Just Sales Jobs
Inside Sales Executive Business Listings & Activation
Just Sales Jobs, Chicago, Illinois, United States, 60290
As an Inside Sales Representative, you will be engaging U.S. small business owners and helping them list their companies for sale on the free online platform that connects sellers with qualified buyers. This is a full-cycle outbound sales role focused primarily on new business development, with a smaller portion dedicated to supporting and managing owners after they've been onboarded. You will contact small business owners with annual revenues between $1-$30 million through high-volume cold calling and video calls, guiding them through onboarding and maintaining relationships. This is a newly created expansion role, reporting directly to the Sales Manager. The base is $50,000 plus uncapped commissions, with on-target earnings of $100,000+ in the first year.
COMPENSATION & BENEFITS
Base Salary: $50,000 with commissions
OTE (Year 1): $100,000-$130,000 (points model)
Company-paid health benefits
Stock options
laptop
Presidents Club trip awards
Company social events
Hybrid Fridays
Unlimited PTO (vacation/sick/personal under one policy)
THE COMPANY & CULTURE Our client is a fast-growing platform building a more transparent marketplace for small‑business acquisitions connecting quality owners directly with qualified buyers and simplifying the process of buying and selling. The platform features vetted, often off‑market U.S. businesses with direct owner contact across categories like software/IT, B2B services, manufacturing, logistics, and home services, and provides a single place for buyers and sellers to connect, exchange NDAs and diligence materials, and make offers reducing friction and avoiding costly middlemen. The Chicago hub in River North fosters a collaborative, with a focus on clear goals, coachability, and high‑energy teamwork.
LOCATION & WORK MODEL
Head Office: Chicago, IL (River North district)
Hybrid work model on‑site Monday to Thursday, optional WFH Fridays after training
First 6 weeks in‑office full‑time for training
Territory: National (U.S.) small business market
Hours: 44 hours per week, Monday to Friday (standard business hours)
THE PRODUCT / SERVICE / SOLUTION A free online marketplace where U.S. small‑business owners list their companies and connect directly with qualified buyers. Sellers join at no cost, and the platform centralizes the deal workflow direct messaging, NDA exchange, diligence document uploads, scheduling intro calls, and submitting offers so both sides can move fast without traditional brokers or added fees.
PROSPECTIVE CUSTOMERS / INDUSTRY FOCUS / DECISION MAKER(S) Target Clients: Owners/CEOs of U.S. small businesses with $1-$30 M in annual revenue
SALES CYCLE / ORDER VALUE / ACCOUNT SIZE Average sales cycle: 12 days from first contact to seller sign‑up (rapid onboarding).
COMPETITIVE ADVANTAGES The only free and fastest way for owners to connect with qualified buyers
TYPICAL DAY & DUTIES
High‑volume outbound (calls + short video intros) to SMB owners; convert to platform sign‑ups.
Work a list‑supplied, national pipeline (no geographic limits)
Run a clean, metrics‑driven process in HubSpot; maintain impeccable CRM.
Move fast: the typical cycle is 12 days from first touch to seller sign‑up.
Hit monthly KPIs and a points quota across onboarding, engagement, offers, and docs.
Provide light post‑listing support (login help, uploads, buyer message triage).
LEADS 100% leads supplied via internal systems
EXPERIENCE, BACKGROUND & EDUCATION REQUIREMENTS
6 months–3 years in inside sales/SDR/BDR or call‑heavy environments
Experience selling services/intangibles (Tech/SaaS/Fintech/Recruitment/Insurance, etc.) is a plus
Comfortable speaking with owner/CEO decision‑makers (often 50+), patient and personable
Strong phone presence, persistence, organization, coachable and team‑oriented
CRM proficiency (HubSpot preferred); Google Workspace basics (Docs/Sheets/Drive)
Education: College diploma
TRAINING & RAMP 23 weeks structured sales training + 12 weeks product/technical training Player‑coach leadership (Sales Manager) with mentorship from top performers Expected to be actively selling by weeks 34; fully ramped in 46 weeks
TECHNICAL SKILLS CRM: HubSpot; plus sales scripts, email templates, brochures
WHY YOU SHOULD APPLY Fast‑growing startup with transparent leadership and monthly all‑hands Clear, data‑driven path to Senior ISR (12–18 months typical) Purpose‑driven work helping owners navigate a major life transition Ambitious, energetic, curious, team‑oriented culture
OTHER SALES JOBS If this job is not ideal for you, please upload your resume for future consideration at https://justsalesjobs.recruiterbox.com/jobs/61ab37640cd048c4b78dc09bcbf58e04
Or visit our website to view other available sales jobs at https://justsalesjobs.ca/jobs/
ABOUT JUST SALES JOBS Just Sales Jobs sources and places Top Sales Talent from Toronto to Kitchener/Waterloo and Cities in between. We use Artificial Intelligence and Machine Learning technologies along with a proven hiring methodology to identify Top Sales Talent.
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COMPENSATION & BENEFITS
Base Salary: $50,000 with commissions
OTE (Year 1): $100,000-$130,000 (points model)
Company-paid health benefits
Stock options
laptop
Presidents Club trip awards
Company social events
Hybrid Fridays
Unlimited PTO (vacation/sick/personal under one policy)
THE COMPANY & CULTURE Our client is a fast-growing platform building a more transparent marketplace for small‑business acquisitions connecting quality owners directly with qualified buyers and simplifying the process of buying and selling. The platform features vetted, often off‑market U.S. businesses with direct owner contact across categories like software/IT, B2B services, manufacturing, logistics, and home services, and provides a single place for buyers and sellers to connect, exchange NDAs and diligence materials, and make offers reducing friction and avoiding costly middlemen. The Chicago hub in River North fosters a collaborative, with a focus on clear goals, coachability, and high‑energy teamwork.
LOCATION & WORK MODEL
Head Office: Chicago, IL (River North district)
Hybrid work model on‑site Monday to Thursday, optional WFH Fridays after training
First 6 weeks in‑office full‑time for training
Territory: National (U.S.) small business market
Hours: 44 hours per week, Monday to Friday (standard business hours)
THE PRODUCT / SERVICE / SOLUTION A free online marketplace where U.S. small‑business owners list their companies and connect directly with qualified buyers. Sellers join at no cost, and the platform centralizes the deal workflow direct messaging, NDA exchange, diligence document uploads, scheduling intro calls, and submitting offers so both sides can move fast without traditional brokers or added fees.
PROSPECTIVE CUSTOMERS / INDUSTRY FOCUS / DECISION MAKER(S) Target Clients: Owners/CEOs of U.S. small businesses with $1-$30 M in annual revenue
SALES CYCLE / ORDER VALUE / ACCOUNT SIZE Average sales cycle: 12 days from first contact to seller sign‑up (rapid onboarding).
COMPETITIVE ADVANTAGES The only free and fastest way for owners to connect with qualified buyers
TYPICAL DAY & DUTIES
High‑volume outbound (calls + short video intros) to SMB owners; convert to platform sign‑ups.
Work a list‑supplied, national pipeline (no geographic limits)
Run a clean, metrics‑driven process in HubSpot; maintain impeccable CRM.
Move fast: the typical cycle is 12 days from first touch to seller sign‑up.
Hit monthly KPIs and a points quota across onboarding, engagement, offers, and docs.
Provide light post‑listing support (login help, uploads, buyer message triage).
LEADS 100% leads supplied via internal systems
EXPERIENCE, BACKGROUND & EDUCATION REQUIREMENTS
6 months–3 years in inside sales/SDR/BDR or call‑heavy environments
Experience selling services/intangibles (Tech/SaaS/Fintech/Recruitment/Insurance, etc.) is a plus
Comfortable speaking with owner/CEO decision‑makers (often 50+), patient and personable
Strong phone presence, persistence, organization, coachable and team‑oriented
CRM proficiency (HubSpot preferred); Google Workspace basics (Docs/Sheets/Drive)
Education: College diploma
TRAINING & RAMP 23 weeks structured sales training + 12 weeks product/technical training Player‑coach leadership (Sales Manager) with mentorship from top performers Expected to be actively selling by weeks 34; fully ramped in 46 weeks
TECHNICAL SKILLS CRM: HubSpot; plus sales scripts, email templates, brochures
WHY YOU SHOULD APPLY Fast‑growing startup with transparent leadership and monthly all‑hands Clear, data‑driven path to Senior ISR (12–18 months typical) Purpose‑driven work helping owners navigate a major life transition Ambitious, energetic, curious, team‑oriented culture
OTHER SALES JOBS If this job is not ideal for you, please upload your resume for future consideration at https://justsalesjobs.recruiterbox.com/jobs/61ab37640cd048c4b78dc09bcbf58e04
Or visit our website to view other available sales jobs at https://justsalesjobs.ca/jobs/
ABOUT JUST SALES JOBS Just Sales Jobs sources and places Top Sales Talent from Toronto to Kitchener/Waterloo and Cities in between. We use Artificial Intelligence and Machine Learning technologies along with a proven hiring methodology to identify Top Sales Talent.
#J-18808-Ljbffr