Top Tech Jobs & Startup Jobs in Boston, MA

Own the end-to-end community experience for MasterClass Executive and Certificates cohorts, including onboarding, engagement, alumni programming, learner support, and retention. Develop community strategy, rituals, playbooks, platforms, automations, and AI-enabled workflows. Manage multiple cohorts, facilitate discussions, support learner leaders and mentors, partner on events, and use engagement insights to improve the learner experience. Requires flexibility for live programming and travel to in-person experiences.

Own MasterClass’s organic social strategy and execution, with a focus on promoting Certificates to professional audiences. Manage content across LinkedIn, Instagram, and YouTube; collaborate with Creative, Marketing, and GTM teams; develop campaigns; optimize performance using audience insights; and communicate recommendations. The role also contributes to evergreen brand initiatives and develops AI-enabled social workflows.

Guide applicants and admitted candidates from consultation through enrollment using phone and email outreach. Explain program value, fees, payment options, curriculum, and alternatives; address objections and remove enrollment blockers. Support employer-sponsored enrollment with ROI materials and communications, maintain accurate CRM pipeline notes, meet contact goals, and share recurring questions with admissions and marketing teams.

Freelance AI Project Reviewer evaluates learner submissions against detailed rubrics, makes consistent pass/fail judgments, and provides constructive written feedback. The reviewer collaborates with product and learning design teams to refine assessment criteria, compares human and AI evaluations for calibration, and documents reasoning to support consistency. This temporary role averages approximately 20 hours per week and requires independent work, strong written communication, and at least five years of assessment or educational feedback experience.