Staff Product Designer, Guest & Discovery

📍 Job Overview

Job Title: Staff Product Designer, Guest & Discovery

Company: Getmyboat & Boatsetter (Collaborative Boating)

Location: United States

Job Type: FULL_TIME

Category: Product Design / UX/UI

Date Posted: 2026-08-11

Experience Level: Senior (10+ years implied)

Remote Status: Fully Remote

🚀 Role Summary

• Lead the end-to-end guest discovery experience for a leading marine recreational marketplace, encompassing search, filtering, refinement, results, map/list views, and listing pages.

• Own the information hierarchy and persuasive elements of the search results card, adapting content and order based on guest intent, data availability, and platform constraints.

• Design interfaces for systems that infer, rank, and predict, ensuring clarity of state and confidence, and creating intuitive correction paths for system inaccuracies.

• Develop structured expressions of experiences and offers that are resilient to summarization, quotation, or rendering by third-party AI assistants and surfaces.

• Drive continuous discovery and iteration within a dedicated pod (Product Manager, Engineering Tech Lead) by prioritizing the most efficient artifact to answer open questions and committing fidelity only when decisions are finalized.

📝 Enhancement Note: This role is positioned as a Staff Product Designer, indicating a senior individual contributor role with significant ownership and influence. The focus on "Guest & Discovery" within a two-sided marketplace (Boatsetter & Getmyboat) implies a deep dive into user acquisition, search optimization, and conversion funnels, which are critical for revenue generation. The emphasis on designing for "surfaces we don't render" and AI assistants highlights a forward-thinking approach to GTM strategy, where user experience must extend beyond owned platforms.

📈 Primary Responsibilities

• Design and iterate on the complete guest journey from initial search query (including natural language and AI-driven inputs) through to successful booking, ensuring a seamless and intuitive experience across both Getmyboat and Boatsetter brands.

• Define and advocate for the optimal information architecture and content strategy for search results cards, balancing persuasive elements with factual accuracy across various data states (e.g., missing photos, limited reviews, price ranges).

• Collaborate closely with Product Management and Engineering to design robust system states, entities, and edge cases that underpin the discovery experience, ensuring data models support efficient and accurate inference.

• Develop strategies for making inferred information legible to users and designing easy correction mechanisms, minimizing user effort and validation labor.

• Partner with engineering to shape structured data outputs that can be effectively leveraged by external AI assistants and third-party platforms, extending the brand's reach and discoverability.

• Conduct direct user research and customer interviews with both guests and operators to uncover unmet needs and identify opportunities for product innovation within the discovery flow.

• Define key performance indicators (KPIs) for discovery features, measure their impact post-launch, and use data to inform future design decisions and product prioritization.

• Contribute to the evolution of the design system by introducing new patterns and ensuring adherence to WCAG 2.1 AA accessibility standards in all designed experiences.

📝 Enhancement Note: The responsibilities clearly indicate a strong focus on information design and system thinking, crucial for optimizing conversion rates in a marketplace. The emphasis on "continuous discovery" and "shipping in days" suggests an agile, iterative product development process where designers are expected to be proactive in identifying problems and opportunities, not just executing briefs.

🎓 Skills & Qualifications

Education: While relevant degrees in Design, HCI, or Information Architecture are welcome, they are not strictly required. The emphasis is on demonstrated experience and impact.

Experience: Substantial professional experience in product design, with a significant portion dedicated to complex, data-driven, two-sided marketplaces.

Required Skills:

• Proven experience leading the design of search, browse, or discovery features within a two-sided marketplace, including relevance surfaces, faceted filtering, availability and pricing display, and map/list views.

• Demonstrated ability to design defensible information hierarchies, articulate the rationale behind element placement and removal, and present clear case studies of complex comparison surfaces.

• Experience designing user interfaces for systems that infer, rank, or predict, with a strong understanding of how to communicate system state, confidence levels, and design effective correction paths.

• A well-formed point of view on the future of search, particularly in an AI-driven landscape, and an understanding of where conversational interfaces are appropriate versus visual, comparative ones.

• Proficiency in designing for both web and mobile platforms, ensuring coherence across brands (Getmyboat and Boatsetter).

• Strong understanding of user research methodologies and the ability to translate user insights into actionable design solutions.

• Deep knowledge of accessibility standards, specifically WCAG 2.1 AA, and the ability to integrate them into design patterns.

• Experience working in cross-functional "pods" or agile teams, collaborating closely with Product Managers and Engineering leads. Preferred Skills:

• Fluency with data modeling, system entities, states, and contracts, enabling close collaboration with engineering on technical design.

• Restraint and exceptional typographic craft, particularly in high-information density surfaces.

• Experience leveraging AI tools within personal design practice.

• Familiarity with search relevance concepts, structured data, and schema work.

• Experience designing for third-party assistant surfaces or AI summarization tools.

• Background in travel, hospitality, or local services search at scale.

📝 Enhancement Note: The "What you need to have done" section directly translates into required skills, emphasizing practical, demonstrable experience over theoretical knowledge. The "what also helps" section provides valuable insights into areas that would make a candidate stand out, particularly technical fluency and domain-specific knowledge.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Submit a portfolio featuring two to three in-depth case studies, focusing on shipped and measured work.

• Prioritize demonstrating the entire design process: identifying and validating the problem, exploring various solutions, making deliberate hierarchy decisions with clear rationale, designing for critical states, and articulating the impact of the shipped work.

• Include at least one case study that highlights a design or approach that did not work, detailing the learnings derived from its failure.

• Roughness in presentation is acceptable; the focus is on the depth of reasoning and the clarity of the design process. Process Documentation:

• Showcase an understanding of designing within systems that infer, rank, or predict, detailing how you communicated system state, confidence, and error correction.

• Demonstrate experience in defining and defending information hierarchy, particularly for dense, comparative surfaces like search results cards.

• Provide evidence of how you collaborated with engineering on system design, data models, and structured data outputs for external consumption.

• Illustrate your approach to continuous discovery, including how you defined success metrics before release and measured impact post-launch.

📝 Enhancement Note: The portfolio requirements are highly specific, emphasizing practical application, iterative design, and measurable outcomes. The request for a case study that "didn't work" is a strong indicator of a culture that values learning from failure and data-driven decision-making. This is a critical differentiator for operations-minded candidates.

💵 Compensation & Benefits

Salary Range: Given the "Staff" title, extensive experience required (10+ years implied), fully remote status within the US, and the nature of the tech industry, a competitive salary range is expected. For a Staff Product Designer in the US, this could typically range from $170,000 to $240,000+ annually, depending on specific experience, location within the US (cost of living adjustments), and negotiation.

Benefits:

• Comprehensive health, dental, and vision insurance.

• Generous Paid Time Off (PTO) policy.

• 401(k) retirement savings plan with company match.

• Stock options or equity in the company.

• Professional development budget for conferences, training, and learning resources.

• Remote work stipend for home office setup and expenses.

• Opportunities for growth and advancement within a rapidly expanding company.

Working Hours: Full-time, with an expectation of high overlap during United States Eastern (ET) hours to facilitate collaboration with the pod and design team. While not strictly defined as 9-to-5, the role requires dedicated focus and availability for team syncs and rapid iteration cycles.

📝 Enhancement Note: Salary estimations are based on industry benchmarks for Staff-level Product Designers in the US tech sector, considering the company's operational domain (marketplace, travel/hospitality tech) and fully remote status. Benefits are standard for senior roles in remote-first tech companies. The emphasis on ET hours is crucial for understanding the collaborative cadence.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology, specifically within the online marketplace and travel/hospitality sector. Collaborative Boating operates Getmyboat and Boatsetter, aiming to simplify the process of booking marine experiences. The company is in a phase of platform convergence, indicating a dynamic and growth-oriented environment.

Company Size: The description implies a growing organization, likely a mid-sized tech company with ambitions to scale. The mention of a "five-person design team" and a "pod" structure suggests a deliberate organizational design focused on agility and cross-functional collaboration, rather than a large, siloed department.

Founded: Getmyboat was founded in 2013, and Boatsetter was founded in 2010. The convergence into Collaborative Boating signifies a strategic move to consolidate market leadership. This history suggests a company with established market presence and a clear vision for future growth.

Team Structure:

• The designer will be part of a five-person design team, reporting to the Director of Design.

• The role is dedicated to a specific "pod" comprising a Product Manager and an Engineering Tech Lead, fostering tight-knit, agile product development.

• Cross-functional collaboration is a core tenet, extending beyond the immediate pod to include direct interaction with guests, operators, and potentially other engineering and product functions. Methodology:

• Problem-Centric Approach: Emphasis on deeply understanding and framing the problem before designing systems or experiences.

• Iterative Design: Rapid iteration and deployment ("shipping in days"), with a focus on continuous discovery and learning from real-world user data.

• Data-Driven Decision Making: Defining success metrics before release and prioritizing measured outcomes over simply shipping features.

• System Thinking: Designing the underlying system (entities, states, contracts) concurrently with the user experience.

• Direct Customer Engagement: Designers are expected to engage directly with users (guests and operators) to build empathy and uncover insights.

Company Website: https://www.getmyboat.com/, https://www.boatsetter.com/

📝 Enhancement Note: The company culture is heavily emphasized as distinct and non-negotiable. Key aspects include a problem-first approach, rapid iteration, data-driven validation, and strong cross-functional collaboration where individuals are expected to "cross lines" and "bet on each other." This suggests a high-performance, agile environment.

📈 Career & Growth Analysis

Operations Career Level: This role is at the "Staff" level, signifying a senior individual contributor with significant autonomy, ownership, and influence over a critical product area (Guest & Discovery). It implies a deep specialization and the ability to tackle complex, ambiguous problems independently. This level often serves as a mentor and thought leader within the design team and for the broader product organization.

Reporting Structure: The designer will report to the Director of Design. However, the primary working relationship will be within a cross-functional pod (Product Manager, Engineering Tech Lead), where decisions are made collaboratively. This structure emphasizes distributed ownership and shared accountability for outcomes.

Operations Impact: The "Guest & Discovery" experience is foundational to the success of a marketplace. The designer's work directly impacts user acquisition, conversion rates, and overall revenue. By optimizing how guests find and choose boats, this role plays a critical part in driving bookings and achieving business objectives. The focus on designing for external surfaces (AI assistants) also positions the role to significantly influence the company's Go-To-Market (GTM) reach and brand perception.

Growth Opportunities:

• Specialization & Deep Expertise: Opportunity to become a leading expert in marketplace discovery, AI-driven search, and information design within the marine recreation sector.

• Cross-functional Leadership: Develop strong collaboration and influence skills by working closely with Product and Engineering leads, potentially influencing broader product strategy.

• Mentorship: As a Staff designer, opportunities will arise to mentor junior designers and contribute to the growth and best practices of the design team.

• Impactful Projects: Work on high-visibility projects that have a direct and measurable impact on business growth and user experience at scale.

• Career Progression: Potential pathways could lead to Principal Product Designer, Design Lead, or specialized roles within product strategy or user research leadership.

📝 Enhancement Note: The "Staff" title is a key indicator of seniority and expected impact. The role's focus on core acquisition funnels positions it as strategically vital for revenue operations and GTM success. The growth opportunities are framed around deepening expertise and influence, which are typical for senior individual contributor paths.

🌐 Work Environment

Office Type: This is a fully remote position. The company operates with a remote-first or remote-heavy model, with a requirement for high overlap during United States Eastern (ET) hours.

Office Location(s): While the role is remote, the requirement for ET hour overlap suggests a concentration of team members and potentially leadership in the Eastern Time Zone of the United States. Specific physical office locations are not detailed, but the remote nature means candidates can be located anywhere within the United States.

Workspace Context:

• Collaborative Environment: Designed for high interaction within small, cross-functional pods. The emphasis is on async communication for broad updates and syncs for critical decision-making and problem-solving.

• Tools & Technology: Expectation to leverage standard design tools, prototyping software, and potentially AI-assisted design tools. Access to design systems and robust product analytics platforms is implied.

• Team Interaction: Regular interaction with Product Managers, Engineering Tech Leads, and other designers. Direct engagement with customers (guests and operators) is also a key part of the role.

Work Schedule: Full-time employment. While specific hours are flexible due to the remote nature, a significant portion of the workday must align with United States Eastern Time hours for effective collaboration. The emphasis on "shipping in days" implies a need for focused, productive work periods and the ability to respond to issues and opportunities quickly.

📝 Enhancement Note: The remote nature combined with ET hour overlap is a critical detail for candidates to consider regarding their work-life balance and collaboration style. The "shipping in days" philosophy suggests a dynamic, fast-paced work environment where efficiency and focus are paramount.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Likely a brief call with a recruiter or hiring manager to assess basic qualifications and cultural fit.

• Portfolio Review & Deep Dive: A dedicated session where candidates present 2-3 case studies from their portfolio. This is where the reasoning, process, and impact of their work will be scrutinized. Expect detailed questions about problem definition, design decisions, trade-offs, and measured outcomes.

• Pod Interview: Meeting with the Product Manager and Engineering Tech Lead from the target pod. This assesses collaboration style, system thinking, and technical fluency. Questions may include hypothetical scenarios related to the discovery experience.

• Director of Design Interview: A final discussion focusing on strategic thinking, leadership potential, design philosophy, and alignment with the company's values and culture.

• Reference Checks: Standard practice for senior roles.

Portfolio Review Tips:

• Tell a Story: Structure your case studies as narratives: problem identification (how you knew it was real), exploration and iteration (what you tried and abandoned), design decisions (hierarchy, states, rationale), and outcomes (what shipped, what changed, measured impact).

• Show, Don't Just Tell: Visually present your work, but ensure the focus remains on the why and how behind your decisions, not just the final UI.

• Embrace Failure: Explicitly include a case study or example of something that didn't work and the lessons learned. This demonstrates maturity and a data-driven mindset.

• Quantify Impact: Whenever possible, use metrics and data to demonstrate the business impact of your designs. If metrics are unavailable, articulate the hypothesized impact and how it would be measured.

• Be Prepared for Technical Depth: Given the emphasis on system design and data models, be ready to discuss technical constraints, trade-offs, and collaboration with engineers at a granular level.

Challenge Preparation:

• Hypothetical Scenarios: Be prepared for questions like: "How would you improve our search results card for users searching for 'something fun for eight people on Saturday'?" or "How would you design an experience for a user interacting with an AI assistant that summarizes boat listings?"

• Information Hierarchy Exercise: You might be asked to critique an existing search results card or propose an improved hierarchy for a given set of data points.

• System Design Thinking: Be ready to discuss how you'd represent states for a boat listing that has no photos but has great reviews, or how you'd design the interaction for a user correcting an AI's summary of a boat's features.

• AI & Search Philosophy: Articulate your views on the evolving landscape of search and AI, and how product design should adapt.

📝 Enhancement Note: The interview process is designed to thoroughly assess not just design skills but also strategic thinking, problem-solving abilities, and cultural fit. The portfolio review is central, and candidates must be prepared to defend their decisions with data and clear reasoning. The emphasis on AI and complex systems suggests a need for forward-thinking candidates.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (highly likely, industry standard), Sketch, Adobe Creative Suite.

• Prototyping & Collaboration: InVision, Principle, Framer.

• User Research & Testing: UserTesting.com, Lookback, Maze.

• Design Systems: Familiarity with building and utilizing design systems.

Analytics & Reporting:

• Product Analytics: Amplitude, Mixpanel, Google Analytics.

• Data Visualization/Dashboarding: Tableau, Looker, Metabase (or similar internal tools).

• A/B Testing Platforms: Optimizely, VWO, internal experimentation tools.

CRM & Automation:

• While not directly a designer's core tool, understanding how CRM data (e.g., Salesforce) and marketing automation platforms (e.g., HubSpot) influence user acquisition and GTM strategies can be beneficial.

• Structured Data & Schema: Understanding of JSON-LD, Schema.org for SEO and AI assistant compatibility.

📝 Enhancement Note: The specific tools are inferred based on industry best practices for product design and the company's operational context (marketplace, data-driven). Proficiency in design and prototyping tools is essential, while familiarity with analytics and structured data formats will be highly advantageous for this role.

👥 Team Culture & Values

Operations Values:

• Problem First, System Second, Experience Third: A deep commitment to understanding the root problem before defining the system that supports it, and then designing the user experience within that system.

• Data-Driven Validation: Decisions are grounded in measurable outcomes. Hitting targets is the baseline; exceeding them through insightful design is the goal. Measurement is integral, not an afterthought.

• Continuous Discovery & Iteration: An agile mindset where work is shipped frequently in small, complete slices, with ongoing learning and adaptation based on real-world performance.

• Ownership & Accountability: Individuals and pods are empowered to own outcomes, take initiative, and make decisions. This fosters a culture of responsibility and proactive problem-solving.

• Radical Candor & Collaboration: Open communication, direct feedback, and a willingness to "cross lines" and support colleagues are highly valued. Trust and mutual respect are foundational.

Collaboration Style:

• Pod-Based Autonomy: Tight-knit collaboration within product pods (PM, Eng Lead, Designer) where decisions are made collectively and rapidly.

• Cross-Functional Integration: Designers are expected to engage directly with customers and work across functional boundaries, not confined to a design silo.

• Async & Sync Communication: A blend of asynchronous communication for broad updates and documentation, and synchronous meetings for critical discussions and decision-making, with a focus on ET hour overlap.

• Design System Adherence & Evolution: Default use of the design system, with new patterns needing to earn their place through demonstrated value and rigorous testing.

📝 Enhancement Note: The company culture is explicitly defined as a set of non-negotiable principles. These values strongly influence how work is done, how decisions are made, and how team members interact, emphasizing agility, data, and proactive contribution.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Ambiguity & AI: Adapting traditional search and discovery paradigms to a world increasingly influenced by AI assistants and natural language interfaces, where the rendering surface is not always controlled.

• Information Density & Persuasion: Balancing the need to present a wealth of comparative information on a small "results card" while making it persuasive and actionable for users.

• System Complexity & Data Inference: Designing intuitive user experiences over complex back-end systems that infer, rank, and predict, and managing the inherent uncertainty and potential for error in such systems.

• Rapid Iteration vs. Grand Vision: Successfully shipping small, iterative updates frequently while maintaining a cohesive, long-term vision for the entire guest discovery experience across two brands.

• Cross-Functional Alignment: Effectively influencing and collaborating with Product Management and Engineering to ensure design vision is realized within system constraints and business priorities.

Learning & Development Opportunities:

• Deep Dive into Marketplace Dynamics: Gain unparalleled expertise in the specific challenges and opportunities of a two-sided marketplace within the marine leisure sector.

• Future of Search & AI: Hands-on experience shaping product strategy at the intersection of traditional search and emerging AI technologies.

• Advanced Information Architecture: Hone skills in designing complex, data-rich interfaces and optimizing information hierarchy for conversion.

• System Design & Data Modeling: Develop a deeper understanding of how data models and system logic directly influence user experience and product capabilities.

• Leadership & Mentorship: Opportunities to mentor junior designers and contribute to the strategic direction of the design team.

📝 Enhancement Note: The challenges identified are directly derived from the job description's emphasis on AI, complex systems, and rapid iteration, framing them as opportunities for growth and skill development.

💡 Interview Preparation

Strategy Questions:

• "How would you approach designing a search results card that needs to be equally effective for a user searching 'boat rental Miami' and another searching 'something fun for eight people Saturday'?" (Focus on flexible hierarchy, data states, and information prioritization).

• "Describe a time you designed an interface for a system that inferred or predicted outcomes. How did you communicate confidence and handle errors?" (Focus on system transparency, user control, and error correction).

• "What are your thoughts on the role of conversational AI in a visual discovery experience like ours? Where do you see the boundaries?" (Focus on your philosophy regarding AI's place in the user journey and your ability to form independent opinions).

• "How would you ensure our listing information is structured effectively to be summarized or displayed by third-party AI assistants?" (Focus on structured data, schema, and designing for external rendering). Company & Culture Questions:

• "How do you align with our 'Problem, then system, then experience' methodology?" (Demonstrate your understanding and preference for this structured approach).

• "Can you share an example of a time you directly engaged with customers to uncover a critical insight that shaped your design?" (Showcase your customer-centricity and proactive research approach).

• "How do you define success for a feature you've designed, and how do you measure its impact?" (Highlight your data-driven mindset and focus on outcomes).

• "Describe a situation where you had to disagree with a colleague or team member on a design decision. How did you handle it?" (Assess your ability to provide constructive feedback and navigate conflict). Portfolio Presentation Strategy:

• Start with the "Why": Clearly articulate the problem, how you validated it, and the business context.

• Show Your Process: Detail your exploration, iterations, and the rationale behind key decisions, especially hierarchy and state design.

• Highlight Trade-offs: Discuss decisions where you had to compromise or make difficult choices, and the impact of those choices.

• Quantify Results: Present the shipped product and its measured impact. If metrics are unavailable or inconclusive, discuss the expected impact and how it would be measured.

• Embrace Roughness: If your portfolio contains rough sketches or early concepts, use them to illustrate your thought process. The reasoning is more important than polished visuals for every artifact.

• Be Ready for Deep Dives: Anticipate detailed questions on specific design choices, system implications, and user behavior.

📝 Enhancement Note: These interview questions are tailored to the specific requirements and culture outlined in the job description, focusing on critical areas like AI, systems thinking, information hierarchy, and data-driven design.

📌 Application Steps

To apply for this Staff Product Designer position:

• Submit your application through the provided link: https://getmyboat.breezy.hr/p/c58c6deaa419-staff-product-designer-guest-discovery

• Curate Your Portfolio: Select 2-3 of your most impactful case studies that clearly demonstrate your experience in marketplace search/discovery, information architecture, and designing for complex systems. Ensure at least one case study includes a failure and its learnings.

• Tailor Your Resume: Highlight experience with two-sided marketplaces, search/discovery design, information hierarchy, AI-influenced interfaces, and cross-functional collaboration. Use keywords from the job description.

• Prepare Your Presentation: Practice walking through your portfolio case studies, focusing on articulating your design process, rationale, and measured outcomes. Be ready to discuss trade-offs and system implications.

• Research Collaborative Boating: Understand the Getmyboat and Boatsetter brands, their market position, and the company's stated values and working methodologies. Prepare to discuss how your approach aligns with theirs.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.