Senior / Principal Product Designer

Role Summary

We are hiring a Senior or Principal Product Designer to join our Product & Technology team in Seattle. Reporting to our Chief Product & Technology Officer, you will work closely with product, engineering, marketing, and cross-functional stakeholders across Operations and Solutions Engineering to build and extend our design system, delivering polished, user-centered experiences across web, mobile, and drive-up kiosks. The level will be determined based on your experience, scope of ownership, and demonstrated impact.

This is a hands-on role for a designer who thrives working on complex, operationally-critical, multiplayer products and can move very quickly without sacrificing quality. Our users are drivers, guards, yard operators, remote ops, VPs of operations, and IT managers at major logistics companies - people working in loud, fast, physical environments where a confusing, inefficient, or oversimplified interface costs real time at a real gate (potentially even backing up traffic into a highway).

Key Responsibilities

• Embrace AI as a core part of the design workflow - across research synthesis, prototyping, documentation, and ideation - and actively look for new ways it can raise the quality and speed of design work across the team.
• Execute high-quality product design work across web, kiosk, and mobile platforms.
• Translate complex logistics and freight data into clear, intuitive, and actionable interfaces.
• Contribute to and maintain design system components and patterns in Figma, Lovable, and design-built prototyping tools.
• Partner with the Product & Technology team to deliver designs that are technically feasible and user-validated.
• Conduct and synthesize user research using Dovetail to inform design decisions.
• Design data visualizations and dashboards that surface meaningful insights for internal and external users.
• Participate in design reviews and contribute structured, high-signal feedback.
• Stay current on AI interaction paradigms and SaaS UX trends and bring relevant ideas to the team.

Qualifications

Shared Across Both Levels

• Lead role - own design for the entire product, end to end, top to bottom.
• Strong focus on interaction design and data-heavy SaaS applications.
• Proven ability to work within systems and contribute to a shared design library, rather than designing individual screens in isolation.
• Experience designing complex workflows, multi-step processes, and data-rich interfaces.
• Demonstrated willingness to adopt and integrate AI tools into daily design practice.
• Strong communication and collaboration skills across distributed teams - Outpost's Product & Technology team spans Seattle (PT), Austin (CT), and LatAm.
• Proficiency with Figma, Lovable, Dovetail, PostHog, ClickUp, Claude, and /or other AI tools.
• Comfort with logistics, freight, IoT, or similarly technical domains is a plus.

Senior Product Designer - Qualifications

• 5-7 years of product design experience.
• Has shipped end-to-end product surfaces and can operate independently on a defined problem area.
• Contributes components and patterns to an existing design system.

Principal Product Designer - Qualifications

• 5-10 years of product design experience, including senior or staff-level scope at a product-led company.
• Has owned a design system end to end - established the architecture, documentation, and adoption model, not just contributed components.
• Sets design direction across multiple product surfaces and influences roadmap and product strategy, not just execution.
• Track record of raising the design bar across a team - mentoring, critique culture, hiring, or establishing practice standards.
• Has designed for at least one domain with hardware, field, or operational constraints (industrial, IoT, logistics, healthcare, fintech ops, or similar).

Success in 12 Months Looks Like

• AI is a native part of the design workflow. Design is actively using Claude for research synthesis, UX copy, and spec writing, and Lovable for rapid prototyping and concept validation - measurably shortening the distance between idea and artifact.
• Designs simultaneously specify the experience and establish reusable patterns and tenets. Outpost's design system is measurably stronger: components are documented, reusable, and actively used by engineering without requiring designer intervention on every implementation.
• Faster cycle time between customer/user feedback > design > spec > engineering, with fewer revision loops due to clearer, higher-fidelity handoff artifacts.
• Every major product surface has a consistent, validated UX that reflects Outpost's design principles and passes internal usability benchmarks.
• Product and design are aligned on priorities, speak the same language in customer-facing conversations, and co-own the quality of what ships.
• Dovetail is populated with synthesized findings from driver, guard, and operator interviews that actively inform roadmap decisions.
• PostHog and product analytics are part of the design workflow, so decisions are grounded in behavioral data, not just intuition.

Benefits

• Comprehensive Benefits Package including Health, Dental, and Vision Insurance
• 401(k) Retirement Plan Matching
• 19 Paid Holidays
• Unlimited PTO
• Friday Team Lunches
• Compensation:
• Senior Product Designer: $170,000-$210,000 base salary, plus equity.
• Principal Product Designer: $180,000-$250,000 base salary, plus equity.

Final level and compensation will be determined based on experience, scope of ownership, and qualifications. A complete compensation and benefits summary will be provided during the interview process.