Posted 4/23/26. We are actively reviewing candidates as long as this posting is up.

Job Summary

We are looking for a Senior Product Designer to join our small, collaborative design team. You will own the design process end-to-end across web and mobile from ideation through prototyping, high-fidelity design, and shipping.

Your initial focus will include work on conversion, onboarding, and subscription experiences: the kind of iterative, experiment-driven design that moves business metrics. But this is not a siloed growth role. You will work across the product, contributing to everything from route planning tools to navigation UX to our design system as the team and roadmap evolve.

You will work closely with product managers, engineers, and design team who have a high touch on all design work. We are a bootstrapped company with an engineering-founder culture, so you will have real ownership and direct impact, but you should be comfortable operating as a senior individual contributor on a small team, not managing people.

We are targeting someone with 3 to 7 years of experience who is proactive, ships fast, and brings a data-informed approach to their work.

Responsibilities

• Own the end-to-end design process for product areas across web and mobile.
• Design and iterate on key surfaces. This includes paywalls, onboarding flows, and subscription experiences using experimentation and data to guide decisions.
• Collaborate daily with product managers and engineers to ship high-quality work.
• Contribute to and evolve our design system and shared component library.
• Create wireframes, prototypes, and high-fidelity designs in Figma.
• Collaborate with design team to focus on product evolution, information architecture, and strategic thinking.
• Explore the frontier of AI-assisted design tools and workflows.
• Present design work to the team and incorporate feedback from cross-functional partners.

Qualifications

• 3 to 7 years of product design experience, with a strong track record of shipping iterative, data-informed work.
• Experience with experiment-driven design. You have run A/B tests, measured outcomes, and used data to iterate. Bonus if that includes conversion, retention, or monetization work.
• Strong portfolio showing end-to-end product thinking. Not just visual polish, but clear problem definition, process, and outcomes.
• Proficiency in Figma.
• Experience designing for both web and mobile platforms.
• Comfort with data. You use metrics and experimentation to validate decisions, not just intuition.
• Familiarity with modern AI-assisted design tools and workflows.
• Self-directed and comfortable operating with ambiguity and defining your own priorities.
• Clear communication skills. You can articulate design rationale to engineers, PMs, and leadership.
• Experience working directly with software engineers and product managers in a collaborative, fast-moving environment.
• Happy as a senior IC, you want to ship great product, not manage a team.
• Experience within the outdoor recreation, health and fitness, or cycling industry is a plus.
• Familiarity with geospatial data, mapping technologies, and location-based services is a plus.
• Experience making design revisions in code and prototyping with production data is a plus

About Ride With GPS

At Ride with GPS, every team member is driven by a single goal: continually shipping a great product that riders love, and to help them go on better rides, more often. In a market crowded with deep-pocketed competitors, we outperform by combining our engineering skills, cycling passion, and modern development tools. Through pragmatic, incremental releases, we deliver high-quality work fast, and take pride in punching above our weight class. Nothing beats the satisfaction seeing real riders using what we’ve built.

We are a profitable and growing mission driven business.

The Team

We are cyclists. We are explorers. We are artists. We are writers. We are parents. We are friends. Above all, we are a group of professionals striving to do the best work of our lives. By joining Ride with GPS, you will become a part of a highly capable team that helps millions of people have a great time on their bikes.

Benefits

We offer a competitive salary as well as health, dental and vision insurance, and a 401k with a 10% match. We strongly believe in testing our own software, and as a result are more than happy to help defray some of the costs of cycling, including offering a one-time new bicycle stipend as well as an annual bike supply budget.

Ride with GPS is a remote first workplace with team members all across North America. We have a small office in Portland, OR that staff is welcome to use as desired.

Twice a year we invite all staff to a central meeting place, to provide an opportunity to work in person, as well as ride together.

How to Apply

Use the application form below to submit your application directly. Please include a paragraph about your relationship to cycling or the outdoors. Being a cyclist is not required, but we find it helpful to all have a common interest that aligns with our professional work. We'll respond in a timely manner and move things forward for promising candidates.

At Ride with GPS, we’re united by a shared mission: to help people go on better rides, more often. We welcome people from all backgrounds and believe that diverse perspectives make us stronger. While we each bring our own beliefs and experiences, we aim to create a workplace that stays grounded in collaboration, respect, and focus. We want to ensure that our time together is spent doing great work in service of that mission. If that sounds like a place where you’d thrive, we’d love to hear from you.