Company Description

The Red Lion Inn, located in Stockbridge, Massachusetts, offers a rich history, warm hospitality, and classic New England charm. Since 1773, the inn has been a welcoming destination for travelers, providing a memorable experience in the heart of the Berkshires. Part of the Main Street Hospitality family, The Red Lion Inn boasts unique lodging options, antiques, art, live music, fine dining, and more. Join our dedicated team committed to creating exceptional guest experiences.

Job Purpose:

The Director of Sales at Main Street Hospitality is a results-driven leader responsible for setting and executing a dynamic sales strategy that drives topline revenue, builds long-term client relationships, and positions the property as a market leader. Equal parts strategist and relationship builder, this role cultivates business across corporate, group, leisure, wedding, and local segments—crafting sales initiatives that reflect the individuality of the property while staying true to Main Street’s values of warmth, integrity, and community connection.

The Director of Sales leads with vision, collaboration, and entrepreneurial spirit, managing the full sales lifecycle from lead generation and proposal development to contracting and client stewardship. This role partners closely with the General Manager, Revenue Management, Marketing, and Operations to ensure that sales strategies align with broader business goals and guest experience standards. As a leader and brand ambassador, the Director of Sales plays a key role in storytelling, positioning, and guest conversion across all touchpoints.

Essential Duties and Responsibilities:

Sales Strategy & Revenue Generation

Develop and execute an annual sales strategy that aligns with property positioning, market dynamics, and revenue targets.
Identify and pursue new business opportunities across group, leisure, corporate, wedding, and social segments.
Maintain a strong pipeline of qualified leads through proactive outreach, networking, partnerships, and inbound lead conversion.
Partner with Revenue Management to set pricing, monitor demand, and optimize channel performance.
Lead quarterly sales forecasting, pacing, and reporting; adjust strategies as needed to meet or exceed revenue goals.

Client Relationship Management

Serve as the lead contact for key accounts, nurturing long-term relationships and delivering personalized, responsive service.
Conduct site visits, develop compelling proposals, and manage all stages of the sales process with professionalism and creativity.
Represent the property at trade shows, sales missions, and industry events to strengthen brand visibility and generate leads.
Collaborate with Catering Sales and Events to ensure seamless transition from sales to execution and maximize guest satisfaction.

Team Leadership & Department Management

Hire, train, and lead sales managers, sales coordinators, and support staff as applicable.
Set clear goals, provide regular coaching, and conduct performance reviews in alignment with Main Street’s leadership philosophy.
Foster a sales culture grounded in collaboration, resilience, and storytelling.
Ensure that all team members are aligned on brand standards, messaging, and service approach.

Collaboration & Cross-Functional Partnership

Work closely with Marketing to develop collateral, content, and campaigns that support sales efforts and seasonal promotions.
Partner with Operations and Front Office to ensure readiness for group arrivals, special requests, and VIP clients.
Collaborate with the Finance team on contract terms, billing, and deposit structures.
Align with the Director of Catering Sales to jointly grow group and event revenue while maintaining operational excellence.

Systems, Reporting & Analytics

Ensure CRM, sales tracking platforms, and lead generation tools are being used effectively and consistently.
Maintain accurate sales data, forecasting models, and KPI dashboards.
Analyze market trends, comp set performance, and internal data to inform strategy and identify growth opportunities.

Brand Stewardship & Community Engagement

Serve as a brand ambassador and property storyteller in all sales engagements and community partnerships.
Leverage local relationships and regional knowledge to enhance the property's visibility and community connection.
Uphold Main Street’s HEART of Hospitality in all client interactions, proposals, and negotiations.

Education & Experience:

· Minimum 7–10 years of progressive experience in hotel sales, including 3+ years in a senior sales leadership role.

· Proven success in driving hotel sales across multiple segments (corporate, group, leisure, wedding, etc.).

· Experience with lifestyle, boutique, or independent hotel brands strongly preferred.

· Proficiency in CRM platforms, PMS, and sales reporting tools.

· Strong understanding of revenue management principles and the sales/marketing funnel.

Professional Characteristics:

· Takes initiative, sets ambitious targets, and holds self and team accountable to results.

· Builds trust and rapport with clients, team members, and stakeholders alike.

· Brings energy, clarity, and storytelling into every proposal, presentation, and interaction.

· Aligns sales tactics with broader business goals and long-term brand building.

· Works seamlessly across departments to ensure cohesion and deliver exceptional guest outcomes.

· Navigates shifting market conditions with composure and adaptability.

· Embodies and models Main Street’s values of kindness, integrity, accountability, and community investment.

Scheduling & Travel:

This is a full-time leadership role that requires schedule flexibility, including availability to work evenings, weekends, holidays, and special events as needed. Occasional travel to attend company meetings, training, or off-site events required.

Work Authorization: Must be eligible to work in the United States.

EEO Statement: Main Street Hospitality is an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability status, protected veteran status, gender identity, or any other characteristic protected by law.

Main Street Hospitality Values:

• We are kind to one another

• We embrace change

• We invest in community

• We act with integrity

• We take responsibility for our actions

I have read and understand the job description as stated above and accept that any of the tasks may be modified or changed. I accept responsibility for knowing the modifications and/or changes in the job description. I can perform the essential functions of this job as listed above, with or without reasonable accommodation.

The Red Lion Inn

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