Senior Product Designer at Fieldguide

📍 Job Overview

Job Title: Senior Product Designer

Company: Fieldguide

Location: United States

Job Type: FULL_TIME

Category: Product Design / GTM Operations Enabler

Date Posted: 2026-08-27

Experience Level: Senior (5-10 years)

Remote Status: Fully Remote

🚀 Role Summary

Lead end-to-end design for complex, ambiguous audit workflows, driving innovation in the assurance and audit practitioner space.
Partner deeply with Product and Engineering teams to influence product strategy, roadmaps, and deliver scalable, high-quality user experiences.
Integrate AI-assisted workflows and leverage AI in daily design practices to enhance auditor efficiency and product capabilities.
Own significant product areas and customer journeys, anticipating downstream impacts and ensuring a cohesive user experience across the platform.
Contribute to the design system, mentor junior designers, and act as a key voice in elevating design craft and standards within the organization.

📝 Enhancement Note: While the role is Senior Product Designer, its focus on automating audit workflows and enabling trust in financial and cybersecurity markets positions it as a critical enabler for Go-To-Market (GTM) and Revenue Operations by streamlining the processes that underpin business assurance. The emphasis on AI integration suggests a forward-thinking approach to product development that will likely impact operational efficiency and data integrity for Fieldguide's clients.

📈 Primary Responsibilities

Spearhead the complete design lifecycle for intricate and undefined audit-related workflows, from initial problem identification to the deployment of user-centric solutions.
Foster close collaboration with Product Management and Engineering to collaboratively define product strategy, influence the development roadmap, and ensure the successful delivery of robust, scalable, and user-friendly implementations.
Drive design execution with a high degree of autonomy, demonstrating effectiveness and adaptability within a rapidly evolving and often ambiguous startup environment.
Translate multifaceted customer needs, synthesized research insights, and strategic business objectives into clear and intuitive user journeys, interaction models, and polished user interface designs.
Maintain a critical balance between rapid iteration and development speed, while upholding high standards for usability, visual consistency, and long-term product integrity and maintainability.
Act as a strong advocate for the end-user's experience, meticulously considering and integrating technical feasibility, regulatory compliance, and overarching business imperatives into design decisions.
Take ownership of a substantial product segment or critical customer journey, proactively identifying and mitigating potential downstream impacts on related workflows, user personas, and overall platform functionality.
Establish and uphold a high benchmark for design quality and influence by actively contributing to the evolution of the design system, providing mentorship and constructive feedback to design peers, and serving as a respected and authoritative design resource within the company.

📝 Enhancement Note: The responsibilities highlight a need for a designer who can not only execute but also strategize and lead within a complex B2B SaaS environment. The emphasis on "ambiguous problem spaces" and "minimal direction" points to a role requiring significant initiative and strategic thinking, common in operations-adjacent product development where understanding underlying business processes is key.

🎓 Skills & Qualifications

Education: A Bachelor's or Master's degree in Design, Human-Computer Interaction, or a related field is typically expected, though equivalent practical experience will be strongly considered.

Experience: A minimum of 6 years of dedicated experience in a Product Design role, with a strong preference for candidates who have specialized in complex, B2B SaaS products.

Required Skills:

End-to-End Product Design: Proven track record of owning and delivering complex product features or entire workflows from conception to launch.
B2B SaaS Expertise: Deep understanding of the nuances and user needs specific to business-to-business software solutions.
AI-Assisted Workflow Design: Demonstrated experience in designing or incorporating AI-driven features, such as review assistance, summarization tools, or intelligent guidance within applications.
User Journey Mapping & Interaction Modeling: Ability to map out intricate user flows and define intuitive interaction patterns for complex tasks.
UI Design & Polish: Exceptional skill in creating visually appealing, consistent, and highly usable user interfaces.
System Thinking: Capacity to understand and design for interconnected systems, anticipating how changes in one area impact others.
Collaboration & Communication: Ability to partner effectively with Product Managers, Engineers, and other stakeholders, articulating design decisions clearly.
Problem Solving & Ambiguity Navigation: Proven ability to tackle ill-defined problems and drive solutions with minimal oversight in fast-paced settings.
Mentorship & Design Leadership: Experience in guiding and elevating the work of other designers through feedback and critique.

Preferred Skills:

Design System Contribution: Experience in developing, maintaining, or contributing to a comprehensive design system.
User Research & Synthesis: Proficiency in conducting user research and effectively synthesizing findings into actionable design insights.
Prototyping Proficiency: Advanced skills in creating interactive prototypes to test and communicate design concepts.
Agile Development Methodologies: Familiarity with agile development processes and iterative design cycles.
Domain Knowledge in Audit/Assurance/Cybersecurity: Prior exposure to or understanding of the audit, assurance, or cybersecurity industries.

📝 Enhancement Note: The requirement for "designing AI-assisted workflows" and "incorporating AI into your daily design practice" is a critical differentiator. This suggests that candidates with experience in operational efficiency tools, workflow automation, or data analysis platforms will be highly valued, as they can translate complex operational needs into intuitive AI-powered solutions.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

End-to-End Case Studies: Showcase 2-3 detailed case studies demonstrating ownership of complex, ambiguous problem spaces from initial research and ideation through to shipped solutions and post-launch iteration.
AI Integration Examples: Include specific examples or case studies where AI was leveraged to enhance user workflows, improve efficiency, or provide intelligent assistance. Highlight the problem, your design approach, and the impact.
B2B SaaS Focus: Prioritize projects that clearly illustrate experience with complex B2B SaaS products, showcasing an understanding of enterprise user needs and workflows.
Systemic Thinking: Demonstrate how you considered downstream impacts, cross-functional dependencies, and the broader product ecosystem in your design process.
Metrics & Impact: Quantify the impact of your design work whenever possible, using metrics related to user adoption, efficiency gains, task completion rates, or user satisfaction.

Process Documentation:

Problem Definition & Research: Clearly articulate the problem space, user needs, and business goals that guided your design decisions for each case study. Include any research methodologies employed.
Design Iteration & Decision Making: Detail the iterative process, including key design decisions, trade-offs made, and how feedback (user, stakeholder, technical) was incorporated.
Collaboration & Hand-off: Illustrate how you partnered with Product and Engineering, and detail your process for design hand-off and ongoing collaboration to ensure successful implementation.

📝 Enhancement Note: For a role emphasizing AI and complex workflows in a B2B SaaS context, the portfolio should strongly highlight a candidate's ability to not just create UIs but to architect efficient processes and leverage technology to solve business challenges. Demonstrating an understanding of how design impacts operational efficiency and data integrity for clients will be crucial.

💵 Compensation & Benefits

Salary Range: $130,000 - $160,000 per year.

Benefits:

Equity: Opportunity to own a stake in a rapidly growing startup.
Competitive Compensation: A strong base salary reflecting the seniority and impact of the role.
Health, Dental, and Vision Insurance: Comprehensive coverage for employees and their dependents.
401(k) Plan: Retirement savings plan to support long-term financial well-being.
Unlimited Paid Time Off (PTO): Encourages work-life balance and provides flexibility for personal needs.
Remote-First Work Environment: Support for remote work, including potential home office stipends.
Professional Development: Opportunities for continuous learning, training, and attending industry conferences.

Working Hours: This is a full-time position, typically requiring approximately 40 hours per week. Given the remote-first nature and the fast-paced startup environment, flexibility may be expected, but a focus on work-life balance is also promoted through policies like unlimited PTO.

📝 Enhancement Note: The salary range provided is within the typical range for a Senior Product Designer in the US tech market, especially for a remote role at a well-funded startup. The benefits package is standard for the industry, with "Unlimited PTO" and "Equity" being attractive components for senior talent in a growth-stage company.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology, specifically focused on SaaS solutions for assurance, audit, cybersecurity, and financial markets. Fieldguide is modernizing the trust economy by providing software that streamlines complex professional services.

Company Size: Fieldguide is a venture-backed startup, likely in the "early to growth stage," with a team size that allows for agility and direct impact. (Based on typical startup funding rounds and growth trajectories).

Founded: Founded in 2018, Fieldguide has a history of innovation and is backed by prominent investors, indicating a solid foundation and growth trajectory.

Team Structure:

The Audit product team is a core component of Fieldguide's offering.
The Senior Product Designer will report to the Director, Product Design, indicating a clear design leadership structure.
Close partnership with Product and Engineering is a defining characteristic of the team's operational model.
The company emphasizes a remote-first culture, fostering collaboration across distributed team members. Methodology:
Agile and Iterative Development: The team ships frequently and operates in tight loops, prioritizing rapid progress and continuous improvement.
AI Integration: A strong emphasis on incorporating AI into both the product and the design practice itself.
Customer-Centricity: Designs are driven by customer needs, research insights, and a deep understanding of auditor workflows.
Data-Driven Decision Making: While not explicitly stated for design, the company's focus on trust and finance implies a strong reliance on data for product development and operational analysis.

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

📝 Enhancement Note: The company's mission to "establish a new state of trust for global commerce" through technology is a powerful differentiator. For a product designer, this means working on solutions that have a tangible impact on critical business functions and professional services, requiring a blend of technical understanding and user empathy. The emphasis on AI suggests a forward-thinking approach to operational efficiency.

📈 Career & Growth Analysis

Operations Career Level: This role is designated as "Senior," indicating a high level of autonomy, responsibility, and the expectation of leadership within the design function. It's beyond an individual contributor role, requiring strategic input and the ability to influence product direction.

Reporting Structure: The Senior Product Designer will report directly to the Director, Product Design. This provides a clear line of mentorship and strategic alignment within the design department. Collaboration will be extensive with Product Managers and Engineering teams.

Operations Impact: The Senior Product Designer will have a significant impact on Fieldguide's core Audit product. By owning complex workflows and integrating AI, they will directly contribute to:

Customer Efficiency: Streamlining audit processes, saving practitioners time and resources.
Product Innovation: Driving the adoption of cutting-edge AI technology within the audit space.
Market Differentiation: Helping Fieldguide establish a competitive advantage through superior user experience and intelligent features.
Revenue Enablement: By improving the core product offering, the designer indirectly supports sales and customer success efforts.

Growth Opportunities:

Design Leadership: Potential to grow into a Lead Product Designer role, managing a specific product area or a team of designers.
Specialization: Deepen expertise in AI-assisted design, complex B2B SaaS product strategy, or specific domains like cybersecurity and financial assurance.
Cross-Functional Influence: Expand influence across product, engineering, and potentially even go-to-market teams through successful project delivery and strategic contributions.
Mentorship Development: Further hone leadership and mentorship skills by guiding junior designers and contributing to the overall design culture.

📝 Enhancement Note: This role offers substantial growth potential, particularly for those interested in the intersection of design, AI, and enterprise operations. The opportunity to shape a core product and contribute to a company mission focused on "trust" provides a unique career path.

🌐 Work Environment

Office Type: Fieldguide operates as a "remote-first" company. This means the primary work environment is virtual, with no requirement to be in a physical office.

Office Location(s): While based in San Francisco, CA, the company explicitly supports remote work across the United States. This allows employees to work from their preferred location within the country.

Workspace Context:

Remote Collaboration Tools: Expect to utilize a suite of digital collaboration tools (e.g., Slack, Zoom, Figma, Notion) for communication, design work, and project management.
Asynchronous Communication: The remote-first model often necessitates proficiency in asynchronous communication, ensuring clarity and context in written updates and documentation.
Flexible Work Arrangements: While core hours may exist for collaboration, remote work offers flexibility in structuring the workday to optimize personal productivity and work-life balance.
Design System & Tools: Access to Fieldguide's design system and a robust set of design and prototyping tools is essential for effective workflow.

Work Schedule: This is a full-time position, generally adhering to standard work weeks (approximately 40 hours). However, the remote-first nature and startup pace may allow for flexibility in daily scheduling, as long as collaboration needs are met and work is delivered effectively.

📝 Enhancement Note: The remote-first nature of Fieldguide is a significant aspect of its work environment. This setup requires strong self-discipline, excellent communication skills, and comfort with digital collaboration tools. It also presents an opportunity for designers to create their ideal workspace, free from traditional office constraints.

📄 Application & Portfolio Review Process

Interview Process:

Initial Screening: A brief call with a recruiter to assess basic qualifications, cultural fit, and interest in the role.
Design Portfolio Review: A dedicated session where candidates present their portfolio, focusing on 2-3 key case studies. Expect questions about your process, decision-making, impact, and experience with B2B SaaS and AI.
Hiring Manager Interview: A deeper dive with the Director, Product Design, to discuss design philosophy, leadership style, approach to complex problems, and mentorship capabilities.
Cross-functional Interviews: Meetings with Product Managers and Engineering leads to assess collaboration style, ability to influence roadmaps, and understanding of technical constraints.
Final Round/Executive Interview: Potentially a conversation with a senior leader to discuss strategic alignment, company vision, and long-term potential.

Portfolio Review Tips:

Tell a Story: Structure your case studies as narratives, clearly outlining the problem, your unique contribution, the process followed, the solution, and the measurable impact.
Highlight AI & B2B SaaS: Emphasize projects that showcase your experience with AI-assisted workflows and complex B2B SaaS environments. Be prepared to discuss how you integrated AI and addressed enterprise-level user needs.
Show, Don't Just Tell: Use visuals, prototypes, and clear diagrams to illustrate your design process and the final product.
Quantify Impact: Wherever possible, present data and metrics that demonstrate the success of your designs (e.g., increased efficiency, reduced errors, improved user satisfaction).
Be Prepared for Process Questions: Expect to be asked about your problem-solving methodology, how you handle ambiguity, your approach to collaboration, and how you give/receive feedback.

Challenge Preparation:

Design Exercise: You may be given a take-home design challenge or a live design exercise focused on a specific problem related to audit workflows or AI integration. Focus on demonstrating your process, problem-solving skills, and ability to think systemically.
AI Integration Strategy: Be ready to discuss how you would approach designing AI-assisted features for auditors, considering user trust, data privacy, and workflow disruption.
Stakeholder Management: Prepare to discuss how you would manage conflicting priorities or feedback from different stakeholders (Product, Engineering, Sales, Customers).

📝 Enhancement Note: The emphasis on AI and complex B2B SaaS workflows means that candidates should prepare to discuss not just UI/UX principles, but also how design can drive operational efficiency and integrate intelligent automation. Demonstrating an understanding of the audit domain, even at a high level, will be beneficial.

🛠 Tools & Technology Stack

Primary Tools:

Design & Prototyping: Figma is the industry standard and highly likely to be the primary tool for UI design, wireframing, and prototyping at Fieldguide.
Collaboration & Communication: Slack for real-time messaging and team communication; Zoom for video conferencing and virtual meetings.
Project Management & Documentation: Tools like Notion, Asana, Jira, or similar platforms are likely used for project tracking, roadmap planning, and documentation.
Design System Management: Tools or processes for managing and contributing to the company's design system.

Analytics & Reporting:

While not directly used by designers for daily tasks, understanding how product analytics tools (e.g., Amplitude, Mixpanel, Google Analytics) are used to measure product performance and user behavior is beneficial. This informs design decisions and impact assessment. CRM & Automation:
Fieldguide's clients likely use CRMs, and the company itself might leverage CRM systems for sales and customer success. While not a direct design tool, awareness of how these systems function and integrate is helpful for understanding the broader business context.

📝 Enhancement Note: Proficiency in Figma is almost certainly a prerequisite. Beyond that, demonstrating adaptability to other collaboration and project management tools common in remote, agile environments is key. A designer's ability to leverage data (even if indirectly) to inform design decisions will be highly valued.

👥 Team Culture & Values

Operations Values:

Drive & Velocity: A strong emphasis on moving fast, shipping frequently, and making progress amidst ambiguity. This requires initiative and a results-oriented mindset.
Craft & Quality: While speed is important, there's an equal value placed on usability, consistency, and long-term product quality.
Customer Focus: Deeply understanding customer needs and using research to inform design decisions is paramount.
Collaboration & Support: A culture that values teamwork, mutual support, and collective growth, even in a remote setting.
Humility & Self-Reflection: A commitment to continuous improvement, both individually and as a team, by being deliberate and reflective.
Inclusivity: Valuing diversity in backgrounds and experiences as a strength for building a better product and team.

Collaboration Style:

Cross-functional Partnership: Seamless collaboration between Design, Product, and Engineering is essential for rapid iteration and successful product development.
Remote Collaboration: Expect a highly digital and asynchronous collaboration style, leveraging tools to maintain connection and clarity across distributed team members.
Feedback Culture: A willingness to give and receive constructive feedback is crucial for elevating craft and ensuring product quality.
Influence & Advocacy: Designers are expected to advocate for user needs and design best practices, influencing product direction through reasoned arguments and strong work.

📝 Enhancement Note: The company culture emphasizes a blend of high performance, collaborative spirit, and a commitment to building a positive and inclusive remote environment. For a designer, this means being proactive, communicative, and open to feedback while contributing to a mission-driven organization.

⚡ Challenges & Growth Opportunities

Challenges:

Designing for Ambiguity: Navigating complex, undefined problem spaces in the audit domain requires strong analytical and problem-solving skills.
Balancing Speed and Craft: Operating at a startup's rapid pace while maintaining high design standards for usability and polish.
Integrating AI Effectively: Designing AI-assisted workflows that are genuinely helpful, trustworthy, and seamlessly integrated into user processes without causing disruption.
Cross-functional Alignment: Ensuring consistent vision and execution across Design, Product, and Engineering, especially in a remote setting.
Domain Complexity: Understanding the intricacies of audit, cybersecurity, and financial assurance processes to design effective solutions.

Learning & Development Opportunities:

AI in Design Specialization: Deepen expertise in how AI can be leveraged to enhance user experiences and operational efficiency.
Complex B2B SaaS Strategy: Gain extensive experience in shaping product strategy for enterprise-level software.
Product Leadership: Develop leadership skills through mentorship, owning critical product areas, and influencing the product roadmap.
Industry Exposure: Learn about the audit and assurance industry, understanding the critical role Fieldguide plays in enabling trust.
Remote Work Best Practices: Master effective communication and collaboration strategies for a distributed team environment.

📝 Enhancement Note: The challenges presented are typical for a senior role in a fast-growing, innovative startup. The growth opportunities are significant, especially for a designer looking to specialize in AI-driven product development and gain experience in a mission-critical B2B SaaS sector.

💡 Interview Preparation

Strategy Questions:

"Describe a complex, ambiguous problem space you tackled end-to-end. What was your process, and what was the outcome?" (Focus on your systematic approach, user empathy, and measurable impact.)
"How do you approach designing AI-assisted workflows to ensure they are helpful and trustworthy for users, rather than disruptive?" (Prepare to discuss user trust, data privacy, and integration strategies.)
"How do you balance the need for speed and iteration in a startup with the importance of usability, consistency, and long-term product quality?" (Highlight your ability to make pragmatic trade-offs and maintain high standards.)
"Tell us about a time you influenced product strategy or roadmaps through your design work. What was your approach to convincing stakeholders?" (Showcase your strategic thinking and communication skills.) Company & Culture Questions:
"What interests you about Fieldguide's mission to establish a new state of trust for global commerce and capital markets?" (Connect your values and career aspirations to the company's mission.)
"How do you contribute to a positive and collaborative team culture, especially in a remote environment?" (Emphasize your teamwork, communication, and mentorship abilities.)
"How do you incorporate user research and customer feedback into your design process?" (Demonstrate your user-centric approach.)
"What are your thoughts on the role of AI in modernizing audit and assurance workflows?" (Show your understanding of the industry and Fieldguide's technological direction.) Portfolio Presentation Strategy:
Focus on Impact: For each case study, clearly articulate the problem, your role, the process, the solution, and most importantly, the measurable impact of your design.
Showcase AI & B2B SaaS: Ensure your presented projects highlight your experience with AI integration and complex B2B SaaS products. Be ready to discuss the specific challenges and solutions related to these areas.
Explain Your 'Why': Be prepared to articulate the rationale behind your design decisions at each stage of the process.
Demonstrate Process: Walk through your design process, including research, ideation, prototyping, testing, and iteration. Use visuals to support your narrative.
Be Ready for Deep Dives: Expect detailed questions about your contributions, challenges faced, and how you collaborated with Product and Engineering.

📝 Enhancement Note: Candidates should prepare to discuss their experience with AI not just as a feature, but as a tool to drive operational efficiency and user value. Demonstrating an understanding of how design impacts business outcomes and client trust will be critical.

📌 Application Steps

To apply for this Senior Product Designer position:

Submit your application through the provided link on Ashby.
Tailor Your Resume: Highlight experience in B2B SaaS, complex workflow design, AI integration, and end-to-end product ownership. Quantify achievements where possible.
Curate Your Portfolio: Select 2-3 strong case studies that best demonstrate your skills in designing for complex, ambiguous B2B SaaS problems, with a clear emphasis on any AI-assisted workflow experience. Ensure your portfolio tells a compelling story of problem, process, solution, and impact.
Prepare Your Presentation: Practice presenting your portfolio case studies, focusing on clarity, conciseness, and highlighting your strategic thinking, design process, and the measurable outcomes of your work. Be ready to discuss AI integration in detail.
Research Fieldguide: Understand the company's mission, product, and the challenges faced by audit practitioners. Familiarize yourself with their values and remote-first 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.

Senior Product Designer