Director, Design

Loop•Chicago, NY

17h•$180,000 - $250,000•Hybrid

About The Position

The Design Team creates exceptional experiences for Loop brands and their customers as we evolve from a post-purchase tool into an autonomous operational intelligence system. They shape how AI-driven decisions get expressed across product surfaces and merchant touchpoints, making complex, autonomous actions legible, trustworthy, and genuinely useful. The Director of Design will lead Loop's design function through a pivotal transition: from designing interfaces that merchants navigate to designing systems that act on their behalf. You will establish and evolve our design system, visual identity, and AI interaction patterns, ensuring that as Loop's engine gets smarter and more autonomous, merchants and shoppers always understand what's happening and why. As the design team leader, you effortlessly transition between a big-picture view and attention to detail. You thrive on collaborating with diverse teams and individuals. You can expect to work in an AI-first product environment, and a product culture that is merchant-centric, trust-obsessed, and product-led. At Loop, we’re intentional about the way we work so that we can do our best work. We call this our Blended Working Environment. We work from our HQ in Columbus, OH, or one of our Hub or Secluded locations, and are distributed throughout the United States, select Canadian provinces, United Kingdom, and Australia. For this position, we’re looking for someone to join us in Columbus, OH; or one of our ET/CT Hub locations. We tried to keep our initial Job Description brief (below), but here's the full version that will tell you more about what is required of the role, and the ideal experience and background to succeed in this opportunity: https://loop-returns.notion.site/director-design-loop?source=copy_link Here's an overview of your responsibilities. Keep in mind that as Loop continues to grow, the challenges we tackle together will evolve across different phases:

Requirements

7+ years of Product and UX Design experience, with meaningful exposure to AI-powered or agent-driven product surfaces.
5+ years of team leadership and management in design, ideally through a significant product platform shift.
E-commerce or fintech experience is highly valued, particularly in environments where design shapes high-stakes transactional trust.
Experience designing B2B products, admin interfaces, merchant dashboards, and customer-facing resolution flows is required.

Nice To Haves

Experience designing for AI explainability, autonomous decision systems, or trust architecture is a strong differentiator.

Responsibilities

Cultivate and empower the design team through hiring, mentorship, and building the culture and processes needed to design for AI-first products.
Embrace a multifaceted role where you'll take ownership of both strategy and execution as Loop transitions from reactive tooling to autonomous operational intelligence.
Collaborate with Engineering and Product teams to make Loop the leading AI-powered post-purchase intelligence platform for independent commerce.
Lead the design vision for surfaces where AI makes autonomous decisions, returns resolutions, shipping exceptions, policy recommendations, ensuring outcomes are always legible, trustworthy, and merchant-controlled.
Lead by example in designing for explainability: creating patterns that translate system decisions into plain-language rationale that merchants and shoppers can read, trust, and override when needed.
Act as the voice of merchant trust: sharing design-informed insights about where AI-driven decisions build or break confidence, and using that perspective to shape how Loop becomes the most trusted autonomous operations platform in ecommerce.