Adding a Design Practice at Lessonly – a Podcast Recap

Maddie Beadle
February 16, 2021

On this episode of Behind the Product, Jaki Clark and Casey Cumbow join us to share their journey of adding a design practice into Lessonly‘s well-established engineering and product development groups. As design and engineering leaders, Jaki and Casey share the techniques, practices, and systems that have helped Lessonly level up over the past 18 months.

Here’s a recap of our conversation hosted by SEP’s Noelle Webster-Milam and Zac Darnell. You can also listen to the full episode here:

Jaki is Lessonly’s Principal Product Designer, and Casey is a Software Engineering Manager. As a duo, Jaki and Casey have made incredible strides in integrating design and engineering at Lessonly even in the face of a worldwide pandemic.

Jaki and Casey’s journey to fully integrate design into their organization took some effort. They implemented new practices and told us about their experiences with dual track agile, cross-functional teams that Lessonly calls squads, validating (and invalidating!) assumptions, and learning how customers use products.

In the early days, Lessonly used design agencies to help move the product forward. As they grew, and moved from “startup mode” to “strategic mode,” it made more sense to bring design in-house. The 

design practice began by “putting out fires” – quickly improving the product before it shipped and focusing on visual-based design – and gradually grew to be more strategic. Listen in on this part of our conversation:

Jaki shared her approach to building a design practice at Lessonly. She began by having one-on-one conversations with as many people as she could. She asked them to map out the design process and point out where they felt like things were going well or where they had some problems. Those conversations revealed that improving the design process should be the top priority.

One of Jaki’s first steps was implementing user research and discovery. The focus has been on pulling design into the delivery process. As a part of this effort, Lessonly has started working in squads, which are small teams made up of people from various disciplines, including engineering, design, and quality assurance. These squads allow them to create and ship faster, and ultimately deliver value to customers faster. Jaki and Casey have noticed that the squads have been empowering for team members. Each squad works differently, figures out what works for them, and is able to collaborate across disciplines more easily. You can hear them share about this process here:

Casey and Jaki shared that user testing and validating assumptions have increased engineers’ confidence that they’re building what’s most valuable. The collaborative approach has also improved the consistency of Lessonly’s users’ experience. Casey explains this here:

Lessonly has also benefited from the designers’ perspectives on what might matter to users. As an example, Jaki shared about a confetti plugin that accompanies their new certification feature. “It’s nothing fancy, but it feels so good,” she explained. “It’s very tangible to customers that something is happening.”  Design has helped Lessonly leverage the strong correlation with perception of usability and how nice something is to look at and to use. Listen to her share about this here:

The way Lessonly incorporates feedback on their product – both from customers and from their employees – has changed as well. The product team’s end-of-sprint meetings have been opened to the entire company. Jaki explains how feedback is shared with the product team here:

What’s next for this duo? They are starting to focus on measuring success as they build out their product function and design system. They’re doing things like gathering customer feedback, measuring use of features, and tracking how many questions customers ask to get certain features working. This helps them keep a better pulse on which features are valuable to customers, what should be sunsetted, and where they might need better enablement. You can hear them discuss their goals for the future here:

That’s the show! We hope you enjoyed this conversation as much as we did. We’re looking forward to reconnecting with Jaki and Casey to hear about the work they’re continuing to do at Lessonly.