Head of Design (North America/Europe - Remote)

📍 Job Overview

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

Company: Hospitable

Location: France (Remote)

Job Type: Full-Time

Category: Product Design / Design Leadership

Date Posted: 2026-08-06

Experience Level: 5-10 Years

Remote Status: Fully Remote

🚀 Role Summary

• Lead the end-to-end design vision, strategy, and execution for Hospitable's product suite, ensuring an intuitive and elegant user experience.

• Build and manage a lean, AI-leveraged product design team, fostering a culture of high expectations and continuous improvement.

• Act as a player-coach, actively contributing to critical design projects while setting the quality bar for the entire design organization.

• Drive data-informed design decisions through research, analytics, experimentation, and customer feedback to demonstrate measurable impact.

• Collaborate closely with Product and Engineering leadership to shape the product roadmap and development priorities.

📝 Enhancement Note: This role is explicitly defined as a "player-coach" position, meaning the Head of Design will not only lead but also actively participate in design execution. The emphasis on AI-leveraged tooling suggests a forward-thinking approach to design processes and team efficiency.

📈 Primary Responsibilities

• Define and champion the overarching design vision and standards for Hospitable's platform, ensuring alignment with long-term company strategy.

• Own the quality bar for the entire product, ensuring all user interactions are intuitive, screens are elegant, and features are a joy to use.

• Lead the design of the highest-stakes projects personally, from initial discovery and user research through to prototyping, visual design, and interaction design.

• Develop and maintain the design language, style guide, and component library, ensuring coherence and consistency as the platform and team scale.

• Proactively identify and eliminate design inconsistencies to reduce overall system complexity.

• Recruit, mentor, and manage a deliberately lean product design team, setting clear operational processes and raising the collective design standard.

• Provide direct feedback and set high expectations to empower designers to produce their best work.

• Act as an equal partner to Product and Engineering leadership in strategic decision-making regarding product development.

• Utilize research findings, product analytics, A/B testing results, and direct customer feedback to inform design choices and quantify their impact.

📝 Enhancement Note: The responsibilities highlight a strong emphasis on both strategic leadership and hands-on execution. The expectation to "reduce complexity" and "kill inconsistency" points towards a need for rigorous process management and a proactive approach to design debt.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio demonstrating equivalent practical experience in design leadership and execution is paramount.

Experience: 5-10 years of progressive experience in product design, with a significant portion in a product-led SaaS environment, demonstrating a proven track record of setting and elevating design quality.

Required Skills:

• Proven ability to set and maintain a high design quality bar within a product-led SaaS company within the last 5 years.

• Demonstrated experience in raising the standard of designers through direct feedback, hiring, and high expectations.

• Hands-on design proficiency, actively contributing to design work within the last 3 years, not solely focused on management.

• Expertise in the full design lifecycle, from discovery and research to shipped features, with a track record of measuring and demonstrating impact.

• Strong product thinking capabilities, enabling shaping of product direction and equal partnership with Product and Engineering leadership.

• High degree of agency and ownership, comfortable operating effectively in a lean, remote, and low-bureaucracy environment.

• Proficiency in modern AI tooling to maximize leverage and efficiency in design processes.

• Advanced skills in research and briefing, going beyond mere visual polish.

• Deep familiarity with core design tools such as Figma for design and Whimsical for mockups. Preferred Skills:

• Experience within the short-term rental, travel, hospitality, or proptech domains.

• Experience developing and scaling design systems and component libraries.

• Familiarity with experimentation frameworks and A/B testing methodologies.

• Experience in building and leading remote design teams.

📝 Enhancement Note: The emphasis on "still hands-on" and "not pure management" strongly indicates that candidates with extensive management-only backgrounds may not be the ideal fit. The preference for specific domain experience suggests that candidates with a background in related industries will have an advantage.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A comprehensive portfolio showcasing end-to-end design ownership, from initial user research and problem definition to final shipped features and their measured impact.

• Case studies that clearly articulate the design challenges, the strategic thinking applied, the design solutions implemented, and the quantifiable business outcomes achieved (e.g., conversion rate improvements, user satisfaction scores, efficiency gains).

• Examples demonstrating the ability to define and maintain a design vision and quality bar, including style guides, design systems, or component libraries.

• Evidence of collaboration with Product and Engineering teams, illustrating how design thinking influenced product strategy and development.

• Demonstrations of how research, analytics, and customer feedback were leveraged to inform design decisions and iterate on solutions. Process Documentation:

• Evidence of established processes for user research, from planning and execution to synthesis and application of findings.

• Examples of how design systems are developed, maintained, and scaled to ensure consistency and efficiency across a growing product.

• Documentation or case studies detailing the implementation and impact of AI tooling within design workflows.

• Examples of how design metrics are tracked, analyzed, and reported to stakeholders to demonstrate value and impact.

📝 Enhancement Note: The portfolio requirements are heavily weighted towards demonstrating impact and process ownership rather than just deliverables. Candidates should be prepared to articulate the "why" and "how" behind their design decisions and their resulting business value, especially in a lean, data-driven environment.

💵 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 approximately $157,619.92 to $201,771.94.

Benefits:

• Equity: Restricted Stock Units (RSUs) with a current grant value of up to $119,400.00, offering participation in the company's long-term value appreciation.

• Performance-Based Incentives: Eligibility for Performance Share Units (PSUs) with a potential annual award of up to $671,637, tied directly to the achievement of clearly defined business performance targets and measurable outcomes.

• Health & Wellness (US Employees): Comprehensive healthcare options including EPO, PPO, and HSA plans.

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

• Time Off: Generous 35 days of paid time off per year, including self-serve public holidays, and parental leave.

• Mental Health Support: Complimentary access to therapists via Slack, provided by [Benefit Provider Name - placeholder].

• Peer Recognition: A virtual coin system through a peer recognition platform, redeemable for gift cards, donations, or monetary rewards.

Working Hours: The standard working hours are 40 hours per week, with an expectation of flexibility and autonomy inherent in a remote, trust-based work environment.

📝 Enhancement Note: The compensation structure includes a significant performance-based component (PSUs), indicating a strong emphasis on driving measurable business results. The salary range is benchmarked using cost-of-living adjustments, reflecting a global approach to compensation for remote talent.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology / Software (SaaS), with a specific focus on the short-term rental and hospitality sector. Hospitable operates within the proptech (property technology) space.

Company Size: Hospitable is a remote-only, global, and trust-based company. While the exact number of employees isn't specified, the description suggests a lean and agile organization that prioritizes impact over bureaucracy. The mention of a "deliberately lean, AI-leveraged design team" implies a smaller, highly effective core team.

Founded: Hospitable's founding date is not explicitly stated, but its emphasis on a fast-moving product roadmap, customer feedback, and iterative improvement suggests a relatively young and dynamic company culture.

Team Structure:

• The design team is described as "deliberately lean" and AI-leveraged, implying a small, highly skilled group focused on core design execution and strategy.

• The Head of Design reports directly to the CEO, Pierre, indicating a high level of visibility and direct impact on company strategy.

• Collaboration is expected to be cross-functional and equal with Product and Engineering leadership. Methodology:

• Data-Driven Decision Making: Research, analytics, experimentation, and direct customer feedback are central to informing design choices and proving impact.

• Agile & Iterative: The company moves fast, thinks boldly, and builds with intention, suggesting an agile development methodology with a focus on rapid iteration and improvement.

• Lean Operations: Emphasis on a lean setup, low bureaucracy, and maximizing leverage, particularly through AI tooling.

• Trust-Based Culture: The company operates on trust, empowering individuals rather than managing them directly.

Company Website: https://hsptb.com/

📝 Enhancement Note: Hospitable emphasizes a culture of radical transparency, trust, and results. The remote-first, global nature of the company, combined with a lean operational model and a focus on AI, suggests an environment where autonomy, proactivity, and measurable impact are highly valued.

📈 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. It is a critical "player-coach" role, requiring both strategic vision and hands-on execution, making it a high-impact position for an experienced design leader.

Reporting Structure: The Head of Design reports directly to the CEO, Pierre. This provides a direct line of communication and influence on company-level strategy and product direction.

Operations Impact: The Head of Design's impact is central to Hospitable's mission of being the best-designed product in short-term rental software. Their work directly influences user acquisition, retention, customer satisfaction, and ultimately, revenue, by making the product effortless and enjoyable to use. They will shape the user experience that drives product adoption and customer loyalty.

Growth Opportunities:

• Leadership Expansion: Potential to grow the design team strategically, building out specialized functions as the company scales.

• Strategic Influence: Opportunity to significantly influence product strategy and company direction through direct reporting to the CEO.

• Skill Development: Continuous learning through hands-on work in a fast-paced SaaS environment, exposure to AI tooling, and collaboration with executive leadership.

• Domain Expertise: Deepen expertise in the proptech and short-term rental industry.

• Equity Growth: Potential for significant long-term financial upside through RSU and PSU grants, tied to company performance.

📝 Enhancement Note: The "player-coach" nature of this role offers a unique growth path for design leaders who want to remain deeply involved in the craft while also shaping organizational strategy and team development. The direct reporting line to the CEO is a significant indicator of the role's strategic importance.

🌐 Work Environment

Office Type: Hospitable is a 100% remote-only company. There is no physical office.

Office Location(s): While the role is based in France, the company hires talent internationally as contractors or employees in the United States, the European Union, and Australia. The ideal candidate is expected to work within a European or North American (up to East Coast) timezone.

Workspace Context:

• Remote Autonomy: A trust-based, low-bureaucracy environment where individuals are empowered to manage their work and schedules.

• Collaborative Tools: Reliance on digital collaboration tools (e.g., Whimsical, Figma, Slack) to facilitate communication and teamwork across distributed teams.

• AI Integration: Expectation to leverage modern AI tooling to enhance design processes and productivity.

• Focus on Output: The culture is focused on results and output, allowing for flexibility in how and when work gets done, as long as objectives are met.

Work Schedule: The standard expectation is 40 hours per week. However, as a remote-first, trust-based company, there's an implicit flexibility in managing one's schedule to achieve objectives, encouraging a results-oriented approach.

📝 Enhancement Note: The fully remote, distributed nature of the work environment requires strong self-discipline, excellent asynchronous communication skills, and a comfort level with digital collaboration tools. The emphasis on trust and autonomy means individuals are expected to be highly self-motivated and accountable.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Application: Submit your application, including a compelling narrative on why this role and mission resonate with you. Applications that demonstrate genuine enthusiasm for building this specific product with Hospitable will stand out.

• Portfolio Review: A deep dive into your design portfolio, focusing on case studies that demonstrate end-to-end ownership, measured impact, product thinking, and collaboration. Be prepared to discuss your process, strategic rationale, and the outcomes of your work.

• Player-Coach Assessment: Discussions and potential exercises to evaluate your hands-on design skills, your ability to set and execute design standards, and your experience leveraging AI tools.

• Leadership & Strategy Discussion: Interviews with the CEO and potentially other leadership team members to assess your strategic thinking, leadership approach, and cultural fit within a lean, remote, and transparent organization.

• Cross-functional Collaboration Simulation: Potential scenarios or discussions to gauge your ability to partner effectively with Product and Engineering leadership.

Portfolio Review Tips:

• Focus on Impact: Clearly articulate the business problem, your role in solving it, the design solution, and the quantifiable results. Use metrics and data to support your claims.

• Showcase Process: Detail your design process, including research methodologies, ideation techniques, prototyping, and iteration. Highlight how you made data-informed decisions.

• Demonstrate Leadership: Include examples of how you've set design standards, mentored designers, or influenced product direction.

• Highlight Collaboration: Provide examples of successful partnerships with Product and Engineering teams.

• Tailor to Hospitable: Emphasize any experience with SaaS, product-led growth, or the short-term rental/proptech industry. Clearly explain why you are passionate about Hospitable's mission.

Challenge Preparation:

• Be prepared for potential design challenges that assess your ability to solve complex problems under constraints, similar to those faced in a lean SaaS environment.

• Practice articulating your design rationale concisely and persuasively, focusing on strategic alignment and business impact.

• Prepare to discuss how you would leverage AI tools to enhance design processes and team efficiency.

📝 Enhancement Note: The application process emphasizes not just skills but also genuine interest and cultural fit. Candidates should proactively demonstrate their understanding of Hospitable's mission and their alignment with its values of transparency, trust, and results.

🛠 Tools & Technology Stack

Primary Tools:

• Design Mockups: Whimsical

• Design & Prototyping: Figma

• AI Tooling: Modern AI tools for design leverage and efficiency (specific tools not named, but expectation is to be proficient in integrating and utilizing them).

Analytics & Reporting:

• Candidates are expected to be proficient in using product analytics and experimentation tools to inform design decisions and measure impact. Specific tools are not listed but would typically include platforms for A/B testing, user behavior analytics, and data visualization. CRM & Automation:

• While not directly a design tool, familiarity with how CRM systems and automation workflows impact user experience within a SaaS product would be beneficial.

📝 Enhancement Note: Proficiency in Figma and Whimsical is a hard requirement. The expectation to leverage AI tooling suggests a need for adaptability and a proactive approach to integrating new technologies into the design workflow.

👥 Team Culture & Values

Operations Values:

• Trust & Autonomy: A core value where individuals are empowered and trusted to manage their work and deliver results, rather than being micromanaged.

• Radical Transparency: Open communication and information sharing across the company, fostering an environment of honesty and mutual understanding.

• Caring & Supportive: A team environment that prioritizes the well-being and professional growth of its members.

• Results & Output Focused: Emphasis on achieving measurable outcomes and delivering high-quality work, with flexibility in how that work is accomplished.

• Intentionality: Building with purpose, ensuring that decisions and actions are aligned with the company's long-term strategy and mission.

Collaboration Style:

• Equal Partnership: Design operates as an equal partner with Product and Engineering leadership, contributing to strategic decisions rather than just executing on them.

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

• Lean & Agile: Collaboration is efficient, with minimal bureaucracy, leveraging digital tools to bridge geographical distances.

• AI-Leveraged: Processes are designed to maximize efficiency and effectiveness through the integration of AI tools.

📝 Enhancement Note: The company culture is built on a foundation of trust, transparency, and a strong focus on results. This implies a need for individuals who are highly self-motivated, proactive communicators, and comfortable working autonomously in a remote setting.

⚡ Challenges & Growth Opportunities

Challenges:

• Setting the Design Standard: Establishing and maintaining a cohesive, high-quality design standard across a rapidly evolving SaaS platform with a lean team.

• Balancing Player & Coach: Effectively managing time between hands-on design execution and team leadership responsibilities.

• Leveraging AI: Successfully integrating and maximizing the benefits of AI tooling within design processes to enhance efficiency and creativity.

• Remote Team Management: Building and nurturing a high-performing, cohesive design team in a fully remote, distributed environment.

• Scalability: Ensuring the design system and processes can scale effectively as the company and product grow.

Learning & Development Opportunities:

• Strategic Impact: Direct influence on product and company strategy through reporting to the CEO.

• Cutting-Edge Tooling: Hands-on experience with modern AI tools and advanced design software.

• Leadership Experience: Opportunity to build and lead a design team from its early stages, shaping its culture and processes.

• Industry Exposure: Deep immersion in the proptech and short-term rental industry.

• Equity Upside: Potential for significant financial growth through RSU and PSU awards tied to company success.

📝 Enhancement Note: The challenges presented are inherent to a fast-growing, lean, remote-first SaaS company. Success will require strong adaptability, proactive problem-solving, and a commitment to continuous learning and process optimization.

💡 Interview Preparation

Strategy Questions:

• "Describe your process for setting and elevating the design quality bar at a product-led SaaS company. Provide an example of how you've done this in a previous role."

• "How do you balance your time between hands-on design work and leading/mentoring a design team, especially in a 'player-coach' capacity?"

• "What are your thoughts on leveraging AI in product design? How would you integrate AI tools into Hospitable's design workflow to maximize efficiency and impact?"

• "Walk us through a time you had to significantly reduce complexity or eliminate inconsistency within a product's design. What was your approach and the outcome?"

• "How would you partner with Product and Engineering leadership to influence product strategy and decide what gets built?" Company & Culture Questions:

• "Why are you specifically interested in Hospitable's mission and this Head of Design role, beyond just the job description?"

• "How do you embody and foster a culture of radical transparency and trust in a remote team?"

• "What does 'results and output focused' mean to you in a work context, and how do you measure success in your own work and your team's?"

• "How do you approach building and leading a deliberately lean, AI-leveraged design team?" Portfolio Presentation Strategy:

• Storytelling: Craft compelling narratives around your case studies, focusing on the problem, your strategic approach, the solution, and the measurable impact.

• Metric-Driven: Be ready to discuss the specific KPIs and metrics you used to define success and demonstrate the ROI of your design work.

• Process Transparency: Clearly articulate your design process, including research, ideation, prototyping, and iteration, and how you made data-informed decisions.

• Tool Proficiency: Be prepared to discuss your experience with Figma, Whimsical, and how you've integrated AI tools.

• Cultural Alignment: Weave in how your values and working style align with Hospitable's emphasis on trust, transparency, and autonomy.

📝 Enhancement Note: Interview questions will likely probe your ability to think strategically, execute tactically, lead effectively, and adapt to a lean, remote, and AI-forward environment. Be prepared to back up all claims with specific examples and quantifiable results.

📌 Application Steps

To apply for this Head of Design position:

• Submit your application through the provided link on Workable.

• Craft a compelling cover letter that specifically addresses why this role and Hospitable's mission are a strong fit for your career aspirations and expertise. Highlight your passion for building this product with the company.

• Curate your portfolio to prominently feature case studies demonstrating end-to-end ownership, measurable impact, strategic product thinking, and collaborative success. Ensure it highlights your hands-on design skills and experience with Figma and Whimsical.

• Optimize your resume to clearly articulate your experience in product-led SaaS, design leadership, and setting quality standards. Quantify achievements wherever possible and include keywords related to design systems, user experience, and AI tooling.

• Prepare for interview questions by practicing your responses to common strategy, leadership, and cultural fit inquiries, and be ready to present your portfolio with a focus on impact and process.

• Thoroughly research Hospitable, its product, market position, and company values to demonstrate a deep understanding and genuine interest during the interview process.

⚠️ 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.