[Hiring] Senior Director, Talent @MasterClass

Role Description

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.

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
  • 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

Qualifications

• 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

Benefits

• Equity
• Comprehensive benefits (medical, dental, vision, flexible PTO, and more)

Salary Range

$183,000 — $220,000 USD