Canvas: A Story of Illustration Liberation

You might be asking yourself, what kind of ding-dong artist would use all this text instead of just having an illustration portfolio? Shouldn’t a competent artist let the images speak on their own? Trust me, I tried making a pure image dump of all the work I’ve done at Canvas, because I’m better with a stylus than a keyboard, and it’s ultimately way easier. But when I included only the pictures, I ignored the conceptual process, conversations with stakeholders, and strategic thinking behind them, which deserve just as much recognition as the deliverables. However, as an empath, I know that even now you still may be thinking, AIN’T NOBODY GOT TIME FOR THAT. In that case, please feel free to only bother yourself with the synopsis and scroll from image to image.


Got hired at a car subscription company during product launch. Didn’t know what I was doing. Created an illustration style guide. It worked, kinda. Trapped myself from being creative. Self-imposed doubt. Made a new illustration style. Freedom.

I joined Canvas in May 2017, as employee 25 and their first illustrator, one week before product launch. Everyone in the office was in full blitz mode. Max Chen, Canvas’ lead product designer, had some illustration needs and calmly laid out the pickle that they were in, with eyes that said, “We just gotta get this done.”

A few weeks ago, the leadership team had agreed that instead of using photos of people, cars, and delivery agents from the photoshoot they’d invested in, they required illustrations to properly showcase the services and benefits of their new car subscription product, a thing completely original to the market at the time. Their overseas freelancer provided a few homepage illustrations to them, but unexpectedly fell off the face of the earth, and they needed me to replicate their simple style to complete the homepage. Here are a couple examples:

Max and the rest of leadership were appeased, but I knew that the homepage images could still use some love. The process for landing on this style felt reactionary, instead of deeply investigated and justified (this was before Canvas had the means to conduct more rigorous customer research). Both product and marketing teams had a few hypothetical personas, but they didn’t truly know yet who our customers would be, and our brand voice guide had some pretty open-ended rules (i.e., “cool, but not too cool”, “educational”, “sound like Matt Damon”). Suddenly, with the pressure of launch gone, I had a brand new challenge: given few constraints, evolve our product illustrations as intentionally as possible.

Truly, this was a colossal task to fit into just a few months. I worked with brand to try to pinpoint where we landed on a spectrum of direct and indirect competitors, as well as companies which might have resonated with our techie customers (i.e., Airbnb, Slack, Everlane). I assembled giant, 20,000 pixel mood boards and ranked sample illustrations within hazy conceptual ranges, such as abstract-to-concrete, and serious-to-whimsical. It was necessary to identify things like how shape language, or level of detail may change from one end of these adjectives to the other. I created and shared many many iterative explorations to hone in on where my own, Canvas’ previous, and Canvas’ future styles synthesized best. I sent, perhaps, too many Google Calendar invites for brainstorming and workshop meetings, so that the teams I was working with would be informed throughout the process, and wouldn’t be blindsided by the end results.

Knowing that I’d have to eventually present all of this work to leadership, I found it important to write a preliminary illustration style guide in a Google Doc, describing the use of line, color, opacity, shapes, etc. as granularly as I could, while including rationale for each aspect which connected them to the brand voice. For example, I felt that a few lines twisted like wire coat hangers to create a single image, was a concise way to demonstrate maturity, thoughtfulness, and simplicity. Light hints of expressive brush strokes made us feel more human in an almost mechanically simple interface. I could fill chapters more about the efforts that took place in order to get to this point, but let’s spare both of us for now.

Leadership was pleased again with the results. However, this time our company identity felt like it had been shifted. I could see illustration being embedded into Canvas’ DNA and I felt like a key part of that contribution. In a data driven world, acknowledging this unquantified cultural impact for myself was significant.

Being the only illustrator presented a lot of challenges. At times, I wasn’t sure if I was on the right course. I formulated my process a lot by looking at the style guides of other companies, as well as trusting in my gut and logic. Being an in-house brand illustrator for a tech company isn’t exactly a skill that’s been passed down through generations, so I’d like to take a moment to give a shout-out to the spectacular Ryan Putnam and Meg Robichaud. Their various Medium posts on developing illustration styles for their own workplaces really guided me forward when I felt stuck. Their writings reminded me that I was driving something useful and meaningful. Google them. Their brains and their work are awesome.

Beyond only making things for the website, I also produced all marketing collateral. Since I made work for both product and marketing teams, it was up to me to negotiate how far I’d allow myself to stretch the style guide when addressing two types of work with very different audiences, at different parts of the funnel. Numerous Facebook ads, for example, would target new prospective customers, and couldn’t be too abstract or convoluted in messaging. In terms of constraints, images made for marketing took on additional liberties beyond the style guide I’d produced.

This was alright and to be expected, but as I began to make more work over the next half-year, I had an urge to try very new and different concepts to tell the brand’s story, but I wasn’t able to do so given the parameters I’d set. The guardrails were too rigid and my initial intent to keep things super minimal for future scalability ended up being limiting. It was at this moment that I realized it was time to liberate myself from my own structures. Fortunately, Canvas needed to make some big changes to its pricing model and core product, which would mean an adjustment in branding, a website overhaul, and an opportunity to revisit our illustration style.

By this point, I’d been fully empowered and given blessings to pursue new creative initiatives. Again, I was positioned to collaborate with marketing and product teams to conduct customer research surrounding homepage illustrations. I spent a few days creating five illustrations to be placed in front of a few dozen people. With surveys and conversations, we evaluated how the illustrations made them feel and assessed the images’ potential to convert. I’ll admit, 7-year-old, socially awkward Kevin didn’t doodle Power Rangers in a variety of styles and strategize which picture had the most sale potential, but 30-year-old Kevin embraces that businesses have needs, and becoming more knowledgeable on how to better meet those needs as a creative makes his day-to-day flow smoother and more buttery. Data, when used correctly, has the potential to remove doubt and mental ambiguity during image making.

I landed on something vastly more freeing. The new style kept the simple pen-tooled shapes, but implemented hand-drawn textures as a way to maintain its approachability. I expanded the color palette to include a lot of colors found in nature, something that brought comfort and ease to our customers. For smaller icons and badges, I paired down to the essentials and made a subset of rules. Also importantly, the marriage of photography and “hand-drawn” illustrations with digitally imbued, shared light source, felt rarer and special to our brand.

Sometimes, I debate whether or not I’d unconsciously and incrementally moved Canvas’ illustration style closer to my own native one. I wonder if I’d been careless in the process. The imposter syndrome in me distrusts myself, but ultimately I realize the need to progress and move forward. Feeling like things are perfect as possible at the moment of execution, is enough. It took me too long to understand that sterilizing my own style and creative brain is a disservice to both myself and the company, and is antithetical to why I was hired. My teammates knew and told me this all along, but I tend to be late with having faith in myself, which is a habit I’m currently undoing. When I observed one of our high performing ads at different refresh stages, I had an uncommon moment of pride. It was then that I connected the evolution of that image to my own personal one.

My day-to-day illustrating immediately felt less strained and I could easily utilize the new style across print, digital banner ads, blog headers, and dinosaurs.

I was energized and excited when I could use the building blocks I’d set to expand the illustration system to include characters.

With other artists, I always wonder what goes on behind the portfolio and what it took for them to get there. I hope you found some benefit in reading about my journey. Thank you for making it to the end! 👋