Founder & Principal Yacht Consultant
Judgment Built Through Experience—On the Water, in the Market, and Across the Table.
Rob Rollick founded Wake & Compass to provide yacht buyers and sellers with something larger brokerage models often struggle to deliver: direct involvement, independent thinking, disciplined market analysis, modern vessel marketing, and clear guidance throughout the transaction.
Principal
Rob Rollick
Founder & Principal Yacht Consultant
Rob Rollick's connection to the water began long before his professional career in yacht sales. Raised around Charleston and the waterways of the Southeast, he grew up boating, fishing, and diving from the Carolinas through Florida. His early maritime experience included working aboard a Magwood Seafood commercial shrimp trawler and aboard the tugboat Orion with Gulf & Orient during work associated with a NOAA navigational-buoy retrofit project.
Those experiences gave Rob an understanding of boats from a working perspective. They also established an appreciation for preparation, mechanical realities, changing conditions, and the importance of making sound decisions before leaving the dock.
Before entering professional yacht sales, Rob developed a broad background in sales, hospitality, consulting, and client service. His experience included work with Waldorf Astoria and Meisel Holding Group, where presentation, communication, discretion, and the quality of the client experience mattered.
In 2011, Rob launched a consulting practice in Massachusetts. That work included advising MIT-affiliated entrepreneurs on strategic planning and infrastructure-related acquisition opportunities across North and South America. The experience strengthened his ability to evaluate complicated opportunities, organize information, identify risk, communicate across different professional disciplines, and approach negotiations with preparation rather than emotion.
Rob's professional yacht career took shape in Newport, Rhode Island—one of America's most respected yachting centers. His experience in yacht sales and client representation exposed him to the strengths of the traditional brokerage model, but also to its limitations. Too often, sellers were given optimistic pricing without enough defensible market analysis. Listings were entered into industry databases without a truly individual marketing strategy. Buyers were shown available inventory without receiving enough independent comparison, risk analysis, or strategic guidance.
Wake & Compass was created to offer a more deliberate approach.
Today, Rob works as a yacht consultant to buyers, owners, and prospective sellers. His work centers on yacht acquisition, buyer representation, market evaluations, vessel positioning, seller strategy, advanced yacht marketing, negotiation, and transaction guidance.
For buyers, the process begins with understanding the mission. How will the yacht actually be used? Where will it cruise? Who will be aboard? What operating, maintenance, transportation, tax, insurance, and ownership considerations may affect the decision? From there, Wake & Compass can research the broader market, compare yachts across regions, identify meaningful differences, investigate potential risks, coordinate with the appropriate professionals, and help the buyer navigate the transaction.
For sellers, Rob's approach begins with market position rather than marketing promises. The objective is not simply to arrive at the highest suggested asking price. It is to determine the most defensible position based on the yacht's age, condition, equipment, engine hours, refit history, location, competition, available inventory, market velocity, and reliable market indicators when available.
That analysis becomes the foundation for a vessel-specific marketing campaign. Wake & Compass combines traditional yacht-industry relationships with modern digital strategy, cinematic presentation, direct outreach, organized follow-up, and measurable campaign intelligence. The yacht is treated as an individual product launch—not simply another database entry.
Rob has also completed professional certification work in artificial intelligence through IBM and incorporates advanced research and data-analysis tools into the Wake & Compass process. Technology is used to broaden research, compare information, organize opportunities, track market activity, strengthen marketing, and pressure-test conclusions.
Technology does not replace relationships, professional judgment, verification, or experience. Pricing decisions, negotiations, recommendations, and transactions remain human-led.
Rob founded Wake & Compass around a straightforward principle: clients deserve to understand what the market is saying, what decision comes next, and why.
Know the market. Navigate the deal.
"A yacht transaction involves far more than finding a boat or uploading a listing. The real work is understanding the market, recognizing risk, creating the right position, and guiding each decision with discipline."
Professional background
Experience That Shapes the Advice
Maritime Foundation
Early experience aboard a commercial shrimp trawler and the tugboat Orion during work associated with a NOAA navigational-buoy retrofit project.
Client Service
Professional experience in sales and hospitality, including work with Waldorf Astoria and Meisel Holding Group.
Strategic Consulting
Founded a Massachusetts consulting practice in 2011, with work that included advising MIT-affiliated entrepreneurs on strategic planning and infrastructure-related acquisition opportunities across North and South America.
Yacht Sales and Consulting
Professional yacht career developed in Newport, Rhode Island, with experience in yacht sales, buyer and seller guidance, vessel evaluation, market positioning, negotiation, and transaction coordination.
Artificial Intelligence and Data Analysis
Professional certification work in artificial intelligence through IBM, applied to market research, organized analysis, modern marketing, and decision support.
IBM AI certification titles will be listed here upon upload of verified credentials.
Services
How Rob Works with Clients
Yacht Acquisition Consulting
Defining the buyer's mission, researching suitable models, comparing markets, identifying material differences, and establishing a disciplined acquisition strategy.
Buyer Representation
Assisting buyers with yacht discovery, market comparison, offer strategy, negotiation, survey and sea-trial coordination, documentation workflow, and communication with appropriate specialists.
Seller Strategy
Evaluating market position, competition, condition, location, presentation, buyer profile, pricing logic, and the decisions necessary before launching a yacht for sale.
Advanced Vessel Marketing
Building an individual campaign around the yacht's strongest defensible story through professional presentation, modern technology, global discovery, direct outreach, organized follow-up, and market feedback.
Market Evaluation
Researching available inventory, comparable models, geographic differences, currency, transportation, taxes, duty, condition, equipment, engine hours, refit history, and reliable market indicators when available.
Negotiation and Transaction Guidance
Helping clients understand the decisions, risks, professional resources, and next steps involved from the initial conversation through closing.
A More Informed Conversation Starts Here.
Whether you are beginning a yacht search, evaluating a potential acquisition, considering a sale, or questioning the position of an existing listing, Wake & Compass can help establish the next course.