Booking Manager

Dream Three • New York, NY

1d • Remote

About The Position

Dream Three is hiring a freelance Booking Manager to proactively pitch and manage live performance bookings, speaking engagements, appearances, and brand deals for its Broadway and touring talent roster. The role manages engagements from outreach or inbound inquiry through negotiation, contracting, advancing, and settlement. The Booking Manager handles day-to-day outreach, negotiation, and booking workflows within approved fee floors, templates, and deal parameters; Dream Three retains final approval authority. This is a hands-on individual contributor position, with the possibility of expanding to additional artists, markets, or brand categories as the roster and the manager’s track record grow.

The engagement is hourly and paid as a 1099 independent contractor. Hours vary with booking volume and confirmed engagement dates. Evening or weekend work around confirmed engagements and occasional travel for advancing or on-site coverage may be required. Candidates may work remotely in the U.S. or in a hybrid arrangement in NYC or LA. The initial engagement and any renewal terms will be agreed upon in writing, and the opportunity is nonexclusive unless otherwise agreed. The start date is as soon as mutually agreed, with reasonable notice periods accommodated. Applicants should apply through Ashby with a résumé and a brief example of a booking, negotiation, or deal personally managed from inquiry through settlement; no cover letter is required. Dream Three is an equal opportunity employer and encourages candidates from historically underrepresented communities to apply.

Requirements

• Relevant experience in talent booking, artist management, live event or tour coordination, or a related field; typically several years, with equivalent practical experience welcome.
• A track record of proactively generating opportunities through outreach, pitching, or business development, rather than only processing inbound requests.
• 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 which matters are routine and which require escalation.
• Strong organization, negotiation, and follow-through, including the ability to manage competing holds, tight deadlines, and last-minute changes.

Nice To Haves

• 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.
• Experience with platforms comparable to Asana, Airtable, and DocuSign.

Responsibilities

• Proactively identify and pitch assigned talent to presenters, buyers, and brands suited to their routing, markets, and categories.
• Manage inbound inquiries and holds; negotiate routine terms within approved fee floors and parameters; and track offers through a decision.
• Prepare deal memos and contracts using approved templates, attach riders and usage-rights terms, and route documents for review and signature through DocuSign.
• Manage paid speaking engagements, personal appearances, and brand or endorsement deals, including usage-rights and category-conflict checks.
• Confirm show-day details, travel, and hospitality arrangements with presenters and the artist’s team.
• Reconcile fees, track invoices and payments, and file executed records in Asana or Airtable.
• Escalate below-floor fees, new brand categories, and conflicting holds early, with a recommendation.
• Coordinate reliable advancing and clear, professional communication with presenters, brands, and artist teams.

What This Job Offers

• Career Level: Mid Level
• Education Level: No Education Listed