Head of Design

Summary

Join Fieldguide, a Series B SaaS startup, as their first Head of Design to lead and mentor a growing design team. You will drive design strategy across multiple product areas, focusing on creating solutions that dramatically reduce administrative effort and enhance operational efficiency for audit practitioners. This role requires a player-coach approach, establishing a design culture that prioritizes business impact, user research, and continuous innovation. You will collaborate closely with various teams and act as a key voice in executive discussions. This is a unique opportunity to be a design thought leader and transform the way work is done in a legacy industry. Fieldguide offers competitive compensation, unlimited PTO, 401k, wellness benefits, technology and work-from-home reimbursement, and flexible work schedules.

Requirements

• 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

Responsibilities

• 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

Preferred Qualifications

• Experience in vertical SaaS
• Expertise in designing for generative AI products
• Knowledge of accounting or audit-adjacent industries

Benefits

• 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