Inside Sales Executive Business Listings & Activation (Digital M&A Platform)

Inside Sales Executive Business Listings & Activation (Digital M&A Platform)

Chicago, IL, USA

About the Job

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 theyve 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