Head of Design (North America/Europe - Remote)

📍 Job Overview

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

Company: Hospitable

Location: Netherlands (Remote)

Job Type: Full-Time

Category: Design Leadership / Product Design

Date Posted: 2026-08-06

Experience Level: 5-10 Years (Estimated)

Remote Status: Remote Solely

🚀 Role Summary

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

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

• Drive end-to-end design ownership from discovery and research through to shipped features, ensuring intuitive user experiences and elegant interfaces.

• Develop and maintain a cohesive design system, language, style guide, and component library to ensure consistency and reduce complexity.

• Collaborate closely with Product and Engineering leadership to shape product strategy and roadmap decisions.

📝 Enhancement Note: The role is explicitly defined as a "player-coach" position, indicating a strong emphasis on hands-on design contributions alongside team leadership. This is crucial for candidates to understand as it differs from a pure management role. The target regions (North America/Europe) and the remote-only nature suggest a need for strong self-management and asynchronous communication skills.

📈 Primary Responsibilities

• Establish and champion the overall design vision and quality bar for the Hospitable platform, ensuring alignment with long-term company strategy and user needs.

• Directly lead the design of high-stakes features and critical user flows, overseeing discovery, research, prototyping, visual design, and interaction design.

• Own the development and governance of the design system, including the design language, style guide, and component library, ensuring scalability and consistency.

• Recruit, mentor, and manage a deliberately lean product design team, fostering their growth and ensuring the highest standard of design output.

• Partner effectively with Product Management and Engineering leadership to define product strategy, prioritize initiatives, and ensure seamless execution of design across the product lifecycle.

• Leverage data, customer feedback, analytics, and experimentation to inform design decisions and demonstrate the impact of design initiatives on key business metrics.

• Champion a culture of continuous improvement and reduce design complexity across the platform, proactively identifying and addressing inconsistencies.

📝 Enhancement Note: The responsibilities emphasize a dual focus on strategic design leadership and hands-on execution. The expectation to "raise the standard of everyone around you" and "keep shipping" implies a need for strong mentorship capabilities and a proactive, results-oriented approach. The emphasis on "data-informed decisions" highlights the importance of analytical skills in design evaluation.

🎓 Skills & Qualifications

Education: While no specific degree is listed, a strong portfolio and demonstrable experience in design leadership and product design are paramount. Candidates with formal education in Design, HCI, or related fields may have an advantage.

Experience:

• 5-10 years of progressive experience in product design, with a significant portion focused on leadership roles within product-led SaaS companies.

• Proven track record of setting and elevating design quality standards within an organization.

• Demonstrated experience in end-to-end design ownership, from initial concept and research to successful feature launch and post-launch impact analysis.

• Hands-on design experience within the last 3 years, showcasing continued proficiency in core design craft. Required Skills:

• Product Design Leadership: Ability to set and execute a compelling design vision and strategy.

• Design Systems: Expertise in developing, maintaining, and scaling design systems, style guides, and component libraries.

• User Experience (UX) & User Interface (UI) Design: Deep understanding of UX principles, interaction design, and visual design best practices for web applications.

• Research & Discovery: Proficiency in user research methodologies, customer feedback analysis, and data interpretation to inform design decisions.

• Prototyping & Design Tools: Expert-level skills in industry-standard design tools such as Figma and Whimsical for mockups and design creation.

• Team Development & Mentorship: Experience in building, leading, and mentoring design teams, fostering high performance and continuous improvement.

• Product Strategy Collaboration: Ability to partner effectively with Product and Engineering leaders to influence product direction.

• Data-Informed Decision Making: Competence in using analytics, experimentation, and user data to validate design choices and measure impact.

Preferred Skills:

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

• Familiarity with modern AI tooling to enhance design processes and team leverage.

• Experience working in a remote-first, low-bureaucracy environment.

📝 Enhancement Note: The "player-coach" aspect is critical, requiring candidates to be both strategic leaders and individual contributors. The emphasis on "still hands-on" means candidates who have transitioned solely into management may not be the best fit. The specific mention of Figma and Whimsical indicates a direct need for proficiency in these tools.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrated Design Leadership: Showcase instances where you set a design vision, established quality standards, and successfully led design initiatives.

• End-to-End Project Ownership: Present detailed case studies of projects you've personally driven from discovery and research through to successful implementation and impact measurement.

• Design System Contributions: Include examples of your involvement in creating, evolving, or utilizing design systems, style guides, or component libraries.

• Data-Informed Design Decisions: Clearly articulate how data, research, and analytics influenced your design choices and how you measured the impact of your work.

• Hands-On Design Craftsmanship: Provide examples of your individual design contributions, showcasing your skills in interaction design, visual design, and prototyping.

Process Documentation:

• Workflow Optimization: Illustrate how you've analyzed and improved design workflows for efficiency and quality.

• System Implementation: Detail your experience in implementing or contributing to design systems and their adoption by teams.

• Performance Analysis: Demonstrate how you've used metrics to track the effectiveness of design solutions and identify areas for improvement.

📝 Enhancement Note: The portfolio is the primary tool for demonstrating "hands-on" experience and "end-to-end ownership." Candidates must be prepared to articulate not just the deliverables but the strategic thinking, problem-solving, and measurable impact behind their design work. The mention of AI tooling suggests including examples of how technology was leveraged to improve design processes.

💵 Compensation & Benefits

Salary Range:

• The total cash budget for this role is between USD $171,000.00 to $218,900.00 annually.

• The exact salary will depend on seniority and the cost of living in the candidate's location.

• For US-based employees, the gross salary range could be between $157,619.92 to $201,771.94.

• Hospitable hires internationally as contractors or employees (US, EU, Australia), with gross compensation adjusted for payroll taxes. Benefits:

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

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

• US Employee Benefits: Healthcare (EPO, PPO, HSA), 401(k).

• Time Off: 35 days of paid time off per year (including self-serve public holidays).

• Parental Leave: Comprehensive parental leave policy.

• Mental Health Support: Access to therapists via Slack through a dedicated platform.

• Peer Recognition: Virtual coins earned through a peer recognition platform, redeemable for gift cards, donations, or monetary rewards.

Working Hours:

• The role is full-time, typically around 40 hours per week. Given the remote, global nature, flexibility is expected, but core availability during European or North American (East Coast) time zones is implied for collaboration.

📝 Enhancement Note: The compensation structure is highly variable, with significant potential upside through RSUs and PSUs. Candidates should understand that the base cash salary is one component, and the performance-based PSUs offer substantial additional earning potential tied directly to company success. The inclusion of specific ranges for US employees and the acknowledgment of international compensation adjustments are crucial details.

🎯 Team & Company Context

🏢 Company Culture

Industry: Software (SaaS) for Short-Term Rentals / Hospitality Technology (PropTech). Hospitable operates within the rapidly growing short-term rental market, providing software solutions that enable hosts to automate and manage their properties.

Company Size: Hospitable is described as a "deliberately lean" company, suggesting a small to medium-sized team. This implies a fast-paced environment with high individual impact and less bureaucracy.

Founded: The founding date is not specified, but the company is described as having a "state-of-the-art product and user experience" and a "fast-moving roadmap," indicating a relatively established yet agile operation.

Team Structure:

• The Design team will be "deliberately lean," with the Head of Design leading "a small team of product designers."

• The Head of Design reports directly to the CEO, Pierre, indicating a high level of visibility and direct access to executive leadership.

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

• Agile & Fast-Paced: The company "moves fast, thinks boldly, and builds with intention," with a "roadmap that moves fast."

• Data-Informed: Decisions are driven by "research, analytics, experimentation, and direct customer feedback."

• Remote-First & Trust-Based: Operates as a "remote-only, global, and trust-based company" where "exceptional work comes from exceptional people — no matter their background, geography, or path."

• Low-Bureaucracy & AI-Leveraged: Emphasizes "low-bureaucracy" and maximizing "leverage from a lean setup and modern AI tooling."

Company Website: https://hsptb.com/

📝 Enhancement Note: The culture is characterized by speed, transparency, trust, and a results-oriented approach. The "remote-only" and "trust-based" aspects are core to how the company operates, requiring high levels of autonomy and accountability from employees. The emphasis on AI tooling suggests integration of new technologies into daily workflows.

📈 Career & Growth Analysis

Operations Career Level: This role represents a senior leadership position, specifically the "first Head of Design." It is a "player-coach" role, meaning it requires both strategic vision setting and hands-on execution. The scope is broad, encompassing the entire product's design quality, system, and team.

Reporting Structure: The Head of Design reports directly to the CEO, Pierre. This elevated reporting structure signifies the strategic importance of design within Hospitable and offers significant visibility and influence at the executive level.

Design Impact: The Head of Design is expected to make Hospitable the "best-designed product in short-term rental software." This involves directly impacting user acquisition, retention, and satisfaction through an effortless and elegant user experience. The role is critical in shaping the product's perceived value and competitive differentiation.

Growth Opportunities:

• Foundational Role: As the first Head of Design, this position offers the unique opportunity to shape the design function from the ground up, establishing processes, standards, and a team culture.

• Team Expansion: Potential to grow the design team significantly as the company scales, moving from a lean setup to a more robust department under your leadership.

• Strategic Influence: Direct reporting to the CEO provides a platform for significant influence on product strategy, company direction, and user experience across the entire business.

• Skill Development: Opportunity to deepen expertise in player-coach roles, AI-leveraged design, and building design systems in a fast-paced SaaS environment.

• Leadership Advancement: Potential to grow into a VP-level role or expand design responsibilities across new product lines or company initiatives.

📝 Enhancement Note: This is a pivotal role for ambitious design leaders who want to build something significant. The "player-coach" dynamic and direct CEO reporting are key differentiators, offering a blend of hands-on contribution and high-level strategic input. The growth potential is substantial, tied to the company's expansion and success in the short-term rental market.

🌐 Work Environment

Office Type: Hospitable is a "remote-only" company. There is no central office; all work is conducted remotely.

Office Location(s): The ideal candidate would work within a European or North American (up to East Coast) timezone to facilitate synchronous collaboration with key stakeholders, particularly the CEO and other leadership team members. While the job posting mentions "Netherlands" as a location, it's within the context of a remote role, implying the candidate would be based remotely in the Netherlands or other specified regions.

Workspace Context:

• Autonomous & Trust-Based: The work environment is characterized by high autonomy and trust. Employees are "trusted, not managed," focusing on results and output rather than micromanagement.

• Collaborative Tools: Expect extensive use of digital collaboration tools (e.g., Slack, Whimsical, Figma) for communication, design, and project management.

• Lean & Efficient: The environment is designed for maximum leverage with minimal bureaucracy, encouraging efficient workflows and smart use of resources, including AI tooling.

• Global Team: Interaction