Director of Sales - Hospitality

Director of Sales – Urban Cowboy Lodge

We are seeking an experienced and dynamic Director of Sales to lead all revenue-generating efforts for Urban Cowboy Lodge.

Urban Cowboy Lodge is multifaceted and dynamic, with multiple outlets serving hotel guests, restaurant diners, bar patrons, weddings, corporate events, and neighbors. We are a team of passionate hospitality professionals committed to delivering exceptional guest experiences both in the Catskills and beyond. The DOS will play a critical role in driving revenue, building meaningful client relationships, and ensuring that every booking reflects the Lodge’s distinctive culture and character.

About Urban Cowboy Lodge

Urban Cowboy Lodge (“The Lodge”) is renowned for its singular hospitality, beautiful setting, and luxe amenities. The Lodge has 38 keys and sits on 200 acres of wilderness, offering both guests and staff expansive nature and a nurturing culture. Amenities include two bars, one restaurant, a pizza outlet, a swimming pool, an outdoor sauna, two treenets, and endless trails and outdoor activities. Its aesthetic is uniquely rustic - detailed, casual, and effortlessly presented. Urban Cowboy Lodge is a place where people arrive as strangers and leave as friends, in both work and play.

Job Overview

The Director of Sales will oversee all sales activity for Urban Cowboy Lodge, including group business, corporate retreats, weddings, private events, and experiential programming. This role is responsible for driving top-line revenue, building long-term client relationships, and maximizing occupancy and event performance across all segments.

This position requires a proactive, highly organized, and commercially minded leader who thrives in a hospitality-driven, experiential environment. You will work closely with Hotel Leadership, Operations, and Events teams to ensure seamless execution from booking to on-site delivery.

Our ideal DOS combines a warm, relational approach with strong commercial instincts. You will communicate the vision and positioning of the Lodge, actively generate new business, and leverage data, market trends, and client relationships to grow revenue.

This is a hands-on role that blends sales strategy, client relationship management, systems oversight, and on-property collaboration, with a strong focus on execution and conversion.

Essential Functions & Responsibilities

Sales Efforts

• Drive revenue and achieve sales goals through proactive outreach, including phone solicitation, email campaigns, virtual presentations, and on-property site tours
• Develop and maintain relationships with new and existing clients across corporate retreats, weddings, private groups, and experiential stays
• Identify and pursue opportunities to grow weekday business, group occupancy, and high-value event bookings
• Respond to all leads and inquiries in a timely manner, ensuring proposals and follow-ups are delivered with speed and precision
• Collaborate with Hotel Leadership and Events teams to align sales strategy with operational execution
• Stay informed on market trends, competitor positioning, and demand drivers within the Catskills and broader experiential hospitality space
• Continuously refine sales strategy, pricing positioning, and conversion processes to maximize revenue and occupancy

Administrative, Systems & Vendor Management

• Own all sales communication channels including inboxes, CRM systems, and third-party booking platforms
• Maintain and optimize systems and workflows for lead management, proposals, contracts, and client tracking
• Develop tailored sales collateral including proposals, decks, event summaries, and group agreements
• Cultivate strong relationships with planners, corporate clients, travel partners, and vendors to expand business opportunities
• Monitor sales performance, pipeline activity, conversion metrics, and pacing reports
• Maintain accurate records of client history, inquiries, and booking trends
• Ensure all sales documentation and processes reflect brand standards and operational clarity

Event & Group Collaboration

• Partner closely with Events and Operations teams to ensure seamless handoff from sales to execution
• Participate in site tours, client walkthroughs, and pre-event planning for high-value bookings
• Support the coordination of logistics for group stays, weddings, and corporate retreats
• Ensure all sold events are communicated clearly to operational teams to guarantee flawless execution
• Maintain ongoing communication with clients leading up to arrival to ensure expectations are aligned and exceeded

Programming & Revenue Development

• Contribute to the development of seasonal programming and experiential offerings that drive occupancy and group demand
• Identify new revenue streams across lodging, events, food & beverage, and experiential packages
• Collaborate with leadership on packaging, pricing strategies, and promotional initiatives
• Build strategic partnerships with external vendors and partners to enhance guest offerings and increase booking appeal

Knowledge, Requirements, and Skills

• 5 years of hospitality sales experience, ideally in hotels, resorts, or experiential travel environments
• Proven track record of achieving and exceeding sales targets across group, corporate, wedding, and event segments
• Strong relationship builder with the ability to convert leads into long-term clients
• Highly organized, with strong CRM, pipeline management, and reporting skills
• Comfortable working in a fast-paced, seasonal hospitality environment
• Strong communicator and storyteller with the ability to “sell the experience,” not just the space
• Analytical mindset with ability to use data, pacing, and market trends to guide decisions
• Proficiency in CRM, Excel, Google Workspace, and hospitality systems (PMS/POS/event tools)
• Collaborative, hands-on, and comfortable working closely with operations teams on property
• Flexible availability including weekends and peak event periods

Compensation

• Base salary of $80,000 - $105,000 annually, depending on experience, with opportunity for incentive compensation based on performance
• Eligibility for health, vision, and dental insurance
• Paid time off and standard employee benefits per company policy
• Employee discounts and access to Urban Cowboy and Dovetail Co properties
• This is an exempt position

If interested, please send your resume and a brief cover letter to Eric Bieber at eric@urbancowboy.com

Disclaimer

We are an equal opportunity employer. We actively respect the right of any qualified individual who performs to Dovetail’s standards to work. Discrimination based on gender, age, race, religion, national origin, marital status, sexual orientation, disability, or any other characteristic not related to performance, ability or attitude protected by state or federal law, will not be tolerated.

Pay: $80,000.00 - $105,000.00 per year

Benefits:

• Dental insurance
• Health insurance
• Vision insurance

Work Location: In person

Salary : $80,000 - $105,000