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Executive Remote Vacation Rental Jobs (NOW HIRING)

Better Talent

Client & Operations Lead

Bradenton, FL · Remote

$60K - $70K/yr

Company Overview TrustFirst Management is a fast-growing vacation rental management company based ... This role reports directly to the CEO and plays a critical role in keeping the business running ...

Trellis

Account Executive (Remote)

ALL premiums covered! * 401k w/ full match up to state limit * Work from anywhere * Flexible vacation policy. You manage your own time Trellis is committed to building a diverse and inclusive ...

Trellis

ALL premiums covered! * 401k w/ full match up to state limit * Work from anywhere * Flexible vacation policy. You manage your own time Trellis is committed to building a diverse and inclusive ...

Aston Carter

REMOTE Entry Level Sales Executive

Houston, TX · On-site +1

$24 - $31/hr

Associate Account Executive (Remote) We are seeking an enthusiastic Associate Account Executive to ... Vacation or Sick Leave) Workplace Type This is a fully remote position. Application Deadline This ...

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How much do executive remote vacation rental jobs pay per year?

As of Jul 6, 2026, the average yearly pay for executive remote vacation rental in the United States is $93,552.00, according to ZipRecruiter salary data. Most workers in this role earn between $58,000.00 and $120,500.00 per year, depending on experience, location, and employer.
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Executive Remote Vacation Rental jobs near you
Client & Operations Lead

Client & Operations Lead

Better Talent

Bradenton, FL • Remote

$60K - $70K/yr

Full-time

PTO

Posted 29 days ago

Job description

Company Overview

TrustFirst Management is a fast-growing vacation rental management company based in Bradenton, Florida, currently managing ~40 properties and scaling rapidly.

Our mission is simple: deliver exceptional guest and owner experiences through strong execution, clear communication, and operational excellence.

We are not building a traditional property management company. We are building a technology-driven, AI-powered operation that leverages automation, data, and smart systems to outperform the industry standard.

If you’re excited about improving processes, working with modern tools, and being part of a high-performance team, you’ll thrive here.

Position Summary

TrustFirst Management is seeking a Client & Operations Lead to take ownership of day-to-day operations and serve as the primary point of contact for owners, guests, and vendors.

This role reports directly to the CEO and plays a critical role in keeping the business running smoothly. You’ll be responsible for managing communication, resolving issues, coordinating vendors, and supporting a remote team, all while maintaining a high standard of service and execution.

This is a hands-on, high-ownership role for someone who is proactive, decisive, and solutions-oriented. As the company grows, this position is designed to evolve into an Operations Manager role.

What You’ll Do

  • Manage owner communication, including updates, issue resolution, and relationship management

  • Coordinate vendors (cleaning, maintenance, etc.) to ensure timely, high-quality execution

  • Handle guest escalations and resolve complex issues to protect reviews and guest experience

  • Act as the primary decision-maker for day-to-day operational needs

  • Support and guide a remote team by providing direction and answering questions

  • Identify inefficiencies and improve processes to increase operational performance

  • Utilize AI tools and automation systems to improve speed and accuracy

  • Hold vendors and team members accountable to performance standards

  • Ensure consistent, high-quality execution across all properties

QualificationsRequired

  • Experience in hospitality, property management, or a customer-facing operations role

  • Strong written and verbal communication skills

  • Proven ability to handle difficult conversations with clients or customers

  • Ability to make independent decisions and solve problems under pressure

  • Highly organized with strong attention to detail

  • Ability to manage multiple priorities in a fast-paced environment

  • Demonstrated ownership mindset (proactive, solutions-focused, accountable)

Preferred (nice to have, but aren't a must)

  • Vacation rental or short-term rental industry experience

  • Experience managing vendors or coordinating service providers

  • Experience supporting or leading remote teams

  • Familiarity with tools such as Guesty, Notion, Conduit, SuiteOp, Turno, or similar platforms

  • Experience working in fast-growing or startup environments

  • Interest in AI, automation, and system optimization

Compensation, Benefits & More

  • Compensation: $60,000 - 70,000 annually based on previous experience

  • Benefits: PTO, flexible work environment, telecommuting options

  • Schedule: Tuesday through Saturday, with Sunday and Monday off. Some flexibility required for occasional evenings or urgent issues. Due to the nature of operations, some flexibility is required, including occasional evenings or weekends for urgent issues or escalations. We operate in a fast-paced environment and prioritize responsiveness, ownership, and outcomes over strict time tracking.

  • Job Type: Full-time

  • Location: Bradenton, FL Area