Account Executive - SMB, AI-Driven Growth

MasterClass; Springfield (IL); Remote; 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 build and scale our SMB sales motion for MasterClass at Work, focused on companies with up to 2,500 employees. You will own the entire sales cycle, from research to close, and create your own book of business.

You’ll run a high-volume outbound motion, use AI to research accounts and personalize outreach, and help define the SMB playbook with sales leadership. This is a builder role with growth opportunity.

Qualifications

• 3+ years of professional sales experience, including at least 2 years in a quota-carrying software sales role.
• Experience owning deals from prospecting through close.
• Comfort with building pipeline from scratch without a fixed playbook.

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.
• Build a high-volume outbound motion focused on smaller deals and shorter sales cycles, continuously testing hypotheses around targeting, messaging, sequences, and go-to-market approaches.
• Use AI and automation as a core part of your sales workflow to research accounts, personalize outreach, automate repetitive work, and increase the quality and volume of your prospecting.
• Help build the SMB sales playbook, partnering with sales leadership to determine what works, establish the right metrics, and turn successful experiments into repeatable processes for the broader team.

Skills

Hunter mentality

Builder mindset

AI proficient

Prospecting

Deal closing

Job description

MasterClass is seeking an entrepreneurial Account Executive to build and scale our SMB sales motion for MasterClass at Work, focused on companies with up to 2,500 employees. You will own the entire sales cycle, from research to close, and create your own book of business.

You’ll run a high-volume outbound motion, use AI to research accounts and personalize outreach, and help define the SMB playbook with sales leadership. This is a builder role with growth opportunity.