Remote: Account Executive (Sales)

Who we are:

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. Step into Nas’ recording studio and Gordon Ramsay’s kitchen, and go behind the big screen with James Cameron. Design your career with Elaine Welteroth, get ready to win with Lewis Hamilton, perfect your pitch with Shonda Rhimes and discover your inner negotiator with Chris Voss.

We’re looking for an entrepreneurial Account Executive to help build and scale our SMB sales motion for MasterClass at Work, focused on companies with up to 2,500 employees.

This is a builder role, not a role where you'll inherit a fully defined sales playbook.

We're looking for a hungry, creative Account Executive who wants to build their own book of business. You'll research where the opportunity is, develop hypotheses about who to target and why, experiment with outreach and automation, and own the sales cycle from first touch through close. This is a high-volume sales motion focused on smaller deals, shorter sales cycles, and companies ready to move quickly with an out-of-the-box solution. You’ll own the entire motion and help us define what great SMB selling looks like at MasterClass.

Build and own your book of business from the ground up, identifying the 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.

You have 3+ years of professional sales experience, including at least 2 years in a quota-carrying software sales role, with experience owning deals from prospecting through close.

You’re a hunter and a builder who is comfortable creating your own pipeline from scratch without relying on an SDR, established territory, or fully developed playbook.

You thrive in a high-volume, fast-moving sales environment and are energized by smaller deals, shorter sales cycles, and consistently creating new opportunities.

You’re AI proficient and naturally experimental, already using AI in your work and excited to find new ways to automate, personalize, and improve your sales motion.

You’re entrepreneurial, curious, and comfortable with ambiguity — you research industries and accounts, develop hypotheses, test new approaches, learn quickly, and build structure where it doesn't yet exist.

We are proud to be an equal opportunity workplace and are committed to equal employment opportunity regardless of race, color, religion, national origin, age, sex, marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or any other characteristic protected by applicable federal, state or local law. In addition, MasterClass will provide reasonable accommodations for qualified individuals with disabilities. If you have a disability or special need, we would like to know how we can better accommodate you.

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