Player-coach design leader · 16 years in product design

I lead design, shape strategy, and stay hands-on.

Design Systems

Architect of high-impact design systems

I lead product design at Tive, a supply chain visibility platform, as a player-coach: I manage a team of designers across web, mobile, and connected hardware while staying hands-on in the work.

Previously: Staff product designer at Built Technologies and Modern Health. Principal design engineer and Head of Design at Anomalie (acquired by David’s Bridal). First designer, hybrid design engineer, and later first lead platform designer at Stitch Fix. Interaction designer at ModCloth.

Player and coach

Where I coach the team and build alongside it.

Design Systems

Architect of high-impact design systems

Owning the system as a product and a platform

  • Design system roadmapping
  • Strategic alignment and prioritization
  • Entire system ownership, from ideation to implementation, migration, maintenance, and evolution

Design and code alignment

  • Token implementation and management
  • Figma-to-code and code-to-Figma alignment
  • Technical architecture

Repeatability

  • Cross-team governance of the design system
  • Contribution and release processes
  • Documentation for humans and machines to understand the system
  • Faster time-to-live while maintaining high quality

Consistency of craft

  • WCAG compliance baked into the design system
  • Visual and interaction designs that are easily tested and highly extensible
  • Design judgment encoded into design system guidelines
  • AI-assisted UI audits, code alignment, and quality assurance

Player-Coach Leadership

A hands-on leader who grows senior designers

Growing a team

  • Managing senior designers
  • Teaching systems thinking
  • Setting individual growth plans

Leading small teams through fast growth

  • Stitch Fix: first design hire, then helped grow the team to 15+ designers and researchers
  • Tive: hired three designers and launched career ladders with individualized growth plans for every level
  • Anomalie: led design as Head of Design through a digital rebrand and transformation

Scaling enterprise products

  • Setting up design processes that meet design teams where they are
  • Establishing repeatable patterns for cross-platform designs and architecture

Product and Business Strategy

Turning ambiguous objectives into clear product direction

Opportunity identification and problem framing

  • Identifying customer problems
  • Risk analysis and solution planning

Product vision and direction

  • Design roadmapping
  • Translating ambiguous objectives into clear product strategy

Strategic prioritization and tradeoffs

  • Balancing customer value, business impact, technical feasibility, and resources
  • Scoping projects, planning release schedules, and aligning with engineering on delivery

Business impact and value creation

  • Connecting decisions to adoption, retention, and revenue opportunities
  • Monetization through user experience
  • Product branding and positioning
  • Anomalie: led a digital rebrand that increased user engagement by 25% and retention by 40%
  • Modern Health: designed a personalized home screen that raised the customer return rate by 25% against a 30-day benchmark

Design Engineering with AI

Prototyping in code and shipping production-ready designs with Claude

Designing in code

  • Proposing and pushing production-ready designs
  • Designing with real data: an object card pattern that renders UI from any data object
  • Using Claude to turn code and API documentation into design documents

AI prototyping for rapid decision-making

  • Prototyping in code with Claude to test product direction before engineering builds it
  • Risk-based design validation that tests product direction earlier and reduces downstream design and engineering rework

Engineering roots

  • First front-end engineer at Stitch Fix
  • Built UI libraries in React and Sass

Work

These are selected examples of the product and systems work that shaped how I lead today. They span design systems, platform architecture, product strategy, accessibility, and operational workflows—often at the intersection of design and engineering.

More Work

Earlier design projects and outcomes.

How I Lead

Career Path

  1. Product designer

    ModCloth

  2. Design engineer

    Stitch Fix

  3. Platform designer

    Stitch Fix

  4. Systems leader

    Built Technologies · Modern Health

  5. Product design lead and manager

    Tive — current

Each step added a lens without dropping the last one—craft, code, systems, and now leadership all still inform how I work. I love coaching designers, partnering deeply with engineering, and complex systemic design challenges.

About Me

A selfie of me and my daughter, Zara

Hey, my name is Brian Cleveland and I'm an unapologetically nostalgic human who fondly reflects on the 80s and 90s. I love watching movies from my childhood, I collect old video games and laser discs, and I love playing Fireball Island and Hero Quest with my kids. In my quote-unquote spare time, I also am a budding home renovation enthusiast who is slowly learning how to DIY one bathroom tile at a time.

I'm reminded daily how lucky I am.

My Design Journey

I love designing with a purpose. As a creative kid who loved art, all of my creations tended to serve a purpose: storytelling through comic book art, pleasure in displaying my pop art, and joy in gifting charcoal drawings. I value designing with good intentions and creating joy for those around me. (My old DeviantArt still exists)

My first design role in a product-driven company was at ModCloth in 2010. I had never before been at a company that was so strategically motivated; we were all moving in the same direction! It opened me up to the world of product design, where you aren't just creating to fulfill something inside yourself, but you're solving real problems for real people through design.

I fell in love with the art of solving problems. From there, I joined ModCloth's head of product to create a startup incubator called Kemists. We were a small team rapidly seeking out problems and generating digital solutions. We started probably a dozen businesses that year, and I learned a lot about the intersection of what people say they want versus what they actually mean. It was constant exposure to user analysis.

Next, I was fortunate to join Stitch Fix when it was just a tiny startup. In my nearly eight years there, I pushed myself to always seek value in my work while providing value to the business. I was a designer-developer hybrid at times, forming some of the closest partnerships I've ever had in my career. At Stitch Fix, I experienced true career growth—and growing pains—at every step of the way. Lifelong relationships developed. I developed.

My hybrid nature and desire to "go wide" as a designer led me to design systems, where I could actively participate in several aspects of the experience, partner closely with my internal users (product teams), and broadly influence the overall user experience. I loved the strategy and deep thinking that went into crafting complex systems. Even more, I loved providing accessibility improvements, automations, and process enhancements to everyone around me.

It's pure joy to make product teams' lives better. It's an adrenaline rush to see my designs across entire ecosystems. I took that passion back to a tiny startup called Anomalie, where we were using technology to provide beautiful, one-of-a-kind, and affordable dresses to consumers. Delight in the software took center stage during my time at Anomalie. I led a team and helped enable our whole organization to embrace design-thinking to make our work efficient yet delightful.

At Modern Health, I met some of the most influential design and product leaders in my career. As part of a team at the cusp of a new type of product, I surrounded myself with people smarter than me and learned at a pace I hadn’t felt in years. Not only were we trying new things at a fast pace, but we cared deeply about what we were delivering. Accessible design was paramount, and user empathy was easy to come by. I used every part of the product I was building, and it felt great to contribute to the growing world of mental health tech.

Later, at Built Technologies, I led design systems with a huge set of unknowns and ambiguity. At most times, this was completely thrilling, and the freedom to create the path forward felt amazing. But eventually, the lack of direction and instability of the future felt stunting in my career. I wanted to continue pushing myself to provide the best value I could.

At Tive, I moved deeply into product design leadership while staying close to the work. I lead a very senior, distributed team across web, mobile, and connected hardware, helping designers take greater ownership while strengthening the systems and operating practices around them. The role has pushed me to combine many threads from earlier in my career: design systems, product strategy, engineering partnership, mentorship, and increasingly AI-assisted ways of exploring and validating product ideas.

Today, I look back fondly on my many creations and partners over the years. I also look forward to pushing myself further, taking on new challenges, meeting new people, and influencing new users of all needs. I am a product designer who is driven by people. I design with a purpose, and that purpose is to spread joy through problem-solving.

Let's Work Together

I am an experienced design leader and manager and I want to help you with AI-enabled design, design-engineering processes, and strategic product initiatives.