Skip to main content

In today's competitive market, delivering an outstanding user experience (UX) is critical for product success. A well-designed UX can lead to higher user satisfaction, increased engagement, and ultimately, improved brand loyalty. But how can product designers, developers, and organizations create user experiences that truly stand out and make a lasting impression on users? In this interview series, we are talking to UX professionals, product designers, developers, and thought leaders to explore "The 5 Best Ways to Elevate Your Product's User Experience." As part of this series, we had the distinct pleasure of interviewing Matthew Goldman.

Matthew Goldman

Matthew Goldman is the Founder of Totavi, LLC, a boutique product consulting firm based in Pasadena, CA. Over the past two decades Matthew founded two VC-backed and acquired companies (Wallaby Financial and Vertical Finance), acted as Chief Product Officer at a public company (Bankrate) and a high-growth startup (Apto Payments) and many things in between. He is a nationally-recognized product management and fintech expert and publishes CardsFTW, a Substack on all things credit and debit cards.

Thank you so much for joining us in this interview series! Before diving in, our readers would love to learn more about you. Can you tell us a story about what brought you to this specific career path?

I was always interested in computers. My older brother was too, and he gave me my first book on software development (the classic book for C by Dennis Ritchie). I came of age at the birth of the World Wide Web and started a small business making websites, running servers, and the like for small businesses and startups. After college, I spent a couple of years doing strategy consulting with Deloitte Consulting but wanted to experience startups. I found a job as a Product Manager at Green Dot Corporation when it was about 60 people and I’ve been doing similar things ever since.

Do you have any mentors or experiences that have particularly influenced your approach to product development and user experience?

On the product side, I have been deeply influenced by my time at AT&T Interactive, where I was Executive Director of Product. My immediate manager Will Hsu (now General Partner at Mucker Capital) taught me that the secret to product strategy (and all strategy) is knowing when to say “no” and saying “no” often. His manager and our Chief Product Officer, David Yoo (now a Partner at NextView Capital) taught me that you must have a compelling vision and sell it to the organization to drive real change–you can’t just respond and react to messages from sales.

On the user experience side my lead product designer at Wallaby Financial, Kenny Chen (now at Google) taught me to balance practicality and ease of use against interesting or new designs. He had to talk me out of some ideas I had!

It has been said that our mistakes can sometimes be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting?

When I was running Wallaby, we kept changing the icon of our iPhone app. We had this multi-color logo (orange, blue, green), and every major new release I changed the color. I thought that was fun and interesting and I was trying to make our app stand out on people's screens. What we learned was users kept losing the app—they couldn’t find it when we changed it. I learned that user behavior can be deeply entrenched, and you have to have a compelling reason to mess with things.

What do you feel has been your ‘career-defining’ moment? We’d love to hear the lead-up, what happened, and the impact it had on your life.

Ultimately, my sale of Wallaby Financial to Bankrate in December 2014 is the single event that most changed my career. I had been a middle manager at AT&T prior to starting Wallaby and when I was at Bankrate I was Chief Product Officer of a public company with a $1B+ market cap. There was a lot in between those steps but I wasn’t sure anyone would have hired me for such a big job, but by taking to a new adventure I was able to rapidly accelerate my career.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

When I was raising capital for Wallaby Financial, I was rejected more than 100 times. I knew that I only had a few months of savings left to support myself and my family. I thought I should just go get a job, but I decided to reboot and give it a new go. I got a new co-founder and CTO, redid my pitch deck, and started an entirely new strategy involving going public with my plans (landing a Techcrunch article with no product). That got me noticed by Founders Fund who led my financing round. I believed 100% in my idea, and I knew that I could find someone else who believed!

Can you share any strategies you have for effectively gathering and analyzing user feedback?

User feedback is so hard to get because of the Observer Effect. This is a physics principle, but it applies to user feedback: when you observe your user you change their behavior. As a result, you have to combine three key methods:
1. Data: Instrumentation to see what users are doing and how they are behaving.

2. Quantitative: Asking users in surveys about preferences and reasoning behind behaviors.

3. Qualitative: Live discussion with users to interact with them and understand their motivations.

Can you share an example of a time when you received user feedback that prompted you to make significant changes to a product's user experience, and how did you approach incorporating that feedback into the development process?

At Wallaby we built an app that made a real-time recommendation to users about what card from their wallet was the best card with which to pay at a retail location. You loaded the app, it geo-located you to a store, and made a recommendation. We saw that users would stop using the app after a while because it trained their behavior—they were often still making the optimal choice, but missing out on changes because they stopped checking. We learned that what they wanted was a push if something interesting was happening. We spent a couple of years developing location services with partners that let us push a message like “You’re at a gas station, use this card” People wanted our advice, and they didn’t want to open the app to get it. That was counterintuitive at first—less time in the app was better if people could get the information they wanted.

How do you balance the need for simplicity and ease-of-use with more complex or advanced features in a product, and what strategies do you use to make sure that users can navigate those features without getting overwhelmed?

I’m a big fan of the “advanced” mode. Most users will be satisfied by an out-of-the-box or simple experience, while some of your heaviest or most advanced users will want more. You can put a setting in the app or experience that unlocks this advanced mode and surfaces more complex users only to those who want them.

What are some of the strategies you’ve used to make your product ‘stickier’ and increase user retention?

All good products solve a problem—whether that is the problem of boredom or the need to pay taxes. The only way to truly make your product sticky is to solve a good problem, not to devise tricks to force people into the app. I hate apps that send you notifications that bury the important news. You must earn your loyalty. So, my strategy is to focus on solving that user problem.

In your experience, what are some of the most effective ways to measure the success of a product's user experience, and how can this data be used to continuously improve the product over time?

The two best ways to measure the fundamental success of a product, which is not just the digital experience, but pricing, support, and all the other things that surround a product is by measuring two questions we should all be familiar with one:
1. Would you recommend this product to a friend?
2. How would you feel if you could no longer use this product?

If your net promotor score is growing, you’re in good shape. If people would be very disappointed that your product disappeared, you have a winner.

Based on your experience, what are your “5 Best Ways to Elevate Your Product’s User Experience”?

1 . Solve a problem
See above!

2 . Make it easy and fast
Use data to understand what the most popular function is and put that front and center, or let users change their home page. Don’t force people to hunt.

3 . Match your design to your underlying experience
One time we put out an “Apple-like” experience on an Android phone. Boy did we make people mad! People are used to OS design conventions, and you have to keep up with them. You’re not so special you can be totally different.

4 . Don’t forget about support
At Wallaby I did customer support for the first year and made sure to give people lots of time and learn from them. At Vertical we had outsourced support and they had bad answers to some questions—we lost a lot of users that way.

5 . Stay focused
Don’t add features that your users don’t care about. Wallaby we had people who wanted to maximize their credit card rewards. We added a bunch of other features like interest rate optimization, cash flow management, etc. but it just cluttered the screen for people who didn’t want that. Just say no!

Is there a person in the world with whom you would love to have a private breakfast or lunch, and why?

Edward Tufte.

For more content like this, subscribe to the Product Manager newsletter.

By Hannah Clark

Hannah Clark is the Editor of The Product Manager. Following six years of experience in the tech industry, she pivoted into the content space where she's had the pleasure of working with some of the most brilliant voices in the product world. Driven by insatiable curiosity and a love of bringing people together, her mission is to foster a fun, vibrant, and inspiring community of product people.