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

MasterClass; Milton (MA); Remote; USD 85,000 - 140,000; Full time

Benefits offered by this job

Equity

Medical, dental, vision benefits

Flexible PTO

Job summary

MasterClass is seeking an entrepreneurial Account Executive to scale MasterClass at Work for SMBs up to 2,500 employees. You will own the sales cycle from first touch through close in a high-volume environment, building your own book of business and defining strategies for faster deals.

You will lead outbound initiatives, capitalize on AI-enabled workflows to personalize outreach, and collaborate with leadership to shape the SMB sales playbook and metrics.

Qualifications

• 3+ years of professional sales experience, including at least 2 years in a quota-carrying software sales role.
• Hunter and builder who can create your own pipeline from scratch.
• Thrives in high-volume, fast-moving sales environments.

Responsibilities

• Own the full sales cycle—from prospecting to close.
• Identify SMB accounts, industries, buyer personas, and use cases with the greatest opportunity.
• Develop hypotheses and experiment with outbound messaging and sequences.
• Leverage AI and automation to research accounts and personalize outreach.
• Partner with sales leadership to define metrics and turn experiments into repeatable processes for the team.

Skills

Sales prospecting

Quota carrying

Job description

MasterClass is seeking an entrepreneurial Account Executive to scale MasterClass at Work for SMBs up to 2,500 employees. You will own the sales cycle from first touch through close in a high-volume environment, building your own book of business and defining strategies for faster deals.

You will lead outbound initiatives, capitalize on AI-enabled workflows to personalize outreach, and collaborate with leadership to shape the SMB sales playbook and metrics.