Senior Director of Talent

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