Account Executive, SMB Growth — AI-Driven Outreach

MasterClass; Hartford (CT); Remote; USD 90,000 - 130,000; Full time

Benefits offered by this job

Equity

Medical

Dental

Vision

Flexible PTO

Other benefits

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 entire sales motion—from prospecting to close—identifying high-potential SMB accounts, developing hypotheses, and executing outreach with AI-powered automation to increase efficiency.

You will build your own book of business, move quickly with shorter sales cycles, and collaborate with leadership to define and improve the SMB sales playbook, while enjoying

Qualifications

• 3+ years of professional sales experience, including at least 2 years in a quota-c carrying software sales role.
• Hunter and builder who creates pipeline from scratch without relying on SDRs or predefined plays.
• Thrives in a high-volume, fast-moving sales environment with smaller deals and shorter cycles.
• Proficient in AI and automation to research accounts and personalize outreach.
• Entrepreneurial, curious and comfortable with ambiguity; evaluates industries and accounts to build structure.

Responsibilities

• Own the full sales cycle from prospecting to close for SMB accounts.
• Identify SMB accounts and use cases with greatest MasterClass at Work opportunity.
• Build and own your book of business with targeted outbound outreach.
• Research accounts, test messaging, sequences, and go-to-market approaches.
• Use AI to automate repetitive work and improve outreach quality and volume.
• Define and contribute to the SMB sales playbook with leadership.

Skills

Account Executive

Outbound prospecting

Quota carrying

AI in sales

Hunter mindset

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 entire sales motion—from prospecting to close—identifying high-potential SMB accounts, developing hypotheses, and executing outreach with AI-powered automation to increase efficiency.

You will build your own book of business, move quickly with shorter sales cycles, and collaborate with leadership to define and improve the SMB sales playbook, while enjoying