Head of Design (North America/Europe - Remote)

📍 Job Overview

Job Title: Head of Design (North America/Europe - Remote)

Company: Hospitable

Location: Spain (Remote)

Job Type: FULL_TIME

Category: Design Leadership / Product Design

Date Posted: 2026-08-06

Experience Level: 10+ Years

Remote Status: Remote Solely

🚀 Role Summary

• Lead the overall design vision, strategy, and execution for a product-led SaaS company specializing in short-term rental software.

• Drive the creation of an exceptional user experience and elegant visual design across the entire platform, ensuring intuitive interactions and joyful feature usage.

• Build, develop, and lead a lean, AI-leveraged product design team, acting as a player-coach to set high standards and mentor designers.

• Own the design system, including the design language, style guide, and component library, ensuring consistency and reducing complexity as the platform scales.

📝 Enhancement Note: This role is explicitly for a "player-coach," meaning the ideal candidate must be comfortable and proficient in hands-on design work while also leading and mentoring a team. The emphasis on AI-leveraged design suggests a forward-thinking approach to design processes and tool utilization. The target markets (North America/Europe) and remote-first nature indicate a need for strong asynchronous communication skills and cross-cultural awareness.

📈 Primary Responsibilities

• Set and evangelize the comprehensive design vision for the product, ensuring alignment with long-term company strategy and market needs.

• Own the end-to-end design quality bar for the platform, from initial discovery and user research through prototyping, visual design, and interaction design.

• Take the lead on the highest-stakes design initiatives, directly contributing to the product's evolution and user experience.

• Develop, maintain, and evolve the company's design language, style guide, and component library to ensure a cohesive and scalable design system.

• Foster a culture of design excellence within a lean team, leveraging AI tools to maximize efficiency and output.

• Conduct and utilize user research, analytics, experimentation, and customer feedback to inform design decisions and measure their impact.

• Collaborate closely with Product and Engineering leadership to define product roadmaps and strategic priorities, acting as an equal partner in decision-making.

• Drive process improvements within the design function, focusing on efficiency, consistency, and reducing complexity.

📝 Enhancement Note: The responsibilities highlight a blend of strategic leadership and hands-on execution. The explicit mention of "reducing complexity as a discipline" and "killing inconsistency before it compounds" points to a strong focus on process optimization and systematic thinking within the design function. The requirement to "partner as an equal with Product and Engineering leadership" underscores the strategic importance of this role within the company's GTM and product development.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio demonstrating equivalent knowledge and practical application of design principles, user-centered design methodologies, and team leadership is essential.

Experience: A minimum of 10 years of experience in design roles, with a significant portion focused on product-led SaaS companies within the last 5 years. Proven experience in setting and raising design quality bars and mentoring designers is critical.

Required Skills:

• Proven track record of setting and executing design vision and quality standards in a product-led SaaS environment.

• Demonstrated ownership of end-to-end design processes, from discovery and research to shipped features, with measurable impact.

• Strong hands-on design proficiency, with recent experience (within the last 3 years) in direct design work, not solely management.

• Expertise in user research, customer feedback analysis, and data-driven decision-making.

• Exceptional product thinking capabilities, with the ability to influence product strategy and roadmap.

• High degree of agency and ownership, comfortable working autonomously in a lean, remote, low-bureaucracy setting.

• Proficiency in modern design tools, specifically Figma for design and Whimsical for mockups.

• Experience in leading and mentoring design teams, providing direct feedback and fostering growth. Preferred Skills:

• Domain experience in short-term rentals, travel, hospitality, or proptech.

• Experience with AI-leveraged design tools and methodologies to enhance efficiency and creativity.

• Familiarity with various analytics and experimentation platforms to validate design hypotheses.

• Experience in developing and managing design systems and component libraries.

• Strong asynchronous communication and collaboration skills, essential for a remote-first global team.

📝 Enhancement Note: The "player-coach" nature of this role heavily emphasizes recent, hands-on design experience. Candidates should be prepared to showcase their individual design contributions and problem-solving skills, alongside their leadership capabilities. The preference for domain experience suggests that candidates with a background in related industries will have a distinct advantage.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A comprehensive portfolio showcasing end-to-end design ownership, highlighting contributions from discovery and research through to launched features and their measured impact.

• Case studies demonstrating strong product thinking, illustrating how design decisions influenced product strategy and business outcomes.

• Examples of hands-on design work, showcasing expertise in Figma and Whimsical, with a focus on user experience, interaction design, and visual polish.

• Evidence of leadership in raising design standards, including examples of mentoring designers, providing feedback, and defining quality bars.

• Documentation or examples of design systems, style guides, or component libraries managed or contributed to, demonstrating an understanding of scalability and consistency. Process Documentation:

• Showcase a structured approach to design discovery, including user research methodologies and problem definition.

• Detail your process for translating insights into actionable design solutions, including wireframing, prototyping, and visual design stages.

• Provide examples of how you use analytics, experimentation, and customer feedback to iterate on designs and measure success.

• Illustrate your approach to collaborating with product and engineering teams throughout the design and development lifecycle.

• Demonstrate how you would establish and maintain a design system and ensure its consistent application across the product.

📝 Enhancement Note: The portfolio is paramount for this role, serving as the primary evidence of a candidate's hands-on skills and strategic thinking. Candidates should focus on telling a story with their case studies, emphasizing the "why" and the "impact" of their design decisions, not just the final deliverables. Demonstrating experience with a lean setup and AI tooling within their process examples will be highly beneficial.

💵 Compensation & Benefits

Salary Range: The total cash budget for this role is between USD$171,000.00 to $218,900.00 per year, with adjustments based on seniority and the cost of living in the candidate's location. For US employees, this translates to a gross salary range of $157,619.92 to $201,771.94.

Benefits:

• Equity: Compensation includes company equity through Restricted Stock Units (RSUs) with a current grant value of up to $119,400.00.

• Performance Incentives: Eligibility for up to an additional $671,637 per year in Performance Share Units (PSUs) tied to clearly defined business performance targets.

• Healthcare (US Employees): Comprehensive health insurance options including EPO, PPO, and HSA.

• Retirement (US Employees): 401(k) plan.

• Paid Time Off: 35 days of paid time off per year, with encouragement to take it, including self-serve public holidays.

• Parental Leave: Generous parental leave policy.

• Mental Health Support: Complimentary mental health and emotional support services available through therapists via Slack.

• Peer Recognition: Access to a peer recognition platform to earn virtual coins redeemable for gift cards, donations, or monetary rewards.

Working Hours: While not explicitly stated, a standard full-time role of 40 hours per week is implied. The remote-first nature suggests flexibility in daily scheduling, with an emphasis on asynchronous communication and meeting availability across North American and European timezones.

📝 Enhancement Note: The compensation structure is highly competitive, with a significant portion allocated to performance-based incentives (PSUs) and equity, indicating a strong alignment with company growth and success. Candidates should be prepared to discuss how their contributions will directly impact these performance metrics. The salary range provided for US employees is an approximation based on the global budget and cost of living adjustments, and actual offers will be finalized based on thorough evaluation.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology, specifically focused on Software as a Service (SaaS) for the short-term rental and hospitality sector (Proptech). Hospitable aims to automate and streamline the operations of short-term rentals.

Company Size: Hospitable is described as a "global, and trust-based company" with a "deliberately lean" design team, indicating a medium-sized, fast-paced organization that values efficiency and autonomy.

Founded: While the founding date is not explicitly stated, Hospitable is presented as an established company with a "state-of-the-art product" and a "fast-moving roadmap," suggesting a company that has successfully navigated its early stages and is focused on growth and innovation.

Team Structure:

• The design team is deliberately lean, with the Head of Design building and leading a small group of product designers.

• The Head of Design reports directly to the CEO, Pierre, signifying a high level of visibility and strategic influence.

• Collaboration is expected to be cross-functional, with the Head of Design acting as an equal partner to Product and Engineering leadership. Methodology:

• Data-Driven: Decisions are informed by research, analytics, experimentation, and direct customer feedback.

• Agile & Iterative: The company moves fast, thinks boldly, and builds with intention, suggesting an agile development approach with rapid iteration cycles.

• AI-Leveraged: Modern AI tooling is integrated into the design process to maximize leverage and efficiency.

• Low Bureaucracy: The environment is characterized by trust and a focus on results, minimizing unnecessary administrative overhead.

Company Website: https://www.hospitable.com/

📝 Enhancement Note: Hospitable's culture is built on trust, transparency, and results. The remote-first, global nature means that strong asynchronous communication and documentation skills are crucial. The "deliberately lean" approach implies that individuals are expected to wear multiple hats and contribute significantly without extensive management layers.

📈 Career & Growth Analysis

Operations Career Level: This role represents a senior leadership position within the design function, equivalent to a Director or VP level in larger organizations, but with a direct hands-on component. It is a critical "player-coach" role, responsible for both strategic direction and tactical execution.

Reporting Structure: The Head of Design reports directly to the CEO, indicating a high level of strategic input and direct access to executive leadership. This provides significant visibility and influence over the company's product direction.

Operations Impact: The Head of Design will have a direct and profound impact on the company's success by:

• Defining and elevating the core user experience, which is crucial for a product-led SaaS business.

• Driving customer acquisition and retention through an intuitive and elegant product design.

• Influencing the product roadmap and strategic priorities by bringing a design-centric perspective.

• Leading the development of a scalable design system that supports rapid product expansion. Growth Opportunities:

• Strategic Leadership: Opportunity to shape the future of design at a growing, remote-first company and build a world-class design function from the ground up.

• Skill Development: Deepen expertise in AI-leveraged design, product-led growth strategies, and leading lean, high-performing teams. Potential to expand into broader product leadership responsibilities over time.

• Impactful Contribution: Directly influence the success of a product used by thousands of hosts worldwide, with significant potential for personal and professional growth tied to company performance through equity and PSUs.

• Domain Expertise: Develop specialized knowledge in the proptech and short-term rental industry, a rapidly evolving market.

📝 Enhancement Note: The direct reporting to the CEO and significant equity/performance bonuses signal that this role is pivotal to Hospitable's growth strategy. The "player-coach" model offers a unique growth path for experienced designers who wish to remain hands-on while also developing leadership capabilities.

🌐 Work Environment

Office Type: Hospitable is a remote-only company. There is no central office; the entire workforce operates remotely across different locations.

Office Location(s): The ideal candidate should be located in a North American (up to East Coast) or European timezone. This facilitates collaboration with existing team members and ensures reasonable overlap for synchronous communication when needed. Specific locations mentioned for potential employee status include the United States, the European Union, and Australia.

Workspace Context:

• Remote Autonomy: The work environment is trust-based, emphasizing autonomy and self-management.

• Collaborative Tools: Extensive use of digital collaboration tools (like Whimsical and Figma) and communication platforms (like Slack) is expected.

• Lean Operations: Expect a low-bureaucracy environment where individuals are empowered to make decisions and drive initiatives.

• Global Team Interaction: Opportunities to collaborate with a diverse, international team, requiring strong asynchronous communication skills and cultural sensitivity.

Work Schedule: While a standard 40-hour work week is typical for full-time roles, the remote setup likely offers flexibility in daily scheduling. The primary requirement is availability within agreed-upon core hours to facilitate team collaboration and responsiveness across the specified timezones.

📝 Enhancement Note: The remote-only nature requires candidates to be highly self-motivated and adept at managing their time and communication effectively. The emphasis on trust and autonomy means that individuals are expected to deliver results without constant supervision.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Application Review: Focus on resume and portfolio quality, looking for strong evidence of hands-on design skills, product leadership, and relevant experience.

• Portfolio Deep Dive: A dedicated session to walk through selected case studies, discussing design choices, problem-solving approaches, and measured impact. Be prepared to articulate your process and rationale clearly.

• Player-Coach Simulation/Challenge: A practical exercise, potentially a design challenge or a strategic discussion, to assess your hands-on design skills, product thinking, and ability to lead and mentor. This may involve working with provided tools like Figma.

• Leadership & Culture Fit Interview: Discussion with the CEO and potentially other leadership team members to assess strategic alignment, cultural fit, communication style, and leadership philosophy.

• Reference Checks: Standard verification of past performance and professional conduct.

Portfolio Review Tips:

• Storytelling: Structure your case studies to tell a compelling story of problem, process, solution, and impact. Quantify results whenever possible.

• Hands-On Focus: Clearly delineate your personal contributions versus team efforts, especially for the "player-coach" aspect. Showcase your design craft.

• Process Clarity: Explain your design process, including how you incorporate research, data, and collaboration. Highlight your experience with Figma and Whimsical.

• Impact Demonstration: Emphasize the business outcomes and user benefits derived from your design work. Connect design decisions to company goals.

• AI & Lean Integration: If applicable, showcase how you've leveraged AI tools or worked effectively in lean, autonomous environments.

Challenge Preparation:

• Figma Proficiency: Ensure you are comfortable and efficient with Figma for rapid prototyping and visual design.

• Product Thinking Scenarios: Practice articulating how you would approach a given design problem within the context of the short-term rental market.

• Design System Concepts: Be ready to discuss principles of design systems and how you would build or evolve one.

• Leadership & Mentorship: Prepare examples of how you have guided and improved the work of other designers.

📝 Enhancement Note: The application process heavily emphasizes the portfolio and practical demonstration of skills. Candidates should tailor their portfolio to highlight leadership in a product-led SaaS context and their hands-on design capabilities. Preparing specific examples for "player-coach" scenarios will be crucial.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The core design tool for creating mockups, prototypes, and final visual designs. Proficiency is essential.

• Whimsical: Used for mockups, flowcharts, and collaborative whiteboarding, indicating a need for strong conceptualization and ideation tools.

Analytics & Reporting:

• While specific tools are not listed, the role requires using "research, analytics, experimentation, and direct customer feedback." Candidates should be comfortable with common analytics platforms (e.g., Google Analytics, Mixpanel, Amplitude) and A/B testing methodologies. CRM & Automation:

• Not explicitly mentioned for the design role, but understanding how design integrates with CRM and marketing automation for user journeys and customer lifecycle management would be beneficial. Other Potential Tools:

• Project management tools (e.g., Jira, Asana) for collaboration with engineering.

• Prototyping tools beyond Figma (e.g., InVision, Principle) may be advantageous.

• AI design tools for ideation, content generation, or workflow automation.

📝 Enhancement Note: Strong command of Figma is non-negotiable. Familiarity with a broad range of design and collaboration tools, including those for research and analytics, will be highly valued. The mention of "AI-leveraged design" suggests an openness to and potential use of emerging AI design tools.

👥 Team Culture & Values

Operations Values:

• Trust & Autonomy: The company operates on a foundation of trust, empowering individuals to manage their work and make decisions without constant oversight.

• Radical Transparency: Open communication and sharing of information are core tenets, fostering an environment where everyone understands the company's direction and challenges.

• Caring & Supportive: Despite the fast-paced, results-oriented environment, there's an emphasis on team members supporting each other.

• Results & Output Focused: The primary measure of success is the quality and impact of the work delivered, rather than hours spent or processes followed rigidly.

• Efficiency & Simplicity: A commitment to reducing complexity and maximizing leverage, particularly through lean operations and AI tooling.

Collaboration Style:

• Cross-functional Partnership: Close collaboration with Product and Engineering is expected, with designers acting as equal partners in decision-making.

• Asynchronous Communication: Given the global, remote nature, effective asynchronous communication through documentation and clear written/recorded messages is crucial.

• Direct Feedback: A culture of providing and receiving direct, constructive feedback to drive continuous improvement and raise quality standards.

• Agile Experimentation: Willingness to experiment, learn from failures, and iterate quickly based on data and feedback.

📝 Enhancement Note: Candidates should highlight their ability to thrive in a remote, asynchronous, and trust-based environment. Demonstrating a proactive approach to communication, collaboration, and feedback will be key to cultural fit. The emphasis on results and efficiency aligns with typical GTM and operations values.

⚡ Challenges & Growth Opportunities

Challenges:

• Building a Design Function: Establishing and scaling the design function within a rapidly growing company, defining processes, and building a team from the ground up.

• Player-Coach Balance: Effectively managing the dual responsibilities of hands-on design work and team leadership, ensuring both strategic direction and high-quality execution.

• Remote Collaboration at Scale: Maintaining strong design cohesion and team culture across distributed global teams, especially as the team grows.

• Rapid Product Iteration: Keeping pace with a fast-moving product roadmap and evolving market demands in the dynamic short-term rental tech space.

• Leveraging AI Effectively: Integrating AI tools into the design workflow in a meaningful way that enhances creativity and efficiency without compromising quality or originality.

Learning & Development Opportunities:

• Strategic Leadership: Opportunity to shape the design direction of a growing SaaS company and build a high-performing team.

• Product-Led Growth Expertise: Deepen understanding and application of product-led growth principles within the hospitality tech sector.

• AI in Design: Become a leader in leveraging AI tools for design innovation and process optimization.

• Cross-functional Influence: Develop strong collaborative relationships and influence across product, engineering, and executive leadership.

• Global Team Management: Gain experience managing and mentoring a diverse, international design team in a remote-first setting.

📝 Enhancement Note: The challenges presented are typical for a foundational role in a growth-stage tech company. Candidates who are comfortable with ambiguity, proactive problem-solvers, and eager to build systems will find this role rewarding. The growth opportunities are significant, offering a clear path for career advancement and skill development.

💡 Interview Preparation

Strategy Questions:

• "How would you define and implement the design vision for Hospitable over the next 1-2 years, considering our product-led SaaS model and short-term rental market?"

• "Describe your approach to building and leading a lean, AI-leveraged design team. How do you set high expectations and foster growth?"

• "Walk us through a complex design challenge you personally led from discovery to launch. What was your process, what tools did you use (specifically Figma), and what was the measurable impact?"

• "How do you ensure design consistency and quality across a platform as it scales? Discuss your experience with design systems and component libraries."

• "How would you balance your hands-on design responsibilities with your role as a team leader? Provide examples of how you've managed this in previous roles." Company & Culture Questions:

• "What specifically about Hospitable's mission and product resonates with you, and why do you want to build this here with us?"

• "How do you approach radical transparency and working in a trust-based, remote-first environment?"

• "Describe a time you had to influence product or engineering leadership with a design recommendation. What was your strategy and the outcome?"

• "How do you measure the success and impact of your design work and your team's contributions?" Portfolio Presentation Strategy:

• Curate Select Case Studies: Choose 2-3 in-depth case studies that best showcase your end-to-end ownership, player-coach capabilities, and impact.

• Focus on the "Why": Clearly articulate the problem, your strategic thinking, and the rationale behind your design decisions.

• Highlight Hands-On Work: Dedicate time to showcase your direct design contributions using Figma, detailing your craft.

• Quantify Impact: Present metrics and data that demonstrate the business value and user benefits of your work.

• Address AI/Lean: If applicable, explain how you've leveraged AI tools or operated effectively in lean environments within your case studies.

• Prepare for Q&A: Anticipate questions about your process, decision-making, and leadership approach.

📝 Enhancement Note: Be prepared to discuss specific examples that demonstrate both your individual design craft and your ability to lead and mentor. The interview will likely assess your strategic thinking, problem-solving skills, and cultural alignment with Hospitable's values.

📌 Application Steps

To apply for this Head of Design position:

• Submit your application through the provided link on Workable.

• Portfolio Customization: Tailor your portfolio to highlight your experience in product-led SaaS, your hands-on design skills (especially in Figma), and your leadership in setting design standards. Prioritize case studies that demonstrate end-to-end ownership and measurable impact.

• Resume Optimization: Ensure your resume clearly articulates your 10+ years of experience, specifically mentioning your background in product-led SaaS and any experience raising design quality bars. Use keywords like "Head of Design," "Product Design," "Design Systems," "Figma," "AI-leveraged design," and "Player-Coach."

• Prepare Your Narrative: Practice articulating why you are passionate about Hospitable's mission and how your unique "player-coach" skillset aligns with the role's demands. Be ready to discuss your approach to building a lean, high-performing design team.

• Company Research: Familiarize yourself with Hospitable's product, target market (short-term rentals), and company values (trust, transparency, results). Understand their remote-first culture and consider how your approach fits within it.

⚠️ 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.