Senior Director, Talent

MasterClass

6d•$183,000 - $220,000

About The Position

MasterClass is seeking a Senior Director of Talent to lead the talent function end to end. The role leads a team of four across talent acquisition and talent relations while carrying a personal slate of instructor bookings, especially for cohort-based programs, the podcast, and live programming. The Senior Director is the senior point of contact for talent across the company and partners with Creative, Production, Marketing, and Go-to-Market to secure instructors and steward relationships through launch and beyond. The role will lead two directors on the booking side and two in talent relations; set team coverage and capacity; negotiate and close agreements; oversee instructor relationships, approvals, and events; and build the function’s intake, deal documentation, fee benchmarks, workflows, and reporting. The position also represents the function’s work and capacity to company leadership. It requires substantial experience working with high-profile talent and their representatives, along with the ability to lead meetings with senior management, agencies, and enterprise partners.

Requirements

At least 12 years of 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 a strong player-coach track record that includes leading while carrying deals.
Ability to manage multiple projects, competing tasks, and self-directed work in a dynamic setting while consistently meeting deadlines with minimal oversight.
Fluency in deal structure, fee benchmarking, and contract terms in partnership with Business Affairs.
Experience with enterprise or brand partners that expect white-glove handling.
Extensive experience engaging with and influencing high-profile individuals and their representation.

Responsibilities

Lead and develop a team of four across talent acquisition and talent relations.
Set coverage and assignments across Core, Marquee, certificates, cohorts, podcast, and events, ensuring every line has an owner.
Arbitrate team workload, protect capacity, and escalate early when demand exceeds it.
Build a development path for the function, including a promotion track into director roles.
Run postmortems on closed deals and launched classes to improve team learning.
Personally book instructors for cohort-based programs, the podcast, and live programming, as well as overflow across classes and certificates.
Negotiate and close agreements directly with talent, agents, managers, and enterprise partners.
Set and maintain fee benchmarks and deal structures, and determine when to walk away from a deal.
Partner with senior sourcing relationships across the company to convert high-tier access into signed instructors.
Pressure-test instructor choices with Creative and Insights for brand fit, audience appeal, and commercial potential.
Oversee instructor relationships from first conversation through launch and re-engagement.
Ensure marketing, social, and editorial approvals move on time across a catalog approaching 400 instructors.
Own escalations on high-profile relationships, including relationships managed through representation.
Oversee instructor-facing events, including dinners, firesides, all-hands appearances, ERG programming, and live cohort weekends.
Partner with Go-to-Market on enterprise and brand-partner relationships requiring white-glove handling.
Own a single intake process for talent requests across the company, with a named owner and due date for each request.
Document negotiating posture, fee benchmarks, and deal terms so they can be used by colleagues who did not close the original deal.
Consolidate recurring meeting load and approval workflows, and champion thoughtful use of tools and technologies, including AI, to reduce manual coordination.
Report on slate coverage, booking pipeline, and instructor cost against plan.
Present ideas in digestible formats and pivot to meet changing priorities and deadlines.
Lead internal and external meetings with senior management, agencies, and enterprise partners.