Key Responsibilities:

Leadership & Team Development

• Lead and mentor a team of stewards, cleaners, and support staff.
• Build a culture of accountability, clarity, and communication.
• Conduct training sessions, meetings, and ongoing performance development.
• Collaborate with leadership on team growth and placement strategies.

Operations & Systems Management

• Develop, document, and refine Standard Operating Procedures (SOPs).
• Oversee scheduling, payroll accuracy, and client onboarding workflows.
• Use platforms like Slack, Google Workspace, and Maid Central to keep systems running smoothly.
• Track performance metrics and identify areas for process improvement.

Client Coordination & Hospitality

• Oversee daily client communication and service delivery.
• Manage scheduling logistics to ensure seamless execution across all job types.
• Serve as a liaison between clients, crew, and leadership to uphold OTF’s service standards.
• Address client needs and concerns with professionalism and care.

What We’re Looking For

• 3–5 years of experience in operations, hospitality/yachting, or service-based management.
• Excellent communication and leadership skills.
• Highly organized with an eye for detail and follow-through.
• Comfortable managing multiple projects in a fast-paced environment.
• Proficient in GSuite, scheduling tools, and CRMs.
• A growth mindset and passion for building teams and systems.

The role (quick snapshot)
This is an entry-level steward role with paid, structured training and room to grow. You will learn the OTF way and provide guest-ready care across many property types: owner-occupied homes, short-term rentals, event and community spaces, coastal cottages, schooners/yachts, and other specialty properties. Land or sea, you will make spaces feel cared for, polished, and ready.

What you will do

• Steward properties: turnovers, linen handling, bed/makeup, staging, trash and fridge checks, and finishing touches.
• Support owner-occupied homes, STRs, event spaces, community workspace upkeep, and vessel/schooner turnovers.
• Perform light maintenance checks, manage inventory and consumables, and submit clear job reports.
• Follow OTF SOPs, green cleaning specifications, and client instructions.
• Communicate professionally with teammates, operations, and clients; be punctual and dependable.

Training and growth

• Paid 3-week training and assessment to learn OTF standards, tools, and systems; we teach you how to win the small battles that add up.
• Successful stewards are offered advanced training (including vessel and specialty instruction), revenue-share jobs, and leadership paths as the company grows.

Our core values: lived daily

• Integrity: accurate reporting, honest work, and doing the right thing.
• Pride: we sweat the small details that make stays feel thoughtful.
• Teamwork: we work like a crew, with clear communication, mutual support, and shared standards.
• Reliability: show up ready, every time.

Personality and team fit: DISC required
Shortlisted candidates are required to complete a DISC Personality Assessment (or a comparable test) as part of our hiring process. This helps us understand how you prefer to work and allows us to make thoughtful matches with teammates and roles.

Who we are looking for

• Entry-level welcome; bring a strong work ethic, curiosity, and a willingness to learn.
• Reliable transportation and a smartphone for scheduling and communication.
• Able to lift about 25–40 lbs and be on your feet; comfortable working in varied environments (homes, event spaces, boats).
• Detail-oriented, punctual, and comfortable following checklists and SOPs.
• Positive attitude, flexible schedule, and coachable.

Compensation

• Beginners: $18–$20 per hour.
• Competitive pay and pathways to revenue-share jobs or specialty work as you advance.

Why join On the Flye?

• Paid, structured training and clear advancement.
• Real variety: work across homes, coastal properties, event spaces, and vessels.
• Crew-first culture, flexible scheduling, and pathways to specialty roles and leadership.
• Meaningful work: you will directly shape guest and owner experiences.

How to apply
Email a short note and your resume to office@ontheflyeclean.com. Tell us: a job you are proud of, how you show up for a team, and one skill you want to grow. Short and human wins.