Responsibilities

• Entrepreneurially own and build a full sales motion from the ground up selling Masterclass products to Enterprise customers.
• Prospect, qualify, negotiate, and close deals independently, ultimately hitting committed sales targets.
• Build a sales plan that identifies which accounts, buyer personas, and verticals represent the biggest untapped revenue opportunity, and go after them.
• Experiment with and adopt AI tools (Claude, Apollo, Sales Navigator, Gong, Salesforce) to build a self-sourced pipeline, and help shape how the broader team uses AI in its sales process.
• Run consultative discovery calls that get at a prospect's real L&D and talent priorities, not a scripted demo.
• Pitch MasterClass at Work, MasterClass Certificates, and MasterClass Executive Programs to HR, L&D, and business stakeholders, adapting the pitch as you learn what resonates.
• Identify and pilot new revenue streams or go-to-market approaches, including new segments, new use cases, and new partnership angles, and bring what works back to the team.
• Partner with Customer Success on a smooth handoff, then drive land-and-expand growth within your own book.
• Forecast your pipeline accurately and hit quota, and flag what's working (or not) in the broader sales motion so it can be refined.
• Proactively surface expansion and renewal opportunities as your book matures.

Requirements

• 4-8 years of full-cycle, quota-bearing SaaS sales experience with a consistent history of meeting or exceeding targets.
• Demonstrated consultative selling skills — deal qualification, discovery frameworks, and pipeline management.
• High intrinsic motivation and an entrepreneurial mindset built for optimizing AI workflows.

Benefits

• In addition to salary, we also offer equity and comprehensive benefits (medical, dental, vision, flexible PTO, and more).