Senior Product Designer

📍 Job Overview

Job Title: Senior Product Designer
Company: Advocate Technologies
Location: New York, New York, US
Job Type: CONTRACTOR
Category: Product Design / GTM Operations
Date Posted: 2026-01-09T11:11:51.718
Experience Level: 3-5 years
Remote Status: Hybrid (2 days/week in office)

🚀 Role Summary

• This role is pivotal in designing and enhancing the core product used by internal review teams and external customers for insurance compliance verification in real estate and business loans.
• Focuses on optimizing workflows, strengthening systems thinking, and delivering a high-quality user interface (UI) within a domain that has significant real-world consequences.
• Emphasizes a "make it work, then make it excellent" mentality, offering significant ownership and direct influence on the product roadmap and development priorities.
• Involves rapid prototyping, including leveraging AI-assisted workflows, to expedite solution exploration and validation.

📝 Enhancement Note: While the title is "Product Designer," the description's emphasis on "workflow design," "systems thinking," "data-heavy, decision-driven interfaces," and "assurance compliance review" indicates a strong alignment with GTM Operations and Revenue Operations principles. The role requires designing operational efficiency within the product itself, impacting how sales and compliance teams function. This suggests a need for candidates who can bridge product design with operational effectiveness.

📈 Primary Responsibilities

• Design end-to-end workflows to accelerate and improve the efficiency of insurance compliance reviews for loans.
• Develop data-heavy, decision-driven interfaces that empower users to make high-confidence decisions efficiently.
• Rapidly prototype solutions, incorporating AI-assisted workflows, to explore and validate design concepts within compressed timelines.
• Collaborate closely with Product Management and Engineering teams to define project scope, manage tradeoffs, and ensure successful product shipment.
• Conduct user research, including scrappy discovery and usability evaluations, to gather insights and pressure-test design decisions with real users.
• Contribute to the development and evolution of Advocate's established design system, "Tyche," ensuring consistency and scalability as the product grows.
• Partner with internal review teams and external customers to understand their challenges and translate needs into effective product solutions.
• Analyze and optimize existing processes within the product to enhance operational throughput and accuracy for insurance compliance.

📝 Enhancement Note: The responsibilities highlight a blend of user-centered design and operational process improvement. The emphasis on "end-to-end workflows," "data-heavy interfaces," and "pressure-test decisions with real users" points to a need for a designer who can think about efficiency, scalability, and the operational impact of design choices, aligning with GTM and RevOps objectives.

🎓 Skills & Qualifications

Education: Bachelor's degree in Design, Human-Computer Interaction, Computer Science, or a related field, or equivalent practical experience.
Experience: 3-5 years of professional experience in product design, with a proven track record of building and shipping successful products.

Required Skills:

• Strong craft and judgment in design, with a focus on shipping high-quality work efficiently.
• T-shaped skillset: demonstrating breadth across product design disciplines (e.g., UX, UI, interaction design) and depth in at least one area (e.g., design systems, complex interaction design, data visualization, advanced prototyping).
• Ability to thrive in ambiguous environments and tackle 0-to-1 problem spaces.
• Demonstrated ability to influence product direction and strategy, rather than solely executing assigned tasks.
• Proficiency in end-to-end workflow design, focusing on operational efficiency and user experience.
• Experience with data-heavy and decision-driven interface design.
• Skill in rapid prototyping, including experience with AI-assisted design tools.
• Experience conducting user research, including discovery, usability testing, and feedback synthesis.
• Ability to collaborate effectively with cross-functional teams including Product Management and Engineering.
• Familiarity with design systems and contributing to their evolution.

Preferred Skills:

• Experience in Fintech, Insurtech, or designing for regulated workflows.
• Experience specifically designing data products or complex analytical interfaces.
• Familiarity with Agile development methodologies and working within a product-led organization.
• Experience with A/B testing and data-driven design iteration.
• Knowledge of business loan or real estate compliance processes.

📝 Enhancement Note: The "3-5 years experience" suggests a mid-level to senior individual contributor role. The "T-shaped skillset" and "ability to influence product direction" indicate a need for someone who can operate with autonomy and strategic thinking, essential for driving operational improvements through design. The bonus points for Fintech/Insurtech are highly relevant to the domain.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase end-to-end product design projects that demonstrate your process from problem identification to shipped solution.
• Include case studies that highlight your approach to designing complex workflows and data-intensive interfaces.
• Demonstrate how you have contributed to or leveraged design systems to ensure consistency and scalability.
• Present examples of rapid prototyping, particularly any use of AI tools or accelerated validation methods.
• Clearly articulate your role in influencing product strategy and decision-making within projects.

Process Documentation:

• Detail your methodology for conducting user research, including scrappy discovery and usability evaluations.
• Explain your process for collaborating with Product and Engineering teams, including how you manage scope and tradeoffs.
• Illustrate your approach to iterating on designs based on user feedback and data.
• Provide examples of how you've translated complex business logic or regulatory requirements into intuitive user experiences.

📝 Enhancement Note: For a role focused on operational efficiency within a product, the portfolio should emphasize the impact of the design on workflows, speed, and confidence. Candidates should be prepared to discuss not just the UI, but the underlying process improvements their designs enabled.

💵 Compensation & Benefits

Salary Range: For a Senior Product Designer role in New York, NY, with 3-5 years of experience, the estimated salary range is typically between $120,000 - $170,000 annually for full-time employees. As this is a contractor role, the hourly rate would likely fall between $60 - $90 per hour, depending on experience and negotiation.

Benefits:

• Employee stock options.
• Health benefits including standard coverage.
• Wellness programs and support.
• Work-from-home stipend.
• Generous Paid Time Off (PTO): 18 days annually, plus local public holidays.
• Paid parental leave.
• Learning & development budget for professional growth.
• Team events and social activities.

Working Hours: Standard 40-hour work week, with flexibility expected to meet project deadlines and collaboration needs.

📝 Enhancement Note: The salary range is an estimate for a comparable full-time role in New York City, as contractor rates can vary significantly based on contract length, benefits inclusion, and specific agency markups. The provided benefits are explicitly listed in the job description.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology, specifically focused on Fintech/Insurtech solutions for loan compliance verification. Advocate Technologies aims to streamline and enhance critical processes within the financial services sector.
Company Size: Advocate Technologies appears to be a growing startup or scale-up, indicated by the "small, nimble design team" and the emphasis on product-led growth. This size suggests an environment where individual contributions have a significant impact and cross-functional collaboration is frequent.
Founded: While the founding date is not specified, the company's focus on modernizing compliance verification suggests it is likely a relatively recent venture or one undergoing significant digital transformation.

Team Structure:

• The design team is described as "small and nimble," implying close-knit collaboration and shared responsibility.
• Design is involved early in the product development lifecycle, indicating a high level of integration with Product and Engineering.
• The organization is "product-led," meaning design and product strategy drive business decisions.
• Cross-functional collaboration is expected to be high, with designers partnering closely with Product Managers and Engineers.

Methodology:

• Advocate Technologies employs a product-led growth strategy, prioritizing user experience and product value.
• Design quality is paramount, with a standard of "high bar or it doesn't ship."
• The team utilizes a mix of established and emerging tools, including Figma for design, Linear for project management, and potentially AI tools for prototyping and ideation.
• Research is integrated into the design process, focusing on scrappy discovery and usability evaluations.

Company Website: tryadvocate.com

📝 Enhancement Note: The company's focus on "insurance compliance for real estate and business loans" places it within a critical but often complex and regulated part of the financial industry. This context is important for understanding the design challenges and the potential for operational improvement through their product.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a Senior Product Designer, indicating a level of experience and autonomy above a standard Product Designer. It requires not just execution but also strategic input, problem-solving in ambiguous areas, and influencing product direction. This level is crucial for driving operational efficiency through design.
Reporting Structure: While not explicitly stated, a Senior Product Designer typically reports to a Head of Design, Design Manager, or potentially a Chief Product Officer in a smaller organization. They would work closely with Product Managers and Engineering Leads.
Operations Impact: The Senior Product Designer will have a direct impact on the operational efficiency of Advocate's clients and internal teams by designing workflows that reduce time, increase confidence, and improve audit trails for insurance compliance. This translates to tangible business value by streamlining a critical but often manual process.

Growth Opportunities:

• Specialization: Deepen expertise in designing for regulated industries (Fintech/Insurtech), complex data visualization, or design systems.
• Leadership: Potential to grow into a Lead Product Designer role, mentoring junior designers and taking ownership of larger product areas or strategic initiatives.
• Strategic Influence: Increased involvement in product strategy, roadmap planning, and cross-functional leadership.
• Skill Development: Utilize the learning & development budget to attend conferences, take courses, or gain certifications relevant to product design, UX research, or specific industry domains.

📝 Enhancement Note: The "Senior" title and the emphasis on influencing product direction suggest that this role is more than just an individual contributor; it's an opportunity to shape how operations are executed within a key industry through product design.

🌐 Work Environment

Office Type: Hybrid work environment, requiring 2 days per week in the New York office. This suggests a blend of focused individual work and collaborative team interaction.
Office Location(s): New York, New York, US. Specific office details are not provided but would be available upon inquiry.

Workspace Context:

• The office environment is designed to foster collaboration between design, product, and engineering teams.
• Access to a set of modern design and collaboration tools, including Figma, Linear, Fibery, Fellow, Cursor, ChatGPT, Storybook, and Slack.
• The design system "Tyche" is actively used, providing a foundation for consistent and efficient UI development.
• Opportunities for direct interaction with team members to discuss design challenges, brainstorm solutions, and receive feedback.

Work Schedule: The role implies a standard 40-hour work week, typical for a contractor position. However, given the startup environment and the nature of product development, flexibility may be required to meet project milestones and critical deadlines.

📝 Enhancement Note: The hybrid model indicates a company culture that values both in-person collaboration and the flexibility of remote work, a common setup for tech companies in major urban centers like New York.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A brief call with a recruiter or hiring manager to assess basic qualifications, experience, and cultural fit.
• Portfolio Review: Presentation of your design portfolio to the hiring team. This is a critical stage where you'll walk through case studies, emphasizing your process, problem-solving skills, and impact.
• Design Exercise/Challenge: Likely a take-home assignment or a live design critique/problem-solving session focused on a specific product challenge related to workflow design, data interfaces, or compliance processes.
• Cross-functional Interviews: Meetings with Product Managers, Engineers, and potentially other stakeholders to assess collaboration skills, systems thinking, and ability to influence product direction.
• Final Interview: Potentially with a senior leader to discuss strategic alignment and long-term vision.

Portfolio Review Tips:

• Focus on Impact: For each case study, clearly articulate the problem, your role, your design process, the solutions you proposed, and the measurable outcomes or impact (e.g., improved efficiency, reduced errors, increased user confidence).
• Workflow & Data Emphasis: Highlight projects that showcase your ability to design complex workflows and data-heavy interfaces, as this is central to the role.
• Process & Rationale: Be prepared to explain why you made specific design decisions, referencing user research, business goals, and technical constraints.
• Design System Contribution: If applicable, showcase how you've contributed to or utilized design systems effectively.
• AI Tool Integration: If you have experience with AI-assisted workflows or prototyping, be ready to discuss how you leveraged these tools.
• Conciseness: Aim for 2-3 in-depth case studies that best represent your relevant skills.

Challenge Preparation:

• Understand the Domain: Research Fintech, Insurtech, and the challenges of insurance compliance verification in real estate and business loans.
• Emphasize Process: For any design challenge, focus on how your solution improves efficiency, accuracy, and user confidence in the compliance workflow.
• Systems Thinking: Be prepared to discuss how your proposed solution integrates with existing systems and workflows.
• Tradeoff Discussion: Practice articulating the tradeoffs involved in design decisions and how you would prioritize features.

📝 Enhancement Note: The emphasis on "make it work, then make it excellent" and "shipping crisp UI into a domain with real consequences" suggests that the interview process will heavily scrutinize practical application, process rigor, and the ability to deliver functional, high-impact designs.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The primary design tool for creating wireframes, mockups, and interactive prototypes. Proficiency is essential.
• Linear: Used for project management and issue tracking, indicating an agile development workflow. Familiarity with modern project management tools is beneficial.
• Fibery / Fellow / Cursor: These tools suggest a focus on collaborative knowledge management, meeting facilitation, and potentially code-based design workflows.
• ChatGPT: Explicitly mentioned for AI-assisted workflows, indicating an interest in leveraging AI for design exploration and ideation.

Analytics & Reporting:

• While not explicitly listed, expect to work with product analytics tools (e.g., Amplitude, Mixpanel, Google Analytics) to understand user behavior and inform design decisions.
• Familiarity with data visualization principles will be key for designing data-heavy interfaces.

CRM & Automation:

• While not directly a CRM role, understanding how product design impacts customer workflows (potentially related to sales or compliance processes managed via CRM) is valuable.
• Experience with tools that facilitate workflow automation within products is a plus.
• Storybook: Used for UI component development and documentation, indicating a strong component-based design system approach.
• Slack: The primary communication tool for team collaboration.

📝 Enhancement Note: The explicit mention of Figma, Linear, and ChatGPT highlights the core technology stack. Proficiency in Figma is non-negotiable. Experience with or openness to AI-assisted design tools is a significant advantage.

👥 Team Culture & Values

Operations Values:

• Quality & Excellence: A commitment to "high standards" and ensuring work "meets a high bar—or it doesn’t ship." This reflects a dedication to delivering robust, high-quality solutions.
• Efficiency & Speed: The role emphasizes "faster, with higher confidence," and "prototype quickly... in hours/days, not weeks," highlighting a value placed on operational efficiency and agile development.
• Ownership & Impact: Designers are expected to have "real ownership and direct influence on what we build next," fostering a culture where individuals are empowered to shape the product.
• Collaboration & Partnership: Close partnership with Product and Engineering is a core expectation, underscoring the importance of teamwork and shared goals.
• Data-Driven Decisions: The role involves working with "data-heavy, decision-driven interfaces" and using "research when it matters," indicating a reliance on data and user insights.

Collaboration Style:

• Integrated Teams: Designers work closely with Product Managers and Engineers from early stages of product development.
• Iterative Design: The process involves rapid prototyping, user research, and continuous iteration based on feedback and data.
• Open Communication: Tools like Slack and potentially Fibery/Fellow suggest a culture of open communication and knowledge sharing.
• Cross-functional Influence: Designers are encouraged to influence product direction, fostering a collaborative environment where design insights are valued across departments.

📝 Enhancement Note: The company's emphasis on "make it work, then make it excellent" and a "high bar" for shipping suggests a culture that balances speed with quality, a crucial aspect for operational technology where reliability is key.

⚡ Challenges & Growth Opportunities

Challenges:

• Complex Domain: Navigating the intricacies of insurance compliance in real estate and business loans, which involves regulated workflows and potentially complex legal/financial requirements.
• Data-Intensive Interfaces: Designing intuitive experiences for data-heavy UIs that require users to make high-confidence decisions.
• Balancing Speed and Quality: Meeting the demand for rapid prototyping and iteration while maintaining a high standard of design quality and product polish.
• 0-to-1 Problem Spaces: Tackling new product areas or features where established patterns may not exist, requiring significant research and strategic thinking.
• Influencing Product Strategy: Effectively advocating for design-led solutions and influencing the product roadmap in a product-led organization.

Learning & Development Opportunities:

• Domain Expertise: Gain deep knowledge in Fintech and Insurtech, specifically in loan compliance processes.
• Advanced Design Skills: Develop expertise in data visualization, complex workflow design, and leveraging AI in design.
• Strategic Product Development: Grow in understanding product strategy, roadmap planning, and cross-functional leadership within a startup environment.
• Design Systems: Contribute to and expand a growing design system, learning best practices for scalable UI design.
• Mentorship: Opportunity to learn from experienced product and engineering leaders within a nimble team.

📝 Enhancement Note: The challenges are directly tied to the role's core responsibilities and the company's industry, offering significant opportunities for professional growth and skill development in specialized areas.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you designed an end-to-end workflow. What were the key challenges, and how did your design improve efficiency or outcomes?" (Focus on process, impact, and problem-solving).
• "How would you approach designing a data-heavy interface for users who need to make high-confidence decisions? Walk us through your process and considerations." (Emphasize data visualization, UI clarity, and decision support).
• "Tell us about a time you had to make significant tradeoffs on a product feature. How did you balance user needs, business goals, and technical constraints?" (Demonstrate strategic thinking and negotiation skills).
• "How do you integrate user research into your design process, especially in a fast-paced environment?" (Highlight scrappy discovery, usability testing, and iterative feedback loops).

Company & Culture Questions:

• "What interests you about Advocate Technologies and our mission to improve insurance compliance verification?" (Research company, industry, and value proposition).
• "How do you see your design skills contributing to a 'product-led' organization like ours?" (Connect your experience to their strategy).
• "Describe your experience working with design systems. How do you balance consistency with the need for innovation?" (Discuss your approach to design systems and their role in scalability).
• "How do you collaborate with Product Managers and Engineers to ensure successful product launches?" (Provide examples of cross-functional teamwork).

Portfolio Presentation Strategy:

• Structure: Begin with a high-level overview of your career and design philosophy, then dive into 2-3 detailed case studies.
• Storytelling: For each case study, frame it as a narrative: the problem, your role, the process (research, ideation, iteration), the solution, and the impact.
• Quantify Impact: Whenever possible, use metrics to demonstrate the success of your designs (e.g., "reduced review time by X%", "increased user confidence scores by Y%", "improved error rate by Z%").
• Process Rationale: Be ready to explain why you made specific choices, referencing user needs, business objectives, and your own design expertise.
• Tooling: Briefly mention the tools used (Figma, AI tools, etc.) but focus more on the process and outcomes.

📝 Enhancement Note: Given the emphasis on "make it work, then make it excellent," interviewers will likely probe deeply into your process, your ability to handle ambiguity, and your direct impact on shipped products. Be prepared to defend your design decisions with clear rationale.

📌 Application Steps

To apply for this operations-aligned product design position:

• Submit your application through the provided link on rippling.com.
• Tailor Your Resume: Highlight experience in workflow design, data-heavy interfaces, Fintech/Insurtech, and your 3-5 years of product design experience. Use keywords from the job description such as "workflow design," "systems thinking," "data-heavy UI," and "user research."
• Curate Your Portfolio: Select 2-3 projects that best showcase your ability to design complex workflows, data-intensive interfaces, and your impact on product efficiency. Ensure each case study clearly outlines the problem, your process, and measurable outcomes.
• Prepare Your Narrative: Practice articulating your design process, decision-making rationale, and how you collaborate with cross-functional teams. Be ready to discuss your experience with design systems and rapid prototyping, including any use of AI tools.
• Research Advocate Technologies: Understand their mission, the industry they serve (Fintech/Insurtech, loan compliance), and their product-led approach to better align your application and interview responses.

⚠️ 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.