Entertainment & Events Manager - The Nest

On Top Of The World Communities; Ocala (FL); On-site; USD 60,000 - 90,000; Full time

Job summary

On Top Of The World Communities’ The Nest at Calesa in Ocala, FL is seeking an Entertainment & Events Manager to design and execute a dynamic calendar of ticketed and community events across the campus.

You will book entertainment, manage budgets, coordinate staffing, and lead on-site event execution to balance guest experience with safety and profitability.

Qualifications

• Bachelor’s degree in hospitality, event management, marketing, communications, or related field preferred.
• Three to five years of progressive experience in event management or related field.
• Experience booking entertainment and negotiating terms is preferred.
• Proficiency with Microsoft Office, especially Excel, Word, PowerPoint, Outlook.

Responsibilities

• Develop and manage the annual event calendar with ticketed and community programming.
• Book entertainment, negotiate fees, and manage contracts with agencies, artists, and vendors.
• Plan staffing, budgets, and on-site event operations for multiple events.
• Monitor attendance, revenue, guest experience, and post-event recaps.

Skills

Budgeting

Reporting

Organization

Project management

Vendor coordination

Guest-service standards

Education

Bachelor’s degree in hospitality or related field

Tools

Microsoft Office Suite

Job description

Job Details

Job Location: OC - Ocala, FL 34481

Position Type: Full Time

Job Summary/Overview

The Entertainment & Events Manager is responsible for creating and executing a dynamic, financially sound calendar of entertainment, community programming, and special events at The Nest at Calesa. This role brings the venue to life through creative activation of the amphitheater, Faregrounds, lawns, pavilions, and other public spaces; books and manages entertainment; develops ticketing and pricing strategy; coordinates event staffing and operating plans; and leads on-site event execution. The Manager serves as the day‑to‑day owner of the event experience, balancing guest appeal, revenue generation, brand alignment, safety, and operational excellence.

Essential Duties and Responsibilities

The following statements describe the principal functions of this position and its scope of responsibility, but should not be considered an all‑inclusive listing of work requirements. Individuals may perform other duties as assigned, including work in other functional areas to cover absences or balance workload. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

Event Calendar, Programming & Creative Activation

Develop, maintain, and continuously improve the annual and rolling event calendar for The Nest, with a mix of ticketed entertainment, free community programming, family events, food and beverage activations, seasonal celebrations, sports‑viewing events, and private or partner opportunities.

Create programming concepts that activate the full Nest campus and align with its brand, guest demographics, operating capabilities, and revenue objectives.

Identify new event ideas, community partnerships, sponsorship opportunities, and repeatable signature programs that build attendance and guest loyalty.

Coordinate calendar priorities with leadership, food and beverage, marketing, facilities, security, and outside partners; avoid conflicts and ensure sufficient lead time for operational and promotional execution.

Monitor attendance, ticket sales, guest feedback, event profitability, and local market activity to refine future programming decisions.

Entertainment Booking, Negotiation & Contract Administration

Research, source, evaluate, and recommend entertainers, agents, promoters, vendors, and event partners appropriate for The Nest’s capacity, audience, budget, and brand standards.

Lead negotiations for artist fees, guarantees, deposits, technical requirements, hospitality needs, cancellation provisions, and other commercial terms within approved parameters.

Prepare deal summaries and coordinate contract review, approvals, execution, certificates of insurance, riders, invoices, deposits, and final payments in accordance with company policy.

Maintain accurate booking records, contract files, payment schedules, artist contact information, production requirements, and post‑event performance notes.

Build and maintain professional relationships with agencies, artists, promoters, local organizations, schools, sponsors, and vendors.

Ticketing, Pricing & Sales

Develop ticketing strategy for each applicable event, including ticket tiers, pricing, on‑sale timing, promotional offers, service fees, comp policies, seating or general‑admission setup, and event capacity controls.

Manage ticketing‑platform setup and accuracy, including event descriptions, ticket inventory, promo codes, reporting, refunds, guest lists, and front‑gate procedures.

Monitor sales pace, forecast attendance and revenue, recommend pricing or promotional adjustments, and communicate sales performance to leadership and marketing.

Coordinate ticketing needs with marketing campaigns, sponsorship benefits, customer‑service procedures, entry protocols, and event‑day box‑office operations.

Event Planning, Staffing & Event‑Day Leadership

Create and distribute event operating plans, timelines, site layouts, load‑in/load‑out schedules, staffing plans, guest‑flow plans, and post‑event checklists for assigned events.

Determine event staffing needs based on event type, attendance, hours, safety requirements, and service plan; schedule and brief On‑Call Event Staff and coordinate support from food and beverage, security, parking, facilities, and vendors.

Lead event‑day execution from pre‑event setup through guest departure and breakdown; serve as the central point of contact for artists, agents, vendors, staff, and internal departments.

Conduct pre‑event staff briefings covering assignments, guest‑service expectations, safety procedures, emergency protocols, venue rules, and escalation paths.

Monitor guest experience, ticketing and entry flow, parking, crowd movement, food and beverage coordination, venue cleanliness, and operational issues throughout the event; make real‑time adjustments as needed.

Prepare post‑event recaps documenting attendance, ticket revenue, expenses, incident reports, lessons learned, guest feedback, and recommendations for future events.

Financial, Compliance & Team Collaboration

Develop event budgets and forecasts; track artist costs, production expenses, ticket revenue, sponsorship revenue, and other event‑related income and expenses against approved plans.

Follow company purchasing, contract, cash‑handling, alcohol‑service, food‑safety, insurance, and recordkeeping requirements.

Ensure events comply with applicable permits, licenses, capacity limits, safety requirements, noise restrictions, and venue policies; coordinate with public safety agencies and vendors as needed.

Work collaboratively with the General Manager, Food and Beverage leadership, CBD Marketing, Facilities, Finance, Human Resources, and outside partners to achieve event and venue goals.

Perform other duties as required.

Qualifications

Education and Experience

Education and Experience: Bachelor’s degree in hospitality, event management, business, marketing, communications, or a related field preferred; equivalent combination of education, training, and relevant experience will be considered.

Three to five years of progressive experience in event management, live entertainment, venue operations, hospitality, ticketing, or a related field; experience at an amphitheater, festival, sports venue, restaurant/entertainment venue, or community destination is strongly preferred.

Demonstrated experience planning and executing events from concept through post‑event review, including budgeting, staffing, vendor coordination, and guest‑service operations.

Experience booking entertainment, negotiating commercial terms, managing contracts, or working with agents, promoters, artists, and vendors is preferred.

Technical Requirements

Proficiency with Microsoft Office Suite, especially Excel, Word, PowerPoint, and Outlook; ability to learn ticketing, scheduling, event‑management, and point‑of‑sale platforms.

Strong budgeting, reporting, organization, and project‑management skills with the ability to manage multiple events and deadlines simultaneously.

Skills and Knowledge

Strong creative judgment and understanding of programming that appeals to families, residents, athletes and visitors, and the broader Ocala/Marion County market.

Knowledge of live‑event operations, crowd flow, vendor coordination, event safety, and guest‑service standards.

Personal Attributes

Creative, entrepreneurial, and guest‑focused

Highly organized and detail‑oriented

Calm, decisive, and solutions‑oriented under pressure

Professional communicator and collaborative team leader

Strong ownership mentality and follow‑through

Honesty and integrity

Adaptable, hands‑on, and comfortable working in a dynamic event environment

Reports to

General Manager, The Nest at Calesa

Supervises

On‑Call Event Staff and event‑day team members, as assigned

Certifications and Licenses

Valid Florida Driver License with an acceptable driving history is required.

Responsible alcohol‑service certification and food‑safety/ServSafe certification preferred; may be required based on operational assignments.

First Aid/CPR/AED certification preferred or willingness to obtain within the timeframe established by company policy.