Outbound Sales Associate

Schooner Woodwind operates two classic Scarano-built schooners offering public sails, private charters,

weddings, and corporate events out of Annapolis. We are hiring a full-time, year-round Outbound Sales

Associate to grow our charter and event business by going out and finding it.

• Proactively identify and pursue new charter and event business through outbound outreach — calls, emails, in-person visits, networking and trade shows.
• Build a book of relationships with corporate clients, event and wedding planners, venues, and local hospitality and tourism partners.
• Develop and work a target list of prospects; own the top of the funnel and drive new leads into the
• Represent Woodwind at expos, industry events, and networking functions to generate leads.
• Maintain an organized prospect pipeline and report on outreach activity, meetings, and new business generated.
• Reactivate lapsed and past clients and pursue referral opportunities.

• Produce content for email newsletters and outbound campaigns to prospects and past clients.
• Support organic social media using Woodwind’s existing photo and video library.
• Help maintain website content and messaging in Woodwind’s brand voice.
• Coordinate with outside marketing contractors or paid-media specialists as needed.

• Experience in outbound sales or business development — hospitality, event, marine, or tourism sales a
• A true hunter: energized by cold outreach, prospecting, and opening new accounts rather than working inbound leads.
• Proven ability to build relationships and generate new business from scratch.
• Strong writing and communication skills for outreach, email, and in-person selling.
• Self-directed and disciplined — able to run an outbound effort through the off-season without daily oversight.
• Familiarity with Annapolis and Capital Region in the local hospitality/event market strongly preferred.
• Comfort with CRM and standard marketing tools.

• Full-time, year-round, salaried position based in Annapolis, Maryland.
• Starting base around 50k with potential for bonus.
• Generous Paid time off
• Health Insurance & retirement benefits available
• Ability to go sailing with friends and family when space if available