Entrepreneurial SMB Account Executive (AI-Driven)

MasterClass; Columbus (OH); On-site; USD 94,000 - 113,000; Full time

Benefits offered by this job

Equity

Medical, dental, vision

Flexible PTO

Job summary

MasterClass is seeking an entrepreneurial Account Executive for SMB sales to build and scale our MasterClass at Work program. You will own the entire sales motion—from researching target accounts to closing deals—with a focus on faster cycles and smaller, high-potential opportunities.

You will leverage AI and automation to research accounts, personalize outreach, and improve outreach efficiency, while collaborating with leadership to define key metrics and repeatable playbooks for the broader

Qualifications

• 3+ years of professional sales experience, including at least 2 years in a quota-carrying software sales role.
• Hunter and builder who creates their own pipeline from scratch without relying on an SDR, established territory, or prebuilt playbook.
• Thrives in high-volume, fast-moving sales environments with smaller deals and shorter sales cycles.
• AI proficient and eager to automate, personalize, and improve the sales motion using AI tools.
• Entrepreneurial, curious, and comfortable with ambiguity; researches industries, tests approaches, and builds structure where it doesn’t yet exist.

Responsibilities

• Build and own your book of business from the ground up, identifying SMB accounts, industries, buyer personas, and use cases with the greatest opportunity for MasterClass at Work.
• Own 100% of your pipeline and the full sales cycle—from account research and outbound prospecting through discovery, pitching, negotiation, and close.
• Develop a high-volume outbound motion targeting smaller deals and shorter sales cycles, testing targeting, messaging, sequences, and go-to-market approaches.
• Utilize AI and automation as a core part of your sales workflow to research accounts, personalize outreach, automate repetitive tasks, and increase prospecting quality and volume.
• Help build the SMB sales playbook in collaboration with sales leadership, turning experiments into repeatable processes for the broader team.

Skills

Pipeline development

Prospecting

Software sales

AI proficiency

Job description

MasterClass is seeking an entrepreneurial Account Executive for SMB sales to build and scale our MasterClass at Work program. You will own the entire sales motion—from researching target accounts to closing deals—with a focus on faster cycles and smaller, high-potential opportunities.

You will leverage AI and automation to research accounts, personalize outreach, and improve outreach efficiency, while collaborating with leadership to define key metrics and repeatable playbooks for the broader