Description
COMPANY OVERVIEW:
iTrip Sarasota & Venice is a locally owned vacation rental management company serving Siesta Key, Lido Key, Venice, and the surrounding area. We manage a portfolio of high-quality short-term rental properties and handle everything from guest support and maintenance to pricing, marketing, and owner relations.
This General Manager role is a core leadership position with wide-ranging responsibilities across operations, team management, owner communications, and overall company strategy. It’s a strong fit for someone who’s ready to take the next step in their career, lead a growing team, and work directly with an owner who has experience building and scaling high-growth companies. You’ll have the autonomy to lead and the backing to succeed.
We’re driven by four core values:
- Guest-Centric Excellence – The guest experience drives everything we do.
- Ideas with Impact – The best ideas win, no matter where they come from.
- Trust and Teamwork – We thrive on openness, respect, and accountability.
- Continuous Growth – We’re always looking to improve and evolve.
We’ve built a strong foundation of tools, systems, and people—and we’re growing in a way that’s smart and sustainable. For the right person, this is an opportunity to step into a meaningful leadership role and help shape the future of the business.
POSITION SUMMARY:
The General Manager is a key leadership role responsible for overseeing the day-to-day operations of iTrip Sarasota & Venice. This person will report directly to the Owner and play a central role in managing the business across multiple functions—operations, owner relations, team leadership, and strategic planning, as well as having an influential role in revenue management, marketing, and our guest services.
On a day-to-day basis, the General Manager will lead our local and remote teams, oversee our field operations and vendor relationships, and serve as the main point of contact for homeowners. The role requires a mix of hands-on problem-solving, team development, and high-level oversight to ensure that guests receive exceptional service and properties are maintained to the highest standards.
This is a great opportunity for someone who thrives in a fast-paced environment, enjoys leading people, and wants to help grow and shape a business. The GM will be empowered to make decisions, improve processes, and collaborate directly with the owner, who has a strong background in scaling high-growth companies.
We’re looking for someone who takes ownership, leads with empathy, and is committed to building a high-performing, service-focused team.
RESPONSIBILITIES:
- Oversee daily operations and overall business performance, reporting directly to the Owner
- Ensure high-quality guest experiences and long-term homeowner satisfaction
- Manage both in-field and office-based tasks, maintaining visibility across the property portfolio
- Partner with property owners to resolve issues, suggest improvements, and identify revenue-generating upgrades
- Collaborate with the revenue management team to optimize pricing and maximize RevPAR
- Analyze operational and performance data to identify trends, challenges, and opportunities for improvement
- Conduct regular property visits to maintain quality standards and spot improvement opportunities
- Lead special projects focused on process improvement, tool implementation, and operational problem-solving
- Manage and support teams in housekeeping, maintenance, guest services, and owner relations
- Foster a culture of accountability, care, and continuous improvement across teams
- Lead with a hands-on approach, staying detail-oriented while keeping a strategic focus on business goals
QUALIFICATIONS:
- 5+ years of experience in hospitality, property management, or operations leadership, preferably in the vacation rental or short-term rental industry
- Proven track record managing cross-functional teams, including field operations, vendors, and remote staff
- Strong experience overseeing housekeeping, maintenance, and quality control processes
- Excellent communication skills with the ability to build trust and rapport with property owners, team members, and vendors
- Data-driven mindset with experience using operational and financial reports to guide decision-making
- Familiarity with revenue management strategies, OTA platforms (Airbnb, Vrbo, etc.), and channel distribution
- Highly organized and process-oriented, with a strong sense of ownership and follow-through
- Technically comfortable with tools like Slack, Google Workspace, and property management systems
- Flexible and resourceful problem-solver with the ability to stay calm and focused under pressure
- Valid driver’s license and reliable transportation; must be willing to travel throughout the service area regularly
- Availability to support operations on weekends or evenings if needed
- Spanish fluency is a plus, but not required
- Local market knowledge of Sarasota, Venice, and Siesta Key is preferred
COMPENSATION & BENEFITS:
Salary: $80,000 - $125,000 Annually