Head of Design

About Us:

Outpost is building the backbone of freight. We’re reinventing how supply chain infrastructure works in America with carrier agnostic truck terminals. As a vertically integrated real estate, operations, and technology company, we acquire and operate mission-critical real estate across the country to serve the largest logistics providers in the world. Backed by $500M from Greenpoint Partners, we’re scaling and building the most valuable logistics network in the country.

We thrive on accountability, integrity, and a shared drive to raise the bar. If you’re excited to reshape the industry alongside a high-performance team with a championship mindset that executes relentlessly, welcome aboard.

Role Summary:

We are seeking an experienced Head of Design at our Seattle, WA, office.

Reporting to the CPTO, the Head of Design will be the team’s first in-house design hire and will be responsible for leading the design of the platform’s user experience, focusing on transforming complex data sets into intuitive and visually compelling interfaces. This role will require a blend of strategic thinking, product design, and visual design, and the ability to work closely with cross-functional teams to solve real-world problems in the logistics and freight management industry.

As a founding member of the team, you will have the unique opportunity to define the design principles, establish best practices, and collaborate closely with product managers, engineers, and executives to deliver an exceptional user experience. Your work will directly impact how many types of users interact with the platform across web, mobile, and drive-up kiosk.

Key Responsibilities:

• Define and execute the overall user experience strategy for the platform, ensuring it aligns with business goals and user needs. You will be a key decision-maker in shaping the product’s design direction.

• Craft powerful yet efficient and visually appealing web and mobile experiences and ensure a seamless, intuitive user experience. You will be responsible for creating and maintaining design systems and establishing a cohesive visual identity.

• Champion user research and testing, conducting interviews, surveys, and usability tests to inform design decisions. Advocate for the end user while balancing business needs and technical feasibility.

• Design sophisticated and dynamic data visualizations that present complex freight and logistics data in ways that are clear, actionable, and visually engaging.

• Partner with product managers, engineers, and executives to understand business requirements and technical constraints, ensuring designs are feasible and meet user needs.

• Stay ahead of industry trends, especially around AI interaction paradigms, SaaS applications, and logistics technology, and apply new insights to continuously improve the product experience.

Qualifications:

• 8+ years of design experience, preferably with a rapid trajectory in seniority within tech companies or startups, with a strong focus on interaction design and data-heavy applications for complex software platforms, ideally in the SaaS, logistics/freight, or IoT industry.

• Proven ability to handle complex data models, creating designs that simplify multi-dimensional relationships (e.g., tools similar to CRM or ATS platforms).

• Full-stack design skills, with a strong grasp of visual design, systems thinking, and user flows.

• Experience designing customer support tools or SaaS applications with intricate workflows and multi-step processes.

• Familiarity with media-based interfaces, such as video navigation or image annotation, and tools that operate akin to workspace editors.

• Extreme career dedication - this will be very hard

Benefits:

• Title Commensurate with Experience

• Comprehensive Benefits Package including Health, Dental, and Vision Insurance

• 401(k) Retirement Plan Matching

• 20 Paid Holidays

• Unlimited PTO

• Friday Team Lunches

Outpost is an Equal Opportunity Employer and Prohibits Discrimination of Any Kind.