I'm Betterment's Product Design Director and I've been designing for the web for 15 years – Chesley AndrewsFeatured

Hi I'm Chesley, I've been designing for the web for 15 years! Currently I'm a Product Design Director at Betterment, running a team that is working to make it simple and easy to manage your money and reach your financial goals.Before that I spent five wonderful years at Etsy designing and managing. And before that I had my own design studio and worked for a startup, a studio and a publisher. I am a mom to two sweet rescue dogs Boomer and Pepper and as of 7 weeks ago, a wonderful daughter named Sophie. I love to draw and paint and have a thing for pattern design.Ask me anything about mentoring, recruiting designers, building a design team, designing a cohesive holistic product, setting up a Meetup talk or happy hour, designing in a highly regulated industry like finance, setting yourself up for a successful parental leave, being pregnant and going on leave when you manage a team and more!
Thanks so much for joining us, Chesley!Please reply in the comments with your questions by Thursday morning (6/20). Chesley may not have time to answer every question, so please upvote the ones you'd most like her to answer.
Hi Chesley! What role should be our first product design hire at iFundWomen? We have designed our product ourselves (clearly) and we now have the resources to hire a proper design team. Design is something we’ve always struggled with. what role should be our first hire? would love any advice. We are solving a big problem, have great traction, customers, etc. Our design needs to Be leveled up big time. Thank you! @KarenCahn
Hi @karencahn! I love iFundWomen! So if it’s your first design hire, I’m assuming they would be asked to design for the web, (apps if you have them) and likely some print and communications work as well right?Not necessarily in this order, but I would look for someone who: 1) is user-centered, meaning they value using research and data to help inform and learn from their work. 2) designs ‘end-to-end’ or is ‘full-stack’, basically meaning they take on their product from beginning to end, research to implementation. At the very least they’re both a UX and UI/visual designer – they can help architect the navigation and user flows, but also create an aesthetically pleasing interface through color, composition, type, spacing, etc. Even better if have research skills or can code.3) understands design systems and can create an accessible design system in partnership with engineering – investing in a design system is so worth it, it makes engineering experiences much much faster and will create a much more consistent and understandable interface for your customers. It sounds like a lot and it is, but it’s worth getting that first hire right as it sets the foundation for everything else to come! Good luck!
This is incredibly helpful. Thank you Chelsea!
Hi Chesley!First off, thank you for taking the time to answer our questions and congratulations on your daughter! I'm biased but I think you picked a great name :) My question revolves around Product and Design team collaboration. I'm one of two Product Designers at a ~25 person startup, and throughout my 2 years here, I've been thinking a lot about how the Design team and the Product team can work better together. It's not always obvious who should have ownership over certain parts of the process, in particular when it comes to research, strategy, and new product features. And in terms of execution, the back and forth can often become unproductive, and things can get missed. All in all: How do you set up your teams for successful Product & Design collaboration? Are there specific similarities or differences with how those teams collaborated at Betterment versus Etsy?Thanks again!Sophie
Hi @sophieolatulippe!I totally agree it isn’t always obvious and every team I’ve worked on at every company does things a little differently. Though it can be stressful, I've come to think of the overlap and tension between product and design at the beginning phases of a project as a healthy thing and always look for designers who see it as part of their role to help shape those questions and decisions, instead of waiting to be told what to design.I haven't found a good standard approach, so what I always encourage is for the team to put in work upfront to decide how are we going to work together and then documenting it. I've seen teams create Asana checklists with different people (or sets of people) assigned to different phases and tasks of a project. Not every project demands the same process and honestly those teams got to a place where they didn't even use the checklist anymore, but the act of creating it forced them to do the critical thinking around how do they work, who does what and when.Another thing, which may seem obvious (but I’ve been surprised in the past) is for designers to have a weekly 1-1 with their PM. An open and regular communication channel is so helpful to the health of that very important partnership. Apologies if this one is obvious too, but regular team retros (or an open way to reflect as a team) is also super helpful for keeping the communication channels open and iterating on how you work as a team.Here's something that we did at Betterment when we wanted to forge a stronger bond between our product and design teams, we had a regular P&D all hands meeting where we should share team and product learnings (wins and fails), but the part everyone loved the most was that we'd kick off the meeting with a PM and a Designer each giving a 5 minute presentation about themselves. Turns out there's a lot you can learn a lot from about someone in just 5 minutes, even if you already knew them! It gave everyone more context, familiarity and appreciation for each other and basically made it easier to talk to each other which always helps everything.
Thank you so much for the detailed answer @chesleyandrews! This is incredibly helpful, and I can totally see us utilizing these tips moving forward.
👋Hello friend! I'm very interesting in hearing about your experience setting up Meetup talks and happy hour. What goals do you have in mind for hosting events like those? And how do you make sure to achieve the goals? Any tactics that you can share?
Hi hi @kuan! So, I started helping out the with NYC Design Systems Coalition Meetup a year or so ago, joining Diana Mounter, Brent Jackson and Tom Takigayama. Diana created the NYC chapter and I've learned a ton from her experience and processes. Our main goal is to create a space for design systems enthusiasts to learn from each other through talks and conversation. Design systems are relatively new and can be hard to figure out and implement, especially retroactively, so it can be really therapeutic and helpful to talk to other people in the thick of it. Each month we plan either a set of lightning talks or a happy hour. Varying the format helps make it sustainable for us to regularly plan and organize these events, and that consistency builds credibility and trust with our audience, so we tend to get a good balance of repeating and new friends. The talks are at different companies around NYC which keeps it interesting (I think) and the happy hour, which is less structured, is usually at the same bar – I think that familiarity helps people feel more comfortable deciding to drop in after work. Diana polled our twitter followers to find out which day of the week is best for them, and it’s Thursdays, so we always aim for that.Another goal of ours is to be a platform for new voices – either new speakers or speakers from traditionally under-represented groups. Some ways we’ve been able to do this is to be explicit on twitter, our website, etc that this is what we’re looking for, which I think helps people feel invited, comfortable and understand they'll be supported. Instead of just waiting for applicants, we proactively reach out to and invite a diverse set of people to talk and we offer to help work with and coach all speakers through developing their talk.
I'm currently actively seeking employment and one area I'm looking to work in is the finance industry. I'd really love to get some tidbits to help with my job search and in being valuable to the company I end up working with.What core areas would you advise paying attention to when designing products for the finance industry? What do you look out for in a product design hire looking to join your team? What advice would you give a product designer looking to get started in designing products for the finance industry?Thank you ♥️💞
Hi @Yami!Designing for finance, be it in Fintech, or a checkout experience, is fun but hard, there’s definitely a gravity and set of challenges to the work that you don’t find in every industry.A few things I’ve realized after designing in the finance and payments space for the past few years: Moving money is an emotional thing and no one is totally rational about it. As a designer, there’s a lot of guiding and educating you need to design in to the experience, it will take strong communication skills and a lot of attention to wording/copy. You’ll find there’s a balance to strike between designing a simple efficient experience with enough guidance and education to help people understand and feel empowered and comfortable with what they’re doing.There’s also lot of information to explain and disclose (definitions, terms, disclosures, etc). It’s a challenge to do that in an elegant and accessible way that’s useful but not overwhelming (especially on mobile!). It takes some nuanced typography and hierarchy skills and a good relationship with your Legal and Compliance team. They’ll be an extra layer of feedback (for good reason) – embrace that team and work with them early and often.Two of the biggest things I look for when hiring is for people who are curious and proactive. They don’t have to know much about finance, but they have to want to and actively try to learn about it. They also need to be low-ego and user-centered, hungry to understand and design for our customers.Hope that's helpful and good luck!
Thanks @chesleyandrews this definitely does help. From a user perspective I can see how guiding and educating is important because there's a lot of finance terms I personally struggle with and often get frustrated about when using Fintech products. Thank you for the insights. You've definitely given me insights into areas to build upon.
I’ve heard great things about you from your team. I’m curious to know; How does your team make your design inclusive and cohesive? What types of data do you use? Qualitative personas or more quantitative user data or a mix?
Hi @rache, oh wow that’s nice to hear :)!At Betterment, we use as many tactics as we can, customer-centricity is one of our core values.We’re currently focused on a big accessibility initiative to make sure our product is usable for the widest set of customers regardless of their condition or situation. We worked with experts to help us understand accessibility best-practices and we use various tools to help us rate how accessible our design components are.Our Product Design team is about 14 people. We have a shared design system that we all use and contribute to, we share our work with each other at least twice a week in a feedback & critique session, we document our work so everyone around the company can consume and comment on it asychronously, and we have opened up UX Reviews (design reviews with leadership) for anyone in the company to watch, so they can leave feedback too.And we have so many other teams focused on helping us to understand our customer, from Data Analytics who help us interpret our A/B tests and analytics and provide insight into customer behavior, to our Customer Experience team who share what they learn from speaking to, chatting and emailing directly with customers day in and day out, to our Customer Insights team who help us send surveys and bring in customers for us to talk to. Our Product Design team is in communication with all of those teams, they their own usability research sessions and have worked to create personas for each of our business lines. I’m a big believer in User Journey maps as well.It sounds like a lot and yet it never feel like enough in practice, so we’re always trying new approaches!
I'm curious about your thoughts on the skillsets of the designers you hired. Did you generally look for product designers that design end to end? How important is their visual design skill, and would less savvy in visual design be a blocker during hiring?
Hi @Yingying!I do look for designers who are end-to-end or ‘full-stack’. Some Product Design roles call for more visual design expertise than others, but I always think solid visual design skills are important. By solid, I mean, they have a good understanding of typography rules and hierarchy, composition, spacing, color, how to use imagery and can work well within a design system. I think basic visual design skills can definitely be learned though! It takes critical examination of designs you think are good, practice (one teacher said I should start by literally re-creating designs I like), and soliciting feedback.
Hi Chelsey, I'd love to know your perspective on hiring generalists and specialists.
Hey neighbor!
Hi @chesleyandrews when working with a complex and regulated market trying to help users navigate their way through how do you begin breaking it down. With user stories, or market conditions. Do you have any tools or frameworks you apply
@chesleyandrews thanks for doing office hours! The finance sector can be intimidating for new customers, and there's a lot of jargon for users to work through as long as they're with you. What's your approach to content in the product and testing for comprehension?
Hi Chesley, thank you for doing this AMA. As a startup, how can we create a minimal design system we can utilize to iterate quickly? I've seen a lot of design systems out there that look very comprehensive, but I don't know if I need that much as a startup? Any example or resource would be appreciated!
@chesleyandrews Hi Chelsey! Thanks for joining us --- can you describe your philosophy on mentorship and its role in designer growth? I'm leading a mentorship program for young girls who are starting to get interested in visual design and design thinking, and I want to set the program up for the girls' success.
Hi @chesleyandrews! Being in web design for 15 years, you've had a front row seat to watching the internet grow and its uses change, including how people view web pages and content. Can you identify any major changes you've made in design or strategy to cater to today's users in comparison to users of 10-15 years ago?