Entrepreneurial SMB Account Executive (AI-Driven Sales)

MasterClass; Nashville (TN); On-site; USD 94,000 - 113,000; Full time

Benefits offered by this job

Equity

Comprehensive benefits

Flexible PTO

Job summary

MasterClass is seeking an entrepreneurial Account Executive to scale our SMB sales motion for MasterClass at Work, focusing on companies with up to 2,500 employees. You will own the entire sales cycle from first touch through close, building your own book of business and leveraging AI to drive outreach.

This is a high-volume role with smaller deals and shorter cycles, requiring a hungry, creative mindset and the ability to craft your own playbook.

Qualifications

• 3+ years of professional sales experience with quota-carrying software sales experience.
• Own deals from prospecting through close.
• Hunter and builder mindset with own pipeline from scratch.

Responsibilities

• Build and own your book of business from the ground up, identifying SMB accounts and use cases with opportunity for MasterClass at Work.
• Own 100% of the pipeline and full sales cycle from research to close.
• Develop a high-volume outbound motion for smaller deals and shorter cycles; test targeting and messaging.
• Leverage AI and automation to research accounts, personalize outreach, and increase prospecting quality and volume.
• Help build the SMB sales playbook with leadership to turn experiments into repeatable processes.

Skills

Sales experience

Quota-carrying sales

New business development

AI proficiency

Outbound prospecting

Negotiation

Hunter mindset

Job description

MasterClass is seeking an entrepreneurial Account Executive to scale our SMB sales motion for MasterClass at Work, focusing on companies with up to 2,500 employees. You will own the entire sales cycle from first touch through close, building your own book of business and leveraging AI to drive outreach.

This is a high-volume role with smaller deals and shorter cycles, requiring a hungry, creative mindset and the ability to craft your own playbook.