Short Term Rentals Portfolio Manager

Upstay is looking for Portfolio Manager 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 maximising 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 Portfolio Manager (PM) at Upstay is the primary relationship owner for a portfolio of approximately 30 homeowner accounts. As a trusted business partner, the PM is responsible for delivering 360-degree performance across each property in their care—driving revenue, managing communications, resolving issues, and maintaining strong satisfaction scores. This role is not transactional. It is strategic, owner-facing, and outcome-driven.

• Be an owner advocate – speak on their behalf internally while maintaining Upstay's integrity.
• Support: meeting preparations, minutes taking, recap sendout & follow up
• Proactively reach out to owners to understand their goals and ensure Upstay meets them.
• Build and maintain strong, trust-based relationships through regular updates and check-ins.
• Cultivate personal connections to better anticipate needs and identify opportunities.
• Respond professionally and empathetically to all owner communications, concerns, or complaints.
• Maintain a strong understanding of regulatory, operational, and revenue-impacting updates.
• Close feedback loops on tasks, escalations, or delays.

OWNER RELATIONSHIP MANAGEMENT & STRATEGY

Core Objective: Build trusted partnerships, not transactions.

• Be an owner advocate – speak on their behalf internally while maintaining Upstay's integrity.
• Proactively reach out to owners to understand their goals and ensure Upstay meets them.
• Build and maintain strong, trust-based relationships through regular updates and check-ins.
• Cultivate personal connections to better anticipate needs and identify opportunities.
• Respond professionally and empathetically to all owner communications, concerns, or complaints.
• Maintain a strong understanding of regulatory, operational, and revenue-impacting updates.
• Close feedback loops on tasks, escalations, or delays.

Support: meeting preparations, minutes taking, recap sendout & follow up

FULL PORTFOLIO OPERATIONS & SERVICE DELIVERY

Core Objective: Own all aspects of the property's performance and ensure owners

don't need to chase answers.

• Manage, delegate, track & communicate progress of tasks & projects ensuring clarity and accountability.
• Stay aware of company goals and strategies so your actions align with team priorities.
• Collaborate with the Onboarding Team to ensure timely and high-quality property launches.
• Coordinate quote approvals using Upstay SOPs and internal workflows.
• Ensure smooth communication and execution on maintenance, guest issues, calendar blocks, and post-onboarding action items
• Monitor and own the communication strategy for revenue concerns and revenue optimization between Upstay and owners in the portfolio including revenue pacing, calendar gap, pricing concerns and overall revenue performance.
• Review guest reviews & listing ratings to identify and hold inter-departmental team members to resolve recurring issues impacting experience and reputation.
• Investigate utility complaints and handle utility outages (for owner-managed accounts).
• Respond to month-end payout concerns, tax notice questions, and dispute escalations.
• Perform month-end audit assignments

Support:

• Weekend & After Hours Coverage Communications
• Follow through with pending items from Onboarding, flag & escalate to PMs as needed & relevant
• Follow through with executions on approved quotes and provide timely updates/communications to inter-departmental teams, PMs and owners until full resolution
• Follow through with new and unresolved warranties tickets for issues requiring warranty involvements
• Follow through with executions on action plans for reviews audit as agreed/discussed with PMs
• Follow through on renewals of insurance policies to ensure all policies are updated/recent. Make sure all insurance policies meet Upstay requirements.
• Follow through with executions on action plans for insurance claims as agreed/discussed with PMs.

PROCESS IMPROVEMENT & DEPARTMENT STRATEGY

Core Objective: Make the Owner Experience team more scalable, efficient, and professional.

• Develop and refine internal processes to increase team efficiency and service consistency.
• Contribute to SOP and FAQ documentation based on recurring owner behaviors or gaps.
• Offer creative solutions to improve task turnaround, owner satisfaction, or tool usage.
• Coordinate with the Portfolio Support Manager to resolve backlog or delays

OWNER-LEVEL REPORTING & INSIGHTS

Core Objective: Deliver clear, confident business updates to owners and internal teams.

• Review and explain monthly P&L reports during owner syncs.
• Prepare and send monthly forecast summaries and portfolio health updates.
• Identify churn-risk owners based on owner satisfaction drops, complaints, or recurring dissatisfaction.
• Track owner pricing restrictions or limitations and their impact on performance.

TEAM COLLABORATION & LEADERSHIP

Core Objective: Strengthen Upstay's internal knowledge and support systems.

• Actively communicate with inter-departmental team members to ensure seamless delivery to owners.
• Delegate and track task completion through PMS.
• Support team development and provide guidance in internal syncs or 1-on-1s.

Handle additional duties as assigned.

• Bachelor's degree in Business Administration, Marketing, Communications, or a related field.
• Minimum of 3-5 years of experience in client relationship management or a similar role.
• Excellent communication, interpersonal, and negotiation skills.
• Strong problem-solving and analytical abilities.
• Ability to prioritize and manage multiple tasks and projects simultaneously.
• Proficiency in using project management tools and software.
• Adept at building and maintaining strong relationships with clients and stakeholders.
• Familiarity with financial reports and an understanding of profit and loss statements.

What You'll Bring

• Bachelor's degree in Business Administration, Marketing, Communications, or a related field.
• Minimum of 3-5 years of experience in client relationship management or a similar role.
• Excellent communication, interpersonal, and negotiation skills.
• Strong problem-solving and analytical abilities.
• Ability to prioritize and manage multiple tasks and projects simultaneously.
• Proficiency in using project management tools and software.
• Adept at building and maintaining strong relationships with clients and stakeholders.
• Familiarity with financial reports and an understanding of profit and loss statements.
• Language: Strong English skills.

Soft skills

• Demonstrated proficiency in verbal and written communication in English or Portuguese , enabling effective communication with property owners, company stakeholders, and team members.
• Self-motivated and capable of multitasking in a fast-paced environment, ensuring timely progress on client-related tasks and project management.
• Adaptability and responsiveness to changing conditions, priorities, technologies, and requirements in order to maintain the highest level of client satisfaction and support department efficiency.
• Professional demeanor and strong time management skills, allowing for effective delegation, guidance, and collaboration with Account Executives and other departments.
• This role typically requires 40 hours on duty and 10 hours on call a week. The candidate needs to demonstrate a resilient and get-it-done attitude and able to work under high pressure.
• Proficiency in creative problem-solving and the ability to address client and organizational challenges using innovative, indirect approaches.

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.

Work Location: Remote

Job Type: Full-time

Application Question(s):

• Are you comfortable working in a remote and dynamic, fast-paced environment that requires constant communications, team collaboration and autonomous execution?

• Do you have a reliable Internet service and computer/laptop/smart phone device to perform your work?

• How many years of leadership/supervisory experience in Hospitality or Account Management do you have?

• How many years of hotel or vacation rental management experience do you have?

• How many years of experience do you have in a team lead/supervisor position?