Big Bear Vacations: Owner Retention Specialist
Company:
Location: Remote
Published: 2026-09-01
Headquarters: Big Bear Lake, California, USA
URL: https://www.bigbearvacations.com/
OWNER EXPERIENCE SPECIALIST
Department: Owner Relations / Owner ExperienceMarket: Puerto Vallarta & Nuevo Vallarta, MexicoReports To: Director of Owner RelationsEmployment Type: ContractorWork Arrangement: 100% Remote / Monday - SaturdayCompensation: USD $1,200 monthlyLanguages: Fluent English and Spanish, written and spoken — required
Position Purpose
The Owner Experience Specialist is the primary point of contact between Naya Homes and our homeowners in Puerto Vallarta and Nuevo Vallarta.
This role is responsible for building and maintaining strong, consistent, and proactive relationships with homeowners in order to support owner satisfaction and retention. Rather than simply reacting to problems after they occur, the Specialist is expected to identify potential concerns early and address them before they become reasons for an owner to consider terminating their relationship with Naya Homes.
The Specialist owns three key outcomes: executing the required owner communication cadence under the 33-Touch Relationship Model; providing homeowners with clear visibility into the condition and performance of their properties; and capturing property content that supports marketing efforts, social media, and owner communication.
The successful candidate will be highly organized, proactive, customer-focused, and comfortable managing a high volume of daily communication while maintaining accurate documentation and consistent follow-up.
Fluency in both English and Spanish, written and spoken, is an indispensable requirement for this position. The Specialist will communicate with homeowners and internal teams in both languages.
Because this is a remote contractor position, the primary focus is on achieving established goals, service standards, and KPIs. The schedule may be flexible as needed to ensure objectives are met, while maintaining the required availability and responsiveness for homeowners and the business.
Core Responsibilities
1. Owner Relationship Management & Communication
Execute 20–25 documented owner interactions per day through calls, email, and text.
Maintain 100% completion of required monthly touches for every assigned owner under the 33-Touch Relationship Model.
Maintain a balance across the three touch types:
Property Visibility: condition updates, inspection findings, photos, and property content.
Personal Relationship: relationship-building communication not directly related to a transaction or problem.
Informative / Value-Driven: performance, pricing, market conditions, and seasonal outlook.
Enter every interaction with a clear purpose and conclude it with a defined next step.
Complete scheduled owner check-in calls on the day they are due and rebook any rescheduled calls before the end of the same business day.
Maintain clear communication regarding availability, support, and expected response times so owners always know who to contact and when they can expect an answer.
Build trust and maintain professional, long-term relationships with homeowners.
2. Property Visibility & Owner Updates
Collect property updates from Operations, Housekeeping, Maintenance, and inspection reports.
Review condition notes and available photos before communicating with owners to ensure updates are specific and accurate.
Translate operational findings into clear, plain-language owner updates, including what was found, what action is being taken, associated costs, and expected resolution timelines.
Respond to all open owner conversations regarding work orders.
Ensure that no work order is dispatched to an owner's property without documented owner approval.
Ensure that every unresolved property issue has a clearly assigned next action and responsible person.
Provide owners with meaningful visibility into the work being performed on their property.
3. Escalation & Churn Risk Identification
Identify early signs of owner dissatisfaction or potential churn, including declining sentiment, slow or short responses, revenue complaints, recurring property condition issues, questions regarding contract terms, or references to other management companies.
Escalate concerns on the same business day.
Add applicable owners to the Owner Churn Board and keep records current as situations develop.
Confirm ownership of the next action for every escalation and ensure each open case has a clearly assigned responsible person.
Communicate potential risks early rather than waiting for issues to escalate.
4. Documentation & CRM Discipline
Log every owner interaction in Monday.com on the same day it occurs.
Maintain the Owner Churn Board on a daily basis.
Schedule all future owner touches and follow-ups before closing out the day.
Prepare a clear next-day action list before logging off.
Complete a weekly CRM documentation self-audit and correct any gaps identified.
Maintain accurate, complete, and timely records of all owner communications.
Daily Operating Rhythm
Start of Day
Log into RingCentral and Monday.com.
Review the Owner Engagement Tracker.
Identify owners due for required touches.
Review notes from inspections, maintenance, turnovers, and operations.
Flag owners with open concerns, negative or declining sentiment, or recent performance or condition issues.
During the Day
Complete scheduled owner check-in calls.
Send required emails and text messages.
Complete scheduled property-content activities remotely or through available internal resources.
Collect and communicate relevant property updates.
Respond to open work order conversations.
Escalate concerns on the same business day.
Maintain consistent follow-up with assigned homeowners.
End of Day
Ensure all owner interactions are documented in Monday.com.
Update the Owner Churn Board.
Schedule future touches and follow-ups.
Confirm that there are zero undocumented conversations.
Prepare the next-day action list.
Weekly Close
Maintain 100% progress toward required monthly owner touches.
Ensure there are no missed follow-ups.
Complete the CRM documentation self-audit.
Review owner sentiment trends.
Identify unresolved owner issues requiring attention.
Identify owners requiring proactive outreach during the following week.
Performance Standards & KPIs
Performance will be measured monthly against the following targets:
Daily owner touches: 20–25 per day.
Required monthly touch completion: 100%.
Documentation accuracy: 95% or higher.
Undocumented conversations: Zero.
Same-day escalation compliance: 100%.
Overdue escalations beyond SLA: Zero.
Owner sentiment trend: Stable or improving.
Overall KPI attainment: 90% or higher.
Retention saves: Tracked and reviewed through the Owner Churn Board.
Sustained performance below the established targets may result in a documented coaching plan.
Accountability Standards
Missed follow-ups are considered a performance issue.
Undocumented conversations are considered a performance issue.
Dispatching a work order without documented owner approval is considered a performance issue.
Early escalation is considered a positive behavior and is recognized accordingly.
Proactive communication is an expectation of the role, not an additional benefit or optional activity.
The Specialist is expected to take ownership of assigned conversations, follow-ups, and open issues through resolution or appropriate escalation.
Qualifications
Required
Fluent English and Spanish, both written and spoken — indispensable.
2+ years of experience in client-facing account management, hospitality, property management, customer success, or a related field.
Demonstrated experience working independently and managing responsibilities in a remote environment.
Strong CRM discipline and a proven track record of documenting work consistently without requiring constant follow-up.
Comfortable initiating a high volume of outbound calls and handling difficult conversations directly and professionally.
Excellent written and verbal communication skills in both English and Spanish.
Strong interpersonal skills and the ability to build trust with clients and maintain long-term relationships.
Highly organized and detail-oriented, with the ability to manage multiple conversations, follow-ups, and priorities simultaneously.
Proactive approach to identifying potential dissatisfaction and escalating concerns appropriately.
Ability to shoot and edit short-form vertical video using a phone and tools such as CapCut, Instagram, or equivalent.
Strong computer skills and ability to work independently with digital communication, CRM, and collaboration tools.
Reliable internet connection and a suitable home-office environment for remote work.
Preferred
Previous experience in short-term rentals, vacation rentals, hospitality, or property management.
Working knowledge of Streamline VRS, Monday.com, or comparable PMS/CRM platforms.
Experience producing content for Instagram, TikTok, Airbnb, or other property marketing platforms.
Understanding of owner statements, management fees, and short-term rental revenue basics.
Familiarity with the Puerto Vallarta / Nuevo Vallarta vacation rental market.
Key Attributes
The ideal candidate will be:
Reliable and consistent: Able to perform repetitive activities consistently and accurately.
Calm and professional: Comfortable dealing with frustrated homeowners without becoming defensive or over-promising.
Highly organized: Capable of managing 20–25 daily conversations while maintaining complete follow-up.
Proactive: Identifies potential issues early and takes action before they escalate.
Accountable: Communicates problems honestly and takes ownership of mistakes.
Relationship-oriented: Genuinely interested in understanding homeowners, their properties, and their needs.
Adaptable: Comfortable working independently in a remote environment and managing priorities without constant supervision.
Strong communicator: Able to communicate clearly and professionally in both English and Spanish.
First 90 Days
Days 1–30
Complete access and onboarding for Monday.com, Streamline, RingCentral, and the Owner Engagement Tracker.
Become confident using the required systems and communication tools.
Review the assigned owner portfolio.
Make introductory contact with assigned homeowners.
Complete shadowing and initial training.
Days 31–60
Execute the full daily communication volume of 20–25 owner touches.
Maintain 100% documentation compliance.
Demonstrate consistent follow-up and proactive communication.
Begin independently identifying and escalating owner concerns.
Days 61–90
Achieve overall KPI attainment of 90% or higher.
Own at least one owner retention case from identification through resolution or successful escalation.
Demonstrate consistent owner relationship management and CRM discipline.
Contribute repeatable content formats or communication practices that can be adopted by other Specialists.
This job description outlines the primary duties and standards of the role and is not an exhaustive list of all responsibilities. Duties may be adjusted according to business needs. Workload structure, escalation pathways, and coaching practices will be administered in accordance with applicable company policies and requirements.
To apply: https://weworkremotely.com/remote-jobs/big-bear-vacations-owner-retention-specialist
