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General Manager

DD Hospitality
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Job Description: General Manager (Operations & Guest Experience)

Company Overview:

We operate a growing portfolio of hospitality, lodging, and destination-driven properties centered around the historic Madison Barracks campus and our flagship inn, Harbor House. Our work blends hospitality, preservation, and long-term placemaking. We are methodically rebuilding an entire historic district into a year-round destination that serves guests, locals, and future generations.

 

The Opportunity

We are seeking a hands-on, high-impact General Manager to oversee the operations of Harbor House, The Venue, and Madison Barracks. This role requires an authentic leader with a "boots-on-the-ground" mentality who can navigate the "organized chaos" of growth with ease. You aren’t just here to manage existing systems; you are here to help build the systems and processes that will allow our campus to scale while remaining agile enough to adapt to the realities of active development.

 

Long-Term Vision

Madison Barracks is being developed as a cohesive, interrelated resort campus, not a collection of standalone businesses. Key initiatives include:

  • Health Club → Spa Transformation: Reopening as a full spa and wellness destination.
  • Historic Theater → Wedding, Arts & Distillery Project: Rehabilitating the theater into a venue and on-site distillery.
  • Marina Integration: Developing shared amenities and guest services across lodging, wellness, and events.

 

Core Values & "Our Why"

We believe great places don’t happen by accident—they are intentionally designed, carefully operated, and stewarded over decades.

  • Ownership over Hierarchy: Initiative and accountability matter more than titles.
  • Long-term Thinking: We optimize for sustainability, reputation, and quality.
  • Operational Excellence: Vision only matters if execution follows.
  • Respect for Place & People: History, guests, staff, and community all matter.
  • Low Drama, High Trust: Direct communication and adult accountability.

 

Key Responsibilities:

Systems Architect & Process Designer

  • The Playbook: Move beyond the "status quo" by building, documenting, and implementing scalable SOPs and operational procedures across all properties.
  • Consistency & Training: Develop and execute consistent training programs to ensure the "Madison Barracks" standard of service is unified across the entire team.
  • Process Improvement: Continuously audit current workflows to identify friction points and engineer better ways to operate.
  • Agile Execution: Maintain a "fluid" approach to management—the ability to pivot priorities quickly as renovation schedules shift.

 

Authentic Leadership & Team Empowerment

  • Lead by example with a "servant leadership" approach.
  • Empower staff to take ownership of the guest journey.
  • Foster a culture of high trust through transparent, real-time feedback and direct communication.

 

Operational Oversight & Stewardship

  • Manage daily operations across a diverse portfolio (Harbor House, The Venue, and Madison Barracks).
  • Act as a "systems thinker" to bridge the gap between creative vision and disciplined execution.
  • Directly oversee the guest journey to ensure every touchpoint reflects our commitment to quality.

 

Qualifications:

  • Experience: Senior operational leadership in hospitality (multi-property, resort, or destination environments).
  • Process Orientation: Proven experience in creating formal procedures and training manuals from the ground up.
  • Leadership Style: "Boots on the ground" approach; you enjoy being visible in the operation.
  • Emotional Intelligence: A calm, professional demeanor with the ability to handle high-pressure situations.
  • Complexity Management: Ability to manage teams, vendors, and diverse property types simultaneously.

 

Nice-to-Haves:

  • Experience with historic properties or adaptive reuse projects.
  • A background in resort, spa, wedding, or event-driven hospitality.
  • Experience working alongside ownership during active renovations or campus expansions.
  • Proficiency in budgeting, forecasting, and performance reporting.

 

Compensation & Benefits

  • Base Salary: $75,000 – $95,000 (Target range, depending on experience and scope).
  • Bonus Structure: Performance-based incentives tied to operational performance, guest experience metrics, and execution of redevelopment milestones.
  • Benefits: Paid Time Off (PTO), workplace flexibility, and significant long-term growth opportunities as our portfolio expands.
  • Onboarding: A comprehensive, structured training and onboarding program is provided to ensure your success from day one.
  • Other: All other pertinent details will be shared during our conversation. 

 

We are looking for a 'people-first' leader—either a recent grad with a solid foundation or someone within their first 5 years of experience—ready to take their next big career leap with a growing brand. I would love to hear about your journey and passion for the Industry, let’s share a conversation!