Head of Design

📍 Job Overview

Job Title: Head of Design

Company: Enter

Location: São Paulo, São Paulo, Brazil

Job Type: Full-time

Category: Design Leadership / Product Design

Date Posted: August 10, 2026

Experience Level: 10+ Years

Remote Status: On-site

🚀 Role Summary

• Lead and build the entire Product Design team at Enter, establishing a cohesive design vision, culture, and operational processes across the company.

• Drive the strategic development and implementation of a robust Design System to ensure consistency, scalability, and technical efficiency across all product touchpoints and institutional materials.

• Champion data-driven decision-making within the design process, institutionalizing discovery methods that leverage qualitative and quantitative evidence to validate design choices and mitigate bias.

• Act as a key strategic partner to Product, Engineering, and Business leadership, influencing product roadmap, priorities, and executive-level decisions with a strong design perspective.

• Elevate the overall quality and technical performance of design deliverables, defining rigorous design review rituals and technical criteria for scalable user experiences.

📝 Enhancement Note: While this role is for a Head of Design, the prompt requires enhancing it for revenue operations, sales operations, and GTM roles. Given the input is for a design leadership position, I will interpret "operations" broadly to encompass the operational aspects of design leadership within a tech company, focusing on process, strategy, team building, and cross-functional collaboration, framing it through an operations lens where possible. This means emphasizing the "how" of design delivery, governance, and strategic integration, akin to how RevOps or SalesOps operates.

📈 Primary Responsibilities

• Design Strategy & Vision: Define and communicate the overarching design vision for Enter, ensuring alignment with business objectives, technical complexity, and user needs across all product domains.

• Team Leadership & Development: Recruit, mentor, and manage a high-performing Product Design team, establishing clear career paths, performance expectations, and fostering a culture of continuous growth and high-quality output.

• Design System Governance: Establish and maintain a strategic Design System, ensuring its consistent application, technical feasibility, and scalability across the entire platform, from user interfaces to marketing collateral.

• Process Optimization: Institutionalize data-informed discovery processes, including user research, usability testing, and analytics, to ensure design decisions are grounded in evidence and user empathy.

• Cross-Functional Collaboration: Serve as the primary design liaison, actively partnering with Product Management, Engineering, and Business Development leadership to shape product strategy, roadmaps, and key company-wide decisions.

• Quality Assurance & Execution: Implement rigorous design review processes and technical standards to guarantee the delivery of polished, accessible, and high-performing user experiences.

• Stakeholder Engagement: Participate in strategic client and stakeholder conversations to ensure the design strategy directly addresses market needs and translates operational complexities into tangible business value.

• Culture Building: Foster and disseminate a strong design culture throughout the organization, enhancing Enter's employer brand and the overall design maturity of the company.

📝 Enhancement Note: The primary responsibilities are translated to emphasize the operational aspects of design leadership. For instance, "Design Strategy & Vision" is framed as strategic planning and operational alignment. "Team Leadership & Development" highlights the operational management of a team. "Design System Governance" is positioned as a core operational framework for consistency and efficiency.

🎓 Skills & Qualifications

Education: Bachelor's degree in Design, Human-Computer Interaction, Computer Science, or a related field, or equivalent practical experience. A Master's degree is a plus.

Experience: Minimum of 10 years of experience in Product Design, with a significant portion focused on leading and scaling design teams within fast-paced technology environments. Proven experience in a "builder" role, establishing design functions or systems from early stages.

Required Skills:

• Product Design Expertise: Deep understanding of UX/UI principles, information architecture, complex user flows, error states, and edge cases for sophisticated digital products.

• Strategic Product & Business Acumen: Ability to translate intricate business strategies into scalable user experience architecture at an enterprise level.

• Data-Driven Design & Research: Proficiency in qualitative and quantitative research methods (usability testing, interviews, funnel analysis, product data analysis) to support design decisions with empirical evidence.

• Team Leadership & People Management: Demonstrated success in managing, mentoring, and growing design teams, including recruitment, performance evaluation, and career path development.

• Design System Development: Experience in establishing, governing, and scaling Design Systems as strategic assets for consistency and efficiency.

• Technical Quality & Review: Capability to conduct rigorous technical reviews of design deliverables, ensuring consistency, accessibility, and interface performance.

• Executive Communication: Exceptional ability to articulate complex strategies clearly and concisely to diverse audiences across all organizational levels, both verbally and in writing.

• Hands-on Problem Solving: Willingness and ability to engage directly in critical design decisions and problem-solving when necessary, complementing team efforts.

• Collaborative Mindset: Proven ability to thrive in collaborative, cross-functional environments, valuing knowledge exchange and collective solution development.

• Resilience & Adaptability: High energy, consistent performance under pressure, and adaptability to ambiguity typical of a high-growth startup.

Preferred Skills:

• Front-End Development Knowledge: Solid understanding of HTML/CSS and familiarity with frameworks like React to effectively communicate technical feasibility with engineering teams.

• AI/LLM Product Design Experience: Prior experience designing interfaces for AI/LLM-powered products, addressing challenges like uncertainty, probabilistic states, and model explainability.

• Regulated Industry Experience: Practical experience in sectors such as LegalTech, FinTech, or other industries where precision, compliance, and reliability are paramount.

• Founding/Scaling Design Teams: Proven track record of building a design area from inception or at an early-stage maturity level.

📝 Enhancement Note: The skills section is structured to highlight the operational execution and strategic leadership aspects of the Head of Design role. "Data-Driven Design & Research" and "Design System Development" are emphasized as operational frameworks. "Team Leadership & People Management" is framed as operational team management, and "Executive Communication" as a key stakeholder management skill.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Case Studies of Impact: Showcase at least 2-3 comprehensive case studies demonstrating significant impact on product strategy, user experience, and business outcomes. Each case study should clearly outline the problem, your role, the process followed, key decisions, and measurable results.

• Design System Contribution/Leadership: If applicable, provide examples of your involvement in the creation, evolution, or governance of a Design System, detailing its components, adoption strategy, and impact on design and development efficiency.

• Team Leadership & Process Examples: Include evidence of your leadership capabilities, such as examples of team growth, process improvements implemented, or mentorship initiatives that elevated team performance and quality.

• Strategic Design Initiatives: Highlight instances where you translated complex business requirements into cohesive design strategies and architectural decisions for large-scale products or platforms.

Process Documentation:

• Discovery & Validation Workflows: Present examples of how you've designed and implemented discovery processes that integrate user research, data analysis, and stakeholder feedback to validate design concepts before significant development investment.

• Design Review & Quality Assurance Protocols: Detail the methodologies and rituals you've established for design reviews, focusing on ensuring quality, consistency, accessibility, and technical feasibility across all design outputs.

• Cross-Functional Collaboration Frameworks: Illustrate how you've fostered seamless collaboration between Design, Product Management, and Engineering, providing examples of integrated workflows or communication strategies that enhance efficiency and alignment.

📝 Enhancement Note: This section focuses on the operational deliverables expected from a design leader. The emphasis is on demonstrating the ability to manage processes, build systems, and lead teams effectively, mirroring the operational rigor expected in RevOps or SalesOps. "Design System Contribution/Leadership" and "Team Leadership & Process Examples" directly relate to operational frameworks and team management.

💵 Compensation & Benefits

Salary Range: Based on market research for Head of Design roles in São Paulo, Brazil, with 10+ years of experience and leadership responsibilities in a high-growth tech startup environment, the estimated annual salary range is R$ 200,000 - R$ 350,000 (Brazilian Real). This range can vary based on the candidate's specific experience, negotiation, and the company's compensation philosophy.

Benefits:

• Comprehensive Health Insurance: Full medical, dental, and vision coverage for employees and dependents.

• Stock Options/Equity: Opportunity to participate in the company's growth through stock options or equity grants.

• Generous Paid Time Off: Ample vacation days, personal days, and national holidays.

• Professional Development Budget: Annual allowance for conferences, training, courses, and certifications to support continuous learning and skill enhancement.

• On-site Perks: Access to a modern office space in São Paulo with amenities, fostering collaboration and a productive work environment.

• Parental Leave: Supportive parental leave policy for new parents.

• Meal Vouchers/Allowance: Contribution towards daily meals.

Working Hours: Standard full-time hours are expected, typically around 40 hours per week. While the role is on-site, the company culture may offer some flexibility in daily scheduling, provided core responsibilities and team collaboration needs are met.

📝 Enhancement Note: The salary range is an estimation based on the role, experience level, and location, incorporating typical tech industry benchmarks for leadership positions in Brazil. Benefits are tailored to what is commonly offered in high-growth tech companies and relevant to attracting and retaining senior talent. The working hours are framed with potential flexibility within an on-site context.

🎯 Team & Company Context

🏢 Company Culture

Industry: Artificial Intelligence (AI) / Enterprise Software / Automation

Company Size: Valued at USD 1.2 Billion (Unicorn status), indicating significant growth and investment. The employee count is likely in the hundreds, growing rapidly.

Founded: Enter was founded with a mission to make Brazil a protagonist in the AI revolution, focusing on applying AI to critical, high-volume manual processes, starting with legal operations and expanding across enterprises.

Team Structure:

• The Product Design team will report directly to the Head of Design.

• The Head of Design will be a key member of the senior leadership team, working closely with executives in Product, Engineering, and Business.

• Cross-functional collaboration is central, with designers working daily alongside product managers and engineers to define and build features. Methodology:

• AI-Driven Operations: The company's core mission revolves around leveraging AI to transform operational efficiency for large enterprises.

• Data-Centric Approach: Decisions across all departments, including Design, are expected to be heavily informed by data and evidence.

• Agile Development: Standard agile methodologies are likely employed, emphasizing iterative development, continuous feedback, and rapid iteration.

• User-Centricity: Despite the technical focus, a strong emphasis is placed on understanding and solving real user problems through empathy and robust research.

Company Website: https://www.getenter.ai/

📝 Enhancement Note: This section contextualizes the Head of Design role within Enter's ambitious AI-focused mission and rapid growth phase. The emphasis on "AI-Driven Operations" and "Data-Centric Approach" highlights the operational environment and decision-making framework.

📈 Career & Growth Analysis

Operations Career Level: This is a senior leadership position, equivalent to a VP or Director level within a larger organization, responsible for building and scaling a critical function from the ground up. It represents a significant step from a Senior Individual Contributor (IC) role into people management and strategic ownership.

Reporting Structure: The Head of Design will report to a C-level executive, likely the Chief Product Officer (CPO) or CEO, given the strategic importance of design in a product-led company. They will directly manage a team of Product Designers.

Operations Impact: The design team's output directly influences product adoption, user satisfaction, operational efficiency for clients, and ultimately, Enter's revenue growth and market position. The Head of Design's strategic decisions will have a profound impact on the company's ability to scale and achieve its mission.

Growth Opportunities:

• Scaling a Design Function: Opportunity to build and shape a world-class design team and establish best-in-class design operations from an early stage.

• Strategic Influence: Deep involvement in executive-level product strategy and company decision-making, contributing to the long-term vision of an AI leader.

• Industry Leadership: Potential to become a recognized leader in AI product design, speaking at conferences and influencing industry best practices.

• Career Advancement: Path to Chief Design Officer (CDO) or a broader Head of Product role as the company scales.

📝 Enhancement Note: This analysis frames the Head of Design role through an operations lens, emphasizing the "building" and "scaling" aspects, strategic influence, and direct impact on business operations and growth, similar to how a Head of RevOps would be viewed.

🌐 Work Environment

Office Type: The role is 100% on-site, indicating a commitment to in-person collaboration and a strong office culture. This suggests a modern, well-equipped workspace designed to foster innovation and teamwork.

Office Location(s): São Paulo, Pinheiros district. This is a well-known business and innovation hub in São Paulo, suggesting accessibility and a vibrant work environment.

Workspace Context:

• Collaborative Hub: The physical workspace is designed to encourage spontaneous interactions, brainstorming sessions, and seamless collaboration between design, product, and engineering teams.

• Technology & Tools: Expect access to the latest design software, hardware, and collaboration tools necessary for high-impact design work.

• Team Integration: The on-site nature facilitates deep integration with product and engineering teams, enabling rapid feedback loops and agile workflow.

Work Schedule: A standard Monday-to-Friday work week is expected. While on-site, the company may offer some flexibility in daily start/end times to accommodate individual needs, provided that team collaboration, meeting attendance, and core work hours are consistently met. The emphasis is on results and collaborative presence.

📝 Enhancement Note: The work environment is described with an emphasis on its operational implications for collaboration, efficiency, and team dynamics, aligning with an operations-focused perspective.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A brief call with HR or a recruiter to assess basic qualifications and cultural fit.

• Hiring Manager Interview: In-depth discussion with the direct reporting manager (likely CPO or CEO) focusing on strategic vision, leadership philosophy, and experience.

• Team & Cross-Functional Interviews: Meetings with key stakeholders from Product, Engineering, and potentially other design team members to evaluate collaboration style, technical depth, and problem-solving capabilities.

• Portfolio Presentation & Case Study: A dedicated session where the candidate presents selected case studies from their portfolio, demonstrating their strategic thinking, process, leadership, and impact. This is a critical stage for assessing practical application of skills.

• Executive/Final Interview: A final conversation with senior leadership to confirm alignment with company vision, culture, and strategic direction.

Portfolio Review Tips:

• Focus on Impact & Strategy: Clearly articulate the business problem, your strategic approach, and the measurable impact of your design work. Quantify results whenever possible (e.g., increased conversion rates, reduced support tickets, improved user satisfaction scores).

• Showcase Leadership & Process: Highlight examples of how you've led teams, improved design processes, mentored designers, and managed design systems. Demonstrate your ability to operate strategically and operationally.

• Tailor to Enter's Context: Emphasize experience with complex products, data-driven decision-making, and ideally, AI or regulated industries. Show how your approach aligns with Enter's mission.

• Structure for Clarity: Organize your portfolio logically with clear case study titles, role definitions, and concise explanations. Use visuals effectively but keep the narrative focused on strategic and operational contributions.

• Be Prepared for Deep Dives: Expect questions about your design philosophy, leadership style, how you handle conflict, and your approach to building and scaling teams and processes.

Challenge Preparation:

• Design Strategy Exercise: You might be asked to outline a high-level design strategy for a hypothetical new feature or product area at Enter, demonstrating your strategic thinking and understanding of their business.

• Process Improvement Scenario: Prepare to discuss how you would assess and improve existing design processes or establish new ones (e.g., for user research, design critiques, or design system adoption).

• Stakeholder Management Scenarios: Be ready to discuss how you would navigate disagreements with product or engineering, or how you would gain buy-in for your design vision from executive leadership.

📝 Enhancement Note: This section provides actionable advice for the application process, focusing on how to present operational capabilities and strategic leadership through the portfolio and interview stages. The emphasis is on demonstrating process ownership, strategic alignment, and leadership impact.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (highly probable for collaborative design, prototyping, and design system integration), Sketch, Adobe Creative Suite.

• Collaboration & Project Management: Jira, Asana, Trello, Confluence for workflow tracking, task management, and documentation.

• User Research & Testing: UserTesting.com, Maze, Hotjar, SurveyMonkey, Google Analytics for data collection and analysis.

Analytics & Reporting:

• Product Analytics: Mixpanel, Amplitude, Google Analytics for understanding user behavior, funnel analysis, and feature adoption.

• Business Intelligence: Tableau, Power BI, Looker (or similar) for broader business data visualization and reporting, enabling data-driven design decisions.

CRM & Automation:

• While not directly a design tool, familiarity with CRM systems (e.g., Salesforce, HubSpot) and marketing automation platforms can provide context for B2B product design, understanding customer journeys and sales processes.

📝 Enhancement Note: This section highlights the operational tools crucial for design leadership, emphasizing how they support process efficiency, data analysis, and cross-functional collaboration. The focus is on the operational utility of these tools in a design context.

👥 Team Culture & Values

Operations Values:

• Data-Driven Excellence: A commitment to using data and evidence to inform all design decisions, ensuring rigorous validation and measurable impact.

• Bias for Action & Iteration: A culture that encourages rapid experimentation, learning from failures, and continuous improvement of both products and processes.

• Customer Obsession: A deep-seated focus on understanding and solving the real-world operational challenges of customers, translating complex problems into intuitive solutions.

• High Performance & Accountability: Expectation of high standards, ownership of outcomes, and a proactive approach to achieving ambitious goals.

• Collaboration & Transparency: Open communication, knowledge sharing, and a collaborative spirit across all teams to build the best possible solutions together.

Collaboration Style:

• Integrated Teams: Design works hand-in-hand with Product and Engineering from ideation through launch, fostering a shared sense of ownership and efficient feedback loops.

• Transparent Communication: Regular syncs, shared documentation, and open channels for feedback ensure everyone is aligned on goals and progress.

• Constructive Feedback Culture: Designers are encouraged to give and receive constructive criticism to elevate the quality of work and foster individual growth.

📝 Enhancement Note: This section translates the company's likely values into an operational framework for the design team, emphasizing efficiency, data utilization, and accountability, which are core tenets of operations roles.

⚡ Challenges & Growth Opportunities

Challenges:

• Translating Complex AI Concepts: Designing intuitive interfaces for AI-driven products that handle complex, often probabilistic, outputs and explanations can be inherently challenging.

• Balancing Innovation with Scalability: Ensuring that design innovations remain scalable and technically feasible across a rapidly growing platform requires careful planning and strong partnerships with engineering.

• Building Design Operations from Scratch: Establishing robust design processes, a comprehensive design system, and a high-performing team in a fast-paced startup environment requires significant strategic effort and execution.

• Managing Stakeholder Expectations: Aligning diverse stakeholder needs and priorities (Product, Engineering, Sales, Executive) with a cohesive and effective design vision.

Learning & Development Opportunities:

• AI Product Design Specialization: Deepen expertise in designing for AI/ML products, understanding user interaction with intelligent systems.

• Design Leadership & Scaling: Gain invaluable experience in building and scaling a design function within a rapidly growing, venture-backed tech company.

• Cross-Functional Strategic Impact: Contribute directly to the strategic direction of an AI company, influencing product roadmap and business outcomes at the executive level.

• Industry Exposure: Engage with cutting-edge technology and potentially present work at industry events, enhancing personal brand and network.

📝 Enhancement Note: This section highlights operational challenges inherent in scaling a design function within an AI startup, framing them as opportunities for skill development and strategic growth, aligning with an operations perspective on problem-solving and continuous improvement.

💡 Interview Preparation

Strategy Questions:

• "How would you approach building a Design System for a complex B2B AI platform from the ground up?" (Focus on your process, governance model, and stakeholder engagement strategy.)

• "Describe a time you had to balance aggressive product timelines with maintaining high design quality. What was your approach?" (Demonstrate your ability to manage operational trade-offs and ensure quality.)

• "How do you ensure design decisions are data-informed and not solely based on intuition, especially in areas with limited historical data?" (Highlight your research methodologies and data analysis skills.) Company & Culture Questions:

• "What are your thoughts on the current state of AI in Brazil and how Enter is positioned to lead?" (Show your understanding of the market and the company's mission.)

• "How would you foster a strong design culture within a company that is primarily engineering and product-led?" (Discuss your approach to influencing and integrating design across departments.)

• "How do you measure the impact of design on business outcomes, and what KPIs would you track for your team?" (Focus on quantifiable results and operational effectiveness.) Portfolio Presentation Strategy:

• Structure for Impact: Begin with an executive summary of your key accomplishments and leadership philosophy. For each case study, clearly state the problem, your role, the strategic approach, key decisions, the operational process you followed, and the measurable results.

• Highlight Leadership & Process: Dedicate specific slides or sections to how you managed teams, mentored designers, established processes, and governed design systems.

• Demonstrate Data-Driven Approach: Show how user research, analytics, and testing informed your design decisions and led to positive outcomes.

• Tailor to Enter's Context: Emphasize how your experience with complex products, AI, and scaling operations makes you the ideal candidate to lead design at Enter. Be prepared to discuss how you'd tackle specific challenges Enter faces.

📝 Enhancement Note: This section provides targeted interview preparation advice, framing questions and presentation strategies in terms of operational impact, strategic leadership, and process execution, making it relevant for candidates approaching the role from an operational mindset.

📌 Application Steps

To apply for this Head of Design position:

• Submit your application through the provided link on Ashby.

• Tailor Your Resume: Emphasize leadership experience, experience in scaling design teams and processes, and any relevant work with complex B2B products, AI, or regulated industries. Use keywords like "Design Leadership," "Product Strategy," "Design Operations," "Team Building," "Design Systems," and "Data-Driven Design."

• Curate Your Portfolio: Select 2-3 of your most impactful projects that showcase strategic thinking, leadership, process implementation, and measurable business results. Ensure your portfolio clearly articulates your role and contributions, especially in team leadership and operationalizing design.

• Prepare Your Narrative: Be ready to articulate your design philosophy, your approach to building and managing a design team, and how you would operationalize design excellence at Enter. Practice presenting your portfolio case studies, focusing on the "how" and "why" behind your decisions.

• Research Enter: Understand their mission, product, target market, and recent funding rounds. Think about how design can strategically support their ambitious goals in the AI space and prepare to discuss specific ideas.

⚠️ 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.

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