Entertainment & Events Manager - The Nest

ON TOP OF THE WORLD COMMUNITIES LLC•Ocala, FL

1d•Onsite

About The Position

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.

Requirements

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.
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.
Excellent written, verbal, presentation, negotiation, and relationship-management skills.
Ability to analyze ticket-sales data, attendance trends, and event financial results and translate findings into practical recommendations.
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.
Ability to work flexible hours, including evenings, weekends, holidays, and extended event days, as required by the event calendar.
Ability to work in indoor and outdoor environments; stand and walk for extended periods; and lift or move supplies up to 30 pounds with or without reasonable accommodation.
Valid Florida driver license with an acceptable driving history.

Nice To Haves

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.

Responsibilities

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.
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.
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.
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.
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.