Senior Product Designer (Contract)

Ollie is seeking a hands-on Senior Product Designer to embed with our digital product team for a 60-90 day engagement. This role is a strong fit for a designer who can move quickly, work through ambiguity, and balance customer needs, business goals, and technical constraints. You will help deliver priority web, app, and subscription work during an accelerated year-end roadmap while maintaining a high bar for craft and execution.

This is a remote, U.S.-based contract role for approximately 20 hours per week, embedded with Ollie’s product design team for 60–90 days, with a target start date of October 1, 2026. 

East Coast–based candidates are preferred, but location within the U.S. is flexible. Candidates should be available during Eastern Time working hours.  

There may be an opportunity to convert to a full-time role at the end of the contract, though conversion is not guaranteed. Individual designers may apply. Small studios may also respond if a named senior designer will be dedicated to the engagement. The potential full-time path applies to an individual designer and may not be relevant to a studio arrangement.

The position collaborates directly with product, engineering, and growth partners and reports to the Lead Product Designer.

What You'll Do:

• Own UX and UI execution for active web and app initiatives, including landing pages, checkout, onboarding, account, and subscription-management flows.
• Increase design capacity so priority initiatives continue moving at pace.
• Translate defined product and growth opportunities into polished, development-ready experiences.
• Develop and rapidly iterate concepts, user flows, prototypes, and A/B test variants in partnership with product managers, engineers, and growth partners.
• Use existing research, product context, analytics, and design-system patterns to make sound decisions and identify gaps or risks early.
• Create high-quality work that is consistent with Ollie’s design system and customer experience standards.
• Prepare clear, production-ready Figma files, interaction details, responsive states, and handoff documentation.
• Join the team’s existing planning, critique, and delivery rhythms, with work prioritized jointly as roadmap needs evolve.
• Partner through implementation, respond to engineering questions, and support design QA as work ships.

Who You Are:

• You have 5+ years of product design experience, with senior-level ownership of shipped digital products.
• You demonstrate strong visual and interaction design craft, systems thinking, and fluency in Figma and Adobe Creative Suite. You’re also comfortable incorporating AI tools into your design process and collaborating within structured product-development workflows using tools such as Jira.
• You have experience in DTC, subscription, e-commerce, growth, or conversion-focused product environments.
• You can move quickly, work through ambiguity, and balance customer needs, business goals, and technical constraints.
• You have experience using AI-assisted design tools—such as Claude, Figma Make, or comparable platforms—to explore concepts, prototype interactions, and accelerate design work. You apply sound judgment when evaluating output quality and handling confidential information, third-party content, and intellectual property.
• You are interested in being considered for a potential full-time Senior Product Designer role after the contract engagement.
• You can begin on or near October 1, 2026 and commit approximately 20 hours per week for 60-90  Days.