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Director, Design

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Loop
Full Time position
Listed on 2026-04-20
Job specializations:
  • Design & Architecture
    Product Designer, UI/UX Design
Salary/Wage Range or Industry Benchmark: 180000 - 250000 USD Yearly USD 180000.00 250000.00 YEAR
Job Description & How to Apply Below

Overview

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. The team spans Product Design, UX Research, and Brand; shaping 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 are 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, but here is 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.

Responsibilities
  • Cultivate and empower the design team through hiring, mentorship, and building the culture and processes needed to design for AI-first products.
  • Serve as the senior leader across Product Design, UX Research, and Brand, connecting the work of each discipline into a unified design strategy.
  • 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, Product, Data, and Marketing 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.
Experience and Qualifications
  • 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.
  • User Research and Brand Design experience is heavily preferred.
  • 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.
  • Experience designing for AI explainability, autonomous decision systems, or trust architecture is a strong differentiator.
Compensation and Benefits

$180,000 - $250,000 a year

This position is eligible for an annual performance bonus expected to be 15% of your base salary, and you will be eligible for benefits such as medical, dental, and vision insurance, flexible PTO, company holidays, sick & safe leave, parental leave, 401k, monthly wellness benefit, home workstation benefit, phone/internet benefit, and equity.

The posted salary range…

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