Find & Apply For Retail Sales Associate Jobs in Annapolis, Maryland

Outbound Sales Associate Position Schooner Woodwind/Running Free LLC 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. This is an outbound, hunter role. Your job is to open new doors — corporate clients, event and wedding planners, hospitality partners, and group organizers — and build the relationships that turn into booked charters. Inbound inquiries are already handled by our inbound Sales Associate; your focus is proactive prospecting, new-business development and closing those leads. Our sales cycle runs year-round even though our sailing season does not. Corporate and event bookings for the summer are secured in the winter early spring and throughout the sailing season, so this role prospects hardest in the off-season and keeps the pipeline full, ahead of each season. Primary Responsibilities — Outbound Sales 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 pipeline. 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. Supporting Responsibilities — Marketing This role also supports marketing that feeds the outbound pipeline: 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. What We're Looking For Experience in outbound sales or business development — hospitality, event, marine, or tourism sales a strong plus.

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. Compensation & Terms Full-time, year-round, salaried position based in Annapolis, Maryland. Starting base around 50k with potential for bonus. Generous Paid time off Ability to go sailing with friends and family when space is available Health Insurance and retirement benefits available Email cover letter and resume to Beth by clicking "Apply for job" button