Now Hiring

Work with us!

59º North Sailing is seeking two professional Lead Skippers to join our team for the 2027 season and beyond. We don't run a sailing school; instead, we schedule real-stakes ocean passages from point A to point B and then must execute on those schedules with little margin for error. These are real ocean passages where we teach our paying crew how to execute them. Our mission is to empower crew members to find their own limits while maintaining the highest standards of safety and seamanship. The best sailing staff make all of this look effortless.

THE ROLES

We are looking for leaders who thrive in a "hands-off director" capacity. You must be able to first properly brief and train the crew prior to departure on a very tight timeline, then step back and let the crew sail the boat, while maintaining the sharp situational awareness required to intervene before a mistake becomes a problem.

  • Lead Skipper (FALKEN): Commanding our 1999 Farr 65. This is a high-performance ocean sailing machine refit specifically for our mission. Supported by a dedicated Bosun. Requires mastery of performance-oriented offshore sailing and large-crew management, and you must be proficient in all aspects of boat maintenance.
  • Lead Skipper (ISBJØRN): Commanding our 1972 S&S Swan 48. A seasonal rotation (Spring–Fall sailing, Winter maintenance) for a "primary fixer" who enjoys the technical intimacy of a classic S&S-designed offshore cruiser-racer. This role will be primarily based in Bergen, Norway.

‍

THE SKILLSET: WEATHER & ROUTING

Safe offshore sailing at 59º North is predicated, first and foremost, on staying "ahead" of the weather.

  • Proficiency: You must be highly proficient in offshore weather forecasting and independent weather routing. You must understand weather models, be able to discuss and teach this to crew prior to a passage and once offshore, and you must understand "certainty" as it relates to weather forecasting & routing.
  • Collaboration: While you will have direct support from professional routers at WRI Inc. and our onshore Mission Control base, you are expected to be the primary decision-maker on board, capable of synthesizing complex data into safe, efficient passage plans, and furthermore, explaining these decisions and their factors to the crew.

‍

THE IDEAL CANDIDATE

  • Humble Authority: You are confident but leave your ego at the dock. You lead by example and are willing to jump into any role — including sailing as a Mate when required.
  • The "Mentor" Mindset: You enjoy managing a diverse group of people with varied ages and goals, ensuring everyone gets the specific experience they came for.
  • Technical Lead: You are comfortable with routine and refit maintenance. You are the primary "fixer" on ISBJØRN and a technical lead on FALKEN.
  • BONUS: Preference given to American citizens who also hold USCG Master Mariner licenses and who are willing to fill-in as skipper on our sister business Schooner WOODWIND, which runs 2-hour tourist daysails based in Annapolis, MD.

‍

QUALIFICATIONS & CONTRACT

  • Contract Type: Rotational ongoing freelance contracts. You’ll be a core part of the 59º North Sailing team, and you'll be expected to participate in other aspects of the business as well, from social media to calendar planning and annual staff training.
  • Licenses: FALKEN: RYA Yachtmaster Ocean (Commercially Endorsed) | ISBJØRN: Norwegian D5L.
  • Legal: Valid B1/B2 Visa (for itineraries starting or ending in the USA) is mandatory.
  • Sustainability: ~150 days at sea per year; rotation-based to ensure you aren't away from home for more than 6–8 weeks at a time.

‍

COMPENSATION & PERKS

  • All-Inclusive: All travel and on-board expenses are covered.
  • Gear: 50% off Helly Hansen pro-deal, plus all job-specific technical clothing and safety gear is provided to you.

‍

HOW TO APPLY

The application process is thorough and includes:

  1. Video Introduction: Tell us your story and your philosophy on leadership.
  2. Professional Sailing CV: Highlighting miles, weather routing experience, and hands-on maintenance.
  3. References: We want to hear from people you’ve led and those you’ve worked for. Bonus points for giving us your worst references and what they’d say about you.

Apply online at: https://forms.59-north.com/jobs