Head of Design

About Fieldguide

‍Fieldguide is an automation and collaboration platform for modern assurance and advisory firms that digitizes the end-to-end engagement workflow on a single platform. Built by former Big Four practitioners and experienced technology leaders, Fieldguide is trusted by top CPA firms to improve margins, win new business, and build stronger client relationships. 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, Y Combinator, Floodgate, Elad Gil, Justin Kan, Qasar Younis, Eric Ries, and more.

About the role

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

We greatly value learning and invest in our team members. As we build the company together, we’ll map your professional interests and goals to ensure you’re learning not only how to be a better engineer, but also growing towards your ideal role in the future.

Fieldguide is committed to building a diverse and inclusive company that celebrates individuals of all backgrounds. We’re an equal opportunity employer and encourage all applicants.