Member Services and Sales

Member Services and Sales — Island Sailing | Portland/Vancouver Area

Full-Time | Thursday–Monday | Base $40,000–$45,000 DOE + Commission

Island Sailing is a sailing school, racing program, and membership club on the Columbia River with over forty years of history and real momentum behind it. Under new ownership, we've grown the membership base significantly, expanded our fleet, built one of the largest and most active racing training programs in the Pacific Northwest, and deepened our roots in the regional sailing community.

We're looking for someone to help us keep that going — and who genuinely belongs in this world. This is a front‑line role with real responsibility. You'll be the first voice many prospective members hear and the ongoing relationship for members already in our community. It blends relationship‑based sales, member experience, and day‑to‑day operational support. If you're a sailor who's also good with people and comfortable in a sales conversation, keep reading.

Island Sailing has worked hard to build something worth protecting: a collaborative, accountable, and genuinely welcoming crew. We're a small team running a large operation, and that means everyone's contribution is visible — the good and the bad. Everyone on this crew shows up fully, engages honestly, and takes the mission seriously. Sailing has more than its share of ego — we've made a deliberate choice to build something different.

The people who thrive here lead with humility, hold our values as a lived standard rather than a talking point, and make those around them better. We're building a crew culture of learn‑it‑alls, not know‑it‑alls. If your identity depends on being the smartest person in the room, this isn't your crew.

Full‑time, Thursday through Monday — our peak operational days as a leisure and instructional business. You'll work directly with ownership and a small, tight‑knit team.

• Own the member experience from first inquiry through onboarding and ongoing engagement — phone, email, in‑person at the club
• Drive membership sales through consultative outreach, follow‑up, and retention conversations
• Manage and maintain member records in our CRM (Zoho); track inquiries, conversions, and renewal pipeline
• Coordinate with instructors and operations to ensure members and students have what they need
• Support event coordination and community programming — regattas, socials, racing events, club gatherings
• Contribute to member communications — campaigns, social content, updates — collaboratively, not solo
• Be the warmth in the room — introduce yourself, be the person who introduces people to each other, initiate conversations, and ensure that no member, student, or visitor ever stands in our space feeling unseen or feeling like a stranger.

This role is not purely administrative, fully remote, or a fit for someone who wants predictable, defined tasks. It's a sailing club: things move, and you'll need to move with them.

First and foremost: you need to have sailed. Not a passing familiarity, not a boat ride — real time on the water, enough that you can speak credibly to a prospective member about what it feels like to heel into a tack for the first time, or why someone who's never left the dock is about to change their life by getting into sailing and joining this club.

ASA 101 certification is the floor. If you have sailboat racing experience on top of that, you move to the front of the line. Our performance racing program is one of the most active in the Pacific Northwest, and someone who already understands that world — the culture, the language, the draw — brings something that cannot be taught in onboarding.

Beyond the water:

• You walk into a room and make it warmer. Our members and students arrive at this club sometimes nervous, sometimes excited, often both. You are frequently the first human being they encounter. That means you notice when someone walks in, you move toward them — not because a script says to, but because your instinct is curiosity about people rather than avoidance of them.
  
  If your natural mode is to wait until someone approaches…