Outside Sales Representative

Jobtailor

Chicago (IL)

On-site

USD 80,000 - 120,000

Full time

14 days+

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Job summary

Jobtailor in Chicago is seeking a results-driven B2B sales professional to drive outbound prospecting, build new accounts, and close multi-site partnerships in the commercial real estate space. You will manage high-velocity outreach and collaborate with internal teams to win opportunities across assigned markets.

Mandarin and English fluency are a plus; CRM experience with Salesforce or HubSpot is preferred, along with a proven track record of quota attainment and strong relationship-building

Qualifications

Minimum 2+ years in B2B sales within CRE or related fields.
Mandarin preferred; English fluency required.
Proven track record hitting quotas.
Experience selling to property management and related buyers.
Strong communication and presentation skills.

Responsibilities

Drive outbound prospecting and build new accounts.
Execute high-volume outreach and convert leads into opportunities.
Navigate complex sales cycles and close multi-site partnerships.
Identify and pursue opportunities across assigned markets.
Build relationships with property groups and portfolio owners.
Manage a high-activity pipeline with strong conversion metrics.
Close long-term, multi-site agreements through consultative selling.
Collaborate with internal teams to refine messaging.
Provide market intelligence on landlord priorities and competition.

Skills

B2B sales

Quota attainment

Relationship building

Hunter mentality

CRM proficiency

Tools

Salesforce

HubSpot

Job description

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, 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

Demonstrates expertise in B2B sales with a focus on commercial real estate and property management, leveraging strong relationship-building skills to drive high-volume outreach and close multi-site partnerships. Proficient in consultative selling and market intelligence to effectively engage property stakeholders and decision-makers.

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