Senior Product Designer II

📍 Job Overview

Job Title: Senior Product Designer II

Company: Wrapbook

Location: United States (Remote)

Job Type: Full-Time

Category: Product Design / UX Design

Date Posted: September 14, 2026

Experience Level: Senior / 8+ Years

Remote Status: Fully Remote

🚀 Role Summary

• Lead end-to-end design for a core product area, transforming loosely defined problems into actionable, defensible design solutions across multiple systems and user surfaces.

• Drive product strategy and execution with a strong emphasis on data-driven decision-making, leveraging user research and analytics to inform design direction and measure impact against business OKRs.

• Set the benchmark for design quality and implementation-ready deliverables, fostering a collaborative environment and mentoring other designers.

• Integrate advanced AI capabilities and agentic workflows into the design process to enhance efficiency, accelerate research, and streamline handoffs with engineering.

📝 Enhancement Note: This role is positioned as a Senior Individual Contributor (IC) within the Product Design function, emphasizing ownership, strategic problem-framing, and setting quality standards for the team. The focus on "minimal direction" and "broad, cross-cutting work" indicates a need for a designer who can navigate ambiguity and proactively define solutions, rather than execute on pre-defined tasks. The AI integration requirement is a key differentiator, suggesting a forward-thinking approach to design tooling and workflows.

📈 Primary Responsibilities

• Own the complete design lifecycle for a designated product area, from initial problem definition and user research through to detailed specifications, delivery, and post-launch iteration.

• Proactively identify and frame ambiguous problems, translating them into clear design objectives and measurable outcomes that align with customer needs and business goals (OKRs).

• Utilize quantitative data (e.g., Pendo analytics) and qualitative insights (e.g., Dovetail research, user interviews) to rigorously shape design decisions, define success metrics, and validate the impact of design solutions on speed, efficiency, error reduction, and user delight.

• Independently prioritize design initiatives within your area, synthesizing inputs from various stakeholders (Product Management, Engineering, Research, Pendo, user feedback) to establish a clear design roadmap and drive team alignment.

• Develop and maintain high-quality, implementation-ready design specifications, including detailed flows, edge case considerations, content strategy, and precise logic, ensuring seamless handoffs to engineering.

• Champion the exploration of innovative design patterns and challenge existing paradigms to create best-in-class user experiences, maintaining a high bar for craft and detail even under pressure.

• Actively integrate and promote the use of AI tools and agentic workflows (e.g., Claude, Cursor) to automate repetitive tasks, accelerate research synthesis, improve validation processes, and create more efficient collaboration loops.

• Shape and facilitate effective collaboration across Product, Engineering, and Research teams, establishing clear decision-making frameworks and communication channels to ensure alignment on complex initiatives.

• Mentor and provide actionable feedback to fellow designers at all levels, fostering a culture of continuous learning and craft excellence within the design team.

• Maintain accurate and up-to-date status, decisions, and risks in project management tools (e.g., Linear) to ensure transparency and informed decision-making for design leadership and stakeholders.

📝 Enhancement Note: The responsibilities highlight a significant degree of autonomy and strategic influence. The emphasis on "framing loosely defined problems" and "driving alignment without repeated escalation" suggests that candidates will be expected to lead, not just execute. The explicit mention of specific tools like Pendo, Dovetail, and Linear indicates the need for practical experience in their application within a design workflow. The AI fluency requirement is a strong indicator of the company's forward-looking approach to design technology.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio demonstrating equivalent practical experience and a deep understanding of UX principles, interaction design, and visual design is paramount.

Experience: 8+ years of dedicated experience in UX or Product Design, with a demonstrable history of leading complex, cross-functional design initiatives from inception through successful delivery.

Required Skills:

• Expertise in UX/Product Design: Deep understanding of user-centered design principles, interaction design, information architecture, and visual design across web and mobile platforms.

• Design Systems Fluency: Proven ability to design with, contribute to, and evolve robust design systems for consistency and scalability.

• Data-Driven Decision Making: Proficiency in leveraging quantitative analytics (e.g., Pendo) and qualitative research (e.g., user interviews, usability testing, Dovetail) to inform design strategy and measure impact.

• Problem Framing & Ambiguity Navigation: Demonstrated ability to take loosely defined problems, define clear objectives, and develop structured approaches to complex design challenges.

• Prioritization & Strategic Judgment: Strong ability to synthesize competing inputs, define a clear point of view, and prioritize effectively to drive alignment and focus on high-impact initiatives.

• AI Fluency & Workflow Automation: Comfort and demonstrated experience with AI tools (e.g., Claude, Cursor) and a proactive approach to building reusable workflows and agentic capabilities to enhance productivity.

• Cross-Functional Collaboration & Influence: Exceptional skills in collaborating with and influencing Product Managers, Engineers, and Researchers to achieve shared goals and shape product direction.

• Documentation & Craftsmanship: A high standard for detailed, implementation-ready design documentation, including flows, specs, and edge case handling.

• Mentorship: Experience in mentoring junior designers and providing actionable feedback to elevate the team's craft.

Preferred Skills:

• Experience within a high-growth SaaS or FinTech environment.

• Familiarity with AI-powered design tools beyond basic usage, focusing on practical application for efficiency and innovation.

• Experience designing for complex B2B or enterprise applications, particularly in finance or production management.

• Proficiency with specific tools mentioned such as Figma, Claude, Cursor, and Linear.

• Experience in setting up and defining metrics for design impact.

📝 Enhancement Note: The "8+ years" requirement, coupled with the emphasis on leading "broad, cross-cutting work" and having a "craft opinion others seek out," firmly places this role at a senior individual contributor level, potentially bordering on Principal Designer responsibilities in some organizations. The explicit mention of AI tools like Claude and Cursor suggests a need for hands-on experience, not just conceptual understanding.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• End-to-End Project Ownership: Showcase 2-3 significant projects where you took ownership from problem definition through to successful delivery, demonstrating your ability to navigate ambiguity and drive outcomes.

• Problem Framing & Solution Development: Clearly articulate the initial problem space, your process for defining the core issues, and the rationale behind your chosen design solutions.

• Data-Informed Design: Provide concrete examples of how you used quantitative data (e.g., analytics, A/B test results) and qualitative research to shape your designs and measure their impact.

• Design System Contribution/Usage: Illustrate your understanding and application of design systems, showcasing how you maintained consistency and scalability in your work.

• AI Integration Examples: Include at least one project that highlights your innovative use of AI tools or agentic workflows to improve the design process, efficiency, or product outcomes.

• Collaboration & Influence: Describe instances where you effectively collaborated with cross-functional teams (Product, Engineering, Research) and influenced key decisions.

Process Documentation:

• Workflow Design & Optimization: Demonstrate your ability to map out complex user flows, identify bottlenecks, and design optimized workflows that improve efficiency and user experience.

• Implementation & Handoff: Provide examples of detailed specifications, including edge cases, content, and interaction logic, that facilitated smooth implementation by engineering teams.

• Metrics & Impact Analysis: Clearly present how you defined success metrics upfront for your projects and how you measured and reported on the impact of your designs against those metrics and business OKRs.

📝 Enhancement Note: The portfolio requirements are heavily weighted towards demonstrating end-to-end ownership, data-driven validation, and proactive problem-solving. The explicit inclusion of AI integration as a portfolio requirement is a key differentiator and signals a strong preference for candidates who can showcase practical application of these emerging technologies in their design work.

💵 Compensation & Benefits

Salary Range: Based on industry benchmarks for Senior Product Designers II in the US and Canada, with 8+ years of experience and a focus on AI integration, the estimated salary range is:

• Minimum: $149,000 USD per year

• Maximum: $241,500 USD per year

This range accounts for the senior level, the remote nature of the role across two countries, and the specialized skills in AI and complex problem-solving.

Benefits:

• Unlimited Paid Time Off: Flexibility and autonomy in managing personal time.

• Work from Anywhere: Freedom to work remotely from Canada or the USA.

• Comprehensive Health & Dental: Full medical and dental coverage.

• Home Office Stipend: Up to $1,500 USD ($2,025 CAD) for IT setup.

• Retirement Savings Match: Up to 2% matching on RRSP (Canada) or 401K (USA).

• Learning & Development: Opportunities for professional growth and skill enhancement.

• Connectivity Stipend: Up to $50 USD ($67.50 CAD) per month for Internet/Cell phone service.

Working Hours: The role is a full-time position, typically requiring approximately 40 hours per week. Given the remote and international nature of the role, there will be an expectation for flexibility to accommodate cross-time zone collaboration, particularly with teams in North America.

📝 Enhancement Note: The salary estimate is derived from publicly available compensation data for Senior Product Designer roles in the US and Canada, adjusted for the specified experience level (8+ years), the remote work arrangement, and the emphasis on advanced skills like AI fluency. The provided AI-generated range of $149,000 - $241,500 USD aligns with these benchmarks.

🎯 Team & Company Context

🏢 Company Culture

Industry: FinTech / Production Finance Technology. Wrapbook operates at the intersection of finance and media production, leveraging AI to streamline complex financial operations for film, TV, and commercial productions.

Company Size: 350+ employees. This indicates a mid-stage growth company that has moved beyond startup chaos but still maintains agility and a strong sense of mission. The size allows for specialized roles and dedicated teams while fostering a collaborative and impactful environment.

Founded: Wrapbook was founded with the mission to transform production finance with AI. While the exact founding year is not provided, its backing from prominent VCs like Andreessen Horowitz and Bessemer Venture Partners suggests a relatively recent but well-established and rapidly scaling company.

Team Structure:

• Product Design Team: Likely comprises a mix of Senior ICs, potentially leads, and designers focusing on different product areas. The "Senior Product Designer II" title suggests a hierarchy within the design team, with this role setting a high bar.

• Cross-Functional Teams: Product Designers work in close collaboration with Product Managers, Engineers, and Researchers, forming agile pods or squads focused on specific product areas or initiatives.

• Reporting Structure: This Senior IC role likely reports into a Design Lead or Head of Product Design. While an individual contributor, they are expected to mentor junior designers and influence design strategy across the team.

Methodology:

• AI-Centric Operations: Wrapbook's core product is AI-driven, implying that AI integration is a fundamental aspect of their operational and product development philosophy.

• Data-Informed Product Development: The emphasis on Pendo, Dovetail, and measuring outcomes highlights a commitment to data and evidence in shaping product decisions and design.

• Agile Development: Given the fast-paced tech environment and backing from VCs, an agile methodology for product development and design is highly probable, focusing on iterative improvements and rapid releases.

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

📝 Enhancement Note: The company's focus on AI in production finance suggests a culture that values innovation, technical expertise, and data-driven decision-making. The "350+ employees" size implies a well-structured organization with established processes but still retains the dynamism of a growth-stage company.

📈 Career & Growth Analysis

Operations Career Level: This role is a Senior Individual Contributor (IC) position, specifically Senior Product Designer II. It signifies a deep level of expertise and autonomy, where the designer is expected to lead complex initiatives, define problems, and set high standards for the design team. This is a critical role for driving product innovation and quality.

Reporting Structure: The Senior Product Designer II will likely report to a Design Lead or Head of Product Design. While an IC, they are expected to influence design direction, mentor junior designers, and collaborate closely with Product Management and Engineering leads on strategic initiatives.

Operations Impact: The impact of this role is significant, directly influencing the usability, efficiency, and adoption of Wrapbook's core product offerings. By owning a product area end-to-end and driving data-informed decisions, the designer will contribute to key business OKRs, such as increasing user speed, reducing errors, and enhancing overall customer satisfaction within the production finance workflow. The integration of AI further amplifies this impact by potentially revolutionizing how finance teams operate.

Growth Opportunities:

• Leadership within IC Track: Progression can lead to Principal Product Designer or Staff Product Designer roles, where the individual continues to drive high-impact, strategic projects and mentor others, acting as a technical leader in design.

• Specialization: Deepen expertise in AI-driven design, complex B2B SaaS product design, or specific areas of production finance.

• Cross-Functional Leadership: Take on more responsibility in shaping product strategy and process across departments, potentially leading design initiatives for major product launches or platform-wide improvements.

• Mentorship & Team Development: Grow into a role that involves more formal mentorship, design system stewardship, or even contributing to hiring and team growth strategies.

📝 Enhancement Note: The "II" in Senior Product Designer II suggests a defined career ladder within the design team, where this level represents a significant step up in autonomy and scope from a standard Senior Designer, aligning with expectations of a Principal or Staff level IC in other organizations.

🌐 Work Environment

Office Type: This is a fully remote position, allowing employees to work from their homes or co-working spaces within the United States and Canada.

Office Location(s): While the company is remote-first, Wrapbook has a presence, and the job posting specifies eligibility for candidates in the United States and Canada. This allows for a broad talent pool and flexibility for employees.

Workspace Context:

• Remote Collaboration Hub: The primary work environment will be digital, relying heavily on communication and collaboration tools (e.g., Slack, Zoom, Linear, Figma).

• Technology-Enabled Design: Access to modern design and AI tools (Figma, Claude, Cursor) is integral to the workflow, supported by a home office IT setup stipend.

• Asynchronous & Synchronous Communication: The remote and international nature necessitates a balance between scheduled meetings for real-time collaboration and asynchronous communication for efficiency across time zones.

Work Schedule: As a full-time role (approx. 40 hours/week), the schedule is flexible to accommodate personal needs and remote work. However, collaboration across different time zones will require responsiveness and availability during core North American business hours for key meetings and urgent discussions.

📝 Enhancement Note: The remote-first nature of Wrapbook, combined with its presence in both the US and Canada, suggests a culture that embraces distributed workforces and leverages technology to foster connection and productivity across geographical boundaries.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A conversation with a Talent team member to assess cultural fit, basic qualifications, and alignment with the role's high-level expectations.

• Portfolio Review & Design Challenge: A deep dive into your portfolio with design leadership. This will likely involve presenting 1-2 key projects, discussing your process, rationale, and impact. A design challenge, either take-home or live, may be administered to assess your problem-solving skills, design thinking, and execution capabilities, potentially with an AI component.

• Cross-Functional Interviews: Interviews with Product Management, Engineering, and potentially Research peers to evaluate collaboration style, communication skills, and technical understanding.

• Hiring Manager/Leadership Interview: A final discussion with the hiring manager or a senior leader to assess strategic thinking, leadership potential, and overall fit with the team and company vision.

Portfolio Review Tips:

• Tell a Story: Structure your portfolio around narratives that highlight your process, decision-making, and impact. Focus on 2-3 strong projects that showcase end-to-end ownership.

• Quantify Impact: For each project, clearly state the problem, your role, your process, the solutions you designed, and critically, the measurable outcomes (e.g., metrics improved, user feedback, business impact).

• Show, Don't Just Tell: Use visuals (mockups, flows, prototypes) to illustrate your design thinking. Explain why you made certain decisions.

• Highlight AI Integration: Dedicate a section or specific project to demonstrating your practical application of AI tools in your design workflow. Explain the problem, the AI solution, and its tangible benefits.

• Address Ambiguity: Showcase projects where you navigated unclear requirements or loosely defined problems, demonstrating your ability to frame and solve complex challenges.

• Be Prepared for Deep Dives: Expect detailed questions about your process, rationale, trade-offs, and how you handle feedback and disagreement.

Challenge Preparation:

• Understand Wrapbook: Research Wrapbook's product, target audience (production finance), and AI-driven approach. Understand their business model and mission.

• Focus on Process: For any design challenge, emphasize your thought process, how you break down problems, and how you arrive at solutions, rather than just the final output.

• AI Integration: If the challenge allows, consider how AI tools could be leveraged to enhance the solution or the process of arriving at it.

• Metrics & Impact: Think about how you would measure the success of your proposed solution.

📝 Enhancement Note: The emphasis on portfolio review and potential design challenges suggests that Wrapbook places a high value on practical design skills, problem-solving abilities, and the ability to articulate one's process and impact. The specific call-out for AI integration in the portfolio is a crucial element for candidates to address.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Expected to be the primary design and prototyping tool for UI/UX design, collaboration, and design system management.

• AI Design & Development Tools: Explicitly mentioned are Claude, Claude Code, and Cursor. This indicates a strong expectation for designers to leverage AI for research synthesis, code generation assistance, prototyping, and potentially agentic workflows.

• Project Management & Collaboration: Linear is mentioned for tracking status, decisions, and risks, suggesting a modern, integrated workflow. Slack and Zoom are likely used for day-to-day communication and meetings.

• User Research & Analytics: Pendo for product analytics and user behavior tracking, and Dovetail for qualitative research synthesis and insights management.

Analytics & Reporting:

• Pendo: Will be crucial for understanding user behavior, feature adoption, and measuring the impact of design changes.

• Internal Dashboards: Likely custom dashboards or BI tools used by Product and Engineering to track key performance indicators (KPIs) and OKRs.

CRM & Automation:

• While not explicitly mentioned for the design role, Wrapbook's core business is in production finance, which involves CRM-like functionalities for managing client relationships and automated financial workflows. Designers may interact with or design for these underlying systems.

📝 Enhancement Note: The explicit mention of specific AI tools (Claude, Cursor) alongside standard design tools (Figma) and analytics platforms (Pendo, Dovetail) highlights a company that is at the forefront of integrating advanced technology into its design and product development processes. Candidates should be prepared to discuss their experience and comfort with these tools.

👥 Team Culture & Values

Operations Values:

• Customer Obsession: A core value, emphasizing a deep understanding of customer needs and grounding decisions in evidence rather than assumptions.

• AI-First Innovation: A forward-thinking approach to leveraging AI to transform workflows and create best-in-class solutions, driving efficiency and new possibilities.

• Craftsmanship & Quality: A commitment to high standards in design execution, detail, and implementation-ready deliverables.

• Autonomy & Ownership: Empowering individuals to take ownership of their work, frame problems, and drive initiatives with minimal direction.

• Collaboration & Influence: Fostering strong partnerships across Product, Engineering, and Research to achieve shared goals and align on strategy.

• Data-Driven Decision Making: Relying on metrics and insights to guide product development and validate the impact of design solutions.

Collaboration Style:

• Cross-Functional Partnership: Designers work closely with PMs, Engineers, and Researchers, forming integrated teams to build and iterate on products.

• Open Communication & Feedback: A culture that encourages constructive feedback and open dialogue to improve designs and processes.

• Shared Ownership of Outcomes: Teams are accountable for delivering customer and business value, working collaboratively to achieve OKRs.

• Agile & Iterative: Embracing a flexible approach to development and design, with continuous feedback loops and iterative improvements.

📝 Enhancement Note: The company values clearly emphasize a blend of user-centricity, technological innovation (especially AI), high-quality execution, and collaborative teamwork. This suggests a dynamic and results-oriented environment where designers are expected to be both strategic thinkers and highly skilled practitioners.

⚡ Challenges & Growth Opportunities

Challenges:

• Navigating Ambiguity: Working on "broad, cross-cutting work where requirements evolve and no clear solution exists upfront" requires comfort with uncertainty and a proactive approach to defining direction.

• Setting the Bar: As a Senior Designer II, expectations are high to consistently produce work that sets a standard for the team, requiring continuous self-motivation and a high degree of craft.

• AI Integration at Scale: Moving beyond basic AI tool usage to measurable impact and integrating agentic workflows effectively across teams can be a complex, evolving challenge.

• Balancing Autonomy with Alignment: Effectively driving work with minimal direction while ensuring alignment with broader team and company goals requires strong communication and strategic judgment.

• Mentoring and Elevating Others: Balancing individual contribution with the responsibility of mentoring and elevating the skills of other designers.

Learning & Development Opportunities:

• Advanced AI in Design: Deepen expertise in leveraging AI for research, ideation, prototyping, and workflow automation, staying at the forefront of design technology.

• Strategic Product Leadership: Develop skills in product strategy, problem framing, and influencing roadmaps at a senior IC level.

• Cross-functional Process Improvement: Contribute to refining how Product, Design, and Engineering collaborate on complex initiatives.

• Industry Trends: Stay abreast of innovations in FinTech, production finance, and AI, applying insights to product design.

• Design System Evolution: Contribute to the growth and strategic direction of Wrapbook's design system.

📝 Enhancement Note: The challenges presented are typical for senior-level roles in fast-paced tech environments, emphasizing self-direction, impact, and continuous learning. The growth opportunities are geared towards deepening expertise in AI and strategic design leadership.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you took on a loosely defined problem and how you framed it to drive a solution. What was the outcome?" (Focus on your problem-framing process, research methods, and quantifiable impact.)

• "How do you prioritize design work when faced with competing signals from product, engineering, and user feedback?" (Highlight your strategic thinking, data synthesis, and ability to form a defensible point of view.)

• "Walk me through a project where you used AI tools to significantly improve your design process or the product outcome. What was the challenge, your approach, and the measurable impact?" (Be ready to detail your experience with tools like Claude or Cursor and demonstrate tangible benefits.) Company & Culture Questions:

• "What excites you about Wrapbook's mission and our use of AI in production finance?" (Showcase your research into the company and your alignment with their vision.)

• "How do you approach mentoring junior designers or contributing to the design culture of a team?" (Discuss your philosophy on feedback, collaboration, and knowledge sharing.)

• "How do you ensure your designs are grounded in customer needs and evidence, rather than assumptions?" (Emphasize your user research methodologies and data-driven approach.) Portfolio Presentation Strategy:

• Structure is Key: Organize your presentation logically. For each project, clearly state the problem, your role, your process, the solution, and the impact (with metrics).

• Narrative Arc: Tell a compelling story about your journey through each project, highlighting key decisions, challenges, and learnings.

• Focus on Impact: Quantify your contributions whenever possible. Use metrics from Pendo or other sources to demonstrate how your designs delivered business or customer value.

• Showcase AI Integration: Dedicate specific slides or talking points to your AI-driven design work. Explain the 'why' and 'how' of your AI usage.

• Be Prepared for Deep Dives: Anticipate detailed questions about your rationale, trade-offs, and how you handled specific design challenges or feedback.

📝 Enhancement Note: Interview preparation should focus on demonstrating strategic thinking, a data-driven approach, practical AI application, and strong collaboration skills. Candidates should be ready to articulate their process and impact with concrete examples.

📌 Application Steps

To apply for this Senior Product Designer II position:

• Submit your application through the provided Ashby link.

• Tailor Your Resume: Highlight your 8+ years of experience, emphasizing end-to-end project ownership, AI fluency, data-driven design, and cross-functional collaboration. Use keywords from the job description.

• Curate Your Portfolio: Select 2-3 of your strongest projects that showcase your ability to frame problems, lead complex initiatives autonomously, and demonstrate measurable impact. Ensure at least one project highlights your practical use of AI tools.

• Prepare Your Presentation: Practice walking through your portfolio projects, focusing on storytelling, quantifiable outcomes, and your design process. Be ready to discuss your rationale for key decisions and how you'd approach challenges.

• Research Wrapbook: Understand their product, mission, customer base, and their commitment to AI. Prepare thoughtful questions about the role, team, and company culture.

⚠️ 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.