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Head of Design

About Us:

Fieldguide is establishing a new state of trust for global commerce and capital markets through automating and streamlining the work of assurance and audit practitioners specifically within cybersecurity, privacy, and ESG (Environmental, Social, Governance). Put simply, we build software for the people who enable trust between businesses.

We’re based in San Francisco, CA, but built as a remote-first company that enables you to do your best work from anywhere. We're backed by top investors including Bessemer Venture Partners, 8VC, Floodgate, Y Combinator, DNX Ventures, Global Founders Capital, Justin Kan, Elad Gil, and more.

We value diversity — in backgrounds and in experiences. We need people from all backgrounds and walks of life to help build the future of audit and advisory. Fieldguide’s team is inclusive, driven, humble and supportive. We are deliberate and self-reflective about the kind of team and culture that we are building, seeking teammates that are not only strong in their own aptitudes but care deeply about supporting each other's growth.

As an early stage start-up employee, you’ll have the opportunity to build out the future of business trust. We make audit practitioners’ lives easier by eliminating up to 50% of their work and giving them better work-life balance. If you share our values and enthusiasm for building a great culture and product, you will find a home at Fieldguide.

About the Role

We're seeking a transformative Head of Design to lead our design team and drive innovation in the future of audit and advisory software. As our first design leader, you'll play a crucial role in shaping the product experience for audit practitioners, focusing on creating solutions that dramatically reduce administrative effort and enhance operational efficiency. This is a unique opportunity to be a design thought leader and transform the way work is done in a legacy industry.

Why Fieldguide?

  • Be the first design leader at a fast-growing, Series B SaaS startup.

  • Drive new bets and bold design moves that will transform an entire industry.

  • Shape the design culture and brand at a company that values design beyond aesthetics.

  • Join a team building solutions for a legacy industry ripe for innovation, with a focus on Agentic AI and user-centric problem solving.

What You’ll Do

  • Lead and mentor a growing design team, taking a player-coach approach

  • Drive design strategy across multiple product areas, including core audit experiences, AI-driven insights, and emerging product lines

  • Establish a design culture that prioritizes business impact, user research, and continuous innovation

  • Collaborate closely with Product, Engineering, and Executive Leadership to align design vision with strategic goals

  • Develop design systems and frameworks that enable rapid iteration and scalable solutions

  • Balance user experience optimization with automation and effort reduction

  • Guide user research, usability testing, and design iteration processes

  • Act as a key voice in executive discussions, advocating for user insights and design-led product development

Who You Are

  • 10+ years in Product Design, with 3+ years of design leadership experience

  • Proven experience leading multidisciplinary design teams in a fast-paced, high-growth environment.

  • Strong portfolio demonstrating expertise in product design, visual design, and design systems in enterprise B2B SaaS design, particularly in complex workflow-driven products.

  • Experience collaborating with cross-functional teams including product, engineering, and marketing.

  • Ability to blend strategic thinking with hands-on design execution

  • Strong understanding of design thinking and user-centered design principles.

  • Passion for leading and mentoring designers at all levels.

  • Excellent communication and presentation skills.

Bonus Points

  • Experience in vertical SaaS

  • Expertise in designing for generative AI products

  • Knowledge of accounting or audit-adjacent industries

More about Fieldguide:

Fieldguide is a values-based company. Our values are:

  • Fearless - Inspire & break down seemingly impossible walls.

  • Fast - Launch fast with excellence, iterate to perfection.

  • Lovable - Deliver happiness & 11 star experiences.

  • Owners - Execute & run the business with ownership.

  • Win-win - Create mutual value & earn trust for life.

  • Inclusive - Scale the best ideas with inclusive teams.

Some of our benefits include:

  • Competitive compensation packages with meaningful ownership

  • Unlimited PTO

  • 401k

  • Wellness benefits, including a bundle of free therapy sessions

  • Technology & Work from Home reimbursement

  • Flexible work schedules

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Average salary estimate

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$120000K
$160000K

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What You Should Know About Head of Design, Fieldguide

At Fieldguide, we're on a mission to redefine the landscape of audit and advisory software, and we're seeking an innovative Head of Design to join our talented team in San Francisco. As the first design leader in our fast-growing Series B SaaS startup, you will play a pivotal role in transforming the way audit practitioners work by creating user-centric solutions that significantly reduce administrative workloads. With a remote-first approach, Fieldguide fosters an inclusive culture where your ideas can thrive. Here, your creativity will not only shape our design culture but also set trends in the industry. You'll lead and mentor a passionate design team, driving strategy across various product areas that aim for operational efficiency and enhanced user experiences. Your expertise in enterprise design will guide our product development towards reducing complexity and elevating usability. Collaborating with cross-functional teams, including Product and Engineering, you'll champion user insights and design-led solutions to achieve our strategic goals. This position provides an exciting opportunity to innovate in a legacy industry, particularly in the realms of Agentic AI and design systems. If you're looking for a role where your contributions genuinely matter and where you can help cultivate a culture of fearless and thoughtful design, Fieldguide might be the perfect fit for you. Join us in our quest to make the world of audit more accessible and efficient for everyone.

Frequently Asked Questions (FAQs) for Head of Design Role at Fieldguide
What are the main responsibilities of the Head of Design at Fieldguide?

The Head of Design at Fieldguide will lead and mentor a growing design team and drive design strategy across multiple product areas. You'll establish a design culture that prioritizes user experience, collaborate closely with Product and Engineering on aligning design vision with strategic goals, and guide the user research and design iteration processes. Your focus will be on enhancing operational efficiency for audit practitioners.

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What qualifications are required for the Head of Design position at Fieldguide?

To excel in the Head of Design role at Fieldguide, candidates should have over 10 years of experience in Product Design, including at least 3 years in design leadership. A strong portfolio showcasing expertise in product design, visual design, and design systems, particularly in B2B SaaS environments, is essential. The ideal candidate will also demonstrate experience in collaborating with cross-functional teams.

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How does Fieldguide prioritize design in its product development?

Fieldguide prioritizes design by establishing a culture that values user research and continuous innovation. As the Head of Design, you will act as a key voice in executive discussions, advocating for user insights and design-led product development. This focus extends to developing design systems that enable rapid iteration and scalable solutions to create business impact.

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What type of work environment can I expect as the Head of Design at Fieldguide?

Fieldguide offers a remote-first work environment, allowing you to work from anywhere while being part of a collaborative team. This inclusive atmosphere encourages creative expression and supports your professional growth, making it an ideal place for a design leader to thrive and drive impactful change.

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What are the growth opportunities for the Head of Design at Fieldguide?

As the Head of Design at Fieldguide, you will have numerous growth opportunities, including shaping the design culture and influencing product strategy in a fast-moving startup. You'll be positioned to drive design innovation across various product lines, allowing you to lead transformative initiatives in a legacy industry and create significant impacts within the organization.

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Common Interview Questions for Head of Design
How have you led design teams in fast-paced environments?

When answering this question, focus on specific strategies you’ve used to lead design teams effectively under pressure. Discuss methods like agile design principles, fostering open communication, and promoting a collaborative atmosphere. Highlight any tools or frameworks you've implemented that encourage rapid iteration while ensuring quality.

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Can you provide an example of a product design project you led from conception to launch?

In your response, share a detailed overview of a project where you oversaw the design process from beginning to end. Detail your role, the challenges you faced, how you collaborated with cross-functional teams, and the impact the final product had on users and the company.

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Describe your approach to user research and usability testing.

Discuss your methodologies for conducting user research, including how you identify target users, formulate questions, and apply findings to influence design decisions. Outline your process for usability testing, ensuring to mention how you iteratively improve designs based on user feedback.

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How do you balance user experience with business goals?

Explain how you approach finding the middle ground between outstanding user experiences and meeting business objectives. Share examples of how you’ve successfully implemented designs that not only prioritize users but also align with strategic business outcomes.

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What design frameworks have you used, and how do they benefit your team?

Provide insights into any design frameworks you have utilized, such as Atomic Design or Design Thinking. Discuss how these models guide your design processes, help maintain consistency, and enable teams to collaborate more effectively on projects.

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What is your philosophy on mentoring junior designers?

Share your views on the significance of mentorship in design. Talk about how you have previously supported junior designers through regular check-ins, structured feedback, and encouraging them to explore their creativity while learning from their experiences.

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How do you keep up with design trends and industry innovations?

Demonstrate your commitment to professional development by discussing how you stay informed about the latest design trends, tools, and techniques. This could include attending design conferences, participating in workshops, or engaging with industry communities online.

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What experience do you have with generative AI in design?

Share specific experiences where you've integrated generative AI technologies into your design process. Explain the benefits and challenges you faced and how they influenced your overall design strategy, particularly in enhancing user experiences.

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Can you explain how you would establish a design culture at Fieldguide?

Outline your vision for creating a design culture that emphasizes collaboration, innovation, and user-centered design. Discuss initiatives you would implement, such as regular design critiques, workshops, and fostering cross-functional team partnerships.

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What role do design systems play in your projects?

Discuss the critical role design systems play in ensuring consistency, scalability, and efficiency in your design projects. Highlight examples where you've developed or utilized design systems to streamline design workflows and improve collaboration among team members.

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DATE POSTED
April 9, 2025

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