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Salary: USD 94,000 - 110,000 / annual
MasterClass is a streaming platform offering 200+ instructors and classes across arts, entertainment, business, design, sports, writing, and more. The company is seeking an entrepreneurial Account Executive to join the MasterClass at Work team, focused on SMB and mid-market accounts up to 2,500 employees.
In this role, you will own the full sales cycle for a defined book of business, including prospecting, discovery, and closing new-logo and expansion deals with L&D, HR, and Talent Management buyers. This is positioned as 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 include:
- 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 while hitting committed sales targets
- Build a sales plan identifying which accounts, buyer personas, and verticals represent the biggest untapped revenue opportunity
- 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 sales
- Run consultative discovery calls focused on prospects' real L&D and talent priorities
- Pitch MasterClass at Work, MasterClass Certificates, and MasterClass Executive Programs to HR, L&D, and business stakeholders
- Identify and pilot new revenue streams or go-to-market approaches, including new segments, use cases, and partnership angles
- Partner with Customer Success on smooth handoffs and drive land-and-expand growth within your book
- Forecast pipeline accurately, hit quota, and flag what's working or not in the broader sales motion
- Proactively surface expansion and renewal opportunities as your book matures
MasterClass is a remote-first workforce with collaborative workspaces in San Francisco and Kitchener, Ontario, and employees across several U.S. states. The company emphasizes learning and development as core to its culture.
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 including deal qualification, discovery frameworks, and pipeline management
- High intrinsic motivation and an entrepreneurial mindset built for optimizing AI workflows
- Location eligibility: AZ, CA, CT, FL, GA, IL, MA, MI, NH, NJ, NY, NC, OH, PA, TN, TX, UT, WA, or Ontario and British Columbia, Canada
