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Executive Assistant

Posted 7 days ago

About Big Bear Vacations

Big Bear Vacations is not just a vacation rental company, we are on a mission to redefine the guest experience in mountain destinations. With decades of trusted service in Big Bear Lake, we’ve built a reputation for quality, consistency, and care across every department, from housekeeping and maintenance to guest services and owner relations. What drives us is not just filling calendars, but creating reliable, memory-making stays that build trust with both guests and homeowners.

We're currently facing exciting and complex provocations that are pushing us to grow and innovate. First, we are expanding our footprint into Mammoth Lakes, California and Puerto Vallarta, Mexico, two very different markets with distinct challenges. These new markets will test our ability to replicate our high-quality systems and culture in new environments, recruit and train teams remotely, and maintain our brand promise across borders.

Second, we're scaling while trying to protect our heart: the personal touch and local care that built our brand. As we automate systems and expand geographically, the provocation is clear, how do we grow without losing the soul of what makes Big Bear Vacations special?

As a company, we’re pushing into new tech, building remote teams, rethinking hospitality workflows, and elevating leadership at every level. We’re not just reacting to growth—we’re building with intention, and we’re looking for people who want to be part of a company that’s not afraid to challenge itself.

 

Our Culture

We are a fast-paced, hands-on team that values efficiency, accountability, and heart. Our leadership team believes in empowering others, staying organized, and creating systems that allow the company to scale without sacrificing quality. If you're looking to support a dynamic, entrepreneurial executive and want to be part of a team that's shaping the future of vacation rental hospitality, this is the place for you.

Apply now

This candidate MUST be able to speak English and Spanish fluently.

This role supports the Chief Operating Officer (COO) of Big Bear Vacations, who leads all operational departments including Housekeeping, Maintenance, Laundry, Remote Operations, and Quality Assurance. The COO is responsible for strategic growth, daily execution, vendor relationships, service quality, and team performance across multiple locations. As the company scales, the Executive Assistant will play a critical part in helping manage communication, scheduling, follow-up, and coordination across departments and teams.

Key Responsibilities: 

1. Flexibility & Adaptability to Executive Schedule 

  • Must be highly flexible and adaptable to a non-traditional, fast-paced executive schedule 

  • Some days may require only a few hours of support, while others may need extended availability (8–12+ hours), including weekends when needed 

  • This role supports an executive who often works 7 days a week during peak periods, so being responsive and dependable, especially when urgent items arise, is essential 

2. Calendar & Schedule Management 

  • Own and maintain the executive’s calendar with precision, coordinate internal and external meetings, calls, appointments, and recurring check-ins across time zones 

  • Proactively block time for deep work, travel, and personal time while avoiding scheduling conflicts 

  • Use tools like Microsoft Outlook, Reclaim.ai, and Teams to ensure schedule visibility and alignment across departments 

3. Email, Communication & Inbox Management 

  • Monitor and triage emails, respond to or flag priority messages, draft replies, and maintain inbox zero 

  • Follow up on unanswered emails or pending replies from key stakeholders 

  • Prepare and send communications on behalf of the COO when needed professional but in the tone of the company 

4. Meeting Preparation & Documentation 

  • Organize agendas for leadership or department meetings, ensure all participants are prepared ahead of time 

  • Attend select meetings to take notes, track follow-ups, and ensure accountability on deliverables 

  • Prepare recap summaries and assign action items in Monday.com or task-tracking systems 

5. Project Coordination & Follow-Up 

  • Help track the progress of ongoing initiatives (e.g., SOP rewrites, software migrations, onboarding processes) 

  • Follow up with team members and vendors to ensure deadlines are met and issues are escalated as needed 

  • Organize documents, checklists, forms, or SOPs and store them in the right folders and platforms (SharePoint, Google Drive, Teams) 

6. Vendor & Team Coordination 

  • Coordinate directly with remote managers (e.g., Pakistan or U.S.-based teams) to ensure alignment across time zones 

  • Manage light HR-style functions like organizing team rosters, time-off tracking, or updating contact lists 

  • Help coordinate between departments like Housekeeping, Maintenance, OAM, and Laundry to relay action items 

7. File & Document Organization 

  • Maintain up-to-date folders for contracts, proposals, policies, and key SOPs 

  • Ensure naming conventions and file structures are followed for easy access 

  • Occasionally draft or edit internal documents, owner communications, or staff memos 

8. Task & Workflow Automation 

  • Help the COO automate routine tasks via Monday.com, Microsoft Power Automate, or Outlook Rules 

  • Assist in setting up forms, templates, and recurring workflows to reduce manual follow-ups 

9. Special Projects & Personal Support 

  • Provide support for one-off initiatives such as meeting decks, trip logistics, conference prep, or external projects 

  • Occasionally assist with personal or family logistics (e.g., booking travel, follow-up reminders, home tasks) 

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