Technical Paid Booking Manager Dream Three New York, NY US 10/20/2026

Playbill, Inc.; New York (NY); Hybrid; USD 34,000 - 62,000; Full time

Job summary

Playbill, Inc. is seeking a freelance Booking Manager to proactively pitch and manage live performance bookings, speaking engagements, appearances, and brand deals for our Broadway and touring talent roster.

You’ll shepherd engagements from outreach through negotiation, contracting, advancing, and settlement, using approved templates and fee floors. You are a sharp negotiator with meticulous follow-through, comfortable coordinating with presenters, brands, and internal teams.

Qualifications

• Experience in talent booking or live events.
• Proven negotiation and contract-follow-through under deadlines.
• Ability to manage deal memos, riders and usage rights.
• Comfort with escalation and quick decision-making.

Responsibilities

• Outreach + Pitching: Proactively identify and pitch assigned talent to presenters, buyers and brands that fit their routing, market and category.
• Inquiry + Negotiation: Manage inbound inquiries and holds; negotiate routine terms within approved fee floors and parameters; track offers to a decision.
• Contracting + Deal Memos: Prepare deal memos and contracts from approved templates; attach riders and usage rights terms; route for review and signature through DocuSign.
• Speaking, Appearances + Brand Deals: Manage non-performance engagements - paid speaking, personal appearances, keynotes, and brand/endorsement deals - including usage rights and category conflict checks.
• Advancing + Logistics: Confirm show-day details, travel and hospitality arrangements with presenters and the artist's team.
• Settlement + Closeout: Reconcile fees, track invoices and payments, and file the executed record in Asana/Airtable.

Skills

Negotiation

Outreach

Organization

Communication

Tools

Asana

Airtable

DocuSign

Job description

ROLE OVERVIEW

We're hiring a freelance Booking Manager to proactively pitch and manage live performance bookings, speaking engagements, appearances and brand deals for our Broadway and touring talent roster. You'll move each engagement from outreach or inbound inquiry through negotiation, contracting, advancing and settlement, working within approved fee floors and templates. Dream Three sets deal parameters and final approval authority; you own the day-to-day outreach, negotiation and booking workflow. This is a hands-on individual contributor role for someone who combines sharp negotiation instinct, meticulous follow-through, and comfort coordinating across presenters, brands and internal stakeholders. There's room to grow into additional artists, markets or brand categories as the roster and your track record expand.

WHAT SUCCESS LOOKS LIKE

• A steady pipeline of proactive pitches runs alongside inbound inquiries for each assigned artist.
• Confirmed engagements are accurately documented, negotiated within approved parameters, and settled with few avoidable discrepancies.
• Holds are resolved on schedule; nothing is represented as confirmed before it is.
• Contracts, riders and usage rights terms are prepared accurately from approved templates and executed without unnecessary back-and-forth.
• Presenters, brands and artist teams receive a reliable advance and clear, professional communication throughout.
• You escape below-floor fees, new brand categories, or conflicting holds early, with a recommendation rather than just a question.

WHO YOU ARE

• You're a self-starter who goes looking for the next opportunity rather than waiting for the phone to ring.
• You are a sharp, organized negotiator who closes loops rather than leaving them open.
• You bring precision to paperwork - deal memos, riders, usage rights - and don't let details slip.
• You stay calm under competing holds, tight deadlines and last-minute changes.
• You know the difference between a routine call you can make yourself and one that needs to go to the principal.
• You welcome direct feedback and take ownership of your negotiations and their outcomes.

KEY RESPONSIBILITIES

• Outreach + Pitching: Proactively identify and pitch assigned talent to presenters, buyers and brands that fit their routing, market and category.
• Inquiry + Negotiation: Manage inbound inquiries and holds; negotiate routine terms within approved fee floors and parameters; track offers to a decision.
• Contracting + Deal Memos: Prepare deal memos and contracts from approved templates; attach riders and usage rights terms; route for review and signature through DocuSign.
• Speaking, Appearances + Brand Deals: Manage non-performance engagements - paid speaking, personal appearances, keynotes, and brand/endorsement deals - including usage rights and category conflict checks.
• Advancing + Logistics: Confirm show-day details, travel and hospitality arrangements with presenters and the artist's team.
• Settlement + Closeout: Reconcile fees, track invoices and payments, and file the executed record in Asana/Airtable.

ROLE REQUIREMENTS

• Relevant experience in talent booking, artist management, live event/tour coordination, or a related field - typically several years; equivalent practical experience is welcome.
• A track record of proactively generating opportunities - not just processing what comes in - through outreach, pitching or business development.
• Evidence of accurate negotiation, contract preparation and follow-through under real deadlines.
• Comfort with deal memos, riders, usage rights language and standard entertainment contract structures.
• Sound judgment about what's routine and what needs escalation.

TOOLS YOU'LL USE

• Asana, Airtable, DocuSign, and designated business-administration tools. Experience with comparable platforms is welcome.

PLUSES

• Experience booking or representing performers, speakers or brand talent.
• Familiarity with tour routing, rider negotiation or entertainment usage rights terms.
• Existing relationships with presenters, buyers or brand partners in relevant markets.

ADDITIONAL DETAILS

• Engagement: Freelance, hourly, 1099 independent contractor.
• Pay: Starting pay reflects demonstrated skills and relevant experience.
• Hours: Actual hours flow with booking volume and confirmed engagement dates.
• Flexibility: Evening/weekend work around confirmed engagements and occasional travel for advancing or on-site coverage may be required.
• Location: Remote (U.S.) or Hybrid (NYC/LA) candidates are welcome.
• Term: The initial engagement and any renewal terms are agreed upon in writing. This is a nonexclusive freelance opportunity unless otherwise agreed.
• Start Date: As soon as mutually agreed; reasonable notice periods accommodated.

SALARY

$25.00 - $45.00 per hour

• NON-UNION