AI-Driven SMB Sales Executive

MasterClass; San Francisco (CA); On-site; USD 94,000 - 113,000; Full time

Benefits offered by this job

Equity

Medical benefits

Flexible PTO

Job summary

MasterClass is seeking an entrepreneurial Account Executive to scale the SMB sales motion for MasterClass at Work, targeting companies with up to 2,500 employees. This builder role requires researching opportunities, creating targeting hypotheses, and owning the entire sales cycle from first touch to close.

The role emphasizes high-volume outbound, experimentation with messaging, and using AI to drive efficiency and deal flow. Applicants in listed U.S. locations encouraged.

Qualifications

• 3+ years of professional sales experience, including at least 2 years in a quota-carrying software sales role.
• Hunter and builder mindset with ability to create pipeline from scratch.
• Comfort with high-volume, fast-moving sales environments and smaller deals.

Responsibilities

• Build and own your book of business from the ground up, identifying SMB accounts and use cases with greatest opportunity for MasterClass at Work.
• Own 100% of your pipeline and the full sales cycle—from prospecting through discovery, pitching, negotiation, and close.
• Build a high-volume outbound motion focused on smaller deals and shorter sales cycles, testing targeting, messaging and go-to-market approaches.
• Use AI and automation to research accounts, personalize outreach, automate repetitive work, and improve prospecting quality and volume.
• Help build the SMB sales playbook with leadership to turn experiments into repeatable processes.

Skills

Account executive

Prospecting

AI proficiency

Sales cycle ownership

Tools

CRM software

Job description

MasterClass is seeking an entrepreneurial Account Executive to scale the SMB sales motion for MasterClass at Work, targeting companies with up to 2,500 employees. This builder role requires researching opportunities, creating targeting hypotheses, and owning the entire sales cycle from first touch to close.

The role emphasizes high-volume outbound, experimentation with messaging, and using AI to drive efficiency and deal flow. Applicants in listed U.S. locations encouraged.