December 16, 2020

Design Leader Insights - Jason

Thank you Jason Carlin, Head of Design at Weedmaps. We love your advice to new designers on understanding what is important to the business...

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Thank you Jason Carlin, Head of Design at Weedmaps. We love your advice to new designers on understanding what is important to the business.

Check out the video below!

On Jason’s career in design:

Alex Smith: Hey Jason, thanks for joining the series today. To get started can you tell us a little bit about your journey and your career in design?

Jason Carlin: Sure yeah absolutely. I have been designing and in some cases developing things for over 20 years. I started off as a front-end engineer back when front-end engineering was a much simpler craft than it is today. I don't know how I could keep up with what they're up to now. I worked in agencies for a bit as a developer. That's where I transitioned to design. I got a really different flavor of what it is to be a designer early on when I made the move from Boston to California. I did a little bit of agency work and hopped into startups as quickly as I could. I found myself accidentally specializing in video startups. I worked at a company called Ifilm, a company called Revere, and then I ended up at YouTube for seven years over at Google. Somewhere in the middle there I helped launch a startup called TextPlus and most recently I helped get a couple things off the ground and did a couple short engagements as a consultant. I've been with WeedMaps now for about a year and a half as the head of design.


On growth in the legal cannabis sector:


AS: Awesome! That's a long journey and you obviously learned some best practices at Google which is always impressive, and WeedMaps is a great place to be. We had some legalization wins this year so it's got to be great for the company.


JC:  Yeah absolutely. We won five states, it's a big deal. We're up to 30-something medical states and 15 probably recreational states if I'm getting those numbers correct. It's been a huge change even in the year and a half I've been here. 


On remote work in design:


AS: It's been a crazy year. 2020 has shaken things up for not only design, but how has that changed design this year and how do you think that's going to change design going forward as we look to 2021 and beyond?


JC:  Design is very collaborative, we call it a full contact sport. Like any job there are a lot of advantages to being in the office and being around people and being collaborative and also friendly and social. Having the entire team suddenly unexpectedly become remote, or you know as we try to think about it more distributed, was a real shock to the system but we've been marveling at WeedMaps over how well it's gone. Productivity hasn't dipped, morale seems to be high, we have this suite of tools that are set up for remote collaboration. 


On Figma and Miro becoming essential tools in design:


AS: What are some of those tools that you're using now that you would consider best in class or recommend for other teams?


JC: Yea I mean the obvious answer is Figma. We switched from Sketch to Figma shortly before this all went down but Figma has been a game changer. We're also using a tool called Miro set up for remote collaboration workshops and white boarding we're using it for story mapping and that's been getting a lot of uptake at WeedMaps across different squads. It's been really useful to help us work cross-functionally with folks who maybe aren't as comfortable getting right into Figma and getting their hands dirty so we can work reliably face to face over video. We can collaborate in design files on Figma, we've got workshops and whiteboarding and miro, the tool set's incredible.


On how to measure design on an organizational level:


AS: So switching gears here a little bit, you've been at a ton of different companies so I think you'll have an interesting perspective on this next question which is how should design be valued and measured effectively by an organization?


JC: Yeah that's the question isn't it? The plight of the designer has always been, well two things the plight of the designer has always been that everybody thinks they can be one. Everybody with eyeballs thinks they can design, but the more important issue is that design can be very hard to quantify value-wise. When you are able to illustrate impact and do what you think is quantifying design it can be really hard to translate that language into something that other functions and leadership can understand. The way I've been thinking about it lately is just the broad topic of business thinking. It's a matter of understanding that you work for a business that you're part of the business and that everything you do can be lovely and wonderful but unimportant unless it is helping the business. It's been interesting trying to evolve that into being even more data-driven and focused on new types of quant and then teaching our design team to work more in data analysis which is not something that most designers are super well versed in. Especially this past year we focused really hard figuring out how to make really well informed decisions and I think that's a huge part of it.  You can't be contributing to business success, or product strategy, or product market fit unless you have more information than assumptions.


On advice to new designers entering the field:


AS: So moving on to new designers entering the field, what advice would you have for them as they graduate either formal education, or some of these quicker form formats that really accelerate them into the field?


JC: I think the first thing I would tell any new designers that your work is valuable. It can be when you're young and when you are in design rather than in something that's a little more quantifiable right off the bat like product and engineering it can be easy to feel a little bit steamrolled and I think it's easy to forget that your work and your time are very valuable. That you can set limits, that you can set boundaries, and that you can speak up and contribute. Mike Monteiro does a talk, I don't know if he's written anything under the name, forgive me here, 'F*ck You, Pay Me.'


AS: I’ve seen that, I didn't recognize his name but I’ve seen the youtube video.


JC: Yeah which is great. It’s him teaching this lesson to young people and I think it's really important. Kind of the flip side of that is when we talked about business thinking is if you do want to be able to speak up you need to understand the reality of product design as distinct from visual and UI and sometimes even UX design. You need to be ready to think strategically about the product and the market, and beyond that you need to be able to understand what the business is going after. 


On design education:


AS: What about education? I kind of mentioned that you know some people are formally graduating from the RISD’s of the world and some people are going through boot camps. What type of education did you have and does it matter?


JC:  You know there's just so many people entering the field from various ways. When I was coming up and when I was starting to do my first hiring there was no really respectable track for really even for creating new interactive media. It really didn't exist yet, especially for design. It's different now. There are you know curricula out there that I think are very respectable. Personally I have zero formal education. I have learned everything that I know on the job, on the spot, and I've faked it until I made it more times than I should probably share. I think that you know the older idea that experience matters more than anything Ii think is absolutely true. If you can learn on the job and if you're truly genuinely interested in your work and in the field and in the work that your peers are doing cross-functionally, I think that's where education is.


On being ineffective leader in design:


AS: So earlier you touched on a sensitive subject I think for any manager, but one that we want to learn more about in design which is how do you balance being a leader, a coach, a mentor, with a designer? How much designing should you do, how much leading should you do?


JC: In my spot as the head of design I should be thinking almost entirely about strategy and about the growth of my team. Any work that I do that's closer to the ground, is I consider creative direction and hopefully not micromanagement. When you get into those kind of middle layers, we've been looking at hiring design leads or design managers. We've been talking about creating a second path for very senior contributors and we're looking at opening a staff designer role and possibly a principal designer role and that area where your career possibly forks or in the past had to fork into management. It can be really sticky and odd and uncomfortable we are looking at design managers where I am we are expecting them to do people management,  organization mentoring, and guidance and also get their hands dirty and be contributing in some way to some projects.I'm excited to see if we can open the staff designer role and get people really motivated to further their career without feeling like they need to stop designing or start managing people or completely abandon their domain knowledge, to pick up something they might be less interested in.


AS: Anything else you'd like to mention as we wrap up here?


JC: It crossed my mind to mention Yonder which is a project that a friend of mine a very brilliant fellow called Jeff Robbins is a series of articles and they've got a podcast where they offer guidance and mentorship to companies that are moving into remote and distributed work. Jeff has run a distributed company Lullabot for years now and he's found it to be an incredibly effective way to work and now that we're all working in a distributed fashion I think it's a good time to find resources like this one's been helpful to me.

AS: Great plug and it sounds super relevant to the distributed work reality that we live in these days. Jason once again thanks again for your time and really enjoyed talking to you today!


JC: Yeah great this has been really fun!