Lead Product Designer

📍 Job Overview

Job Title: Lead Product Designer

Company: Keep Company

Location: Bethesda, Maryland, United States

Job Type: FULL_TIME

Category: Product Design / UX/UI

Date Posted: March 12, 2026

Experience Level: 2-5 years

🚀 Role Summary

• Lead end-to-end product design initiatives for a mission-driven SaaS platform focused on human connection in the workplace.

• Drive the design of core user experiences across a multi-tenant platform, encompassing client program management, impact reporting, and AI-driven interactions.

• Champion human-centered design principles in an AI-saturated landscape, ensuring the product enhances human judgment rather than replacing it.

• Develop and maintain a scalable design system to ensure product coherence and consistency as the company grows.

• Collaborate closely with Product, Engineering, Client Success, and Founders, translating user insights and business needs into actionable product design decisions.

📝 Enhancement Note: This role is positioned as the "first dedicated Product Designer," indicating a high degree of autonomy and foundational impact. The emphasis on "human connection," "AI-powered features," and "cognitive prosthetic" suggests a unique intersection of UX, applied cognitive science, and responsible AI design within the B2B SaaS space.

📈 Primary Responsibilities

• Lead the full product design lifecycle for high-impact projects, from initial discovery and user research through interaction design, prototyping, and final delivery to engineering.

• Design intuitive and efficient core admin workflows for HR and L&D leaders to confidently configure, launch, and manage mentoring, coaching, and group programs with minimal friction.

• Create sophisticated data and reporting experiences that empower non-technical decision-makers to quickly understand program effectiveness, identify intervention points, and demonstrate ROI to stakeholders.

• Shape the user experience for human interaction with AI features, ensuring transparency, trustworthiness, and ease of comprehension in AI-driven suggestions, recommendations, and summaries.

• Advocate for and implement human-centered design principles, pushing back against purely efficiency-driven defaults and leveraging expertise in applied cognitive science and HCI to ensure the product augments human judgment.

• Build, evolve, and evangelize a scalable design system and shared interaction patterns to maintain product coherence and accelerate design velocity as the company scales.

• Foster close, collaborative relationships with Product Managers, Engineers, Client Success teams, and company Founders, acting as a key partner in turning user insights and business requirements into thoughtful, impactful product decisions.

• Cultivate a research-driven approach within the design process, conducting lightweight studies, synthesizing user feedback, and utilizing evidence to inform and validate product direction.

📝 Enhancement Note: The responsibilities highlight a strategic design leadership role, emphasizing the need for a designer who can not only execute but also influence product strategy and champion user-centricity. The specific mention of "AI-powered features" and "cognitive prosthetic" indicates a need for expertise in designing for complex human-AI collaboration.

🎓 Skills & Qualifications

Education:

• BS or MS in Human-Computer Interaction (HCI), Cognitive Science, Behavioral Design, or a closely related field.

Experience:

• 3–5+ years of hands-on, applied product design experience.

Required Skills:

• Proven ability to lead end-to-end product design for complex systems, with a portfolio showcasing work on data-heavy or AI-adjacent B2B products, rather than consumer-facing UX.

• Strong data visualization and information architecture skills, with a track record of designing dashboards and reporting interfaces that are easily understood and utilized by non-technical users.

• Demonstrated systems thinking capabilities, with experience in designing interaction models and shared patterns for broad reuse across a platform.

• High proficiency in Figma, including advanced use of component libraries, auto-layout, and design tokens.

• Experience collaborating effectively with engineers and product managers in a cross-functional setting, understanding the impact of design decisions on engineering complexity.

Preferred Skills:

• Applied experience with HCI/AI principles, such as designing for human oversight of automated systems, appropriate reliance on AI, explainable AI (XAI) UX, or human-in-the-loop (HITL) design.

• Familiarity with established AI UX heuristics and guidelines (e.g., Google PAIR, Microsoft HAX, Stanford HAI).

• Experience designing recommendation surfaces or agentic interfaces where users must critically evaluate and act upon AI-generated output.

• Experience with multi-tenant SaaS architecture, including designing for Role-Based Access Control (RBAC) patterns and tenant-level configuration UX.

• Background or familiarity with HR tech, Learning & Development (L&D) platforms, or enterprise workflow tools.

📝 Enhancement Note: The required experience level (3-5 years) combined with the "Lead" title suggests this individual will be the primary design voice, setting standards and processes. The emphasis on B2B SaaS and data-heavy/AI-adjacent systems is crucial for portfolio selection.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase end-to-end design processes for complex B2B SaaS or enterprise software projects, demonstrating problem definition, user research, ideation, prototyping, and final design solutions.

• Include case studies that highlight your approach to designing data-heavy interfaces, reporting dashboards, or AI-integrated features, emphasizing how you translated complex data into actionable insights for non-technical users.

• Demonstrate your ability to design for scalability and consistency through examples of design system contributions, reusable components, or established interaction patterns.

• Present work that reflects systems thinking, illustrating how you considered the broader product ecosystem and designed for reuse and maintainability.

Process Documentation:

• For each case study, clearly outline the design process followed, including methodologies used for user research, ideation, and validation.

• Detail how user insights and business requirements were synthesized to inform design decisions, with specific examples of trade-offs made.

• Illustrate the iterative nature of your design process, including how feedback (from users, stakeholders, or engineering) was incorporated to refine solutions.

• Document the rationale behind key design decisions, particularly those related to data visualization, information architecture, and human-AI interaction.

📝 Enhancement Note: The portfolio is critical for this role, especially given it's the "first dedicated Product Designer." It needs to prove not just visual design skills but also strategic thinking, research rigor, and experience with complex B2B SaaS challenges, particularly those involving data and AI.

💵 Compensation & Benefits

Salary Range:

• The base salary range for this position is $125,000 - $165,000 per year.

• This range is determined by factors such as the candidate's experience, skills, and alignment with the role's scope.

Benefits:

• Competitive salary and meaningful equity package.

• Comprehensive health benefits.

• 401k retirement savings plan.

• Flexible Paid Time Off (PTO).

Working Hours:

• Standard full-time position, typically around 40 hours per week.

• The remote-first nature offers flexibility, but core collaboration hours will be expected.

📝 Enhancement Note: The salary range provided is specific and competitive for a Lead Product Designer role in the US market, especially considering the equity component. Benefits are standard for a growing tech company.

🎯 Team & Company Context

🏢 Company Culture

Industry: Software / SaaS (specifically focused on HR Tech, Employee Experience, and Human Capital Management)

Company Size: Startup/Growth Stage (Venture-backed, recognized by Techstars, Forbes, SHRM)

Founded: [Founding date not provided, but described as venture-backed and growing]

Team Structure:

• As the first dedicated Product Designer, you will likely work very closely with the Product and Engineering teams, reporting to a Head of Product or potentially a Founder.

• The design function will be nascent, offering an opportunity to shape its processes and culture.

Methodology:

• The company emphasizes a mission-driven approach, focusing on making "human connection an intentional, scalable asset."

• Their product combines technology with coaching and mentoring to deliver "transformative employee experiences."

• There's a clear awareness of the evolving work landscape, with a focus on strengthening "culture, retention, and performance" in the age of AI.

• The design approach is expected to be research-grounded and human-centered, even as AI capabilities are integrated.

Company Website: https://www.keep-company.com/

📝 Enhancement Note: Keep Company appears to be a mission-oriented startup in the HR Tech space, aiming to leverage technology to enhance human connection at work. The culture likely values innovation, collaboration, and a user-centric approach, with a strong emphasis on the "human layer" of work.

📈 Career & Growth Analysis

Operations Career Level: Lead Product Designer

• This role represents a significant step up from a mid-level Product Designer, offering ownership of core product areas and the opportunity to establish design practices.

Reporting Structure:

• Likely reports directly to a senior leader such as the Head of Product, VP of Product, or one of the Founders.

Operations Impact:

• The designer will directly influence the core user experience of the SaaS platform, impacting how clients manage programs, understand data, and interact with AI.

• This role has the potential to significantly improve employee experiences, strengthen company culture, enhance retention, and boost performance for Keep Company's clients.

Growth Opportunities:

• Design Leadership: A clear path to design leadership is explicitly mentioned, with the opportunity to grow the design team as the company scales. This could involve hiring, mentoring, and defining the design team's vision.

• Strategic Influence: High-level collaboration with founders and senior leaders provides opportunities to influence product strategy and company direction.

• Skill Specialization: Deepen expertise in designing for complex B2B SaaS, human-AI interaction, data visualization, and applied cognitive science within a real-world product context.

• Foundational Impact: Opportunity to build and own critical design systems and foundational design processes for a growing company.

📝 Enhancement Note: This is a high-impact, growth-oriented role for a designer looking to make a significant mark. The "Lead" title, combined with the "first dedicated designer" status, points towards a clear trajectory into design leadership and strategic product influence.

🌐 Work Environment

Office Type: Remote-first

Office Location(s): Bethesda, Maryland, United States (primary location, but role is remote)

Workspace Context:

• Remote-First: The company operates on a remote-first model, offering flexibility and autonomy.

• Collaborative Environment: While remote, the company emphasizes collaboration. Periodic in-person team sessions are planned to foster connection and strategic alignment.

• Tools & Technology: Expect access to standard design tools (Figma mentioned) and a tech stack typical of a modern SaaS company. The emphasis on human-centered design and AI interaction will shape the specific tools and workflows used.

• Team Interaction: Regular interaction with Product, Engineering, and Founders is expected, fostering a dynamic and communicative work environment.

Work Schedule:

• Standard full-time work schedule, with flexibility inherent in a remote-first setup.

• Core collaboration hours will be necessary for effective cross-functional teamwork.

📝 Enhancement Note: The remote-first nature with periodic in-person gatherings is a common model for growing tech companies. This setup requires strong self-discipline and proactive communication skills from the designer.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Review of resume and portfolio against the outlined requirements.

• Portfolio Presentation & Discussion: Likely a session where the candidate walks through 1-2 key case studies from their portfolio, focusing on their process, decision-making, and impact. Expect questions about their experience with B2B SaaS, data visualization, and complex systems.

• Cross-Functional Interviews: Conversations with Product Managers, Engineers, and potentially Founders to assess collaboration style, technical understanding, and cultural fit. Questions may focus on how you approach problem-solving, handle trade-offs, and integrate into a fast-paced team.

• Design Challenge (Potentially): While not explicitly stated, some companies may include a small design exercise or a take-home challenge to assess specific skills, especially around problem-solving or ideation.

• Final Interview: Likely with senior leadership or founders to discuss overall strategic alignment, long-term vision, and final fit.

Portfolio Review Tips:

• Focus on B2B SaaS & Complexity: Prioritize case studies that showcase your experience with enterprise software, complex workflows, data-heavy interfaces, or AI-adjacent features. Avoid purely consumer-focused projects unless they strongly demonstrate transferable skills in complex problem-solving.

• Showcase Your Process: Clearly articulate your design process, from research and discovery to iteration and delivery. Explain why you made certain decisions and how you validated them.

• Highlight Impact & ROI: Quantify the impact of your designs whenever possible. For this role, focus on how your designs improved efficiency, usability, data comprehension, or stakeholder buy-in for clients.

• Demonstrate Systems Thinking: Include examples that show your ability to design reusable components, patterns, and contribute to or build design systems.

• Address Human-Centered & AI Elements: If you have projects involving AI, explain your approach to ensuring transparency, trust, and human oversight. Articulate how you balance AI capabilities with human judgment.

• Be Concise and Clear: Structure your portfolio for easy understanding, with clear headings, visuals, and concise explanations.

Challenge Preparation:

• Be prepared to discuss your approach to designing for complex user needs and stakeholder requirements.

• Think about how you would tackle designing a dashboard for non-technical users or an interface for interacting with AI suggestions.

• Practice articulating your design rationale clearly and concisely, anticipating questions about trade-offs and engineering implications.

📝 Enhancement Note: The emphasis on "complex, data-heavy, or AI-adjacent systems" in the portfolio requirements is a strong signal for what the interviewers will be looking for. Candidates should tailor their portfolio presentation to highlight these specific areas of expertise.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Explicitly mentioned as a required proficiency. Expect to use it for wireframing, prototyping, UI design, and likely collaboration on design system components.

• Prototyping Tools: Beyond Figma's capabilities, other tools may be used for more advanced prototyping or user flow mapping.

• User Research Tools: Platforms for conducting remote usability testing, surveys, and interviews (e.g., UserTesting.com, Lookback, SurveyMonkey, Typeform).

Analytics & Reporting:

• Data Visualization Tools: Familiarity with best practices for presenting data clearly and effectively is key. While specific tools aren't mentioned, the output will be consumed by users of these tools.

• Analytics Platforms: Understanding how users interact with the platform and how data is tracked (e.g., Amplitude, Mixpanel, Google Analytics) can inform design decisions.

CRM & Automation:

• Internal Tools: While not directly designing CRM/automation, understanding how the platform integrates with or complements existing enterprise workflows (e.g., HRIS, LMS) is beneficial.

• Design System Management: Tools or processes for managing design tokens, component libraries, and documentation.

📝 Enhancement Note: Figma proficiency is a hard requirement. The role also implies a need for strong data visualization skills and an understanding of how users consume insights from complex systems, even if the designer isn't building the analytics backend.

👥 Team Culture & Values

Operations Values:

• Human Connection: Central to the company's mission; expect this to permeate design decisions, aiming to enhance rather than detract from human interaction.

• Intentionality & Scalability: Designing solutions that are deliberate, well-thought-out, and can grow with the company and its user base.

• Integrity & Trust: Particularly important for AI-powered features and handling sensitive user data related to development and performance.

• Data-Driven Insights: Using research and analytics to inform design, but balanced with human-centered principles.

• Collaboration: High emphasis on working closely with cross-functional teams.

• Impact-Oriented: Focus on delivering tangible value to clients and participants.

Collaboration Style:

• Cross-functional Partnership: Close working relationships with Product Managers and Engineers are essential for effective product development.

• Open Communication: "High context, low bureaucracy" suggests an environment where ideas can be shared freely and feedback is actively sought.

• User-Centricity: A shared commitment to understanding and solving user problems through thoughtful design.

• Iterative Development: Expect a dynamic environment where designs are continuously refined based on feedback and data.

📝 Enhancement Note: The company's mission to "make human connection an intentional, scalable asset" is a core value that should be reflected in the designer's approach, especially when dealing with AI.

⚡ Challenges & Growth Opportunities

Challenges:

• Establishing Design Function: As the first dedicated designer, you'll be responsible for defining processes, setting standards, and building the design system from the ground up.

• Balancing Human & AI: Designing interfaces that leverage AI effectively while maintaining transparency, trust, and augmenting human judgment, rather than replacing it, is a complex challenge.

• Complex B2B SaaS Workflows: Designing for enterprise users often involves intricate workflows, multiple user roles, and significant data management, requiring a deep understanding of user needs and business objectives.

• Communicating Design Value: Effectively articulating design decisions and their impact to non-design stakeholders, especially founders and engineers.

• Rapid Growth Environment: Adapting to the fast-paced, evolving nature of a venture-backed startup.

Learning & Development Opportunities:

• Design Leadership Path: Explicitly stated opportunity to grow into a design leadership role and build a team.

• Strategic Product Influence: Direct involvement in product strategy and roadmap decisions.

• Specialized Expertise: Developing deep knowledge in human-AI interaction design, applied cognitive science in UX, and complex B2B SaaS design.

• Building from Scratch: Gaining invaluable experience in establishing design systems, processes, and best practices within a growing organization.

• Mentorship: Potential to learn from founders and experienced team members in a collaborative environment.

📝 Enhancement Note: The primary challenge is also the greatest growth opportunity: the chance to build and shape the design function of a promising startup.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to advocate for a human-centered approach when a more 'efficient' or AI-driven solution was proposed. How did you present your case?" (Focus on your process, research, and communication skills).

• "Walk us through your process for designing a complex dashboard or reporting interface for non-technical users. What were the key challenges and how did you address them?" (Highlight data visualization, information architecture, and user research).

• "How would you approach designing the interaction between a user and an AI suggestion feature to ensure trust and appropriate reliance?" (Demonstrate understanding of AI UX principles and cognitive load).

Company & Culture Questions:

• "What excites you about Keep Company's mission to enhance human connection in the workplace?" (Connect your values to the company's mission).

• "How do you see your role contributing to our 'human-centered design in an AI-saturated landscape' philosophy?" (Show you understand the nuanced approach required).

Portfolio Presentation Strategy:

• Select Relevant Projects: Choose 1-2 case studies that best demonstrate your experience with B2B SaaS, data visualization, complex workflows, and ideally, AI-adjacent features.

• Structure Your Narrative: For each project, follow a clear story: the problem, your role, the process (research, ideation, design, testing), key decisions and rationale, and the outcome/impact.

• Quantify Impact: Wherever possible, use metrics to demonstrate the success of your designs (e.g., improved task completion time, increased user adoption, stakeholder satisfaction).

• Highlight Systems Thinking: Show how your designs contribute to scalability and consistency, perhaps through examples of component usage or design system contributions.

• Be Prepared for Deep Dives: Anticipate detailed questions about your design choices, research methods, and how you handled technical constraints or trade-offs.

📝 Enhancement Note: Candidates should prepare to defend their design decisions with clear rationale rooted in user research, business goals, and design principles, particularly concerning the intersection of human interaction and AI.

📌 Application Steps

To apply for this Lead Product Designer position:

• Submit your application through the provided link on the Keep Company careers page.

• Portfolio Customization: Ensure your portfolio prominently features projects that demonstrate your experience with B2B SaaS, complex data visualization, and designing for AI-adjacent features. Tailor your case study selection to align with the "human-centered design in an AI-saturated landscape" philosophy.

• Resume Optimization: Highlight your 3-5+ years of experience, specifically mentioning your background in B2B SaaS or enterprise software. Use keywords from the job description such as "end-to-end product design," "data visualization," "information architecture," "systems thinking," "Figma," and "human-centered design."

• Cover Letter Focus: In your cover letter, articulate what specifically excites you about Keep Company's mission to enhance human connection through technology and how your design philosophy aligns with their approach to AI. Share your vision for building a design function from the ground up.

• Company Research: Familiarize yourself with Keep Company's product, target market (professional services organizations), and their stated values. Understand their unique position at the intersection of HR Tech, AI, and human connection.

⚠️ 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.