Head of Design

At Coast, we're building the financial infrastructure powering America's fleets. AI is fundamentally changing how fleets run their financial operations, and we're shaping the tools this new era requires.

Founded in 2020, Coast has become the payments and expense management platform of choice for the 500,000 fleets and 40 million vehicles that keep the country moving — giving fleet owners and operators control, visibility, and trust over how their businesses spend.

Simplicity is our competitive advantage. In an industry where complexity is the norm, we're building something opinionated and focused: software that field workers and fleet managers actually want to use. Every member of our fully co-located team is a builder who cares deeply about bringing modern, well-crafted tools to the trades — an industry that's been underserved for too long. This mindset drives everything we do, from product decisions to hiring choices.

We're looking for a Head of Design to join the team.

In this role, you will lead by making, not managing. Someone who sets direction, establishes standards, and grows a team while staying close to the work. This is a true player-coach role: you'll lead a small but talented design team while also acting as the primary designer on one of our product squads. We don't need a design politician or a gatekeeper. We need someone in builder mode — opinionated, hands-on, and excited to shape what great looks like at Coast from the inside out.

Location & work mode

Coast is an in-person company. This role is based out of our New York City office, where our full team works together day to day. We believe great products are built by people who are in the room together — collaborating closely, moving fast, and holding each other to a high bar.

What you'll do

• Pair closely with engineering and product to initiate and complete roadmap projects, no hand-offs
• Spot opportunities to redesign or refine key screens and flows, as well as smaller quality issues and “paper cuts” as you use Coast
• Create mockups, prototypes, and high-fidelity visuals to communicate ideas and describe their execution
• Guide and inspire fellow designers through collaborative critique of work-in-progress
• Use and improve our lightweight design system components
• Help with hiring new teammates that can elevate our team and product

What we’re looking for

• 10+ years designing software, with at least 3+ years leading a design team
• A track-record of demonstrating both systems thinking and exceptional craft
• Ability to drive quality, business impact, and delight across a portfolio of products
• A player-coach mentality — you lead by doing, not just directing
• Courage to ask questions, experiment, and advocate for what you feel is right
• Humility to accept feedback, adapt your thinking, and iterate toward the best solution
• Experience with prototyping in Figma (and beyond with tools like AI, HTML/CSS)
• Ability to distill problems and feedback, then design clear, focused solutions
• Capable of transforming existing design processes into AI-assisted workflows
• Effective written and verbal communication skills

What we offer

You'll have a high-impact role with real ownership and the opportunity to shape the future of Coast’s products and services

• Competitive salary ($205,000—$230,000 USD) and equity
• Company-sponsored 401(k)
• Medical, dental, and vision insurance
• Flexible paid time off (vacation, personal well being, paid holidays)
• Paid parental leave
• $400 accessories allowance (a keyboard, mouse, headphones, etc.)
• Education stipend
• Tools to help manage your financial wellness, including webinar, and access to an equity tax advisory service 
• Free lunch on Fridays

Learn how we think

• The $40M push to modernize fleet paymentspodcast with our founder and CEO, Daniel Simon
• Fueling the Financial Operating System for Fleets: Our Partnership with CoastICONIQ Series B blog post