DIRECTOR

OF

OPERATIONS 

 

Job Title: Director Of Operations

Location: Tops’l Farm, Waldoboro, ME
Type: Seasonal Leadership Position  • April- November  

Our mission is to offer spaces and experiences for guests to better connect with themselves, the people they love, and nature. 

How we get there as a team is nurtured with equal care. 

The Opportunity 

Tops'l Farm is seeking an exceptional leader to serve as Director of Operations for our 10th anniversary season. This is not a traditional hospitality management role—it's an opportunity to steward an experience that matters deeply to the people who come here and the team that makes it possible. 

As Director of Operations, you will be the senior leader on-property, overseeing all aspects of our seasonal business model: elegant weekend weddings (130+ guests) and intimate midweek retreats (22 guests average). You'll manage department heads across culinary, events, property, and hospitality—ensuring seamless execution while our founder transitions to other growth focused projects. 

We're looking for someone who leads with both competence and heart. Someone who understands that how we treat each other behind the scenes shapes every guest experience. Someone who can hold high standards while creating an environment where people want to do their best work. 

About Tops'l Farm 

Nestled on 83 acres in Waldoboro, on Maine's midcoast, Tops'l Farm has spent a decade cultivating a reputation for authentic, Maine-rooted hospitality. Our 1860s restored farmhouse, working farm, and collection of thoughtfully designed cabins create an environment where guests disconnect from the ordinary and reconnect with what matters. 

We are not a luxury resort. We are not a rustic barn venue. We exist in the space between—sophisticated but not stuffy, elevated but grounded. Our guests come for the experience of real Maine: the smell of salt air mixing with garden roses, meals crafted from ingredients grown steps from the kitchen, and the kind of unhurried pace that allows genuine connection. 

In 2026, we will host 18+ weddings, 14+ retreats during peak season, and special programming including our 10th Anniversary Celebration. Our culinary program, led by our in-house chef, has become a destination in itself. Our team is small, talented, and deeply committed to the Tops'l vision. 

Our Culture 

At Tops'l, we believe the guest experience begins with the team experience. We can't create spaces for connection if we don't practice connection ourselves. This shapes everything about how we work: 

  • We solve problems together. When something goes wrong, we're more interested in fixing it than assigning blame. 

  • We communicate directly and kindly. Hard conversations happen with respect. Feedback is given to help people grow. 

  • We protect each other's wellbeing. Seasonal hospitality is intense. We build schedules that allow for rest and lives outside of work. 

  • We trust each other. Micromanagement doesn't live here. We hire capable people and let them do their jobs. 

  • We take pride in craft. Whether it's a perfectly plated dish, a beautifully set table, or a well-organized storage room—details matter because they add up to something guests can feel. 

The Director of Operations sets the tone for all of this. You will model the culture we want to create. Your energy, your communication style, your approach to problems—these ripple through the entire team. 

The Role 

Core Responsibilities 

  • Operational Leadership: Serve as the senior decision-maker for all day-to-day operations, ensuring both wedding weekends and midweek retreats execute flawlessly 

  • Team Leadership: Direct oversight of department heads including Executive Chef, Small Events Manager, Property Manager, and Beverage Manager; create an environment where people thrive 

  • Culinary & F&B Partnership: Work closely with in-house culinary on menu execution, food costs, vendor relationships, and kitchen operations; oversee beverage program including inventory, ordering, and bar service coordination 

  • Guest Experience: Maintain quality control across all touchpoints; handle escalated guest concerns with grace and authority 

  • Financial Stewardship: Monitor labor costs, food costs, and operational expenses against budget; approve purchases and vendor contracts within established parameters 

  • Problem-Solving: Be the calm in any storm—weather emergencies, vendor failures, staffing gaps, guest issues—you navigate challenges so they don't escalate 

  • Systems & Process: Implement and maintain operational systems; document processes; ensure consistency and efficiency across all departments 

  • Strategic Partnership: Participate in monthly strategic meetings with ownership; bring solutions and recommendations, not just problems 

What You Won't Do 

This is a leadership role, not a hands-on production role. You won't be cooking, serving, or cleaning—you'll be ensuring the people who do those things have what they need to succeed. You won't be planning weddings—you'll be ensuring our event coordinators execute them beautifully. You won't be mowing lawns—you'll be ensuring our property team maintains our standards. 

Schedule & Compensation 

Position Details 

Season: April 1 – November 30th, 2026 

Hours: 45-50 hours/week during peak season (May-October); 30-35 hours/week shoulder season 

Schedule: Primarily Wednesday through Sunday during peak season; flexibility required for events 

Reports to: Owner (Sarah Pike) via weekly check-ins and monthly strategic meetings 

Compensation Package 

Competitive Base Salary + Housing + Performance Bonus + Meals (during events)  

We are eager to hire the best person for this role and look forward to learning more about your compensation requirements.  

 

Who You Are 

Required Experience 

  • 5+ years in hospitality operations management (hotel GM, restaurant GM, event venue operations, winery/vineyard operations, or similar) 

  • Demonstrated food & beverage management experience—you understand kitchen operations, food costs, menu planning, and bar program management 

  • Proven track record of managing teams of 10+ people across multiple departments 

  • Strong financial acumen—comfortable with budgets, P&L statements, labor cost analysis, and expense management 

  • Availability to live on or near property in midcoast Maine for the season 

Ideal Background 

  • General Manager of a boutique hotel, inn, or resort 

  • General Manager of a high-end restaurant or restaurant group 

  • Operations Director for a winery, vineyard, or farm-to-table venue 

  • Catering Director or Director of Operations for a premier event venue 

  • F&B Director transitioning into broader operational leadership 

Who Thrives Here 

Beyond skills and experience, we're looking for alignment in how you approach work and people: 

  • You lead by example. You don't ask your team to do anything you wouldn't do. Your standards start with yourself. 

  • You're solutions-oriented. When something goes wrong, you've already thought through options before bringing it forward. You fix; you don't just flag. 

  • You communicate with clarity and care. You can have hard conversations without being harsh. You give feedback that helps people grow. 

  • You stay calm under pressure. Events are live performance. Things go sideways. You navigate without drama. 

  • You genuinely care about people. Guests and team alike. Hospitality isn't a performance for you—it's an expression of who you are. 

  • You appreciate beauty and craft. The details matter to you because they add up to something meaningful. 

What You'll Love About This Role 

  • Real Authority: You're not a figurehead. You make decisions, lead the team, and own the outcomes. 

  • Exceptional Setting: 83 acres of midcoast Maine beauty—working farm, restored farmhouse, gardens, and salt air minutes away. 

  • Talented Team: You'll work alongside a celebrated chef, experienced event coordinators, and committed hospitality professionals who care about their craft. 

  • Mission-Driven Work: This isn't corporate hospitality. We create experiences that help people connect with what matters most. 

  • Growth Opportunity: For the right person, this role could expand into year-round leadership as the business evolves. 

  • 10th Anniversary Season: You'll be part of a milestone year, helping us celebrate a decade of creating meaningful gatherings. 

This Role Is Not For You If... 

  • You need constant validation or direction to feel confident 

  • You avoid difficult conversations or conflict 

  • You have great ideas but struggle with execution and follow-through 

  • You prefer large corporate structures with clear hierarchies 

  • You think "good enough" is good enough 

  • You see this as a stepping stone rather than an opportunity to pour yourself into something meaningful 

How to Apply 

Please send your resume and a cover letter to hello@topslfarm.com In your cover letter, we'd love to hear: 

  • Your most relevant hospitality leadership experience 

  • How you've built or shaped team culture in a previous role 

  • A time you navigated a significant operational challenge 

  • What draws you to this opportunity and to Maine 

Timeline: We are interviewing candidates in January with an ideal start date of mid-March 2026 for onboarding and training before our May 1 season launch. 

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Tops'l Farm is an equal opportunity employer. 

We believe diverse perspectives strengthen our team and enrich our guests' experiences.