Little Philly Sea Adventures Anna Maria Island & Palma Sola Bay, Florida Anticipated Start:
Mid-February 2027
Starting Position:
Part-time, with opportunity to grow into a full-time, year-round leadership role
Starting Pay:
Approximately $27/hour, based on experience
Bonus Opportunity:
Performance-based bonuses may be added as the position and business grow
Vehicle Requirement:
Candidate must own or legally control a reliable truck capable of safely towing company boats and jet ski trailers
ABOUT LITTLE PHILLY SEA ADVENTURES
Little Philly Sea Adventures creates memorable experiences on the water through boat rentals, jet ski rentals, and guided adventures for families, couples, groups, local residents, and visitors to the Anna Maria Island area. We are more than a rental company. Our goal is to make every customer feel welcomed, prepared, safe, and excited about their time on the water. Our current operation includes two pontoon boats and six jet skis serving Anna Maria Island and Palma Sola Bay. As we prepare for the 2027 season, we are looking for a dependable, experienced, hands-on Operations Manager who can take ownership of daily execution, lead the operations team, protect our equipment, and help build a more organized and scalable operation.
WE ARE RECRUITING EARLY TO FIND THE RIGHT PERSON
The anticipated start date is approximately mid-February 2027. We are recruiting early because this is not a position we intend to fill simply to fill it. This absolutely must be the right fit. The Operations Manager will be trusted with customers, employees, boats, jet skis, trailers, schedules, launch procedures, safety standards, and routine operating decisions. Experience is important, but so are character, judgment, reliability, accountability, communication, leadership, and follow-through. We are willing to take the time necessary to find someone who fits our work ethic, customer-service philosophy, and long-term direction.
POSITION OVERVIEW
This is not an office-only management position. It is a hands-on leadership role overseeing daily boat rental, jet ski rental, and guided-adventure operations throughout Anna Maria Island and Palma Sola Bay.
The position requires someone comfortable:
Working outdoors and around the water Driving a truck while towing boats and jet ski trailers Launching and retrieving boats and personal watercraft Coordinating employees and customer schedules Communicating directly with customers Monitoring weather and marine conditions Managing equipment readiness Solving operational problems in real time The right person will bring structure, organization, accountability, and calm decision-making to an operation where conditions can change quickly because of weather, traffic, equipment issues, employee availability, ramp congestion, or customer schedule changes. The Operations Manager reports directly to the owner and may make routine operational decisions within company policies. Major financial, staffing, pricing, legal, partnership, or expansion decisions remain with ownership unless specifically authorized.
CORE RESPONSIBILITIESDAILY OPERATIONS & DISPATCH
Review reservations and prepare the operating plan for each day. Review the following day's schedule in advance. Determine which boats, jet skis, trailers, employees, fuel, and supplies are needed. Coordinate equipment movement between storage, launch areas, docks, and approved delivery locations. Ensure each rental is properly staffed and employees understand arrival times, locations, and responsibilities. Coordinate launches and returns efficiently to reduce delays, unnecessary trips, fuel usage, and payroll expense. Adjust operations when bookings, weather, traffic, staffing, customer timing, or equipment conditions change. Keep ownership informed of significant cancellations, staffing issues, equipment problems, safety concerns, and customer situations. Ensure equipment is returned, inspected, secured, and prepared for the next rental. Identify potential problems before they affect customers and handle routine operational details without requiring the owner to manage every step.
OPERATING AREA
This position currently covers Anna Maria Island and Palma Sola Bay only . Responsibilities include coordinating approved launch and customer meeting locations, moving equipment between storage and launch areas, accounting for traffic, parking, tides, weather and ramp congestion, and maintaining professional relationships with local personnel, customers, and the public. Equipment may not be staged, launched, delivered, or operated in unauthorized areas. This position does not currently include Casey Key or another separate operating location.
PERSONAL TRUCK & TOWING REQUIREMENT
The Operations Manager must own or legally control a dependable truck capable of safely towing Little Philly Sea Adventures' pontoon boats and jet ski trailers. Occasional access to another person's truck is not sufficient. The approved truck must be consistently available during scheduled working hours.
The candidate must:
Maintain the truck in safe mechanical condition with current registration. Hold a valid driver's license and acceptable driving record. Have demonstrated towing and trailer-backing experience. Be comfortable launching and retrieving boats and personal watercraft. Understand trailer connections, hitches, safety chains, straps, electrical connections, lighting, tires, load security, and towing capacity. Be able to back trailers at busy ramps and in confined areas. Immediately report accidents, citations, mechanical issues, or insurance concerns affecting safe use. The truck and driver must be approved before transporting company equipment.
COMMERCIAL VEHICLE INSURANCE
Little Philly Sea Adventures will cover the cost of commercial vehicle insurance required for the Operations Manager's approved truck while it is authorized for company operations. The candidate must cooperate with the insurance approval process and provide required driver, vehicle, registration, ownership, and driving-history information. Commercial insurance eligibility is a condition of employment because towing company equipment is an essential part of the role. Company-paid coverage does not make Little Philly Sea Adventures responsible for the employee's personal vehicle payment, depreciation, registration, routine maintenance, personal repairs, or unauthorized use.
TEAM LEADERSHIP & SCHEDULING
Create employee schedules based on reservations and seasonal demand. Avoid unnecessary payroll expense during slower periods and maintain an on-call plan when appropriate. Confirm employee availability and communicate schedule changes. Assign launch, retrieval, check-in, safety, fueling, cleaning, inspection, delivery, and closing responsibilities. Set expectations for punctuality, communication, appearance, customer service, safety, and equipment care. Train employees on company procedures and customer-experience standards. Document repeated attendance, performance, safety, or equipment concerns. Address employee issues professionally and build a culture of reliability, accountability, respect, and teamwork. Recommend training, corrective action, staffing changes, or termination when appropriate. Final hiring, compensation, disciplinary, and termination decisions remain with ownership unless otherwise authorized.
CUSTOMER EXPERIENCE
Our customers are not simply renting equipment. They are trusting us with an experience. The Operations Manager must ensure every customer receives friendly, professional, accommodating, and safety-focused service.
Responsibilities include:
Confirming reservation details, arrival instructions, identification, and required documentation. Conducting or supervising check-in and safety orientation. Explaining operating boundaries, restricted areas, return times, fuel expectations, damage responsibility, and emergency procedures. Making reasonable accommodations when possible while consistently enforcing company policies. Responding professionally to delays, complaints, weather questions, and schedule changes. Escalating significant refund requests, charge disputes, accidents, injuries, or major customer issues to ownership. Protecting and strengthening the company's five-star reputation. Convenience, speed, and revenue never come before customer or employee safety.
FLEET READINESS & EQUIPMENT MANAGEMENT
The Operations Manager will help oversee the readiness of the company's two pontoon boats, six jet skis, trailers, and operating equipment.
Responsibilities include:
Performing or assigning pre-rental and post-rental inspections. Documenting equipment condition before and after rentals. Checking fuel, batteries, trailer tires, lights, straps, registrations, keys, and required safety equipment. Ensuring boats and jet skis are clean and customer-ready. Identifying and documenting mechanical problems, cosmetic damage, warning lights, battery issues, propeller damage, trailer concerns, and maintenance needs. Immediately removing unsafe equipment from service. Coordinating approved maintenance and repairs and maintaining organized records. Ensuring equipment is rinsed, cleaned, flushed, charged, secured, and stored correctly. Monitoring required safety and operating equipment. Helping establish preventative-maintenance routines. Unsafe equipment will never be returned to service simply because a reservation is scheduled.
LAUNCHING, RETRIEVAL & TRAILER OPERATIONS
Inspect the truck, trailer, hitch, straps, lights, tires, and safety equipment before towing. Verify trailer connections and secure boats and jet skis correctly. Coordinate safe and efficient launches and retrievals. Prevent unauthorized or inexperienced employees from towing company equipment. Account for traffic, ramp conditions, water depth, tides, parking, weather, and congestion. Document damage and immediately report accidents, citations, breakdowns, or unsafe conditions. Maintain safe and professional driving behavior while towing.
SAFETY, COMPLIANCE & RISK MANAGEMENT
Verify customer age, identification, boater-safety, waiver, and operating requirements. Confirm required safety equipment is present and serviceable. Monitor forecasts, radar, tides, wind, visibility, storms, and marine conditions. Distinguish between inconvenient weather and unsafe conditions and delay or stop operations when necessary. Follow company procedures for weather delays, rescheduling, cancellations, credits, and refunds. Respond appropriately to disabled equipment, overdue renters, accidents, injuries, unsafe behavior, and emergencies. Coordinate on-water assistance or recovery when necessary. Document accidents, injuries, damage, law-enforcement interactions, and reportable incidents. Cooperate professionally with authorities, marinas, ramp personnel, and emergency responders. Follow applicable boating laws, local requirements, insurance requirements, and company policies. Safety concerns, accidents, injuries, equipment failures, and compliance issues must never be ignored or concealed.
RESERVATIONS, EXPENSES & REPORTING
The Operations Manager will monitor reservations and company communication channels, identify scheduling conflicts, communicate customer instructions and changes, coordinate same-day opportunities when appropriate, and avoid bookings that cannot be fulfilled safely and professionally. The Operations Manager must protect company pricing, avoid unauthorized discounts, and follow approved policies regarding deposits, credits, cancellations, refunds, fees, damages, and late returns. Company fuel cards, equipment, and supplies may only be used for authorized business purposes. Fuel purchases, receipts, employee hours, maintenance issues, damage, incidents, and unresolved customer concerns must be documented according to company procedures. The Operations Manager may not authorize significant repairs, reimbursements, discounts, refunds, purchases, or financial commitments outside delegated authority. Customer, employee, financial, operational, legal, and company information must remain confidential.
PERFORMANCE EXPECTATIONS
Performance will be evaluated based on reliability, punctuality, completed rentals, customer satisfaction, employee performance, scheduling accuracy, fleet readiness, equipment care, safety compliance, documentation, expense awareness, safe towing, problem-solving, communication, and accountability. Performance-based bonuses may eventually be tied to defined operational measurements and will be documented separately.
REQUIRED QUALIFICATIONS
Experience in operations, hospitality, recreation, marine services, rentals, tourism, transportation, logistics, customer service, or another fast-moving service environment. Experience supervising employees or coordinating a team. Strong organization, scheduling, problem-solving, verbal, and written communication skills. Professional and patient customer-service skills. Ability to remain calm when circumstances change and work independently within established policies. Comfortable working outdoors in Florida heat, humidity, wind, and changing weather. Physically capable of helping launch, retrieve, secure, inspect, clean, and prepare equipment. Must own or legally control a reliable truck with adequate towing capacity. Previous towing, trailer-backing, launching, and retrieval experience. Valid driver's license and acceptable driving record. Ability to meet commercial insurance requirements. Weekend, holiday, early-morning, and peak-season availability. Comfortable using smartphones, email, text messaging, reservation systems, digital forms, and basic business software. Dependable, honest, safety-conscious, organized, and accountable. Candidates must be willing to complete company training and any legally permitted background, driving-record, reference, or insurance-eligibility review.
PREFERRED QUALIFICATIONS
Marine or watersports experience, pontoon or Yamaha WaveRunner experience, knowledge of Florida boating requirements, FareHarbor or similar software experience, CPR/First Aid certification, basic mechanical awareness, seasonal-team leadership, and familiarity with Anna Maria Island and Palma Sola Bay are preferred.
SCHEDULE & COMPENSATION
The anticipated start date is approximately mid-February 2027 . The position will begin part-time , with hours determined by reservations, seasonal demand, staffing requirements, and operating conditions. Boat and jet ski rentals do not follow a traditional Monday-through-Friday schedule. The Operations Manager must be available during high-demand periods, including weekends, holidays, early mornings, spring break, and peak portions of spring and summer. Hours may be lighter during slower periods and increase significantly as reservations increase. Starting compensation is expected to be approximately $27/hour , based on experience and demonstrated ability. Little Philly Sea Adventures will cover required commercial vehicle insurance for the approved towing vehicle while authorized for company operations. The long-term goal is to grow this into a full-time, year-round leadership position . Future compensation may include salary and performance incentives as responsibilities and the business grow. This position does not include ownership or equity in Little Philly Sea Adventures.
WHO WILL SUCCEED IN THIS ROLE?
The right candidate sees what needs to be done and acts before a problem becomes an emergency. They review schedules, communicate with employees, inspect equipment, monitor weather, prepare for customers, and keep the operation organized. They are equally comfortable leading and doing—whether coordinating reservations, towing and launching a boat, preparing jet skis, helping customers, documenting damage, or reorganizing the day when conditions change. They communicate clearly, follow through, keep ownership informed, respect the boundaries between leadership and ownership, and understand that we are not simply renting equipment—we are helping customers create meaningful experiences and lasting memories on the water.
OUR HIRING PHILOSOPHY
We are recruiting early because we intend to be selective. Towing and marine skills are important, but this position also requires leadership, sound judgment, accountability, customer service, safe equipment handling, and respect for company policies and assets. We would rather continue searching than put the wrong person into a role that is critical to the success of Little Philly Sea Adventures.
HOW TO APPLY
Please submit a resume or detailed summary of relevant experience along with responses addressing: Your experience managing employees or daily operations. Your experience with boats, jet skis, trailers, hospitality, rentals, tourism, or outdoor recreation. Your experience towing, backing, launching, and retrieving boats or personal watercraft. The year, make, model, towing capacity, and general condition of the truck you would use. Your experience handling customers and changing operational conditions. Your weekend and holiday availability beginning around mid-February 2027. Why you believe you would be a strong fit for Little Philly Sea Adventures. What dependable leadership means to you. Your desired hourly compensation. Whether you are comfortable starting part-time with the opportunity to grow into a full-time position. When you would be available to begin training or orientation. Qualified applicants may be asked to complete interviews, reference checks, driving-record and insurance review, a towing-vehicle inspection, trailer-handling assessment, customer-service scenarios, and a paid working interview or training period when appropriate. Little Philly Sea Adventures is an equal-opportunity employer. Employment decisions are based on business needs, qualifications, reliability, judgment, performance, and the ability to fulfill the responsibilities of the position.
Pay:
$27.00 - $30.00 per hour Expected hours: 10.0 - 40.0 per week
Benefits:
Employee discount Flexible schedule People with a criminal record are encouraged to apply