Sales Exec & Account Manager - Real Estate

OSG is looking for a talented individual to join our Sales team.....

OSG's Sales Executive & Account Manager - Real Estate is responsible for driving new business growth by selling print, mail, and communication solutions to real estate–related clients, with a primary focus on Property Management Companies, large Homeowners Associations (HOAs), and real estate organizations. This role identifies new prospects, builds long-term client relationships, and delivers tailored solutions that support compliance, resident communications, and operational efficiency.

Additionally the Executive will manage an established book of customers in the assigned geographic area with the ability to receive referrals, perform cross sell and upsell to those customers.

The ideal candidate is a consultative sales professional who understands the real estate or HOA environment and can confidently present print and mail services such as statements, notices, ballots, compliance mailings, and large-scale print and digital communications.

• Prospect, qualify, and close new business within the HOA, property management, and real estate sectors
• Develop and maintain a strong pipeline through outbound calls, referrals, networking, and industry events
• Conduct needs assessments to understand client communication, compliance, and mailing requirements
• Present and sell customized print and mail solutions, including variable data printing, presort mailing, and secure communications

• Build trusted relationships with board members, property managers, and real estate decision-makers
• Serve as the primary point of contact during onboarding and early implementation
• Partner with internal production and operations teams to ensure smooth execution of client programs
• Retain and grow existing accounts through upselling and cross-selling services

• Stay informed on Property Management, HOA and real estate compliance requirements related to mailings and resident communications
• Monitor market trends, competitor offerings, and client needs to identify new sales opportunities
• Accurately maintain CRM records, forecasts, and sales activity reports

• 5+ years of B2B sales experience, preferably in print, mail, or real estate–related services
• Bachelor’s degree in Business, Marketing, Communications, or a related field required or equivalent combination of education and experience.
• Proven track record of meeting or exceeding sales goals
• Strong prospecting, negotiation, and closing skills
• Excellent communication and presentation abilities
• Proficiency with CRM systems and Microsoft Office

• Experience selling to Property Management Companies, HOAs, or real estate organizations
• Knowledge of print production, mailing services, USPS regulations, or data-driven communications
• Existing relationships within the HOA or property management industry
• Consultative selling approach
• Relationship-building and account management
• Strong organizational and time-management skills
• Ability to explain complex services in clear, client-friendly terms
• Self-motivated with the ability to work independently and collaboratively
• Position located out of Carol Stream, IL Corporate Office (remote as needed)
• Territory assigned is the Midwest and Upper Midwest
• Local and regional travel may be required for client meetings and industry events
• Health Insurance (EPO & HRA options)
• 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.