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Salary: USD 183,000 - 220,000 / annual
MasterClass is a streaming platform offering 200+ instructors and classes across arts, entertainment, business, design, sports, writing, and more. The Senior Director of Talent leads the end-to-end talent function, owning instructor booking and relations across original classes, certificate programs, cohort-based programs, live events, and podcasts.
You will lead a team of four (two directors on booking, two in talent relations) while personally carrying a slate of deals, especially for the company's newest and fastest-growing product lines. You'll be the senior point of contact for talent across the organization, partnering closely with Creative, Production, Marketing, and Go-to-Market teams.
Key responsibilities include:
**Team Leadership:** Develop and lead the talent team across acquisition and relations; set coverage and assignments across all product lines; arbitrate workload and protect capacity; build career development paths and promotion tracks; run postmortems on closed deals and launched classes.
**Talent Acquisition:** Personally book instructors for cohort programs, podcasts, and live programming; negotiate and close agreements with talent, agents, managers, and enterprise partners; set and maintain fee benchmarks and deal structures; convert high-tier access into signed instructors; pressure-test instructor choices for brand fit and commercial potential.
**Talent Relations & Lifecycle:** Oversee instructor relationships from initial contact through launch and re-engagement; ensure marketing, social, and editorial approvals move on schedule across ~400 instructors; own escalations on high-profile relationships; oversee instructor-facing events (dinners, firesides, all-hands, live cohort weekends); partner on enterprise and brand-partner relationships requiring white-glove handling.
**Operations & Systems:** Own a single intake process for all talent requests company-wide with named owners and due dates; document negotiating posture, fee benchmarks, and deal terms for team reusability; consolidate meeting load and approval workflows; champion use of new tools and AI to reduce manual coordination; report on slate coverage, booking pipeline, and instructor costs.
**Requirements:**
- 12+ years professional experience in talent booking, talent relations, or representation at an agency, streamer, network, production company, or speakers bureau
- At least 4 years in a similar leadership role
- Demonstrated record of closing high-profile talent and negotiating directly with their representation
- Experience leading a team or strong player-coach track record leading while carrying deals
- Ability to manage multiple projects, juggle competing tasks, and self-direct in dynamic settings with minimal oversight
- Fluency in deal structure, fee benchmarking, and contract terms in partnership with Business Affairs
- Experience with enterprise or brand partners expecting white-glove handling
- Must present ideas clearly, pivot to changing priorities, and lead internal/external meetings with senior management, agencies, and enterprise partners
