Upstay is looking for a Listing Strategy Supervisor to join our team! Get Your Resume Ready!

Who We Are

Upstay operates and optimizes short-term rentals to create ROI for homeowners and unforgettable vacation homes for guests. Based in Orlando, Florida, Upstay offers short-term rentals across the United States, Eastern Canada, and South America. Our team of 160+ employees manages 400+ properties on behalf of owners. We treat every property in our portfolio as an investment with a focus on maximizing profit without sacrificing best-in-class hospitality for our guests.

What We Do

We build great communities that bring the tools and sensibilities of the world’s best hotels and apply these principles to our vacation rentals, short-term rentals, and modern hotels.

How We Do It

We are accountable for every aspect of our property’s creation and existence. Site selection, acquisition, development, design, construction, furniture manufacturing, laundry and property management are all looked after by our in-house teams which translates to higher standards in our properties, service, and customer expectations.

What Matters to Us

We are committed to providing compliant and locally beneficial short-term property rentals that add value to our guests. We work with local governments and homeowner associations to develop standards and provide industry-wide leadership so our guests can relax and enjoy their time with us.

What You’ll Do The Listing Strategy Supervisor oversees launching and managing listings for our properties on Guesty (property management software), Online travel agents (OTAs) and other short-term rental platforms, working collaboratively with Revenue, Marketing, Owner Experience, and Guest Experience teams to maintain high listing quality.

- Oversee all onboarding operations from a listing standpoint to ensure a successful launch. Collaborate with the listing team and other departments for new and existing markets, ensuring that we have the necessary information to complete the onboarding.




- Oversee health and optimisation of all listings and accounts in our portfolio, and conduct regular audits of listings across platforms to identify areas for improvement.
- Keeping up to date with all platform updates (Guesty, OTAs, etc.) ensuring that any updates given that will affect a listing’s optimization and planning accordingly.
- Month-end reports - collaborate with the finance team regarding feedback from month-end, investigating reservations with missing or incorrect fees/taxes and resolving any issues.
- Researching potential new OTA connections via Guesty or otherwise, and discussing with the revenue team and other departments it may impact.
- Serve as the point of contact, in collaboration with the Head of Revenue and Distribution, for all existing and potential OTA contacts and account managers, maintaining a good working relationship with each.
- Regularly track OTA performance across the portfolio and per market and report to the revenue team for any areas of improvement or success
- Explore the use of AI platforms and tools to aid the team and improve reporting, processes and procedures.
- Work closely with the compliance team regarding licensed listings/markets, taking necessary action whenever a compliance issue arises. Ensuring the team carry out regular, proactive spot checks on all licensed listings/markets and that accounts are compliant as per SOPs.
- Collaborate with the listing team and other necessary departments for offline listings, strategizing approaches for offline listings to bring them back online,utilising account managers for assistance when needed.
- Train and onboard new employees, sharing knowledge and best practices.
- Create and update standard operating procedures (SOPs)



for the department to ensure consistency and efficiency.
- Conduct performance appraisals and give continuous feedback to the team, guiding them in their daily tasks, aligned with the Upstay’s culture and values.
- Spearhead other projects as requested by the Head of Revenue and Distribution that are related to the department.
- Actively participate and contribute with the improvement of company procedures and processes.
- Follow all Upstay’s procedures and guidelines and, legal applicable regulations
- Promote safe behaviour in the workplace.
- Promote a professional and cooperative working environment, based on mutual respect and trust.

What You’ll Bring

- 2+ years of management experience in hotel rooms division or short term rental field, experience working with distribution channels, experience with Guesty highly preferred.
- College diploma or bachelor’s degree, preferably in hospitality or business management.
- Advanced user of Microsoft Office, Google Drive, Slack, Guesty, Airbnb, Booking.com highly preferred.
- Highly organized, with exceptional attention to detail
- Critical thinking and problem solving skills
- Comfortable with tech and software
- Passionate and enthusiastic about the short-term rental industry
- Proven verbal and written communication skills in English
- Self-motivated and able to multitask in a fast-paced environment
- Professional attitude with strong time management skills
- Flexibility to work on weekends and public holidays.

Equal Employment Opportunity

We're proud to be an equal opportunity employer and all applicants will be considered. At Upstay we celebrate and support the differences between our employees' including race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, and Veteran status. Diversity is essential to our growth, and we’ve concluded that we’re stronger together.

Last Thing

If this isn’t the job for you, perhaps you have a friend who would be a perfect fit? Send them this job posting.

📌 Listing Strategy Supervisor (Colombia)
🏢 Upstay
📍 Colombia