Staff Product Designer, Guest & Discovery

Company

Collaborative Boating operates Boatsetter and GetMyBoat, the two largest marketplaces for getting on the water, now converging into one platform. Guests arrive wanting something specific — a fishing trip, a sunset cruise, a birthday on a pontoon — and we connect them to the captains, operators, and owners who can make it happen. Finding and booking a day outside should be as easy and intuitive as booking a flight.

The problem

Search is changing under us. Guests arrive with intent expressed in natural language, increasingly through an AI assistant instead of a search box, and increasingly on a surface we don't own. Answering that with a chatbot is the obvious move and the wrong one: choosing between boats is a parallel, visual, comparison task, and a conversation is sequential. The work is holding both — a visual discovery experience built for comparison, and a compact, structured expression of a listing that holds up when a third-party assistant renders it in a layout we didn't design.

The center of gravity is the search results card. It's the smallest unit of persuasion we have: a handful of facts, ordered, that a guest uses to decide whether to look closer. Which facts earn a place, in what order, and how that adapts from "boat rental Miami" to "something fun for eight people Saturday" — that's the problem. It's an information design problem before it's a visual one.

What you'll own

The end-to-end guest discovery experience — search, filtering and refinement, results, map and list, the listing page, and the paths in from organic search and AI assistants. Coherence across both brands and web plus mobile is yours.

The information hierarchy of the results card, defended with evidence, across guest intents and every state the data actually produces: missing photos, no reviews yet, a price range instead of a price, partial availability.

Interfaces over a system that infers. Make what it inferred legible, make correcting it easy, and reduce verification labor rather than creating it — a guest who has to double-check our answer has been handed our work.

Surfaces we don't render. With engineering, shape the structured expression of an experience, an offer, and an operator so it survives being summarized, quoted, or laid out by someone else's assistant.

Continuous discovery with your pod — a Product Manager and an engineering tech lead. Choose the cheapest artifact that answers the open question; spend fidelity when a decision is actually being committed.

How we work

Five things worth knowing before you apply. They aren't universal, and here they aren't negotiable.

• Problem, then system, then experience
• Discovery is ongoing, not a handed off spec
• We ask what moved, not what shipped
• We ship in days, not quarters
• We cross lines, and we bet on each other

What you need to have done

• Held substantial ownership of search, browse, or discovery in a two-sided marketplace — relevance surfaces, faceted filtering, availability and pricing display, map plus list, comparison.
• Designed information you can defend. Walk us through a dense comparison surface you built: why each element is there, why it's ordered that way, what you removed, and what removing it cost.
• Designed over a system that infers, ranks, or predicts — communicating state and confidence in real time, and designing the correction path for when the system is wrong.
• Formed a point of view on search in an AI-driven world, including where conversation doesn't belong. We'd rather you disagree with us than agree quickly.

What also helps

Fluency with entities, states, and contracts alongside your tech lead. Restraint and typographic craft in high-information surfaces. AI tools in your own practice. Search relevance literacy, structured data and schema work, third-party assistant surfaces, or travel, hospitality, and local-services search at scale are each a plus rather than a requirement.

Your portfolio

Send work, not a slide deck about process. Two or three cases at depth. For at least one: the problem and how you knew it was real, what you tried and abandoned, the hierarchy decisions and their rationale, the states you designed for, what shipped, and what it changed. Include something that didn't work. Roughness is fine — we care about the reasoning.

Practicals

Remote, with high overlap in United States Eastern hours. You'll join a five-person design team, report to our Director of Design, and be the dedicated designer in this pod. Relevant degrees in design, HCI, or information architecture are welcome and not required — portfolio and shipped, measured work outweigh credentials.