Outside Sales Representatives, Chicago

Life Space Digital • Chicago, IL

5d • $45,000 - $68,000

About The Position

Life Space Digital is 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. The role involves developing territory strategies, cultivating new relationships, and guiding deals from prospecting through close. It is suited to a high-performing sales professional with real estate aptitude, the ability to build trust and open doors from scratch, and motivation to exceed targets in a fast-scaling environment.

Life Space Digital deploys digital screens in high-traffic office, multifamily, and retail environments, delivering content and targeted advertising to building occupants and visitors. The company partners with property owners to modernize buildings, improve tenant experiences, and create new revenue opportunities through digital media.

The representative will identify and pursue new business across assigned markets, build relationships with property groups and portfolio owners, manage a high-activity sales pipeline, and close long-term, multi-site agreements through consultative selling. The role also includes collaborating with internal teams to improve messaging and sales processes, and sharing market intelligence. The base pay range is $45,000–$68,000, with uncapped commission. Pay may vary based on job-related knowledge, skills, candidate location, and experience.

Requirements

• At least 1 year of B2B sales experience; exposure to commercial real estate, property management, multifamily, hospitality, or facility management buyers is relevant.
• Proven success in quota attainment through high-activity prospecting and relationship-building.
• Strong hunter mentality and ability to create opportunities, build trust quickly, and close deals independently.
• Excellent communication and presentation skills, including the ability to engage property executives and decision-makers.
• Comfort with ambiguity and motivation to build something from the ground up.

Nice To Haves

• Bilingual fluency in English and Mandarin is preferred; candidates without native Mandarin may be considered if they demonstrate market-relevant experience.
• Experience selling into property-related verticals, with an understanding of building management, buying decision-makers, and how to position value to property stakeholders.
• Experience with CRM systems such as Salesforce or HubSpot.

Responsibilities

• 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.
• 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, the competitive landscape, and emerging opportunities.

Benefits

• Medical coverage with employer-covered premiums up to 100%.
• Dental plan.
• Vision coverage.
• Talkspace therapy package and access to mental health support.
• Commuter benefits for in-office employees.
• Short-term disability coverage.
• 401(k) retirement savings plan with company match.
• Paid time off for vacation, personal time, and holidays.

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: No Education Listed