General Manager – Position Description
Position Information
Position Title
General Manager
Reports To
The Board of Trustees, Harborside Inn
Property Location
3 South Water Street, Edgartown, MA 02539, Martha's Vineyard, Massachusetts
Employment Type
Full-Time, Exempt, Salaried
Primary Season
April through November (Peak Operational Period)
Year-Round Responsibilities
Pre-season preparation (January–April); post-season wind-down and planning (November–December); off-season oversight
Proposed Start Date
September 2026
FLSA Status
Exempt – Year round salary
Role Summary
The General Manager (GM) of the Harborside Inn is a hospitality leader who is present on-site, hands on when needed and takes pride in running an exceptional boutique hotel and time share. The GM will be the primary face of the property to guests, staff, vendors, and the broader Martha's Vineyard community, serving as the embodiment of the property's values in every interaction.
The GM must possess strong operational, financial, and leadership skills and the ability to build and retain a high-performing seasonal team while delivering consistently exceptional guest experience.
Above all, the GM is entrusted with the owner’s vision: a boutique timeshare and hotel that distinctly reflects Martha's Vineyard — unhurried, gracious, beautifully maintained, and unforgettable. The GM will operate with significant autonomy and entrepreneurial latitude, supported by an engaged Board who brings resources, trust and a collaborative spirit to the partnership. This is an opportunity for a seasoned hospitality professional to truly lead, shape, and grow a property they can be proud of.
Key Responsibilities
Operations & Guest Experience
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Oversee all aspects of daily hotel operations, ensuring consistently exceptional service standards across all guest touchpoints — arrival, accommodations, amenities, and departure.
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Develop, implement, and continuously refine Standard Operating Procedures (SOPs) to deliver a seamless, luxury-caliber guest experience that reflects the property's boutique ethos.
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Monitor and respond to online guest reviews across platforms (TripAdvisor, Google, Booking.com, Expedia), maintaining and elevating the property's digital reputation.
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Personally resolve escalated guest concerns with professionalism, empathy, and swift action, turning challenges into loyalty-building moments.
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Manage room inventory, rates, and reservations in collaboration with the PMS platform, ensuring optimal occupancy and revenue performance throughout the season.
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Oversee property amenities, dock space, swimming pool, public spaces, and guest-facing areas to ensure they are consistently maintained at the highest standard of presentation.
Team Leadership & Human Resources
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Recruit, hire, onboard, train, schedule, supervise, and evaluate all hotel department heads and staff, with particular emphasis on building a motivated, high-performing seasonal workforce.
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Foster a positive, inclusive, and accountable team culture where staff feel valued, heard, and equipped to deliver their best work each day.
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Develop and administer seasonal staff onboarding and training programs, ensuring all team members are fully prepared and operationally ready by opening day.
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Manage staff housing, scheduling logistics, and island-specific Human Resource (HR) considerations (including transportation, work authorization, and workforce sourcing strategies common to island resort markets).
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Conduct regular performance conversations, administer corrective action fairly and consistently, and proactively address retention risks within the team.
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Work closely with the Board of Trustees to facilitate their vision and strategy and keep them informed of plans, issues and activities.
Financial Management
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Develop, manage, and report on the annual operating budget, with full accountability for revenue, expenses, and Gross Operating Profit (GOP) performance.
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Analyze financial statements, Average Daily Rate (ADR), Revenue Per Available Room (RevPAR), occupancy trends, and departmental cost performance on an ongoing basis, identifying opportunities and risks in real time.
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Negotiate and manage vendor contracts, purchasing agreements, and supplier relationships with an eye toward quality, cost-efficiency, and reliability on-island.
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Prepare monthly financial performance reports and end-of-season financial summaries for the owner, with clear narrative analysis and forward-looking recommendations.
Sales & Marketing
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Collaborate with the Board of Trustees and any marketing partners to develop and execute a seasonal marketing and revenue management strategy that maximizes occupancy, ADR, and ancillary revenue.
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Market revenue generating events in collaboration with the Board.
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Maintain and evolve the property's brand presence across web sites, digital channels, On Line Travel Agencies (OTAs), and direct booking platforms, ensuring the hotel's positioning is compelling and competitive within the Martha's Vineyard market.
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Cultivate relationships with travel agents, local event organizers, wedding planners, corporate accounts, and other group or leisure demand generators.
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Identify and capitalize on shoulder season opportunities, including packages, local partnerships, and programming that extend the property's relevance beyond peak summer months.
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Identify and explore new revenue opportunities that will enhance the financial status of the Inn.
Vendor & Community Relations
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Build and maintain strong relationships with island-based vendors, contractors, and service providers, ensuring reliable, high-quality support for the property's operational needs across the season.
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Engage actively and positively with the Martha's Vineyard business community, local government, and island stakeholders, serving as an ambassador for the property's reputation and values.
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Coordinate with ferry companies, transportation providers, and island infrastructure partners to ensure seamless logistics for guests, staff, and supplies throughout the season.
Facilities & Seasonal Readiness
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Lead the annual pre-season opening process, including property inspection, maintenance project completion, deep cleaning, supply procurement, systems testing, and staff readiness — ensuring the hotel is fully guest-ready on opening day.
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Oversee the post-season closing process, including property winterization, maintenance scheduling, inventory reconciliation, and capital improvement planning for the following year.
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Manage ongoing preventive maintenance programs, property improvement projects, and capital expenditure planning in collaboration with the Board of Trustees.
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Ensure full compliance with all applicable health, safety, fire, licensing, permitting and regulatory requirements applicable to the property and its operations.
Required Qualifications
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Bachelor's degree in Hospitality Management, Hotel Administration, Business Administration, or a related field — or equivalent professional experience demonstrating progressive growth in hotel leadership.
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Minimum of 5 years of progressive time share and/or hotel management experience, with at least 2–3 years in a General Manager or senior leadership role.
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Prior experience managing a seasonal resort; island, time share or destination properties strongly preferred; demonstrated understanding of the operational and staffing dynamics unique to seasonal hospitality.
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Experience with managing a time share and/or condo or a similar type of property.
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Strong financial acumen, including experience with budgeting, Profit and Loss (P&L) management, revenue management, and financial reporting.
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Demonstrated success in building, leading, and retaining high-performing teams in high-turnover seasonal hospitality environments.
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Proficiency with Property Management Systems (PMS); experience with systems such as Opera, Cloudbeds, Little Hotelier, or equivalent platforms.
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Excellent interpersonal, written, and verbal communication skills; ability to engage effectively with Boards, guests, staff, vendors, and community partners alike.
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Proven track record of delivering outstanding guest satisfaction results and maintaining strong online review performance.
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Must be able to work a flexible schedule, including weekends and holidays during peak season, and maintain availability and responsiveness as required by the demands of a boutique time share and hotel operation.
Preferred Qualifications, but not Required
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Prior experience working in the Martha's Vineyard market, or in comparable New England coastal resort destinations such as Nantucket, Cape Cod, Newport, or coastal Maine.
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Established vendor and trade relationships within the Martha's Vineyard or broader southeastern Massachusetts region.
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Bilingual language skills (Spanish or Portuguese a particular plus, given regional workforce demographics).
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Certified Hotel Administrator (CHA) or other professional hospitality certification.
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Experience with event management, wedding services, or private event hosting in a boutique hotel setting.
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Familiarity with island-specific logistics, seasonal workforce sourcing (including J-1 visa programs), and ferry/supply chain management.
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Compensation & Benefits
The anticipated salary range for this position is $125,000-$160,000 annually, with final compensation determined based on experience, qualifications, and demonstrated success in comparable hospitality leadership roles.
The General Manager is also eligible for an annual performance-based bonus and a comprehensive benefits package, which may include:
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Performance bonus opportunity
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Housing assistance or employer-provided housing
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Medical, dental, vision and life insurance
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401(k) retirement plan with employer contribution
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Paid time off and holidays
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Opportunity for ongoing professional development
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Additional benefits as offered by the Harborside Inn
Compensation and benefits are reviewed periodically and may be adjusted based on performance, market conditions, and organizational need
