ABOUT US
We are a privately held group of internationally impactful companies operates across consumer packaged goods, hospitality, technology, real estate, non-profit, and venture funding. Led by a highly entrepreneurial, self-made founder and supported by a team of high-performing executives, the organization has a global footprint with active interests across the United States, Canada, Europe, and the Caribbean.
Our family has a deep and enduring connection to the ocean where time on the water brings clarity, connection, and calm. Yachting is part of our rhythm and a reflection of our values. Our vessels are maintained to uncompromising standards, operated with quiet precision, and managed with the same professionalism and discretion that define our organization.
We’re seeking a captain who combines technical mastery with personal maturity, a mariner and manager in equal measure. Someone who can lead crew, oversee maintenance, and navigate with confidence, while fostering an atmosphere of respect, readiness, and ease onboard.
The ideal candidate is steady under pressure, self-sufficient in problem-solving, and composed in communication. They take genuine pride in their craft, anticipate needs before they’re voiced, and deliver excellence in every detail. Above all, we’re looking for a captain who embodies precision, loyalty, and discretion and who treats the vessel as both responsibility and art form.
WHAT YOU'LL DO
As Captain, you will command a diverse fleet operating across multiple countries, including smaller work and pleasure craft in Canada, a 50-foot day boat and 100-foot regional cruiser in the Bahamas, and a 200+ foot global expedition yacht now in acquisition. You will oversee and operate all vessels, ensuring safety, precision, and readiness at all times. This is a hands-on leadership role requiring technical mastery, sound judgment, and disciplined execution. You will build and manage a flexible crew across regions, oversee maintenance and refits, and lead vessel purchases and sales when required. You will manage the fleet with cost-conscious discipline, maximizing efficiency and identifying income opportunities where appropriate. The expedition yacht will run a limited off-season charter program, which you will organize and oversee.
When the family is aboard, you will captain day trips, regional cruises, and extended global expeditions spanning the Bahamas, Caribbean, Arctic, Northwest Passage, Canada, the Azores, Europe, Iceland, and the Galápagos. When they are away, you will manage crew, budgets, and operations with quiet precision. Security and discretion are paramount. You will safeguard both people and property, maintain readiness across all locations, and be prepared for travel through challenging or unstable regions. Firearms or formal security training is a plus.
The ideal candidate has proven success managing multi-vessel fleets, global passages, and refits ranging from under $1M to $10M with verifiable results. A broker’s license and experience in vessel acquisition, sales, or property oversight are valuable advantages. Above all, this role demands initiative, composure, and pride in craft. You will lead by example, setting a tone that is professional yet relaxed, disciplined yet approachable, ensuring every experience reflects the family’s high standards of excellence and trust.
WHO YOU ARE
- A seasoned mariner with a minimum of five years in command of vessels 100 feet or greater, backed by deep operational experience in the Caribbean and Bahamas.
- You are equally comfortable single-handing smaller craft (50ft) with precision as you are commanding a full bridge team aboard a 200-foot expedition yacht.
- Brings mastery of navigation, seamanship, and the judgment required to operate a yacht as a disciplined, high-performing enterprise.
- Equally confident on the bridge or in the engine room, with advanced mechanical, electrical, and systems knowledge including hydraulics, HVAC, and vessel electronics.
- Maintains the yacht to flawless standards through proactive maintenance and reliability oversight.
- Composed and decisive under pressure, able to troubleshoot complex issues and navigate demanding conditions with clarity, calm, and control. Leads with quiet authority, ensuring safety, order, and confidence at all times.
- Operates with absolute discretion, professionalism, and integrity in all interactions. Understands the nuances of private family service, anticipates needs without intrusion, and upholds confidentiality as a matter of principle.
- Prioritizes safety above all else through rigorous operational discipline, compliance, and proactive risk management. Ensures every voyage meets the highest standards of technical, legal, and ethical responsibility.
- Runs the vessel with precision and accountability maintaining detailed logs, budgets, inventories, and maintenance schedules.
- Oversees all operations with an ownership mindset and seamless coordination with shore-based management.
- Leads with steadiness and respect, fostering trust and pride among a small, close-knit crew.
- Communicates clearly, sets high expectations, and cultivates a culture of professionalism and mutual accountability.
- Acts as a trusted extension of ownership, proactive, transparent, and aligned with the family’s standards and pace. Balances autonomy with consistent communication to maintain confidence and trust.
- Thrives in lean, hands-on programs and remote cruising environments where foresight, adaptability, and independence are essential. Excels in managing logistics, sourcing, and execution without reliance on large support networks.
- Maintains impeccable standards of presentation and performance. Every aspect of the vessel from tender operations to guest experience reflects excellence, care, and the quiet precision expected at the highest level of private ownership.
RESPONSIBILITIES
- Command and operate the vessel safely and confidently across Caribbean cruising grounds, ensuring precision in navigation, seamanship, and overall voyage execution.
- Oversee and participate directly in all maintenance and technical operations, maintaining mechanical, electrical, and hydraulic systems at peak performance through proactive service and inspection.
- Plan and execute itineraries in collaboration with ownership, management, and local agents, balancing operational efficiency with guest experience and environmental conditions.
- Maintain the vessel in impeccable condition at all times — managing refits, repairs, and scheduled servicing with foresight, quality control, and disciplined documentation.
- Manage all operational budgets, provisioning, and compliance requirements in accordance with maritime, Flag State, ISM, and ISPS standards.
- Uphold the highest standards of safety, security, and discretion, ensuring every voyage is executed with professionalism and care while delivering a seamless luxury experience.
- Navigate and operate the vessel with confidence, overseeing all bridge operations, routing, and watchkeeping to the highest professional standards.
- Conduct and supervise all engineering functions, including troubleshooting, diagnostics, and routine servicing of onboard systems to ensure reliability and performance.
- Execute docking, mooring, and anchoring procedures independently and with precision, maintaining full vessel control even in challenging conditions.
- Operate and maintain tenders for guest transfers, provisioning, and shore access, ensuring reliability, safety, and readiness at all times.
- Lead and manage a small seasonal crew, including Cook/Stew and contracted professionals, setting clear expectations and ensuring service excellence throughout.
- Control maintenance budgets and operating expenditures with discipline, forecasting costs accurately, sourcing efficiently, and maintaining clear financial accountability.
WHAT YOU'LL BRING
- Minimum of five years’ experience as Captain on yachts of comparable size or larger, with a proven record of command, operational excellence, and reliability.
- Demonstrated versatility operating vessels from 50 to 200 feet, including hands-on operation, docking, and systems management without reliance on large support teams.
- Valid 200GT Captain’s License (Yachtmaster Offshore, USCG, or equivalent), with all required certifications maintained in good standing.
- Advanced engineering knowledge with hands-on proficiency across mechanical, electrical, hydraulic, and HVAC systems; capable of troubleshooting and resolving issues independently.
- Extensive Caribbean and Bahamian cruising experience with deep knowledge of regional waters, ports, and anchorages.
- Strong leadership presence with the ability to motivate, direct, and maintain discipline among a small crew while fostering respect and professionalism.
- Exceptional communication, situational awareness, and problem-solving skills; maintains composure, judgment, and clear decision-making in dynamic conditions.
- Prior experience in marine engineering or as a dual-role Captain/Engineer is highly valued, reflecting a hands-on, technical leadership style.
- Fluent in English with strong written and verbal communication skills; able to interact professionally with owners, guests, and service providers.
- Demonstrated history of excellence, integrity, and longevity in previous roles, supported by strong verifiable references.
- Comfortable operating under Cayman registry and capable of managing voyages across the Caribbean, U.S., Canada, and potentially South America.
- Prior experience with private family ownership and extended Caribbean or Bahamas cruising is a significant advantage.
- Prior military, Coast Guard, or naval background is considered an asset, reflecting the discipline, precision, and reliability valued in this role.
Note: Applications from professional couples are welcomed, particularly where a partner brings Stew or Chef experience aligned with family standards.
COMPENSATION
A highly competitive base salary will be offered, commensurate with experience and the standards expected at this level of command.