Director of Sales

Chesapeake Search Partners has partnered with a boutique hospitality ownership group to identify a Director of Sales to lead commercial strategy across two upscale waterfront hotel properties in the Baltimore market.

Position Overview
The Director of Sales will own the revenue strategy and sales performance across both properties, driving growth across group, catering, and corporate segments. This role leads a small, agile sales team and is responsible for setting direction, building accountability, and elevating overall sales effectiveness.

This is a highly visible leadership position that blends strategic planning with active business development. The ideal candidate brings a strong understanding of hotel revenue drivers, thrives in a multi-property environment, and is comfortable engaging directly with key clients while guiding team performance.

Key Responsibilities

Shape and execute sales plans to increase revenue production across group, catering, and corporate business segments
Provide day-to-day leadership and development for a small sales team, including goal setting and performance management
Evaluate sales activity, pipeline health, and conversion metrics to drive continuous improvement
Generate new business through direct outreach, client meetings, and industry engagement
Oversee corporate RFP responses and maintain visibility into account production and booking trends
Partner closely with property leadership and revenue management to align pricing, positioning, and inventory strategies
Stay informed on local market dynamics and competitor activity to refine sales approach
Maintain ownership of key client relationships and participate in high-impact negotiations
Guide group and event sales strategy, ensuring strong coordination from initial inquiry through execution
Work cross-functionally with operations and F&B teams to support successful group experiences
Ensure accuracy and consistency in sales systems, reporting, and forecasting processes
Support brand alignment across digital channels, marketing initiatives, and third-party platforms
Act as an ambassador for both properties within the local business and hospitality community
Qualifications

Bachelor's degree in hospitality, business, or related field preferred
5+ years of progressive hotel sales experience, ideally within boutique, lifestyle, or urban properties
Experience supporting group, catering, and corporate sales channels
Prior leadership or team mentorship experience strongly preferred
Solid understanding of hotel revenue strategy, sales analytics, and market positioning
Ability to manage competing priorities across multiple properties
Track record of building and maintaining strong client relationships
Experience working with CRM/PMS platforms and standard business tools
Strong communication skills with a proactive, solutions-oriented approach