Outside Sales Representatives (Chicago)

What We Offer

• Healthcare: Medical coverage to keep you and your family healthy (employer covered premiums up to 100%)
• Dental: Comprehensive dental plan
• Vision: Vision coverage for eye care and eyewear
• Talkspace Therapy Package: Access to mental health support
• Commuter Benefits: Assistance for in-office employees’ commuting costs
• Short-Term Disability: Financial protection in case of temporary disability
• 401(k): Retirement savings plan with company match
• Paid Time Off (PTO): Generous leave for vacation, personal time, and holidays

Responsibilities

• Drive outbound prospecting and relationship-building with new accounts
• Navigate complex sales cycles and close multi-site partnerships
• Identify and pursue new business opportunities across assigned markets
• Build relationships with property groups and portfolio owners from initial contact through partnership
• Manage a high-activity pipeline with strong conversion metrics and deal velocity
• Collaborate with internal teams to refine messaging and improve sales processes
• Provide market intelligence on landlord priorities, competitive landscape, and emerging opportunities

Requirements

• 2+ years of B2B sales experience, ideally with exposure to commercial real estate, property management, multifamily, hospitality, or facility management buyers
• Bilingual fluency in English and Mandarin is preferred; candidates without native Mandarin may be considered if they demonstrate market relevant experience
• Proven success in quota attainment through high-activity prospecting and relationship building
• Experience selling into property-related verticals preferred — you understand how buildings are managed, who makes buying decisions, and how to position value to property stakeholders
• Strong hunter mentality with the ability to create opportunities, build trust quickly, and close deals independently
• Excellent communication and presentation skills with the ability to engage property executives and decision-makers
• Comfortable with ambiguity and motivated by the opportunity to build something from the ground up
• Experience with CRM (Salesforce, Hubspot) systems preferred

Qualifications

• Not specified

Skills

• Not specified

Benefits

• Healthcare: Medical coverage to keep you and your family healthy (employer covered premiums up to 100%)
• Dental: Comprehensive dental plan
• Vision: Vision coverage for eye care and eyewear
• Talkspace Therapy Package: Access to mental health support
• Commuter Benefits: Assistance for in-office employees’ commuting costs
• Short-Term Disability: Financial protection in case of temporary disability
• 401(k): Retirement savings plan with company match
• Paid Time Off (PTO): Generous leave for vacation, personal time, and holidays

Pay

• The base pay range for this position is $54,000-$81,000 with an uncapped commission structure.

Schedule

• Not specified