Drew Montgomery — Lead Product Designer + Strategist + Advocate + Builder

A designer from the 3rd world, bringing a diversity of thought and a unique lived experience to the 1st world.

I empower millions of people while generating hundreds of millions in revenue by turning insights into experiences for startups, entrepreneurs, and corporations.

Born and raised in Jamaica, now living in Toronto, I’ve seen two sides to the story of technology. Coming from a place with limited access to a hub of innovation, I always questioned how to bridge the gap. Then I discovered user experience design.

My belief that access to technology is a right, not a privilege, guides my design decisions. I help make the world more equitable through my work.

As a creative thinker and problem solver, I enjoy straddling the line of marrying human needs with business goals. Creating great products comes from truly understanding the people using them. Humans willingly incorporate useful and enjoyable experiences into their daily lives.

I’ve designed products that have empowered millions while generating millions of dollars for world-renowned companies. My versatility spans mobile product design (iOS and Android), B2B, SAAS, B2C and AI-driven experiences. I excel in environments that value user research, behavioural data, empathy, diversity, accessibility, and inclusion.

When not designing, I’m either mentoring other designers or teaching kids code, in the mountains skiing, playing soccer or travelling the world. Experiencing different cultures heavily influences the way I solve problems.

21 countries and counting.

Experience

Maryam K.

UX Design Manager, TD

“Drew is one of the most naturally talented designers I've ever worked with. He was the key designer on MyTD Rewards. Besides bringing fresh ideas to the team, he worked on creating high fidelity prototypes and proof of concepts for executive demos; as well as, working closely with vendors such as Moven to bring alignment across all the TD apps. His calm character and his sense of humor made it always fun to work with."

Tamar H.

Founder, Tech Spark AI

“Andrew Montgomery is unparalleled in his dedication and expertise. When I sought to empower underprivileged students with UX design knowledge, he supported our culturally relevant lessons and sparked genuine passion within our students. Entrusted with my AI vision, Andrew navigated my needs with unmatched professionalism, attention to detail, and efficiency; always aligning with my original vision. His blend of skill, patience, and deep understanding makes him the only UX designer I'd trust wholeheartedly with my vision. Simply put, Andrew understands the assignment, every single time."

Phil S.

Senior Product Design Manager, Wayfair

“Drew fully embraced the challenges, opportunities, and responsibilities of becoming a product designer at Wayfair. His hard work, ability to learn, and leadership have been evident…He eagerly and quickly assumed great responsibility…which was very impressive. I greatly appreciate his ability to work independently and with initiative. Further, his teammates, colleagues, and I all recognize that he is an effective collaborator, gifted creative problem-solver, and design thinker. He exhibits actions, behaviors, and attitudes that Wayfair highly values"

  • “Drew is one of the most naturally talented designers I've ever worked with. He was the key designer on MyTD Rewards. Besides bringing fresh ideas to the team, he worked on creating high fidelity prototypes and proof of concepts for executive demos; as well as, working closely with vendors such as Moven to bring alignment across all the TD apps. His calm character and his sense of humor made it always fun to work with."

    Maryam K.

    UX Design Manager, TD Bank

  • “Drew fully embraced the challenges, opportunities, and responsibilities of becoming a product designer at Wayfair. His hard work, ability to learn, and leadership have been evident…He eagerly and quickly assumed great responsibility…which was very impressive. I greatly appreciate his ability to work independently and with initiative. Further, his teammates, colleagues, and I all recognize that he is an effective collaborator, gifted creative problem-solver, and design thinker. He exhibits actions, behaviors, and attitudes that Wayfair highly values"

    Phil S.

    Senior Product Design Manager, Wayfair

  • “Andrew Montgomery is unparalleled in his dedication and expertise. When I sought to empower underprivileged students with UX design knowledge, he supported our culturally relevant lessons and sparked genuine passion within our students. Entrusted with my AI vision, Andrew navigated my needs with unmatched professionalism, attention to detail, and efficiency; always aligning with my original vision. His blend of skill, patience, and deep understanding makes him the only UX designer I'd trust wholeheartedly with my vision. Simply put, Andrew understands the assignment, every single time."

    Tamar H.

    Founder

  • “I had the pleasure of working with Drew during the early design phase of the Haul & Pull Up app. The insights, critical thinking, and expertise that he was able to provide was integral in dictating the distinct look and feel of our platform. Like his designs, working with Drew is seamless and uncomplicated. He brings a level of professionalism that stresses communication and efficiency, while still maintaining a personal touch. I've already recommended him to several peers of mine and will continue to do so in the future."

    Brannon C.

    Co-Founder, Haul & Pull Up

  • “Mr. Montgomery came highly recommended to us through a mutual friend to design our web application. His end result was impeccable and he delivered more than we expected. He went above and beyond to bring out vision to fruition. His work ethic, professionalism, thoroughness, attention to detail and passion for his craft as a UI/UX designer is unmatched! It was our pleasure working with him and we look forward to collaborating more with him in the future."

    Shardonnay G.

    Co-Founder, ChairShare

Skills

Product Discovery
& Design Strategy

Unlock the full potential of your idea

I specialize in uncovering market opportunities, problem framing and scoping, defining user needs, and crafting strategic plans to ensure your product aligns perfectly with your vision and your customers' demands. Let's turn your concept into a well-defined, market-ready solution.

Product &
UX Design

Crafting user-centric data-informed experiences

A first-principles design thinker who leads user-first design strategy and implements UX methodology to improve conversion, task completion, and user engagement. I work collaboratively with you and your team to solve complex user problems while driving business outcomes, saving costs, increasing revenue and de-risking going to market by using design to align your product with the mental models of your user base.

Visual Design,
Concepting, & Prototyping

Bringing ideas to life, pixel by pixel

With an eye for detail and a passion for creativity, I breathe life into concepts. From sketches to interactive prototypes, I transform ideas into visually striking, functional designs that resonate with your target audience. I’ve designed award-winning proof-of-concepts instrumental in securing millions in funding for multiple startups.

No Code
App Building

Transform your ideas into functional apps

I have the expertise to build functional apps without writing a single line of code. Whether it's a simple MVP or a complex project, I can turn your vision into reality quickly and cost-effectively.

AI-Driven Experiences

AI Experiences

Mobile App Design

B2B Design

B2C Design

Responsive Web Apps

SAAS Design

E-Commerce

FinTech

EdTech

Retail

Logistics

Supply Chain

Manifest your Vision

Whether you want to manifest a new vision or redefine an existing product, together we can take your idea to the next level. I prefer working remotely but I’m always open to an adventure.