Head of Design

📍 Job Overview

Job Title: Head of Design

Company: PermitFlow

Location: New York City, New York, USA

Job Type: FULL_TIME

Category: Design Leadership / Product Design / GTM Operations Enablement

Date Posted: May 11, 2026

Experience Level: 10+ Years (AI-derived)

Remote Status: Hybrid (New York City Office)

🚀 Role Summary

• Lead and scale the design function at PermitFlow, transforming it into a strategic partner across Product, Engineering, GTM, Customer Success, and Operations.

• Drive product design and brand design initiatives, ensuring a cohesive and high-quality user experience for complex B2B SaaS workflows.

• Own the design system architecture, quality standards, critique processes, and cross-functional collaboration models to enable design at scale.

• Act as a player-coach, contributing hands-on design work while building and mentoring a team of talented designers.

• Leverage AI tools to enhance design workflows and set the future vision for design at PermitFlow.

📝 Enhancement Note: While the raw job title is "Head of Design," this role has significant implications for GTM Operations and Sales Operations by shaping the user experience of a B2B SaaS product critical for construction workflows. The emphasis on complex workflows, data-dense interfaces, and customer-facing product aspects directly impacts how sales and operations teams leverage the platform and communicate its value. The AI-derived experience level of "10+" suggests a senior leadership role requiring extensive experience in scaling design functions and strategic product input. The hybrid nature implies a need for strong in-person collaboration with Product and Engineering in the NYC office.

📈 Primary Responsibilities

• Establish and grow PermitFlow's design organization, fostering a culture of strategic partnership with Product, Engineering, and other business units.

• Recruit, hire, and develop a high-performing team of product and brand designers, providing mentorship and career development opportunities.

• Define and implement PermitFlow's overarching design strategy, encompassing design system governance, quality assurance, critique frameworks, and collaborative workflows.

• Execute hands-on design work for critical product areas, setting the benchmark for design quality and user experience.

• Oversee and evolve the company's design system to ensure consistency, scalability, and adherence to brand guidelines across all product touchpoints.

• Implement robust quality standards and review processes to guarantee that shipped products align with design intent and user needs.

• Collaborate closely with executive leadership to align design efforts with key business objectives, driving improvements in activation, retention, and customer satisfaction.

• Champion the integration of AI tools within the design process, exploring new methodologies and workflows to enhance team efficiency and innovation.

• Partner with GTM and Operations teams to ensure the product design effectively supports user workflows, data accessibility, and overall operational efficiency.

📝 Enhancement Note: The responsibilities highlight a blend of strategic leadership and hands-on execution, typical for a Head of Design in a growing startup. The emphasis on partnering with GTM, Customer Success, and Operations is crucial for a B2B SaaS product like PermitFlow, as design directly impacts user adoption, efficiency, and satisfaction within these functions. The "player-coach" aspect means candidates must be comfortable leading and doing.

🎓 Skills & Qualifications

Education: Not explicitly stated, but a Bachelor's or Master's degree in Design, HCI, or a related field is typically expected for such a senior role.

Experience:

• 8+ years of progressive experience in product design, with a strong focus on B2B SaaS products.

• 3+ years of direct experience leading and managing design teams, preferably within a high-growth startup or technology company context.

• Proven track record of building and scaling design functions from an early-stage to a more mature organizational level. Required Skills:

• Expertise in B2B SaaS product design, particularly with complex workflow products, data-dense interfaces, and domain-expert users.

• Exceptional design craft across typography, layout, spacing, hierarchy, color, interaction design, and overall polish.

• Strong systems thinking capabilities, extending beyond individual screens to holistic design solutions.

• Proven ability to build and manage design teams, including hiring, mentoring, and performance management.

• Player-coach mentality: capable of hands-on design execution while leading and developing a team.

• Active fluency and practical integration of AI tools within daily design workflows.

• Experience establishing and governing design processes, including critique rituals, quality gates, and design-engineering collaboration models.

• Excellent communication, presentation, and interpersonal skills, with the ability to influence cross-functional stakeholders and leadership.

• Strategic thinking combined with a strong bias for action and hands-on execution. Preferred Skills:

• Experience in brand design and its integration with product design.

• Familiarity with the construction technology (ConTech) industry or complex regulatory/workflow environments.

• Experience designing for AI-powered products or integrating AI into user workflows.

• Deep understanding of design system architecture and governance.

• Experience in user research methodologies and translating insights into design solutions.

📝 Enhancement Note: The requirements emphasize a blend of deep design expertise, leadership acumen, and a forward-thinking approach to AI integration. The "player-coach" requirement is critical for a startup environment where leaders often need to roll up their sleeves. The specific mention of "complex workflow products" and "data-dense interfaces" is highly relevant for operations roles that rely on efficient management of intricate processes.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A comprehensive portfolio showcasing a range of B2B SaaS product design work, with a focus on complex workflows and data-dense interfaces.

• Examples demonstrating the ability to define and evolve design systems, including their architecture, governance, and impact on product consistency and scalability.

• Case studies detailing your experience in building and scaling design teams, including hiring processes, team structure, and mentorship strategies.

• Demonstrations of hands-on design work, highlighting your craft, problem-solving skills, and strategic approach to user experience challenges.

• Evidence of successful collaboration with Product and Engineering teams, showcasing how design integrated into development cycles. Process Documentation:

• Case studies that illustrate the establishment and refinement of design processes, such as critique frameworks, quality gates, and design-engineering collaboration models.

• Examples of how you've integrated AI tools into your design workflow, demonstrating efficiency gains or novel approaches to design challenges.

• Documentation or examples of design system governance, including how standards are maintained and evolved.

• Examples of how design has directly influenced business metrics like activation, retention, or customer satisfaction.

📝 Enhancement Note: For a Head of Design role, the portfolio is paramount. It needs to showcase not just individual design skills but also the ability to build and scale a design function, manage complex systems (like design systems), and drive business outcomes through design. The emphasis on process documentation is key for demonstrating leadership capabilities in defining how design operates within the organization.

💵 Compensation & Benefits

Salary Range: $250,000 - $300,000 per year.

Benefits:

• Competitive salary and meaningful equity in a high-growth company.

• Comprehensive health coverage: 100% company-paid base medical, dental, and vision insurance for employees.

• Healthcare Flexible Spending Account (FSA).

• 401(k) savings plan for retirement.

• Generous paid time off: Unlimited PTO and paid family leave.

• Home office and equipment stipend to ensure a productive remote work setup.

• Daily in-office lunch and dinner provided for employees working at the NYC office.

• Commuter benefits (pre-tax transit and parking).

Working Hours: Standard full-time hours, typically 40 hours per week, with flexibility expected in a startup environment, especially for a leadership role.

📝 Enhancement Note: The salary range is competitive for a Head of Design role in New York City, reflecting the experience level and leadership responsibilities. The benefits package is robust, indicating a commitment to employee well-being and work-life balance, which is attractive to senior professionals. The mention of in-office meals suggests a strong emphasis on in-person collaboration for hybrid employees.

🎯 Team & Company Context

🏢 Company Culture

Industry: Construction Technology (ConTech) / Applied AI. PermitFlow operates at the intersection of AI and the construction industry, a sector ripe for digital transformation.

Company Size: High-growth startup, having recently raised a $90M Series B. This indicates a rapidly scaling organization with a dynamic, fast-paced environment.

Founded: PermitFlow was founded with the mission to redefine how construction projects are managed using AI. The company has achieved significant traction, processing over $20B in development.

Team Structure:

• The design organization is expected to grow from a small team under this leadership role into a well-staffed, strategic function.

• Designers will partner closely with Product Management, Engineering, GTM (Sales, Marketing), Customer Success, and Operations teams.

• The Head of Design will report to senior leadership, likely the CEO or a VP of Product, and will be instrumental in shaping the product vision and execution. Methodology:

• PermitFlow leverages applied AI to tackle complex information challenges in construction.

• The company emphasizes data-driven decision-making and a focus on delivering tangible business value (speed, accuracy, visibility) to its clients.

• Design processes will need to be efficient, scalable, and integrated with AI-driven workflows.

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

📝 Enhancement Note: PermitFlow is positioned as an innovative leader in the ConTech space, leveraging AI to solve significant industry pain points. This implies a culture that values technological advancement, problem-solving, and direct business impact. The growth stage suggests opportunities for significant influence and career acceleration.

📈 Career & Growth Analysis

Operations Career Level: This is a senior leadership role (Head of Design), equivalent to a Director or VP level within a design organization. It demands strategic vision, team-building expertise, and the ability to influence product direction.

Reporting Structure: The Head of Design will likely report to the CEO or a VP of Product, working closely with other C-suite executives and department heads. This provides high visibility and direct impact on company strategy.

Operations Impact: The design function under this leader will directly impact the usability, efficiency, and adoption of PermitFlow's AI platform. This has downstream effects on sales effectiveness, customer onboarding, operational efficiency for clients, and overall customer satisfaction and retention. Strong design is critical for a complex B2B SaaS product.

Growth Opportunities:

• Organizational Scaling: Opportunity to build and shape a design function from the ground up, establishing its processes, culture, and strategic importance within the company.

• Product Strategy Influence: Direct involvement in defining the product roadmap and strategy, influencing the future direction of an AI-powered platform in a massive market.

• Leadership Development: Experience leading a growing team, honing management and mentorship skills in a high-growth startup environment.

• Industry Expertise: Deepen knowledge in Construction Technology and the application of AI in enterprise workflows.

• Advancement: Potential to move into a VP of Design or broader product leadership role as the company continues to scale.

📝 Enhancement Note: This role offers significant growth potential, not just in terms of managing a larger team but also in influencing the strategic direction of a rapidly scaling AI company. The ability to build a function from the ground up is a key differentiator for career advancement.

🌐 Work Environment

Office Type: Hybrid work model with a physical office presence in New York City. This suggests a blend of remote flexibility and in-person collaboration.

Office Location(s): New York City, New York, USA.

Workspace Context:

• The hybrid model necessitates a workspace that supports both remote productivity and in-office collaboration.

• The office environment likely fosters interaction between design, product, and engineering teams, crucial for agile development and design-led innovation.

• Access to provided meals in the office can enhance team cohesion and facilitate spontaneous working sessions.

• The company provides stipends for home office setups, ensuring employees have the necessary tools and comfort for remote work.

Work Schedule: While a standard 40-hour workweek is implied, the startup environment often requires flexibility. The focus will be on delivering results and driving impact, with the hybrid model offering some control over work location.

📝 Enhancement Note: The hybrid model in NYC indicates a need for strong remote collaboration tools and processes, alongside the benefits of in-person interaction for strategic discussions and team building. This environment is suitable for experienced professionals who can manage their time effectively across locations.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Review of resume and portfolio to assess experience, leadership capabilities, and design craft.

• Hiring Manager/Team Interview: Deeper dive into design philosophy, team management experience, and AI integration strategies.

• Portfolio Presentation: A comprehensive presentation of key design projects, focusing on problem-solving, process, impact, and leadership. This is where the "player-coach" aspect and design system governance will be scrutinized.

• Cross-functional Interviews: Meetings with Product, Engineering, and potentially GTM/Operations leaders to assess collaboration skills and strategic alignment.

• Executive/Founder Interview: Final discussion on vision, culture fit, and strategic contribution to PermitFlow's growth.

Portfolio Review Tips:

• Showcase Leadership & Scale: Highlight instances where you've built or significantly scaled a design team and function. Detail the challenges and your solutions.

• Demonstrate Process & Systems: Clearly articulate your approach to design systems, critique, quality gates, and cross-functional collaboration. Use case studies to illustrate these processes in action.

• Quantify Impact: Wherever possible, use metrics to demonstrate the business impact of your design decisions and leadership, especially concerning activation, retention, and customer satisfaction.

• Highlight AI Integration: Showcase how you've actively incorporated AI tools into your design workflow, explaining the benefits and any novel approaches.

• B2B SaaS & Workflow Focus: Emphasize your experience with complex B2B SaaS products, data-dense interfaces, and user workflows, as this is core to PermitFlow's product.

Challenge Preparation:

• Be prepared to discuss hypothetical scenarios related to scaling a design team, managing design debt, prioritizing feature design, and integrating AI into the product development lifecycle.

• Practice articulating your design philosophy and leadership approach clearly and concisely.

• Be ready to defend your design decisions and processes with clear reasoning and data.

📝 Enhancement Note: The interview process will be rigorous, focusing on both individual design excellence and the ability to lead and scale a function. A strong portfolio that demonstrates strategic thinking, process maturity, and quantifiable impact is essential. The emphasis on AI and B2B SaaS workflows implies candidates should tailor their examples accordingly.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (highly probable for modern design teams), Sketch, Adobe Creative Suite.

• Design Systems: Tools for managing component libraries, documentation, and governance (e.g., Zeroheight, Storybook, or custom solutions).

• AI Design Tools: Candidates are expected to be proficient with AI tools integrated into their daily workflow (e.g., AI-powered image generation, AI-assisted content creation, AI for design exploration, prompt engineering for design).

• Collaboration & Project Management: Jira, Asana, Trello, Slack.

Analytics & Reporting:

• Product Analytics platforms (e.g., Mixpanel, Amplitude) for understanding user behavior and product engagement.

• Tools for A/B testing and experimentation.

• Dashboarding tools (e.g., Tableau, Looker) for visualizing design impact and business metrics.

CRM & Automation: While not directly managed by Design, understanding how CRM (e.g., Salesforce) and automation platforms impact user experience and data flow within a B2B context is beneficial.

📝 Enhancement Note: Proficiency with modern design tools like Figma is expected. The explicit mention of AI integration suggests the company is forward-thinking and likely uses AI for various aspects of design and product development. Understanding how design impacts the B2B customer journey, including sales and operations touchpoints, is also valuable.

👥 Team Culture & Values

Operations Values:

• Innovation: Embracing new technologies like AI to solve complex problems in the construction industry.

• Impact-Driven: Focusing on delivering measurable business value and tangible results for customers and the company.

• Collaboration: Fostering strong partnerships across Product, Engineering, GTM, and Operations to achieve shared goals.

• Excellence: Maintaining high standards in design craft, product quality, and strategic thinking.

• Scalability: Building systems, processes, and teams that can grow efficiently with the company.

Collaboration Style:

• Highly collaborative, with designers embedded within product pods or working closely with cross-functional teams.

• Emphasis on open communication, constructive critique, and shared ownership of product outcomes.

• Agile methodologies likely influence the pace and iterative nature of collaboration.

📝 Enhancement Note: PermitFlow's culture appears to be one of innovation, rapid growth, and a strong focus on solving real-world problems with technology. The design leader will be expected to embody these values and foster them within their team.

⚡ Challenges & Growth Opportunities

Challenges:

• Scaling Design: Building a robust design function and design system from an early stage to support rapid company growth.

• AI Integration: Defining and implementing effective AI-powered design workflows in a fast-evolving landscape.

• Industry Complexity: Designing for a complex, data-intensive industry (construction) with domain-expert users.

• Balancing Strategy & Execution: Effectively managing both strategic vision and hands-on design work in a demanding startup environment.

• Cross-functional Alignment: Ensuring design is a strategic partner and not just an execution arm for Product and Engineering.

Learning & Development Opportunities:

• Leadership Growth: Developing skills in team building, mentorship, and strategic leadership within a high-growth tech company.

• AI in Design: Becoming an expert in leveraging AI to transform design processes and product development.

• ConTech & AI Domain: Gaining deep expertise in the construction technology sector and the impact of AI on enterprise workflows.

• Strategic Impact: Directly contributing to the growth and success of a well-funded, innovative startup.

📝 Enhancement Note: The challenges presented are typical for a senior leadership role in a scaling startup, offering significant opportunities for professional development and impact.

💡 Interview Preparation

Strategy Questions:

• "How would you approach building a design team from the ground up at a Series B company like PermitFlow?"

• "Describe your philosophy on design systems and how you'd govern one in a fast-paced environment."

• "How do you see AI transforming the future of product design, and how would you integrate these tools into our workflow?"

• "Walk me through a time you had to balance hands-on design execution with team management responsibilities."

• "How would you ensure design quality and consistency across a rapidly growing product and team?" Company & Culture Questions:

• "What excites you about PermitFlow's mission and the construction technology industry?"

• "How do you foster a collaborative design culture that partners effectively with Product, Engineering, and GTM/Operations?"

• "Describe your experience working with domain-expert users and complex workflows."

• "What are your expectations for how design can impact business metrics like activation and retention?" Portfolio Presentation Strategy:

• Structure your presentation around key themes: Leadership & Team Building, Design Systems & Process, Complex B2B SaaS Solutions, and AI Integration.

• For each project, clearly articulate the problem, your role, the design process, the solution, and the quantifiable impact.

• Be prepared to discuss the trade-offs you made and why.

• Highlight how your work directly addresses the needs of B2B users and complex workflows.

• Showcase your AI fluency by discussing how AI tools were integrated or how the product itself leverages AI.

📝 Enhancement Note: Candidates should prepare to speak extensively about their leadership philosophy, their experience scaling design functions, and their vision for AI in design. The portfolio presentation is a critical opportunity to demonstrate these capabilities.

📌 Application Steps

To apply for this Head of Design position:

• Submit your application through the provided Ashby link.

• Curate Your Portfolio: Ensure your portfolio prominently features B2B SaaS product design, design systems, team leadership, and AI integration. Tailor examples to showcase experience with complex workflows and data-dense interfaces.

• Optimize Your Resume: Highlight leadership experience, team-building achievements, and quantifiable business impact. Use keywords related to AI, B2B SaaS, design systems, and design leadership.

• Prepare Your Presentation: Rehearse your portfolio presentation to clearly articulate your strategic vision, process, and leadership approach, focusing on how you can build and scale PermitFlow's design function.

• Research PermitFlow: Understand their mission, product, target market, and recent funding rounds. Consider how design can uniquely support their growth and their customers' operational needs.

⚠️ 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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