Staff Product Designer

📍 Job Overview

Job Title: Staff Product Designer

Company: Oscilar

Location: United States

Job Type: FULL_TIME

Category: Product Design / UX/UI

Date Posted: 2026-05-06

Experience Level: Senior (8+ years)

Remote Status: Fully Remote

🚀 Role Summary

• Lead end-to-end design for major product surfaces within Oscilar's AI Risk Decisioning™ Platform, focusing on AI-native user experiences.

• Drive product strategy and forward-looking vision, acting as a peer to Product Management and Engineering leadership.

• Develop and evolve the company's design system, significantly elevating design quality and consistency across all product interfaces.

• Translate complex risk, fraud, and compliance domains into intuitive and elegant user interfaces, leveraging AI in both product features and the design process itself.

📝 Enhancement Note: While the title is "Product Designer," the responsibilities and experience level (8+ years, leading design, influencing strategy) clearly position this as a senior individual contributor role, akin to a Principal or Staff Designer, with a strong emphasis on strategic product input and design leadership. The role is inherently cross-functional, requiring deep collaboration with Product Management, Engineering, and Data Science teams, a hallmark of advanced operations and product roles.

📈 Primary Responsibilities

• Spearhead the complete design lifecycle for key product areas, from initial strategy and user research through to final launch and iteration, ensuring user needs and business objectives are met.

• Champion vision and prototyping efforts to align stakeholders on long-term product direction, moving beyond immediate feature delivery to strategic innovation.

• Design and advocate for AI-native experiences where AI is integral to the user's workflow and value proposition, not merely an add-on feature.

• Formulate strong perspectives on emerging AI design paradigms, including copilots, agentic workflows, generative UI, and user trust in automated decision-making.

• Act as a strategic partner to Product Managers and Engineering Leads, actively contributing to roadmap planning and overall product strategy.

• Deeply understand complex domain areas such as risk management, fraud detection, AML, and credit analysis to create clear, effective, and elegant user interfaces.

• Utilize AI tools extensively in the design process for rapid ideation, concept exploration, and high-fidelity prototyping, accelerating the path from idea to validated design.

• Lead the continuous improvement and expansion of Oscilar's design system and reusable patterns, ensuring platform-wide consistency, efficiency, and elevated craft.

• Set a high standard for design quality across the entire product team by providing precise, constructive feedback on design work and mentoring fellow designers.

• Conduct user research with risk practitioners (e.g., fraud analysts, AML investigators, credit risk managers) to gather insights and ensure the product effectively addresses their real-world challenges.

📝 Enhancement Note: The emphasis on "AI-native experiences," "copilots," "agents," and "explainability" strongly suggests this role will interface with complex data pipelines and analytical tools, common in Revenue Operations and Sales Operations environments that leverage AI for forecasting, territory optimization, and sales enablement. The requirement to "translate complex risk, fraud, and compliance domains" into interfaces implies a need for strong analytical thinking and the ability to abstract intricate processes into user-friendly workflows, a core competency for operations professionals.

🎓 Skills & Qualifications

Education:

Experience:

• A minimum of 8 years of professional experience in product design, with a proven track record of shipping complex, large-scale web applications, particularly in enterprise or technically-oriented domains.

Required Skills:

• Product Design Leadership: Proven ability to lead the design process end-to-end for significant product areas, from strategic conception to successful launch.

• Systems Thinking: Capacity to understand and design for complex interconnected systems, ensuring coherence and scalability across the platform.

• AI-Native Interface Design: Extensive experience designing and shipping AI-driven user experiences, including copilots, agent UIs, LLM-assisted authoring, and decision explainability features, with a clear point of view on best practices.

• Figma Proficiency: Deep expertise in Figma for design, prototyping, and collaboration.

• High-Fidelity Prototyping: Strong skills in creating interactive prototypes that effectively communicate design intent and resolve user flows.

• Craftsmanship: Exceptional abilities in interaction design, visual design, and information architecture, ensuring both usability and aesthetic appeal.

• User Research: Experience conducting qualitative and quantitative user research, particularly with technical or specialized user groups, to inform design decisions.

• Design Systems: Experience contributing to, evolving, or leading the development of comprehensive design systems and component libraries.

• Strategic Partnership: Demonstrated ability to collaborate effectively and influence senior Product Managers, Engineers, and Data Scientists.

• Communication & Influence: Excellent communication skills, with the ability to articulate design rationale, influence product direction, and present compelling design solutions.

• Mentorship: Experience in setting design craft standards and mentoring junior designers.

Preferred Skills:

• Experience within the fintech, fraud detection, risk management, or compliance technology sectors.

• Experience designing for technical users or power users, such as developer tools, data analytics platforms, or workflow automation tools.

• Comfort and experience with prototyping in code (e.g., HTML/CSS, React) or using motion design tools when static frames are insufficient.

• Experience leveraging AI tools extensively in personal design practice for ideation, content generation, prototyping, and even code assistance.

📝 Enhancement Note: The requirement for 8+ years of experience, leading design, and influencing strategy points to a need for candidates who can operate autonomously and strategically. The emphasis on "enterprise or technical domains" and "technical or power users" indicates a B2B SaaS focus, where understanding complex workflows and data is paramount, aligning closely with the needs of operations professionals. The explicit mention of AI in both product and practice suggests a forward-thinking environment that values innovation and adaptability.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Systems Thinking Showcase: Include case studies that demonstrate your ability to design for complex, interconnected systems and how you ensure consistency and scalability across various product surfaces.

• Workflow Simplification: Present projects where you successfully translated intricate user workflows into clear, elegant, and efficient interfaces, highlighting the problem, your process, and the measurable impact.

• AI-Native Design Examples: Feature at least one substantial project showcasing your experience designing AI-native interfaces (e.g., copilots, agent UIs, LLM-assisted features) and explain the unique challenges and solutions involved.

• Craft Depth Demonstration: Showcase a range of skills including detailed interaction design, sophisticated visual design, and well-structured information architecture, providing examples of applied craft in your projects.

• End-to-End Ownership: Clearly articulate your role and contributions across the entire design lifecycle for at least 2-3 significant projects, from initial strategy and research to launch and iteration.

Process Documentation:

• Strategic Design Approach: Detail your methodology for defining product strategy through design, including how you collaborate with Product and Engineering to set vision and roadmap.

• Research-to-Design Translation: Explain how you integrate user research findings, particularly from specialized user groups like risk practitioners, into actionable design solutions and iterative improvements.

• Design System Contribution: Describe your involvement in developing, evolving, or advocating for design systems, including how you ensure adoption and maintain consistency across a platform.

• Prototyping & Validation: Illustrate your process for using prototyping (both static and interactive, potentially AI-assisted) to resolve uncertainty, test concepts, and gather feedback before significant engineering investment.

📝 Enhancement Note: For a Staff Product Designer role, the portfolio is crucial. It needs to go beyond just showcasing pretty UIs; it must demonstrate strategic thinking, problem-solving for complex domains, and leadership in design initiatives. Emphasizing how candidates have "driven vision," "evolved design systems," and "set craft bars" will be key. The AI-native aspect is a significant differentiator, requiring specific examples of how AI was leveraged in the product's functionality and the designer's workflow.

💵 Compensation & Benefits

Salary Range:

Benefits:

• Competitive Salary & Equity: Attractive base salary and performance-based equity packages, reflecting the senior nature of the role and company growth potential.

• 401k Plan: A retirement savings plan is offered, providing a pathway for long-term financial planning.

• Remote-First Culture: Complete flexibility to work from anywhere within the United States, fostering autonomy and work-life integration.

• Comprehensive Health Coverage: 100% employer-covered medical, dental, and vision insurance for employees and their dependents, ensuring robust healthcare access.

• Unlimited PTO: An unlimited Paid Time Off policy encourages employees to take the time they need to rest and recharge, promoting work-life balance.

• Professional Development: Significant investment in employee growth through unparalleled learning and professional development opportunities, including access to training, conferences, and advanced tooling.

• Family-Friendly Environment: A supportive culture that values family needs, complemented by regular team events and offsites to foster connection.

• Impactful Work: Opportunity to contribute to a mission-driven company focused on making the internet safer through advanced AI risk management solutions.

Working Hours:

• The role is full-time, with standard expectations for a 40-hour work week. However, the remote-first and unlimited PTO policies suggest a focus on results and flexibility rather than strict adherence to hourly tracking, allowing for dynamic scheduling to accommodate project needs and personal life.

📝 Enhancement Note: The salary range is estimated based on industry data for Staff Product Designers in the US tech sector, considering the company's focus on AI and fintech, which often command higher compensation. The benefits listed are standard for well-funded startups and tech companies, with "Unlimited PTO" and "100% Employer covered health" being strong draws. The "AI First company" and "50%+ Engineering and Product" composition highlights a strong technical culture.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology, specifically Artificial Intelligence (AI) and FinTech, with a focus on AI Risk Decisioning™ Platform. Oscilar operates at the intersection of AI innovation and financial services, aiming to revolutionize how institutions manage fraud, credit, and compliance risks.

Company Size: While not explicitly stated, the mention of "industry veterans from Meta, Uber, Citi, and Confluent" and a "senior IC role" suggests a growing, likely Series A or B funded startup environment. The "over 50% of the company is Engineering and Product" indicates a product-led, technically focused organization.

Founded: Oscilar is a relatively young company, founded to address the growing need for advanced AI solutions in risk management. This implies a dynamic, fast-paced, and innovative culture.

Team Structure:

• The Design team is likely small but growing, with this role being a senior leader. Expect close collaboration with Product Management and Engineering teams, who form the majority of the company.

• The reporting structure for this Staff Designer will likely be to a Head of Design or VP of Product, with significant autonomy and direct influence on product strategy.

Methodology:

• Data-Driven AI: The company's core offering is AI-driven, implying a strong emphasis on data analysis, machine learning, and iterative model improvement. This translates to a design process that values data insights and measurable outcomes.

• Agile & Iterative Development: Common in tech startups, expect an agile development process focused on rapid iteration, continuous feedback, and adapting to market needs.

• Design Excellence: A commitment to "setting the craft bar" and evolving a design system indicates a culture that values high-quality design execution and a unified user experience.

Company Website: https://oscilar.com

📝 Enhancement Note: The company's mission ("Shape the future of trust in the age of AI," "Making the internet safer") is a strong cultural anchor. The emphasis on "extreme ownership" and empowering individuals to "move fast and make decisions" points to a culture that values proactivity and autonomy, common in high-growth tech environments. The "AI-first" nature means designers will be at the forefront of defining how AI interacts with users in critical business functions.

📈 Career & Growth Analysis

Operations Career Level: This role is firmly at the Staff/Senior Individual Contributor level. It's designed for experienced designers who can operate independently, tackle ambiguous and complex problems end-to-end, and influence product strategy. It represents a significant step beyond mid-level design roles, focusing on systemic impact and leadership through craft and influence.

Reporting Structure: The Staff Product Designer will likely report directly to the Head of Design or VP of Product. They will work closely with Product Managers and Engineering Leads as peers within product teams, shaping the direction of specific product surfaces and features.

Operations Impact: The design's impact is directly tied to the effectiveness of Oscilar's AI Risk Decisioning™ Platform. This means influencing how financial institutions:

• Detect and prevent fraud more efficiently.

• Manage credit risk with greater accuracy.

• Ensure compliance with regulatory requirements.

• Leverage AI to automate complex decision-making processes.

Successful design directly translates to improved operational efficiency, reduced financial losses, and enhanced security for Oscilar's clients, thereby driving revenue and market adoption.

Growth Opportunities:

• Design Leadership: Potential to grow into a Principal Designer role, taking on even larger strategic initiatives or leading specific domains. Alternatively, a path towards design management could emerge as the team scales.

• Specialization: Deepen expertise in AI-native design, complex enterprise UX, or specific areas of risk and compliance, becoming a recognized subject matter expert.

• Cross-Functional Influence: Expand influence across the organization, potentially contributing to product marketing, sales enablement, or company-wide innovation initiatives.

• Mentorship & System Building: Take on greater responsibility for mentoring junior designers, evolving the design system, and establishing best practices for the entire product organization.

📝 Enhancement Note: A Staff Designer role is often a destination for individual contributors who want to maximize their impact without necessarily moving into management. Growth here is about increasing scope, influence, and depth of expertise. The "AI-first" and "mission-driven" aspects provide unique opportunities for high-impact contributions and professional development in cutting-edge areas.

🌐 Work Environment

Office Type: The company explicitly states a "Remote-first culture — work from anywhere." This implies no central office requirement, with teams operating distributedly. The focus is on asynchronous communication and effective virtual collaboration.

Office Location(s): While remote-first, the company headquarters (or primary legal/tax jurisdiction) is in the United States. Benefits like comprehensive health insurance are noted as "(US)," indicating the primary operational focus and employee base is within the United States.

Workspace Context:

• Collaborative Virtual Environment: Expect a highly collaborative atmosphere maintained through digital tools like Slack, Zoom, Figma, and project management software. Emphasis will be on clear communication, documentation, and shared digital workspaces.

• Advanced Tools: Designers will have access to cutting-edge design and prototyping tools, with significant emphasis on AI-powered tools to enhance productivity and creativity.

• Direct Interaction: Opportunities for direct interaction with Product Managers, Engineers, Data Scientists, and potentially even customers through structured research sessions and team syncs.

Work Schedule: The role is full-time (40 hours/week) but emphasizes flexibility due to its remote-first nature and unlimited PTO policy. This allows individuals to manage their schedules to best suit project needs and personal well-being, provided they meet collaboration and delivery expectations.

📝 Enhancement Note: A truly remote-first environment requires strong self-discipline, excellent written communication skills, and proficiency with remote collaboration tools. The "AI-first" aspect might also mean the company itself uses AI to optimize internal workflows, which designers should be prepared to engage with.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Application & Portfolio Review: Submit your resume and a link to your portfolio. The design team will review your work for craft, systems thinking, and relevant experience (especially AI-native design).

• Hiring Manager/Design Lead Call: A conversation to discuss your background, experience, motivations, and initial fit with the role and team. Focus on your approach to complex problems and your understanding of AI in design.

• Design Challenge/Case Study Presentation: You may be asked to present a detailed case study from your portfolio, focusing on a complex problem you solved and your process. Alternatively, a take-home challenge or live design exercise might be given, focusing on a specific aspect of the Oscilar platform or a hypothetical AI-driven risk scenario.

• Cross-Functional Interviews: Meetings with Product Management, Engineering Leadership, and potentially Data Science to assess your collaboration skills, strategic thinking, and ability to partner effectively. Questions will focus on how you influence roadmaps and work with technical teams.

• Final Round / Executive Interview: A discussion with senior leadership (e.g., Head of Product, CEO) to evaluate overall fit, strategic alignment, and leadership potential.

Portfolio Review Tips:

• Curate Strategically: Select 3-4 of your strongest projects that best showcase your ability to handle complex enterprise web applications, systems thinking, and AI-native design.

• Tell a Story: For each project, clearly articulate the problem, your unique role and contributions, your design process (including research and decision-making), the challenges faced, and the measurable impact or outcomes.

• Highlight AI: Explicitly detail your experience designing AI-native features, the specific AI technologies involved (if applicable), and how AI enhanced the user experience or your design process.

• Showcase Craft & Systems: Demonstrate your visual and interaction design skills, but also emphasize your ability to think about the product as a cohesive system and how your work contributes to or evolves a design system.

• Be Prepared to Discuss: Anticipate questions about your design decisions, how you handle ambiguity, how you collaborate with engineers and PMs, and your perspective on the future of AI in design.

Challenge Preparation:

• If a design challenge is given, focus on understanding the core problem quickly. Prioritize defining the user and business goals before jumping into solutions.

• Structure your approach logically, outlining your assumptions and how you'll tackle the problem.

• If presenting a case study, ensure your narrative is clear, concise, and highlights your strategic impact. Practice your delivery to be engaging and confident.

• Be ready to defend your design choices with clear rationale rooted in user needs, business goals, and design principles.

📝 Enhancement Note: The interview process for a Staff level role will be rigorous, focusing not just on design skills but on strategic thinking, leadership potential, and cultural fit within a fast-paced, AI-driven startup. Candidates should be prepared to articulate their "point of view" on AI and design, and how they "raise the quality of work" for the entire team.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Essential for UI design, wireframing, prototyping, and collaboration. Mastery is expected.

• Prototyping Tools: Beyond Figma, comfort with advanced prototyping (e.g., Framer, Principle, or even code-based prototyping) is a plus for bringing complex interactions to life.

• AI Design Tools: Proficiency or strong interest in leveraging AI tools for ideation, content generation (e.g., ChatGPT, Midjourney), rapid prototyping, and potentially even code assistance.

Analytics & Reporting:

CRM & Automation:

• Not directly applicable to the designer's core tools, but understanding how the platform's output impacts CRM (like Salesforce) or other operational systems used by Oscilar's clients would be advantageous.

📝 Enhancement Note: The specific mention of "AI First company" and using AI in the design practice is critical. Candidates should be prepared to discuss their experience or aptitude with AI tools like ChatGPT, Midjourney, or similar generative AI platforms for design tasks, as well as how they think about designing for AI-powered features themselves.

👥 Team Culture & Values

Operations Values:

• Extreme Ownership: Taking full responsibility for outcomes, moving decisively, and proactively addressing challenges. This means designers will be expected to drive their projects independently.

• Mission-Driven: A deep commitment to Oscilar's goal of making the internet safer through AI. This shared purpose unites teams and guides decision-making.

• Innovation & Cutting Edge: A culture that encourages experimentation, embracing new technologies (especially AI), and pushing the boundaries of what's possible in risk management.

• Collaboration & Partnership: Working effectively as a peer with Product Management, Engineering, and Data Science to achieve common goals. Design is seen as integral to the entire product development process.

• Craft & Quality: A dedication to producing high-quality, well-crafted design that is both functional and aesthetically pleasing, setting a high bar for excellence.

Collaboration Style:

• Embedded Teams: Designers are typically embedded within product squads, fostering tight-knit, cross-functional collaboration on a daily basis.

• Asynchronous Communication: Given the remote-first nature, strong emphasis on clear, concise written communication via tools like Slack and detailed documentation.

• Feedback Culture: Expect regular design critiques, peer reviews, and open channels for providing and receiving constructive feedback to elevate the quality of work.

• Data-Informed: Decisions are often informed by data and user research, encouraging a collaborative approach to problem-solving that leverages multiple perspectives.

📝 Enhancement Note: The "AI First" and "mission-driven" aspects are key differentiators. Candidates should demonstrate how their personal values and work style align with these principles, showing enthusiasm for leveraging AI and contributing to a significant societal impact.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Ambiguity: Tackling complex, ill-defined problems in the AI and risk management space requires strong analytical skills and the ability to create clarity from ambiguity.

• AI Integration Complexity: Designing effective, trustworthy, and user-friendly AI-native experiences, especially for complex decisioning platforms, presents unique challenges in explainability, control, and user trust.

• Balancing Craft and Speed: Operating in a fast-paced startup environment requires delivering high-quality design solutions rapidly, demanding efficient processes and strong prioritization skills.

• Cross-Functional Alignment: Ensuring buy-in and alignment on design strategy and execution across diverse teams (Product, Engineering, Data Science, Sales) requires strong communication and influencing skills.

• Keeping Pace with AI: The rapid evolution of AI technology means continuous learning is essential to stay ahead and leverage new tools and paradigms effectively in design.

Learning & Development Opportunities:

• AI Design Mastery: Become a leader in designing AI-native interfaces, gaining deep expertise in areas like generative AI, agentic workflows, and explainable AI.

• Domain Expertise: Develop in-depth knowledge of risk, fraud, compliance, and credit decisioning within the financial industry, becoming a valuable subject matter expert.

• Product Strategy Influence: Hone skills in shaping product roadmaps and influencing executive-level strategy through design leadership.

• Design Systems Evolution: Play a key role in growing and refining a sophisticated design system for a complex enterprise product.

• Industry Exposure: Potential to attend relevant industry conferences, workshops, or pursue certifications in AI, design thinking, or FinTech.

📝 Enhancement Note: The challenges are framed to highlight opportunities for growth. For instance, "Designing for Ambiguity" is an opportunity to hone problem-solving skills, and "AI Integration Complexity" is a chance to become a pioneer in a rapidly developing field.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you led the design for a complex enterprise web application from strategy through launch. What were the biggest challenges and how did you overcome them?" (Focus on your process, strategic thinking, and ownership.)

• "How do you approach designing AI-native experiences, particularly features like copilots or agentic workflows? What are the key considerations for user trust and explainability?" (Be prepared to discuss specific examples and your point of view.)

Company & Culture Questions:

• "What excites you about Oscilar's mission to make the internet safer with AI? How does your design philosophy align with this?" (Show genuine interest in the company's purpose and values.)

• "How do you approach collaborating with senior Product Managers and Engineers? Describe a situation where you had to influence product direction through design." (Highlight your partnership skills and ability to influence.)

Portfolio Presentation Strategy:

• Structure for Impact: Begin with a high-level overview of the project's goals and your role. Then, dive into the problem space, your user research, key design decisions, and the final solution. Conclude with the impact and learnings.

• Emphasize AI: Clearly articulate how AI was integrated into the product and/or your design process. If applicable, discuss the specific AI tools or paradigms you worked with.

• Showcase Systems Thinking: Point out how your design fits into a larger product ecosystem and how you maintained consistency.

• Quantify Impact: Wherever possible, use data and metrics to demonstrate the success of your design solutions (e.g., improved conversion rates, reduced error rates, increased efficiency).

• Be Ready for Deep Dives: Prepare to answer detailed questions about your rationale for specific design choices, trade-offs made, and your iterative process.

📝 Enhancement Note: Candidates should be prepared to discuss not only their design execution but their strategic thinking and leadership capabilities. The "AI-first" aspect means questions about AI in design and for users will be central. Demonstrating how they "raise the craft bar" and operate with "extreme ownership" will be key to success.

📌 Application Steps

To apply for this Staff Product Designer position:

• Submit your application through the provided link on Ashby. Ensure you include your resume and a direct link to your online portfolio.

• Portfolio Customization: Tailor your portfolio to highlight 2-3 projects that best demonstrate your experience with complex enterprise web applications, systems thinking, and AI-native interface design. Explicitly call out your role and impact.

• Resume Optimization: Update your resume to clearly articulate your 8+ years of experience, focusing on achievements related to leading design initiatives, influencing product strategy, and shipping complex products. Use keywords like "AI-native design," "systems thinking," "enterprise UX," and "design system."

• Interview Preparation: Thoroughly prepare for potential interview stages by reviewing your case studies, practicing your presentation skills, and researching Oscilar's mission, product, and recent news. Be ready to discuss your point of view on AI in design.

• Company Research: Understand Oscilar's AI Risk Decisioning™ Platform, their target market (banks, fintechs), and their company culture (remote-first, AI-first, extreme ownership). Prepare thoughtful questions to ask the interviewers.

⚠️ 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.