Senior Director, Talent Booking

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. We put you in the room with the creators, thinkers, makers, and leaders who have changed the world so you can change yours.

Members get unprecedented access to 200+ instructors and classes across various fields, including Arts & Entertainment, Business, Design & Style, Leadership, Writing, and more. Step into Issa Rae’s writing session and Gordon Ramsay's kitchen. Go behind the big screen with James Cameron. Start your career with Martha Stewart. 

About The Role:

Leads the talent function end to end. Owns booking for our newest lines, leads a team of four, and is the single senior point of contact for talent across the company. Player-coach: carries a slate and leads the people who carry the rest.

Job Overview:

As Senior Director of Talent, you'll lead the team that finds, signs, and stewards the instructors behind everything we make — original classes, certificate programs, cohort-based programs, live events, and our podcast. You'll carry your own book of business, personally closing talent for our newest and fastest-growing lines, while leading two directors on the booking side and two in talent relations. You'll partner closely with Creative, Production, Marketing, and Go-to-Market to convert access into signed instructors and to keep every relationship healthy long after launch. A credible closer and a steady leader, you'll bring order to how talent demand enters the company, build the deal infrastructure this function has run without, and represent talent's work — and its limits — to company leadership.

Responsibilities:

TEAM LEADERSHIP

•   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; ensure no line runs unowned
•   Arbitrate load across the team and protect capacity; escalate early when demand outpaces it
•   Build the development path this function has not had, including a promotion track into director roles
•   Run postmortems on closed deals and launched classes to compound what the team learns

TALENT ACQUISITION

•   Personally book instructors for cohort-based programs, podcast, and live programming, plus 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 across the slate; know when to walk
•   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

TALENT RELATIONS AND LIFECYCLE

Relationship Ownership

•   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 those managed through representation

Events and Partner Programming

•   Oversee instructor-facing events: dinners, firesides, all-hands appearances, ERG programming, and live cohort weekends
•   Partner with Go-to-Market on enterprise and brand-partner relationships that expect white-glove handling

OPERATIONS AND SYSTEMS

•   Own a single intake for every talent request across the company, with a named owner and a due date
•   Document the function's negotiating posture, fee benchmarks, and deal terms so they are usable by someone who did not close the original deal
•   Consolidate recurring meeting load and approval workflows; champion thoughtful use of new tools and technologies — including AI — to reduce manual coordination
•   Report on slate coverage, booking pipeline, and instructor cost against plan

GENERAL

•   Must be able to present ideas in digestible formats, and able to pivot to meet changing priorities and deadlines
•   Extensive experience engaging with and influencing high-profile individuals and their representation
•   Ability to lead internal and external meetings with senior level management, agencies, and enterprise partners

Requirements:

•   12+ years minimum professional experience in talent booking, talent relations, or representation at an agency, streamer, network, production company, or speakers bureau, with at least 4 years in a similar leadership role
•   Demonstrated record closing high-profile talent and negotiating directly with their representation
•   Experience leading a team, or a strong player-coach track record where you led while still carrying deals
•   Adept at managing multiple projects, juggling competing tasks, and self-directing in a dynamic setting, 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 who expect white-glove handling