SMB Account Executive — AI-Driven, High-Volume Outreach

MasterClass; Nashville (TN); Remote; USD 70,000 - 110,000; Full time

Benefits offered by this job

Equity

Medical, dental, vision benefits

Flexible PTO

Job summary

MasterClass is seeking an entrepreneurial Account Executive to build and scale our SMB sales motion for MasterClass at Work, targeting companies with up to 2,500 employees.

You’ll own the entire sales cycle—from account research and outbound prospecting through discovery, pitching, negotiation, and close. This is a high-volume, fast-moving role focused on smaller deals, with an emphasis on experimentation and AI-driven efficiency.

Qualifications

• 3+ years of professional sales experience.
• 2+ years in a quota-carrying software sales role.
• Hunter and builder who can create pipeline from scratch.

Responsibilities

• Own the full sales cycle from research to close.
• Build and manage a high-volume outbound motion for SMBs.
• Experiment with targeting, messaging, and sequences.
• Utilize AI to automate and personalize outreach.
• Help define and scale the SMB sales playbook with leadership.

Skills

3+ years sales

quota-carrying SaaS

hunter mentality

AI-enabled selling

high-volume outbound

Tools

CRM software

AI tools

Job description

MasterClass is seeking an entrepreneurial Account Executive to build and scale our SMB sales motion for MasterClass at Work, targeting companies with up to 2,500 employees.

You’ll own the entire sales cycle—from account research and outbound prospecting through discovery, pitching, negotiation, and close. This is a high-volume, fast-moving role focused on smaller deals, with an emphasis on experimentation and AI-driven efficiency.