Outside Sales Representatives, Chicago

Life Space Digital is reshaping the out-of-home media landscape through the deployment of digital screens in high-traffic office, multifamily, and retail environments. Our platform delivers content-rich experiences and targeted advertising directly to building occupants and visitors — starting in elevators, lobbies, and shopping center concourses. Backed by an experienced leadership team and aggressive growth targets, we are scaling across key U.S. markets with a focus on speed, precision, and long-term value for our partners.

We are seeking Outside Sales Representatives to drive growth across key markets by building strategic partnerships with owners, developers, and operators in the office and multifamily space. You will develop territory strategies, cultivate new relationships, and guide deals from prospecting through close. This role is suited for a high-performing sales professional with strong real estate aptitude, proven ability to open doors and build trust from scratch, and the drive to exceed targets in a fast-scaling environment.

We partner directly with leading property owners to modernize buildings, elevate tenant experience, and unlock new revenue opportunities through digital media. At Life Space Digital, we combine high design with smart technology to redefine what people expect from everyday spaces.

Your Focus in the Sales Funnel:

• Drive outbound prospecting and relationship-building with new accounts

• Execute high-volume outreach and convert leads into qualified opportunities

• Navigate complex sales cycles and close multi-site partnerships

What you'll get to do in this role:

• 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

• Close long-term, multi-site agreements through consultative selling and value demonstration

• Collaborate with internal teams to refine messaging and improve sales processes

• Provide market intelligence on landlord priorities, competitive landscape, and emerging opportunities

Who you are:

• 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

Life Space Digital offers a comprehensive benefits package for full-time employees, including:

• 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

The base pay range for this position is $60,000-$90,000 with an uncapped commission structure. Base pay offered may vary depending on job-related knowledge, skills, candidate location, and experience.