Account Executive (MasterClass at Work) - SMB & Mid-Market Sales

MasterClass is the streaming platform where the world’s best come together so anyone, anywhere, can access and be inspired by their knowledge and stories. Members get unprecedented access to 200+ instructors and classes across a wide variety of fields, including Arts & Entertainment, Business, Design & Style, Sports & Gaming, Writing, and more.

We’re a remote-first workforce with collaborative workspaces in San Francisco and Kitchener, Ontario, and employees in several U.S. states.

The Role

We’re seeking an entrepreneurial Account Executive to join our MasterClass at Work team, focused on SMB and mid-market accounts up to 2,500 employees. In this role, you’ll own the full sales cycle for a defined book of business—prospecting, running discovery, and closing new-logo and expansion deals with Learning & Development (L&D), HR, and Talent Management buyers. This is a great fit for someone with a couple years of quota-bearing experience who is ready to run their own book of business, with mentorship from senior AEs as they build toward a full enterprise territory.

Key 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 identifying 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.