THE COTTAGES ON THE KEY

Operations Runner

Company Summary

At The Cottages on the Key, we're more than a vacation rental company—we're a fast-growing team that's redefining hospitality on Florida's Gulf Coast. Every day is different, every role has an impact, and every team member has the opportunity to grow.

• Work with an amazing team. We hire people who care about doing great work and supporting one another. Our culture is built on trust, teamwork, and a shared commitment to creating unforgettable experiences for our guests and homeowners.

• Grow your career. As we continue to expand, so do the opportunities for our team. We believe in promoting from within, developing talent, and giving employees the chance to take on new challenges and leadership roles.

• Make a real impact. You're not just another employee. Your ideas are heard, your work matters, and you'll see the direct results of your efforts every day.

• No two days are the same. Whether you're helping guests create lifelong memories, solving challenges in the field, improving homes, or working with homeowners, every day brings something new.

• Work in paradise. Our properties are located on Siesta Key, Lido Key, and Anna Maria Island—some of the most beautiful beach destinations in the country.

• We invest in innovation. We embrace technology, continuously improve our processes, and encourage new ideas that make us better for our guests, homeowners, and employees.

• Be part of something bigger. We're an ambitious company that's constantly growing and looking for people who want to grow alongside us.

Position Summary

The Operations Runner reports directly to the Maintenance Supervisor and plays a key role in ensuring our vacation homes are guest-ready and maintained to The Cottages on the Key's high standards. This position supports daily operations by performing light maintenance, completing arrival and departure inspections, responding to guest requests, coordinating vendor and supply runs, and assisting with property presentation and special projects. Working closely with the Maintenance, Quality Control, and Housekeeping teams, the Operations Runner helps deliver exceptional guest experiences through proactive service, attention to detail, and the flexibility to support multiple departments in a fast-paced environment.

Key Responsibilities

• Conduct arrival-day quality inspections to ensure each property meets The Cottages on the Key standards. Complete the required inspection template, identify any issues, and perform or coordinate all necessary corrective actions and work orders to ensure the home is fully guest-ready prior to arrival.

• Replace light bulbs, batteries, air filters, and smoke detector batteries.

• Maintain the cleanliness and organization of maintenance storage areas.

• Respond promptly to guest concerns and help create a positive guest experience through proactive service.

• Assist with special guest requests and deliveries, including ice deliveries, beach equipment transportation, housekeeping supplies, and other guest-related support services.

• Perform vendor and supply runs as needed, including pickups and deliveries from approved vendors, suppliers, and local partners such as Morton's, local bakeries, and other business partners.

• Assist with unit arrivals by ensuring homes are guest-ready, including power washing, garage organization, grill cleaning, outdoor area preparation, and other property presentation tasks.

• Support turnover operations by working closely with Quality Control, Housekeeping, and Maintenance teams to ensure homes meet company standards prior to guest arrival.

• Perform departure inspections on our higher-level homes to ensure everything is in order.

• Assist management with special projects, operational support tasks, and miscellaneous assignments as business needs require.

• Demonstrate flexibility and a sense of urgency by supporting multiple departments and responding to changing priorities throughout the workday.

Growth Path

The Operations Runner role is a common entry point into TCOK's Maintenance and Operations teams. Runners who show reliability and initiative are considered first for advancement into Maintenance Technician, Quality Control, and other operations roles as the company grows.

Required Qualifications

• Valid driver's license and reliable transportation.

• Basic maintenance and handyman experience preferred.

• Comfortable working independently, while also staying responsive to direction and shifting priorities from management.

• Excellent communication and customer service skills, with confidence interacting directly with guests and homeowners.

• Highly adaptable and willing to support multiple departments as operational needs arise throughout the day.

• Demonstrates initiative and a sense of urgency in responding to guest, housekeeping, and maintenance needs.

• Ability to multitask and maintain a professional attitude during busy periods and high-occupancy seasons.

• Strong organizational and time-management skills.

• Ability to lift up to 50 pounds and perform physical work outdoors, including in Florida heat and humidity.

Compensation, Benefits & Schedule

Pay: $45,000–$48,000 annually

Benefits

• Health insurance (eligible after 90 days of employment).

• Two weeks paid vacation.

Schedule

• Full-time, flexible schedule, must be available to work major holidays, and weekends.

• Includes after-hours coverage, 5:00 PM–11:00 PM, as scheduled.

• Participates in an on-call rotation for after-hours guest and property needs.

Vehicle & Equipment

• Company vehicle is not provided; employee must provide their own reliable transportation for vendor and supply runs.

• Employee must provide their own basic hand tools and equipment for light maintenance tasks.