Head of Design

📍 Job Overview

Job Title: Head of Design

Company: Rain Technologies Inc.

Location: United States

Job Type: FULL_TIME

Category: Design Leadership / Product Design

Date Posted: 2026-05-04

Experience Level: 10+ Years

Remote Status: Fully Remote

🚀 Role Summary

• Lead and expand the product design team, overseeing the design of Rain's core mobile application, employer web portal, and internal administrative tools.

• Drive the expansion and maintenance of the company's global design system and visual language to ensure consistency and scalability across all platforms.

• Spearhead end-to-end design for new, impactful initiatives, including AI-powered financial assistants, card products, lending solutions, and personal finance management (PFM) tools.

• Direct the creation of marketing collateral, contribute to brand evolution, and manage motion design efforts, potentially leveraging freelance resources.

• Foster strong collaboration with Product Management and Go-To-Market (GTM) teams to translate loosely defined requirements into intuitive, user-centered features and products.

📝 Enhancement Note: While the title is "Head of Design," given the emphasis on product, engineering, and marketing collaboration, and the mention of leading a design team, this role is positioned as a senior design leadership position with significant product strategy influence, rather than purely a brand or marketing design head. The "Project Scope" section further solidifies this by detailing product features and system expansion.

📈 Primary Responsibilities

• Product Design Leadership: Oversee the entire design lifecycle for Rain's mobile app, employer portal, and internal tools, ensuring high-quality, user-centric design solutions.

• Design System Management: Develop, maintain, and evolve the global design system, ensuring its adoption and scalability to support rapid product development and growth.

• New Initiative Design: Lead the design strategy and execution for innovative features such as AI financial assistants, card products, lending solutions, and PFM tools, from concept to launch.

• Brand & Marketing Collaboration: Work closely with the Marketing team to develop compelling collateral, contribute to brand evolution, and manage motion design projects to enhance Rain's market presence.

• Cross-Functional Partnership: Collaborate effectively with Product Managers and Engineering teams to translate business requirements into intuitive user experiences and actionable design specifications.

• Team Development: Build and scale the design team by hiring and mentoring at least one additional designer by the end of the year, fostering a culture of innovation and excellence.

• UX Problem Solving: Proactively identify and solve complex UX challenges, leveraging design thinking principles to define requirements and deliver optimal design outcomes.

📝 Enhancement Note: The responsibilities detail a blend of strategic leadership (team building, design system ownership, new initiatives) and hands-on execution (overseeing app/portal design, marketing collateral), indicating a senior role expected to both guide and contribute directly. The mention of "GTM teams" suggests a close alignment with go-to-market strategies, impacting product positioning and messaging.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a Bachelor's or Master's degree in Graphic Design, Interaction Design, Human-Computer Interaction, or a related field is typically expected for leadership roles in design. Equivalent practical experience will also be strongly considered.

Experience: A minimum of 10+ years of progressive experience in product design, with a significant portion focused on mobile applications within the fintech sector. Proven experience in a leadership or management role, demonstrating the ability to build and guide design teams.

Required Skills:

• Product Design Expertise: Proven track record of designing and shipping complex mobile applications, particularly within the fintech industry.

• Leadership & Management: Demonstrated ability to lead, mentor, and grow a design team, fostering a collaborative and high-performing environment.

• Design Thinking: A strong grasp of design thinking methodologies to proactively define problems and develop innovative solutions.

• Figma Proficiency: Expert-level command of Figma for UI/UX design, prototyping, and collaboration.

• Claude Design Proficiency: Expert-level command of Claude Design (or similar advanced design/collaboration tools) for complex design workflows and team interaction.

• Design System Development: Experience in creating, expanding, and maintaining robust design systems and visual languages.

• UX Problem Solving: Aptitude for identifying and resolving complex user experience challenges with creative and effective solutions.

Preferred Skills:

• Motion Design Direction: Experience directing motion design projects, either directly or through managing freelance resources.

• AI/ML Product Design: Familiarity with designing user experiences for AI-powered features, such as financial assistants.

• Fintech Product Innovation: Experience designing for card products, lending solutions, or personal finance management (PFM) tools.

• Brand Strategy: Understanding of brand evolution and its impact on product design and marketing collateral.

• Agile/Scrum Methodologies: Experience working within agile development environments, collaborating closely with engineering teams.

📝 Enhancement Note: The requirement for "expert in Figma and Claude Design" is highly specific and indicates a need for deep technical proficiency in these tools. The "hands-on leader" description implies that candidates should be comfortable with individual design contributions, not just management. The fintech and mobile application experience is crucial due to the nature of Rain's product.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• End-to-End Product Case Studies: Showcase 2-3 comprehensive case studies detailing your involvement in the entire design process for complex mobile applications, ideally in fintech. Emphasize problem definition, user research, ideation, design iterations, prototyping, and final shipped product outcomes.

• Design System Examples: Include examples of a design system you have contributed to or led, highlighting its structure, components, guidelines, and how it supported product consistency and scalability.

• Fintech Product Innovation: Highlight specific projects involving innovative fintech features such as AI assistants, card products, lending, or PFM tools, demonstrating your understanding of user needs and industry best practices.

• Leadership & Teamwork: Provide examples that demonstrate your leadership capabilities, ability to collaborate with cross-functional teams (Product, Engineering, Marketing), and how you've mentored or guided other designers.

Process Documentation:

• Workflow Design & Optimization: Demonstrate how you approach designing and optimizing user workflows for complex applications, ensuring efficiency and intuitive navigation.

• User Research & Testing: Showcase your methods for conducting user research, usability testing, and incorporating feedback into the design process to validate solutions.

• Cross-Functional Collaboration: Illustrate your process for collaborating with Product Managers and Engineers, including how you translate requirements into design specifications and manage design handoffs.

• Metrics & Impact: Where possible, quantify the impact of your design decisions using relevant metrics (e.g., conversion rates, user engagement, task completion times, reduction in support tickets) linked to your projects.

📝 Enhancement Note: Given the "hands-on leader" expectation and the "high design volume" and "many new features to own," the portfolio should clearly demonstrate both strategic thinking and tactical execution capabilities. The emphasis on fintech and complex mobile apps means case studies in these areas will be paramount.

💵 Compensation & Benefits

Salary Range: $180,000 - $230,000 USD per year.

Benefits:

• Flexible Paid Time Off (PTO): Encourages a healthy work-life balance with adaptable time-off policies.

• Comprehensive Health Coverage: Medical, Dental, and Vision insurance plans to support employee well-being.

• Life & Disability Insurance: Provides financial security for employees and their families.

• Parental Leave: Offers support for new parents during a significant life event.

• Monthly Stipend: A flexible allowance for expenses, potentially covering home office setup, wellness, or other needs.

• Equity Options: Opportunity to share in the company's success through stock options.

• Bonus: Performance-based bonus structure, aligning individual and company achievements.

Working Hours: While specific hours are not detailed, a standard full-time role typically involves approximately 40 hours per week. Given the remote nature and the emphasis on results, there may be flexibility in scheduling, provided core responsibilities and collaboration needs are met.

📝 Enhancement Note: The stated salary range of $180,000-$230,000 USD for a Head of Design with 10+ years of experience in a fully remote US-based role is competitive and aligns with industry benchmarks for senior leadership positions in established, well-funded tech companies. The inclusion of equity and bonus further enhances the total compensation package.

🎯 Team & Company Context

🏢 Company Culture

Industry: Fintech / AI Financial Health Platform. Rain operates at the intersection of financial technology and artificial intelligence, aiming to improve the financial well-being of millions of employees. This industry demands innovation, data security, and a strong user-centric approach.

Company Size: The description implies significant growth, serving 3.5 million employees and having raised $150M in venture funding. While exact employee count isn't stated, it suggests a scaling startup or growth-stage company, likely in the 100-500 employee range, with a dynamic and fast-paced environment.

Founded: Founded with a mission to revolutionize financial health for employees, Rain is established enough to have secured substantial funding and a large user base, indicating a mature product and business model.

Team Structure:

• Design Team: The Head of Design will lead the existing product design team and is responsible for hiring at least one additional designer. This suggests a growing, potentially lean, but impactful design function.

• Cross-Functional Collaboration: The role requires close collaboration with Product, Engineering, and Marketing/GTM teams, indicating a matrixed or integrated team structure where design is a key partner in product development and market strategy.

• Reporting: While not explicitly stated, a Head of Design typically reports to a VP of Product, Chief Product Officer (CPO), or potentially a CTO, depending on the organizational structure.

Methodology:

• Data-Driven Decisions: Rain likely emphasizes data analysis to understand user behavior, optimize financial tools, and measure the impact of its platform. Design decisions are expected to be informed by user data and performance metrics.

• Agile Development: Given the rapid growth and focus on shipping new features, an agile or iterative development methodology is probable, requiring close partnership between design and engineering.

• User-Centricity: The core mission of improving financial health underscores a commitment to understanding and addressing user needs through thoughtful design.

Company Website: https://rainapp.com/

📝 Enhancement Note: The company's focus on AI and financial health, coupled with significant funding and a large user base, suggests a data-rich environment where design plays a critical role in translating complex financial concepts into accessible and actionable user experiences. The "hyper growth" phase implies a need for adaptable, scalable design solutions.

📈 Career & Growth Analysis

Operations Career Level: This role is at a senior leadership level, specifically "Head of Design." It signifies a strategic position responsible for defining and executing the design vision, managing a team, and influencing product direction. This level demands not only exceptional design skills but also strong leadership, strategic thinking, and business acumen.

Reporting Structure: The Head of Design will likely report to a senior executive, such as a VP of Product, Chief Product Officer (CPO), or potentially a CTO. This position has direct reports within the design team and works closely with other department heads.

Operations Impact: The Head of Design has a profound impact on Rain's success by shaping the user experience across all touchpoints, directly influencing user adoption, engagement, retention, and ultimately, the company's ability to achieve its mission and financial goals. Their work is critical to translating the company's AI and financial health mission into tangible, user-friendly products that drive business outcomes.

Growth Opportunities:

• Team Expansion & Leadership: Opportunity to build and scale a high-performing design team, defining its structure, processes, and culture.

• Product Strategy Influence: Play a key role in shaping the product roadmap and design strategy for innovative financial products and AI features.

• Design System Ownership: Drive the evolution of a comprehensive design system that underpins the entire product suite, impacting thousands of users.

• Industry Impact: Contribute to a mission-driven company that is making a significant positive impact on the financial health of millions of employees.

• Potential for advancement: As the company grows, opportunities may arise for broader design leadership roles (e.g., VP of Design) or specialization in areas like AI product strategy.

📝 Enhancement Note: The role offers significant strategic impact and the chance to build a design function from a growing stage. The emphasis on "owning the product experience end-to-end" and "shaping the product experience" highlights the high level of autonomy and influence this leadership position provides.

🌐 Work Environment

Office Type: Fully Remote. This indicates that the company embraces distributed workforces, offering flexibility in location for employees within the United States.

Office Location(s): While fully remote, the company is based in the United States. Timezone alignment (e.g., "America/Chicago" derived) might be beneficial for collaboration, but the remote nature suggests a focus on asynchronous communication and flexible scheduling.

Workspace Context:

• Collaborative Environment: Despite being remote, the emphasis on collaboration with Product, Engineering, and Marketing teams suggests a strong culture of virtual teamwork, utilizing collaborative tools for design reviews, brainstorming, and project management.

• Tools & Technology: Employees will have access to industry-standard design and collaboration tools, including Figma and Claude Design, and likely other project management and communication platforms.

• Operations Team Interaction: Regular virtual meetings, Slack channels, and project management tools will facilitate interaction and knowledge sharing among the design team and with other departments.

Work Schedule: A standard full-time schedule (approximately 40 hours per week) is expected. However, the fully remote nature often allows for greater flexibility in managing work hours, with a focus on meeting deadlines and collaboration requirements rather than strict adherence to a 9-to-5 schedule. This flexibility is beneficial for design work that often requires deep focus and can be performed at optimal times.

📝 Enhancement Note: The fully remote aspect is a key feature, requiring strong self-discipline and excellent communication skills. The company culture, as described, emphasizes owning work and adapting quickly, which aligns well with a remote setup that relies on proactive communication and task management.

📄 Application & Portfolio Review Process

Interview Process: The company notes a typical interview process duration of about 4 weeks. This usually involves several stages designed to assess skills, experience, and cultural fit.

• Initial Screening: A recruiter or hiring manager will review applications and conduct an initial screening call to assess basic qualifications and interest.

• Portfolio Review & Design Challenge: Candidates will likely present their portfolio, showcasing relevant case studies. A design challenge or exercise may be assigned to evaluate problem-solving skills, design thinking, and proficiency with tools like Figma.

• Cross-Functional Interviews: Interviews with Product Managers, Engineers, and potentially Marketing leads to assess collaboration style, communication, and ability to integrate design into the broader product development lifecycle.

• Leadership Interview: A final interview with a senior executive (e.g., CPO, CEO) to evaluate strategic vision, leadership potential, and overall cultural alignment.

Portfolio Review Tips:

• Focus on Impact: Clearly articulate the "why" behind your design decisions and quantify the impact of your work using relevant metrics (e.g., user satisfaction, engagement, conversion rates, efficiency gains).

• Showcase Process: Detail your design process for each case study, from problem definition and research to iteration and final implementation. Highlight how you used design thinking to solve complex problems.

• Highlight Leadership: For this role, emphasize examples of your leadership, team management, and cross-functional collaboration. Showcase how you've mentored designers and influenced product strategy.

• Fintech & Mobile Expertise: Prioritize case studies that demonstrate your experience with complex mobile applications and, ideally, the fintech domain.

• Design System Contribution: If applicable, clearly present your contributions to design systems and how they benefited product development.

Challenge Preparation:

• Understand Rain's Product: Research Rain's AI Financial Health Platform, its target audience, and its key features. Understand the competitive landscape.

• Design Thinking Practice: Be ready to articulate your design process and how you approach ambiguous problems.

• Tool Proficiency: Ensure you are comfortable demonstrating your skills in Figma and any other tools mentioned.

• Communication: Practice articulating your design decisions clearly and concisely, explaining the rationale and trade-offs.

📝 Enhancement Note: The 4-week interview process suggests a structured but potentially thorough evaluation. A strong portfolio that directly addresses the requirements (fintech, mobile, leadership, design systems) will be critical. The "hands-on leader" aspect means candidates should be prepared to discuss specific design contributions and problem-solving approaches.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Essential for UI/UX design, prototyping, and collaborative workflows. Expect to use it extensively for creating wireframes, mockups, and interactive prototypes.

• Claude Design: Mentioned as a key tool, likely referring to a comprehensive design platform or suite that may include advanced collaboration, design system management, or prototyping capabilities beyond standard Figma. Deep proficiency is required.

• Motion Design Tools: Proficiency or experience directing work in tools such as Adobe After Effects, Principle, or similar, for creating animations and micro-interactions.

Analytics & Reporting:

• Product Analytics Platforms: Likely candidates include Amplitude, Mixpanel, or similar, for tracking user behavior, feature adoption, and conversion funnels.

• Data Visualization Tools: Experience with tools like Tableau, Looker, or even advanced Excel/Google Sheets for presenting data insights to stakeholders.

CRM & Automation:

• CRM Systems: While not directly a design tool, understanding how design impacts CRM data and user journeys (e.g., in the employer portal) is beneficial. Salesforce or similar platforms might be relevant in a broader GTM context.

• Project Management & Collaboration: Tools such as Jira, Asana, Trello, or Slack will be crucial for managing tasks, tracking progress, and facilitating communication within remote teams.

📝 Enhancement Note: The explicit mention of "Figma and Claude Design" as expert-level requirements is a significant indicator of the expected technical toolkit. Candidates should be prepared to discuss their proficiency and how they leverage these tools for complex design challenges and team collaboration.

👥 Team Culture & Values

Operations Values:

• Mission-Driven: A deep passion for Rain's mission to improve financial health, motivating a commitment to creating impactful and accessible financial tools.

• Diversity & Inclusion: Embraces diversity across its global team, fostering an inclusive environment where all voices are valued.

• Ownership & Accountability: Individuals take ownership of their work, driving initiatives forward and being accountable for outcomes.

• Data-Guided Actions: Decisions are informed by data analysis, ensuring that design and product strategies are effective and user-centric.

• Speed & Adaptability: Operates with agility, working quickly and adapting to new challenges and market changes in the fast-paced fintech industry.

• Personal & Professional Growth: Fosters an environment where employees can grow personally and professionally, encouraging continuous learning and development.

Collaboration Style:

• Cross-Functional Integration: Design is integrated into product development and GTM strategies, requiring seamless collaboration with Product, Engineering, and Marketing.

• Open Communication: Given the remote setup, an emphasis on clear, proactive, and open communication is essential for effective teamwork.

• Feedback Culture: Encourages a culture where constructive feedback is shared and received to continuously improve designs and processes.

• Shared Ownership: While design leads its domain, there's a sense of shared ownership for product success across all functions.

📝 Enhancement Note: The company culture emphasizes a blend of purpose-driven work, individual accountability, and adaptive teamwork, which is typical for successful growth-stage tech companies. The "own what we do and let data guide our actions while working quickly and adapting to new challenges everyday" quote encapsulates this ethos.

⚡ Challenges & Growth Opportunities

Challenges:

• High Design Volume & Pace: The sheer volume of new features and initiatives (AI assistants, card products, lending) presents a challenge in managing design bandwidth and maintaining quality across all projects.

• Scaling Design Systems: Evolving and maintaining a global design system to support rapid product expansion while ensuring consistency and accessibility for millions of users.

• Leading a Growing Team: Building and scaling a design team effectively, including hiring, onboarding, and fostering a strong team culture in a remote environment.

• Balancing Innovation with User Needs: Driving innovation in fintech while ensuring that complex financial products are intuitive, trustworthy, and accessible to a broad user base.

• Remote Collaboration: Effectively leading and collaborating with a distributed team, ensuring clear communication and alignment across different time zones and locations.

Learning & Development Opportunities:

• Strategic Design Leadership: Opportunity to shape the design strategy for a rapidly growing fintech company and influence product direction at a high level.

• Team Building & Mentorship: Develop leadership skills by building, mentoring, and growing a design team.

• Fintech & AI Innovation: Gain deep experience in designing cutting-edge AI-powered financial products and innovative solutions in the fintech space.

• Design System Mastery: Deepen expertise in managing and scaling complex design systems for a large user base.

• Industry Exposure: Contribute to a company making a significant impact on financial wellness, gaining insights into the broader fintech landscape.

📝 Enhancement Note: The challenges are directly tied to the company's growth phase and the nature of its product. Successfully navigating these will provide significant opportunities for professional development and career advancement.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you led a design team through a period of rapid product expansion. What were the biggest challenges, and how did you overcome them?" (Focus on leadership, team management, and process adaptation.)

• "How would you approach designing an AI-powered financial assistant for users who may be skeptical of AI or new to financial management tools?" (Assess design thinking, user empathy, and approach to complex/sensitive product areas.)

Company & Culture Questions:

• "What excites you most about Rain's mission and our approach to AI Financial Health?" (Gauge alignment with company mission and understanding of the product.)

• "How do you foster a collaborative and innovative culture within a remote design team?" (Assess leadership style and remote team management strategies.)

Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly define the problem, your role, the process you followed, your key contributions, the decisions you made (and why), and the measurable outcomes.

• Highlight Leadership: Explicitly point out instances where you led, mentored, or influenced cross-functional teams. Quantify successes where possible.

• Showcase Figma/Claude Proficiency: Be ready to discuss your workflow and advanced techniques within Figma and Claude Design. If possible, show interactive prototypes.

• Address Fintech Nuances: Explain how your design decisions considered the specific challenges and opportunities within the fintech sector (e.g., security, trust, complexity, regulation).

• Be Prepared for Questions: Anticipate questions about trade-offs, challenges encountered, and alternative solutions you considered.

📝 Enhancement Note: The interview process is likely to be rigorous, focusing on both strategic leadership and hands-on design execution. Candidates should be prepared to articulate their process, demonstrate problem-solving skills, and clearly show how their experience aligns with Rain's specific needs in fintech and AI product design.

📌 Application Steps

To apply for this Head of Design position:

• Submit your application through the provided link on jobs.ashbyhq.com.

• Tailor Your Resume: Highlight your 10+ years of experience, focusing on leadership roles, fintech, mobile application design, and successful product launches. Quantify achievements where possible.

• Curate Your Portfolio: Select 2-3 of your strongest case studies that best demonstrate expertise in complex mobile apps, fintech, design systems, and leadership. Ensure they clearly articulate your process and impact. Be ready to discuss your specific contributions and decision-making.

• Prepare Your Presentation: Practice presenting your portfolio, focusing on storytelling, clear articulation of your design process, and highlighting leadership contributions. Be ready to discuss your proficiency with Figma and Claude Design.

• Research Rain Technologies: Understand their mission, product, target audience, and recent funding rounds. Prepare thoughtful questions about their design challenges, team structure, and future vision.

⚠️ 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.