UX/UI Designer, Toronto ⇄ Tokyo

In a world optimized for engagement, I design for curiosity.

With a background in business consulting and music, I create products that balance systems thinking with human experience, encouraging deeper, more intentional interaction.

Case studies

Four ways of shaping how people find music, move through space, train, and see: from full product research to visual identity.

Case Study 01: Product Design & Research

Cued

Role: UX/UI Design & Research (lead)

Cued is a global network of artists, listeners, spaces and scenes: sets, sessions, and voices from cities around the world, built for people who actually listen and want to break free from the algorithm.

Cued front page
Type · Concept project
Role · UX/UI design & research (lead)
Status · Prototype & user testing

The Challenge

Music discovery platforms prioritize efficiency and engagement over meaningful exploration: search is purely retrieval-based, taste is treated as static, and opaque algorithms reinforce repetition instead of expanding perspective, with little transparency, no sense of growth, and few incentives to explore deeply.

The Approach

Being a musician myself, I ran field research across venues, cars, and homes to understand people's real relationship with music, narrowing it to three types of listeners and three types of musicians, then benchmarked against existing platforms to define the core question: how do we get people away from their algorithms and back to curiosity?

Stage 1
Field Listening

In-context interviews across venues, cars, and homes with listeners and musicians.

Stage 2
Persona & Journey Mapping

Narrowed to three audience types and three musician types; mapped and recorded their journeys.

Stage 3
Competitive Analysis

Analyzed where existing platforms fall short against what we'd learned.

Stage 4
Core Question

How can we build a platform that moves people away from their algorithm and back toward curiosity?

Target audience

Understanding the Audience

We segmented listeners into the average listener, the extreme listener, and the listener who doesn't care much about music, and musicians into the eager early adopter, the tentative performer, and the up-and-coming artist looking for mentorship, each with different needs from a platform like Cued.

Empathy map Affinity mapping

Empathy & Synthesis

Interviews across listeners and musicians surfaced recurring themes, from algorithm fatigue to the desire for real community, which we clustered into an affinity map to spot where the strongest opportunities for change were.

POV with actionables

Defining the Problem

How might we make a platform that gets people away from their music algorithms and back to curiosity?

This point-of-view statement, and the actionable HMWs behind it, became the north star for every feature decision that followed.

Persona

Meet the Persona

To keep decisions grounded, we built a persona representing the everyday listener, someone who still loves music but has stopped actively searching for anything new, and used him to pressure-test every feature we designed.

Customer journey

Mapping the Day

Mapping a day in the persona's listening life, from the drive to work to winding down at night, showed us exactly where the current experience falls flat, and where Cued could step in.

Early Lo-Fi Sketches

Once the research pointed toward "curiosity over algorithm," the earliest sketches worked through how that idea holds up across a full experience: a radio-style player, discovery cards for surfacing new artists, a lightweight blog for storytelling, and a landing page pitching the concept itself.

Landing page sketch Discovery page sketch Scrolling functionality sketch

Where It Stands, and Where It's Heading

Cued is currently in prototype and user-testing; next steps are validating the interpretive search flow and the taste-map concept with real listeners. As principal designer, I'm rebuilding search, recommendations, and interaction design around exploration, not consumption: interpretive search for emotional queries, taste maps that show how a listener evolves, and adaptive discovery balancing familiarity with serendipity, with thoughtful friction, social features without performative pressure, and privacy that stays visible, not buried.

Reflection: this project made the parallel impossible to ignore. Mapping a listener's journey is the same discipline as mapping an employee's: the tools change, the question doesn't: where do they get stuck, and what's the smallest fix? Working it end-to-end convinced me this is a change of medium, not a career pivot.

Freelance, Web Design

Free Fitness

Role: Web design (desktop & mobile)

Designed full desktop and mobile wireframes for a good friend's gym here in Canada, mapping out the complete user experience across booking, class programs, and location pages to create a clear, intuitive flow for members.

  freefitness.ca
Free Fitness desktop
Desktop layout
Free Fitness mobile
Mobile layout
Visual & Cultural Design

SentoSensations

@sentosensations ↗

Jointly organised by indie publication sankaku and electronic musician Demsky, SentoSensations is a one-day festival of art, live music, and food. The first event was held in November 2022 in Denki-yu, one of Tokyo's most iconic bathhouses.

At its core, a sento like Denki-yu has an important social role: bringing a community together. SentoSensations celebrates our community and all the creativity, culture, and craft that they have to offer in a very special venue.

Denki-yu is a beloved public bathhouse in Kyojima. It was a key location in Wim Wender's Perfect Days (2023), and has been in business for 102 years as of 2024. It is managed by Okubo Katsuhito, who will appear on the second talk panel of SentoSensations.

SentoSensations main room
Event poster Live performance DJ set Setting up Attendees Crowd, bubbles
Graphic Designer & Visual Communication

Designed 500+ posters, websites, and visual identity systems for artists and cultural events, applying typography, layout systems, and visual hierarchy to create cohesive brand communications and visually compelling materials that enhance clarity, recognition, and audience understanding.

Drifting Air poster Alchemy tour poster Pintology vinyl release poster Drifting Air poster Drifting Air Instagram post Drifting Air poster Sengoku Daitoryo poster Drifting Air poster

Two skills carry through every project, both learned long before UX entered the picture.

Two of the skills I lean on most, carried over from a decade in learning design, facilitation, and music.

Benchmarking

Before helping clients improve cross-functional communication, we first identify performance gaps and provide constructive feedback to improve efficiency, collaboration, and overall workplace effectiveness.

Relevance to UX

Benchmarking plays an important role throughout the design thinking process, particularly during the empathize, ideate, and testing stages, it uncovers inefficiencies, clarifies user needs, and surfaces opportunities for meaningful improvement.

Example

At Woven by Toyota, I developed the benchmarking framework for the Learning & Development team, which became the team standard, mapping tailored learning journeys and giving coaches a structured assessment to run before any program begins.

Material Curation

Curation is the process of selecting, organizing, and shaping information or experiences to create meaning, filtering through complexity to make something intentional, human, and valuable.

Relevance to UX

In UX, every choice, from information hierarchy and user flows to visual layout and interaction, is an act of curation: filtering out unnecessary complexity so experiences feel intuitive and human-centered.

Example

As the artist behind Demsky, I curate emotional experiences through sound, space, and community, including SentoSensations, a festival held in one of Tokyo's oldest bathhouses. At Woven by Toyota, I curate learning pathways for engineers, organizing complex material into clear, scalable programs.

AI-Enabled Practice

How AI shows up in my research, design, and delivery.

"AI is a capability enabler. People and human oversight first, tools second."

Enterprise Adoption
Woven by Toyota, "Wovey"
  • Accelerated curriculum development, documentation, content creation, and workshop design
  • Used AI to synthesize complex information and improve communication clarity across engineering and business teams
  • Promoted AI-assisted workflows while keeping human oversight, accuracy, and user-centered design front and center
Product Design & UX
Where AI shows up in practice
  • User research synthesis and persona development
  • Journey mapping and feature prioritization
  • UX writing and information architecture
  • Design iteration, usability evaluation, and stakeholder communication
Research & Problem Solving
Turning volume into insight
  • Accelerated qualitative research through AI-assisted synthesis of community feedback, industry trends, and competitor analysis
  • Transformed large volumes of information into actionable insight
  • Supported structured decision-making, brainstorming, and opportunity identification
Content & Communication
Faster, clearer delivery
  • Created and refined learning materials, executive presentations, proposals, and technical documentation
  • Improved drafting, editing, summarization, and knowledge sharing across projects
Alan Demsky

About

My path into UX design has been shaped by years in music, learning design, education, and community-driven work. Originally from Toronto and now based in Tokyo, I spent years touring as a musician across Canada, the United States, Europe, and Asia, experiences that deepened my understanding of storytelling, emotion, and how people connect through shared experiences.

Alongside music, I founded a business teaching mathematics and chess, which led me into learning & development, facilitation, and communication coaching with teams across cultures and industries. That work kept pulling me toward the same question: how do you make an experience more intuitive, inclusive, and meaningful for the people inside it? UX/UI design became the natural next step.

To ground the transition, I completed certifications through the Interaction Design Foundation (IxDF) in user-centered design, UX research, interaction design, and design thinking.

Benchmarking Curation & Information Architecture Facilitation & User Research Figma Visual Systems Design Journey Mapping Workshop Facilitation IxDF Certified
Toronto
Musician & founder, math & chess education business
Origin
On the Road
Touring musician across Canada, the US, Europe, and Asia
Music
Woven by Toyota
Learning & development, benchmarking framework lead
L&D
IxDF
Certified in user-centered design, UX research, interaction design & design thinking
Certification
Tokyo
Co-founder, SentoSensations · Principal designer, Cued
Present

Let's talk

I'm looking for my first role in UX/UI. If you're hiring, or just want to talk shop, I'd love to hear from you.

Opens your email app, addressed to alandemsky@gmail.com.