client meetings and industry events
• A team that rewards hustle, not just tenure
  
  

This role is based out of our Carol Stream, IL office or remote in Phoenix, AZ area.

Ready to break into sales with a company that'll actually teach you the craft? Apply now.

Benefits

• Health Insurance (EPO & HRA options)
• Dental Insurance
• Vision Insurance
• Short & Long Term Disability
• Flexible Spending Accounts
• Life Insurance
• Accident & Critical Illness Insurance
• Company 401(k) Matching Contribution
• Paid Time Off (PTO)
• Employee Assistance Program (EAP)
  
  

OSG offers equal employment opportunity and will not discriminate on the bases of race, religion, color, sex (including pregnancy, gender identity, and sexual orientation), parental status, national origin, age, disability, family medical history or genetic information, political affiliation, military service, or other non-merit based factors.