Design Leadership Interview with Will DiMondi
Hi Will! What do you do at DoorDash?
I manage a talented design team who builds merchant and agent experiences at DoorDash.
Tell me about how you became a designer.
While growing up, I always thought I would inherit the family business of construction supplies selling blocks and concrete, but my dad ended up selling the company in high school. At the time, I was attending a trade school, which, in addition to the standard curriculum, each student had a specific shop or trade. These focuses included everything from blue-collar occupations such as carpentry and welding to more technology and business-related professions such as electrical engineering and visual communications. I was initially pursuing business and masonry, but when my dad sold the company, I had the opportunity to change my focus to whatever I want.
At first, I had no idea what I wanted to do, but after chatting with my parents, my mom said I had spent an ungodly amount of time on the computer, creating graphics here and there in Photoshop and MS Paint. So that’s when I decided to change my focus to television and media, which included everything from studio productions of the morning announcements, 3D animation, and making websites in Dreamweaver. That’s when I really discovered my love for design!
How was your career journey from thereon?
My career has positioned me to be in quite a few places, both geographically and industry-wise. In college, I was fortunate enough to have a series of internships at smaller agencies and startups. After graduation, I continued to pursue the agency route. Doing a yo-yo between NYC and Hilton Head (Bluffton for those who are more familiar with The Lowcountry!), I worked for a couple of agencies for a lot of different types of brands. Both big and small name food and beverage, payments, and consulting companies. One opportunity that stood out to me was the work I was able to do on American Express OPEN, where I helped define the interactive experiences of the Small Business Saturday campaign for a couple of years. Getting a purview on how hard it is for small business owners in the modern economy was eye-opening. I also finally realized that I’m much better at creating experiences that help people rather than trying to come up with creative ideas on how to sell things — which lead me to throw in the towel on the agency side and search for something in-house.
After working within a very corporate environment for a couple of years, I wanted to experience what it’d be like to be in an ambiguous environment with more obscurity from a design and product perspective. That’s when I decided to join Zenreach as the first designer but eventually built a team to help make the foundation of a stable design function — both in branding/marketing and product design perspective. This was where I was able to continue to pursue my passion for creating experiences for small and local business owners.
After being at an earlier stage startup for a couple of years, I decided to join Apple. The stability and organization of how they’ve systematized software and hardware releases intrigued me. During my time there, I worked with two other designers in a joint effort to redesign the Reminders app for both iOS and macOS completely. Don’t get me wrong, the opportunity to learn how to design a perfect product (and Keynote slides!) was great, but I was longing for a faster-paced environment again — which led me to DoorDash!
What made you decide DoorDash?
Well, given the slow process at Apple, it was definitely the pace — and getting back to focusing on creating valuable products for merchants that ultimately support local economies. Also, the problems we’re trying to solve are hard, and we’re one of the only companies that are thriving in that ambiguity. Everyone here brings their all every day and is here to make a lasting, but positive impact.
What makes DoorDash unique from other companies you’ve been at so far?
First, a lot of other places I’ve worked for had a more significant emphasis on what their competitors are doing versus focusing on customers. I’ve even been guilty of it as well. Sure I’ve done my fair share of user research and testing, but I never truly understood what it meant to be customer-obsessed before I joined.
Second, a lot of tech companies focus on solving problems by solely concentrating on the digital side of the problem. DoorDash has a significant focus on understanding and solving problems in both the online and offline worlds. If that means going on a Dash to test a feature yourself or doing a merchant visit to understand a restaurant’s operations first hand, folks here will do whatever it takes to ensure they fully understand a problem before diving into solutions.
How did you become a design manager?
While at Zenreach, I was taking on all things design — from product to branding and marketing. Within the first couple of months, I was getting somewhat overwhelmed with the amount of work that I was taking on, so that’s when my manager suggested that I should maybe hire someone to help me with the workload. At the time, the thought of being a manager was very foreign. But after reflecting on my career before Zenreach, it was evident that I was making a natural progression to a management path. In addition to being a trusted friend (and part-time HR manager), my fellow peers always approached me, asking for thoughts and opinions on their designs, which I was always more than willing to give.
That said, I went from knowing nothing about being a manager to setting rigorous goals to hire designers for various functions, defining career ladders, and eventually consolidating all design assets and experiences with a brand redesign.
Do you have any advice for the designers who are considering becoming a manager someday?
Oh boy, there’s a lot, but I think the biggest thing to realize is that management is a selfless pursuit. Once you’re responsible for managing others, it’s not about you anymore, but about your team and their success.
There are also a lot of designers who think that becoming a manager is the only natural progression in their career, but this couldn’t be further from the truth. The industry will always need senior leaders who can help guide a team’s execution output. I’ve had more than a few inspiring mentors throughout my career, and if they had taken the management path, I would have never had the opportunity to learn from them.
How do you think your team would describe your leadership style?
Hmm, I think they’d describe me as personable, selfless, and trustworthy. We have a very trusting and open relationship amongst the Merchant and Agent design team — to the point where we’re almost like a small family. Some have even said that I’ve been their favorite manager in their career so far. 🙂
What kind of culture do you strive to build as a manager?
I try to create a culture of trust, honesty, and openness. At DoorDash, the feedback is considered as a gift to better themselves. I love that we have a feedback-rich culture.
As you continue to build up the Merchant Design team at DoorDash, what qualities are you looking for in a designer?
The issues we’re trying to solve at DoorDash are hard, so I’d like someone that can confidently apply an end-to-end design process towards big and ambiguous problems. Also, as I previously mentioned, we’re customer-obsessed, so designers need to deploy a great deal of empathy when performing research and validating their solutions.
What kind of tips would you provide to the designer candidate who might be interested in applying to DoorDash?
First, when meeting with a hiring manager for the first portfolio review, be sure to display your entire end-to-end process — from research to the quantitative and qualitative outcomes of the feature or product that was shipped.
Second, for those that are planning to come in for an onsite, be sure to take up the opportunity to solicit feedback on your presentation from your hiring manager. At this point in time, we want to be your champion and set you up for success. This is also an excellent time for you to evaluate your hiring manager further.
And Lastly, don’t get too worked up and nervous over the whiteboarding sessions. Treat this as any other whiteboarding session that you would experience in your current or previous job.
Now on the personal side… What do you do for fun?
I’m really into landscape photography and music, so you can usually find me chasing sunsets or going to a show on the weekend!
Since you work at DoorDash, I must ask this question. What’s your favorite food?
Pasta by far. My family is predominantly Italian, so I grew up eating a lot of homemade Italian food. Although I can’t have my Aunt Irma’s homemade Italian food out here in California, The Italian Homemade Company has done a great job in easing my cravings — and better yet, they’re on DoorDash!
Fun fact, I love pasta so much that I got a custom license plate made that says PAAASTA.
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