Zac Darnell: Welcome to Behind the Product, a podcast by SEP, where we believe it takes more than a great idea to make a great product. We've been around for over 30 years, building software that matters more, and we've set out to explore the people, practices, and philosophies to try and capture what's behind great software products. So, join us on this journey of conversation with the folks that bring ideas to life. Hey, everybody, welcome to Behind the Product. I'm your host, Zac Darnell, and joining me as my co- host for this show is Noelle Webster-Milam. Did I say that right?

Noelle Webster-Milam: You sure did.

Zac Darnell: Bam. I'm good. Well, okay. I had some practice. Let's be honest. How are you, Noelle?

Noelle Webster-Milam: I'm doing pretty good today. How are you, Zac?

Zac Darnell: I'm doing well. Noelle, what do you do at SEP?

Noelle Webster-Milam: I am the director of UX at SEP, so I'm splitting my time between making sure that we are keeping an eye on just health within the organization when it comes to UX practices and keeping current and relevant and also looking at new opportunities coming into the door, making sure that we're looking from that lens and making sure that we get a good cross-functional team solving our problems for our clients. I also practice UX on our time so that I don't get old and crusty and propose something that's not relevant.

Zac Darnell: That's probably a good attribute of that role. I love that. So, your experience and role and just way of thinking is perfectly relevant for our conversation today. We sat down with Jaki and Casey. Jaki Clark is the design leader. I think her title is principal product designer at Lessonly. And then Casey Cumbow is one of the engineering managers at Lessonly. They've both been there working together for a little over a year, year and a half. I think Casey's actually been there coming up on three years. So, it was wonderful to talk to them about our topic of the day, which is integrating a design practice into an existing technology company and their story and their journey through that. So, thank you again for joining me for that. I appreciate it.

Noelle Webster-Milam: Yeah. I sure had fun talking to them. They were a fantastic duo.

Zac Darnell: I have to say, it was a very fun conversation. They definitely have a very fun dynamic with each other. Just hearing about the last 15 months- ish, especially thinking about the last six months and what we've been dealing with here in 2020 and the strides that they've been able to make at Lessonly is just kind of a cool story. What was maybe one thing that you found kind of laced into that conversation that you thought was really interesting?

Noelle Webster-Milam: That's a good question. I saw them talk about the journey of organizationally what was going on before they brought in Jaki and saying that they went from everything about design was visual and then everything kind of went into a transaction sort of state. Then they started to get a little like, " Maybe we should be a little more focused on this" and kind of went strategic, which is what we usually see with most organizations in their design maturity journey. And I hate to say design maturity, because this is kind of like a whole organization maturity into accepting design into its problem-solving space. So, if you look at the Nielsen Norman Group, or Envision did a lot of studies about design maturity, and Jared Spool has a whole thing about design maturity, you kind of go from this there's nothing to there's one person, then there's a team and they're overloaded, but it's like putting out fires. They're never really looking at something from a holistic point of view. Then you kind of get embedded into a team as a designer, and then you get to a point where the whole company is thinking about solving problems with design. It's not really about design anymore. It's just how you do it. That's where everybody's kind of striving to be. That was pretty clear that they were on track to get to that point.

Zac Darnell: Yeah. That's such a good point. I feel like there's a lot in that that we dove into with them. Tactically, I loved hearing about practices like dual- track agile, something that we definitely talk a lot about at SEP, this idea of cross-functional teams that they call squads, the engineering team feeling more confident that they're building the right thing first, and this idea that it's okay to invalidate assumptions, it's just important to do that as it is to validate assumptions, and having a better grasp on how their customers are using a product after it's been released rather than releasing and forgetting. We talk about and read about, but to actually hear from a company and a group of people that have embraced the thinking, the practices, the philosophies, the disciplines to kind of do it better and to feel better about it, that was just a very encouraging story. I'm excited to hear 12 months when we have a followup kind of how it's going from here.

Noelle Webster-Milam: Zac, that's such a good point. In the past when I've been on project teams and we've had all of the different cross-functional minds coming together to solve a problem, we just got so much more out of bringing that whole person to the conversation for all the things that they've learned and trying to solve the problem together with those mindsets. We just get much further faster because of all that we're inviting into that inclusionary problem-solving space.

Zac Darnell: That's such a good point and something you and I have talked about in the past. It's this idea that this isn't necessarily a new thing. Right? This thinking, these techniques, these practices, they've been around for quite a while. It's maybe taken some industries a little bit longer to catch up. I don't know what you ... Would you say that that's true?

Noelle Webster-Milam: It's so spotty. To make a general sweeping statement feels crunchy to me, but I would say that there are some folks that are out there trying to learn all of the newest things and apply them on their projects every day, and they're probably meeting some sort of obstacle because not everybody's tracking with them, and that's the point of all of this is bringing everybody along into this journey. So, I'd encourage everyone, no matter where you are in that maturity journey, just to make sure that you're not running out so far in front of everyone else, that you're taking the steps together, because there's a whole slew of organizational and just position issues that may occur if you just kind of try to be so far out in front of everything without bringing everyone else along into the journey.

Zac Darnell: Yeah. That's a good point. Well, without further ado, I think Jaki and Casey talking about their story together, we appreciate them sharing their journey with us, and we hope all of you find some wisdom in this. So, enjoy the show. Hey, everybody. Welcome to Behind the Product. Today we're joined by Jaki Clark and Casey Cumbow, both with Lessonly. We were actually chatting before the show, and we all thought it would be fun if Jaki and Casey introduce each other for the intro. So, Jaki, would you like to kick us off?

Jaki Clark: Yeah. Hi. So, my name's Jaki, and I love to brag on Casey. Casey's a manager of engineering at Lessonly, and she's one of my favorite people. I'm so excited she's joining us today for the chat. She is a former educator. She is a Tech 25 Standout Star for 2020. She's pretty much a rockstar. And she handles a lot of tasks around management of engineering at Lessonly.

Zac Darnell: Awesome. That's a wonderful intro for you there, Casey.

Casey Cumbow: I'm blushing, if you could see me. That was so nice, Jaki. Thank you. Jaki is our principal product designer. She came onboard a little over a year ago, and instead of just saying, " Hey, we're doing these things," she took the time to get to know folks on a human level and understand the problems from their perspective before working on solutions. She's grown the design team from her and one other person to her and five people, and we're also continuing to grow. She also has time on the calendar each week for designers to work on professional development and share what they've learned, which is just so many ta- da emojis and party poppers, because, as a manager, that's amazing to be so intentional about that. She puts learners first, provides the best user experience. She's great at what she does. Also, on the side, she offers to provide feedback on people's resumes to help them find new jobs, which is freaking awesome. And she sews and makes masks!

Zac Darnell: Thank you so much for that intro. All right. We're talking about kind of the last couple three years maybe in Lessonly's history. Thematically, it's this idea of bringing design into an existing product engineering firm and talking about that journey. I know that each of you carry different tenures of Lessonly and you've got some stories even prior to when you guys were there. So, I'm really excited to dive into that. The first thing that I'm wondering about... At some point in Lessonly's journey, there was a recognition that design was important and that we need to bring the practice and discipline of design into the company. I don't know. Could you talk a little bit about what maybe led up to that decision and kind of what influenced that for the company?

Casey Cumbow: In the early days of Lessonly, Max, our founder and CEO, along with Wassim, one of first front-end focused engineers, handled most of the design. The designs that they didn't have a good grasp on, we outsourced. We used some agencies to help us get up and running. That was mainly because of the size of where we were and our capacity. It just made more sense to kind of lean on different agencies to help us build great designs and kind of move the product forward. That reached a threshold though when we wanted to be able to iterate more quickly and work on several different areas of the application at once, and we kind of just reached a threshold and it made more sense to bring it in- house. I think that was the primary reason, and to allow Wassim to focus more on engineering and Max to do the things CEOs do.

Jaki Clark: Yeah. I think when we look... We talked to some folks for historical reference, because I've only been at Lessonly for a little over a year as the principal product designer. I think they were very scrappy, early stages, and I think a lot of folks are. Max, our CEO, I think just really likes design. I think another life he probably would be a designer. He has pretty good instincts. Then worked with some agencies. I actually think maybe everyone in Indianapolis has probably had a hand in Lessonly at some point. Studio Science helped, Innovatemap helped, a bunch of contractors here and there, which I think is kind of lovely. Then over time, like Casey had mentioned, they went from being more startup, sort of panic like, " Okay, what are we going to build next? What are we going to build next?" And then they started I think doing more strategic work. " Okay, we're going to build this feature next. This is a big feature, and we're going to work with a Studio Science or Innovatemap to build that feature." Then as the product team grew, changed, we actually changed from more of a sort of loosey goosey format to a squad- based format once we changed leadership. And that squad- based format has one of every type of person, designer, QA, product management.

Zac Darnell: Like a cross- functional team?

Jaki Clark: Yeah. Then we kind of reached scale, so where it became necessary to work on all of the functionality at one time to keep it moving forward rather than project by project, which I think is a pretty natural progression for most product teams. So, it became necessary to hire in the first full- time designer who's truly design, rather than front- end, and then they hired in a second one, and then I was hired in to kind of build out the full practice after we started to really do really well, scale, and start looking at large- scale squads.

Zac Darnell: Okay. I want to ask about that here in a second, because I'm sure it's been a great journey, but I'm sure it's not without its challenges at the same time. Just to level set, what was the team size, structure like maybe just before bringing on those first couple of designers, and roughly how many engineers, how many different teams?

Casey Cumbow: That's a great question. I joined three years ago as engineer number maybe eight or so, and the product and engineering team was about 10 of us. At that point in time, we had one designer. So, I believe he was probably brought on... I think he was here for about a year or so before I joined. So, a team of 10- ish had one designer at that point. That's all the information I have though.

Zac Darnell: No, no. That's fair.

Jaki Clark: I think what's maybe more important is the way in which design has changed, so less about head count and more about the type of work that's being done. I've been at Lessonly for about a year, and change, there's still a big design backlog. I can't even imagine what that first designer felt like coming in and being like, "Oh my gosh, there's so much to do," because engineering kind of had a head start on them for a long time. So, I think for the first, if I can speak for somebody who I actually don't know very well, based on my understanding, is they were playing a lot of catch-up, a lot of like, "Design this screen. Design this screen. Design this screen. Make this screen a little bit better than the agency gave us, and something has changed, and you need to change it." It was I think a little bit more like what I call field medic mode where you're just trying to sew up stuff as fast as you can before it ships and less about the kind of product design I like to do, which is looking at what is our opportunity for problems to solve for our customers, what's the value to them, how are we proving out the value before we invest a lot of time and money on the discovery process, and then go build it. So, be a partner in the product, rather than just the person who makes it pretty before it goes out to customers.

Zac Darnell: Right. Maybe to put it simply, it sounds very tactile versus strategic, very transactional service ticket versus integrated, part of the team.

Jaki Clark: Yeah. And this is to say, I think if I was the only designer with 10 or 11 engineers, I'd do the exact same thing. There's literally no other option. But now that the business had kind of decided to invest in it as a true discipline, you have the opportunity to be more strategic.

Zac Darnell: One of the things I was thinking about as I was kind of preparing for the show was were there identifiers or elements of Lessonly's products that made it obvious that" Man, we could really use a more strategic view of design as part of our team, as part of our company." Were there things that were manifesting to users and customers that were like, " Ah, man, we could have done that better"?

Jaki Clark: I think it's two things. We're basically a learning management system. That is ultimately what our functionality is, primarily. And the learning management system space is very crowded. There are lots of types of learning management systems for schools, for professional folks, for different types of things. I think as they kind of really nail down that core LMS functionality in the first four and change years, then they started looking where should we go next. That's a lot harder. It's relatively easy to get great at the thing you're already good at. It's a lot harder to figure out where your business goes next. How do you continue to push it? What do our customers want? Where's the value prop? What makes sense for the direction of our business? So, it feels like since I have started our discussion has really... I haven't really worked on, and my team hasn't really worked on, the core LMS functionality hardly at all. It's really been about how do we continue to innovate for our customers, how do we continue to kind of push and solve problems that they maybe even don't know how to articulate that they have, but that's part of our job as detectives. Right? So, I think it was less about not valuing that at the beginning. It was more just like they kind of knew what their core value prop was, and now we're continuing to push that in a really exciting way.

Noelle Webster-Milam: That's really a fantastic evolution that's happened that you've described, from the point of everything being very visual- based, and, I'm going to be blunt, it's like putting out fires. This sounds like the triage sort of mentality. Casey, I'm really curious, as design has changed across Lessonly, how has engineering responded to the way that you are holistically thinking about solving problems as a cross- functional team?

Casey Cumbow: I think the fact that we have a whole design discipline, and Jaki has introduced a lot of positive change around user testing and verifying our assumptions and let's build the right thing, versus the thing that we think our customers want and will be helpful for them, it's increased our confidence in what engineers are working on are the most value things and they're going to provide just customers with everything they didn't even know they wanted, which is really exciting. I think another big advantage is just the consistency piece that we have with someone like Jaki helping us kind of grow the whole discipline and thinking about designs systems and how do we be more consistent and how do we provide the best user experience possible. It's fantastic. There's also a lot of fun things going on with how do we collaborate better, engineers and design. How do we work together? How do we pair? How do we share before we're ready and get feedback on our implementation of something? So, that's been really, really exciting.

Jaki Clark: Yeah. And we are by no means experts or perfect at it either. We are still a work in progress. I think it was when I started I was kind of focused on building out a team, hiring design, starting user research. User research really wasn't a thing we did, and I felt like it was really important. As part of that, we implemented a discovery process, which some folks might know as dual-track agile, so discovery and delivery. That meant we actually pulled engineering forward into the process rather than just having them what I would call downstream. We would pull some engineers, not everybody. That was okay. There were some bumps in that just this is new, it's hard, it's a new process. Now I feel like we worked out some of those bumps where we're feeling better. This last quarter, Casey and our other engineering manager and other leaders in engineering have been great partners with design, because now we're trying to pull design it's not really forward, it's not backward... We're trying to pull them into the delivery process, whatever direction that is, so that they are truly partners, not just on the front piece, not just handing over mock-ups, but actually starting to build in more true conversation around execution. We actually have a squad right now who it's on the smaller side just as an experiment, and the designer is not building out full mock-ups. The designer and the front- end engineer are pairing. And it's going so fast and so quick, and we're very excited. I'm very excited about it.

Zac Darnell: When you break down that wall and you put everybody in a room together, it's amazing how quick you can move. That's cool.

Jaki Clark: Yeah. I really think that's probably how squads were always meant to be, but for whatever reason it just kind of never gelled until with this new squad, I think because they started fresh maybe. Maybe that helped. But we're definitely doing some exciting things that are still in progress, but we'll see how we can continue to improve.

Noelle Webster-Milam: That's fantastic to hear that it's gaining such headway within the organization, dual- track and pairing and mobbing and all those things that you do together to actually do something-

Jaki Clark: What's mobbing?

Noelle Webster-Milam: Mobbing is a whole slew of people around an experience that's being built, whether it's prototyping or coding, and everyone contributes to that thing, and somebody's at the wheel. Then you switch in and out who's kind of got the reins.

Jaki Clark: Oh. That's cool.

Noelle Webster-Milam: But it's a whole team experience. It sounds like that's what you're doing anyways.

Jaki Clark: Kind of, kind of.

Noelle Webster-Milam: It's just not labeled. Right? I'm curious with the leading indicator that this is going well, where might you use that as influence for how design and engineering pair together going forward and how you build product?

Jaki Clark: That's a great question. I think one thing that we love as a company is speed, because we're still relatively small. Lessonly is about, what, 180- ish people. We're not a big company. So, we would love to build a ship faster, create faster, deliver value faster to customers. I think it takes the right sort of pairing, the right designer and engineer combo. Both of the two folks that we mentioned like working a little loose. Not everyone loves that functionality. One thing I think is really interesting about Lessonly and the squad setup is there's a lot of empowerment of squads. So, we have I think, what, gosh, Casey, like six- ish squads?

Casey Cumbow: Six, I think.

Jaki Clark: For us at the not- in- a- squad, at sort of the management level, it's a little bananas, because each squad works a little differently, but they work differently in a way that works for them, which is really empowering and really exciting. So, I think what we'll see is probably it happens squad by squad as they kind of work out the kinks amongst themselves and figure out what works for them, and honestly, just truly see how much easier, more fun, more collaborative it is. We try not to do too much top- down so that it feels like they're making the best decision for them. Every once in a while, we have to do some stuff top- down. But I hope that we'll see adoption that way as they see what the benefits are.

Casey Cumbow: Yeah. I'd also add there I think it's interesting that our experiment with the pairing is going just super well, better than we ever could have hoped for, and that's a really, really great sign. I think their personalities... Like you said, Jaki, those two individuals really like the high level of collaboration, and they like just going with the flow and moving really fast. I'd be interested to see if that works for that kind of front- end engineer/ designer combo on other squads or if we need to do some experimentation on what it could look like and what feels right for different people. So, I think I'm really hopeful and exciting that we can keep moving forward and want to see what it could look like. But just I've realized and learned just different squads operate differently, and we have that autonomy, which is very positive, that people can figure out what works for them, and it could look different across squads. But for folks like Jaki or myself, who we kind of bop around and hang out on different squads, it's sometimes hard to get up to speed, because people are doing things differently, which isn't a bad thing, but it's hard to kind of keep a pulse on everything if people are operating in very different ways. So, advantages and some disadvantages. We're making progress.

Zac Darnell: I kind of want to go a little bit back in time. Jaki, you started about a year and some change, a year and a half- ish ago.

Jaki Clark: Yes.

Zac Darnell: Do you remember walking in day one and thinking through, " Okay, here's what I need to get done in my first..." Let's just say 30/ 60/90. What were some of the first challenges you felt like you had to tackle, and what was that like?

Jaki Clark: I did actually attempt to read the book in the first 90 days.

Zac Darnell: Yes.

Jaki Clark: I think I got through the first two weeks and then was like, "Whaa!" and put it by the wayside. But it is a good book if anybody goes to a new job. It's kind of an interesting story for me. It's not I don't think what I've done at other places. I didn't have this tactic that I'm going to talk about at other places. It just kind of happened this way.

Zac Darnell: Sure.

Jaki Clark: So, I had already booked a vacation before going to Lessonly. So, I knew I was going to work there for two weeks and then go on basically a week of vacation. I highly recommend. That's a great idea, if you can swing it. What ended up happening is I worked there for two weeks, and I was going to be out for a week, and I knew everything would leave my head. Everything I just learned was just going to fly out of my head on vacation. So, I spent the first two weeks setting up one- on- one conversations with as many people as I could, QA, engineering, design, some folks outside of product in customer support and things like that. I asked them to map out the design process, if there was one, and where they felt like things were going well or where they had some problems. Doing that fact- finding mission for the first two weeks, I learned that the design process was something that they struggled with. There really wasn't a formalized one, and that meant that... Lessonly has one product. We are the one product. We don't really have the luxury of multiple products, which means everyone in the company cares a whole lot about that one product. We were getting lots of comments kind of here and there, everyone trying to be helpful, but the comments weren't always coming back in at the right time, and we were being kind of reactive as a product team to that feedback and to customers. So, I kind of took all this information, digested it, and then met with the head of product before I left on vacation, and I made a mind map of all of the things I felt like I was hearing and that I felt like we needed to be better at. And I will say that, in my interview, my interview was like 75% design system. And I was like, " Okay, that's fine. We can do design system. No big deal." But as I was listening to the team and observing their interactions with each other, it felt like that wasn't the most urgent need. It was on the design map, like making the product look great, creating a design system, but on the map was also things like making database decisions and using user testing to inform our product strategy and creating some sort of formalized design process so everyone knows where everything's at and there's no surprises for people in the company, for people in product, et cetera, doing a better job for design of communicating what we were thinking. The smartest thing I've ever done to date, and I'm giving this to all of you for free, is I made this mind map, and I handed it to him. I said, "I need you to star the three most important things that we're going to do for the first six months," or three months, or whatever. "You know your desires. You know your needs better than I do." And he did not star the design system. He starred user testing and design process and I think one other thing as well. And that to me really helped communicate expectations, because I think if I hadn't done that, I would have assumed, "Okay, well, I'm seeing these other problems, but I guess I'll just do the design system, because that's what we talked about in the interview." I think it was a nice way to help communicate expectations. So, I'd recommend that exercise honestly to anybody when they start any job, because ultimately you're being hired in as a brain. You're not being hired in as just a set of hands. So, I think that helped say, "Here's my perspective. What do you think?" Now a year later, we're kind of just getting to the design system, because all of those other pieces in the map have kind of worked themselves out, and we're doing nicely on them.

Zac Darnell: Wow.

Casey Cumbow: Yeah. Real quick, as a team member, Jaki joining us and taking that approach was so reassuring. I'm trying to think of all of the words I can use here.

Jaki Clark: That's nice.

Casey Cumbow: But it was just so nice. I mean, she took everyone's perspective into consideration. She got to know folks. It wasn't someone coming in, saying, " Here's what we're doing. You're doing everything wrong." It was like, " Let me hear your concerns and understand where you're coming from and figure out where we're at," so she has more information on where we should go next. Yeah, everyone should do that.

Zac Darnell: I mean, I'm by no means an expert in this space, but it kind of sounds like you did some user research on your coworkers.

Jaki Clark: For sure. Right. It's not magic. It's just like eating your own dog food. Right?

Zac Darnell: That's awesome.

Jaki Clark: There's nothing secret about it. It's just the process.

Zac Darnell: I love it. Oh, man. I'm going to take that advice, although I'm never starting a new job. I'm never leaving SEP.

Jaki Clark: Right. I mean, who would?

Zac Darnell: I won't have an opportunity to. That's really cool. I love the idea of" Okay, I hear what you're saying. However, here's some information that you may not necessarily be aware of. Hey, I'm out for vacation." You had that naturally built in. " When I get back, let me know what you want to work on." That's fantastic.

Jaki Clark: Yeah. And I would imagine it would look different for person and every organization and every type of job, but for me I was looking at what's the value to the business. The value to the business is building the right thing for our customers. Design systems are awesome. They have great return on investments. But I would say the return on investment for creating a design system on a product that... I use the word legacy really lovingly, there are parts that are-

Zac Darnell: It's been around for a little while.

Jaki Clark: Seven years, which in web terms is a long time. While that is for sure valuable, and we are doing that work right now, it to me wasn't the most urgent need. It was creating functional value for customers first and then creating operational value, which is I think valuable but less so for the product team.

Zac Darnell: That's really cool.

Noelle Webster-Milam: There are so many times I feel like I have conversations with designers or even just overall team members where it's like... A team is a system. It literally has moving pieces within it. Designers and engineers are very empowered by understanding unconsciously what's going on and taking a look and using your own toolkit, like you said, eating your own dog food. I love the term dogfooding. Being able to recognize and use your own practices and methods, looking at yourself introspectively, and then your team as an ecosystem and being able to apply that and look for the best opportunity is something that I think is just kind of running under the radar but is so foundational to the success of especially how you've grown organizationally to getting to the point where you are. If you had not taken that step, you would have been creating some sort of ginormous design system-

Jaki Clark: Right.

Noelle Webster-Milam: ...applied some quote, unquote lipstick to the situation. It would still have the undercurrent issue of usability issues or designing the wrong thing or not hitting whatever market with the right thing that, like you said, Casey, they didn't know that they needed.

Zac Darnell: That's a good point and kind of an interesting segue. So, okay. Fast forward to now, I guess, how have you seen the product itself be impacted by this evolution and this integration of design discipline at Lessonly?

Jaki Clark: That's a good question. Casey, I'd be curious about your perspective as not an outsider, but you're on a different part of the space than I am.

Casey Cumbow: Yeah. I mean, it's definitely helped us increase our confidence that we're building the right thing. Right? Also started user testing for a thing and realized, yeah, that's not right. So, rather than hoping for the best, diving in, spending months of time and effort delivering the feature, we've said, "Hey, no, let's pause. Let's gather more information. Let's ask our questions, and maybe here's the problem we're trying to solve over here versus this other one." So, it's definitely, definitely helped there, I mean, hugely. We were doing that at all before. So, we were at level zero, and now I think we're doing a fantastic job there, which has inspired confidence in the delivery crews, engineers, product folks, to be able to more confidently talk about the thing that we're building and know that we're building the right thing and what we're investing our time in is the most important thing. I think also increased confidence in just the user experience, that we're paying attention to the right things and we know our customers, because we're talking to them. We're talking to our users way more than we ever did before, which is really fantastic and valuable for 9, 000 different reasons, obviously. I also love just the level of collaboration that we've seen recently. We've had some road bumps. Right? We've had engineering making a decision to reduce scope and removing some core thing that design felt very passionately about, and we didn't have a conversation. Right? That's not okay. And we've worked through some of those challenges and figured out how to avoid them and prevent then from happening in the future. So, definitely have our challenges, but there's just been so many great things.

Jaki Clark: Thanks, Casey.

Zac Darnell: I mean, even just the two main nuggets there, feeling confident that you're building the right thing... I can't tell you how many times I've had teams come and" We're not really sure if this is..." It's demotivating in some ways to not have that feeling. So, to have it is almost like having jet fuel behind a team moving forward. That's awesome. In some cases, invalidating an assumption is almost sometimes more important to your point of not wasting time on something.

Jaki Clark: Oh, so important.

Zac Darnell: Right?

Jaki Clark: It's actually my favorite thing.

Zac Darnell: Like, " Oh, we were wrong. Yes!"

Jaki Clark: We were so wrong! Let's kill it! I probably say the words" let's kill it" more than is appropriate for a workplace, because I really like being open to broad possibilities but then pivoting when it's not the right fit. Thank you, Casey, for that really lovely answer. I'm so glad you're here.

Casey Cumbow: One thing to add there is I think we've gotten better at verifying and validating our assumptions upfront. But what we are now working on is validating the effectiveness and the usage of the thing we actually get out there, which we're very much so working on improving. But up until recently, we would launch a big, new thing and just let it go and not really revisit it. So, in the spirit of killing things... That sounds very bad. Sorry.

Jaki Clark: Sunsetting. I think sunsetting is the word we like to use.

Casey Cumbow: Sunsetting. We're working to do more of that, to keep a better pulse on what features are super valuable to customers, what's no one using, what could we get rid of, and that is something that we definitely need to improve, but we've made a lot of progress recently.

Jaki Clark: I think one other part of just having more designers around is, for the most part, the other parts of our organization and for sure our customers, they're not technical people. So, we can talk about... I mean, performance is critical, performance like site loading performance, uptime, back-end architecture. Those are all incredibly critical. We don't exist without them. But as far as value delivered, there's nothing like... We kind of joke... There's a feature that we launched recently. We launched a certifications feature. And we spent a lot of time talking about the confetti that goes along with that certification, and it's just a fun little JavaScript I think plugin or something like that, and it's nothing fancy, but it feels so good.

Zac Darnell: Are you talking about virtual confetti?

Jaki Clark: Virtual confetti. I mean, we don't mail it to your house or anything. It's just on the screen.

Zac Darnell: Okay. I didn't know if you were sending glitter bombs to people. I wasn't sure.

Jaki Clark: Oh my god. That's a great idea. We should do that next. That is very tangible to customers and to our folks that like, "Oh, something is happening. Oh, that's exciting." Something has changed in the UI. It's very obvious. There's obvious value even if it's just kind of a fun little thing. So, I think the added value of additional design is there is a high correlation with perception of usability and how nice something is to look at and to use. Maybe they're not always a direct correlation, but I think the more that we put that polish in... It's not that our value prop as a company has changed. It's just that we're putting on a little bit of fresher clothes, and we're kind of presenting ourselves in a way that feels modern, it feels like it's delivering on our powerfully simple training software promise, and I think that's really important. It's not just quote, unquote a coat of paint. It's really trying to communicate the value that we bring to our customers.

Zac Darnell: Well said.

Noelle Webster-Milam: I'm curious too. Jaki, you and I have talked about this a little bit. So, how has this outwardly virally made its way across Lessonly as an organization? How are people bringing content to the product team or shared knowledge across the company for all these different divisions that are around? I'm sure there's a wealth of knowledge. Given where you might seek feedback at certain points in time in the development process or even after something is launched, if you're monitoring it or maintaining it or looking for improvement, what are the channels that were there, and maybe you tapped into, or that you have created in order to have those open communications at the organization?

Jaki Clark: Yes. Great question. Before I started, I would say they were doing some things. They had customer experience account managers on each of our squads as weighing in of their perspective of a customer's wants and needs from a business perspective, and I thought that was great, and we still continue to do that to some extent. I think some squads have it, some don't. I would say our Slack channels are pretty open, meaning if you're really interested in what's happening on our learn squad, you can join the Slack channel and follow along and ask questions. Other than that though, I do think there are some folks that, because they had been at Lessonly a long time and had seen it grow, I think they felt more empowered to go ask questions and go poke the bear a little bit and give feedback. I guess there was a committee meeting for, again, a handful of people. There wasn't really an open line of" Hey, we would like your feedback communication." I think there was maybe a Google form. If you heard customer feedback or if you had an idea, you could send it to the product team. We're still doing that, but it's a little bit more formalized now. We use Productboard to capture either from a customer of from you're hearing on a prospect call of you're hearing your own brain, because you're smart and you use our product too. So, I think those are all great, and I think those are really handy mechanisms. We also have our customer support feed go into that, and I think that's really helpful. The couple things that we changed, number one, we're all in the same building now, or at least we were when we were in COVID. So, we were actually in separate buildings, which it's hard to be in separate buildings. I think we felt a little distanced because of that naturally, because Lessonly had grown quite a bit and they needed more space. So, the product team had moved to another building. Once we kind of got all back in the same building, it felt a lot better. It felt like you could run into people and talk with them about the product and what you were making. Then one of the things that we started doing, Casey was actually super helpful in instrumenting this as well, was every three weeks we do three- week sprints. We call them something else, but they're three- week sprints basically. And we would share out every three weeks within the product team. That's great, but I wanted the opportunity to get feedback from lots of people, because lots of people have... They talk with customers or prospects all day long too, or they have four, five years of experience of being at Lessonly, so they have a great perspective. So, we actually opened up our end- of- sprint team share to the company, and we said, when we were in person, "We'll be in the kitchen," which is our shared, nice space in the building. "We'll be in the kitchen. Come swing by. We'll have a recording." Then we implemented a process that they wouldn't ask questions in the meeting, because that would just be chaos, because, A, we had a lot to share, and then B, that's how you get derailed really quickly. So, we said, "If you have feedback, fill out this form," and the form actually goes to a Slack channel that says product weekly updates. Then we actually have the discussion in front of the whole company about their questions or about their ideas or about what they love or about what they think is really risky and they have a lot of concerns about. So, it becomes less of a ... It's no longer secret. We've kind of taken the mask away and said, "Anybody is welcome. We would love to have you. We're excited to have you. We think it's an honor for you to spend an hour of your time with us every three weeks. This is an important... We have one product. Everyone should be excited about what's coming." I think that worked really well for us for it to feel like an open discussion, and then that's I think generated more organic discussion as a result of it, which I think is really cool.

Noelle Webster-Milam: That's really awesome. You're inviting so many voices that may not necessarily... They may have an opinion or they may have a thought, and that channel's open. That's so amazing that you're inviting them all in and being so inclusive within your organization.

Jaki Clark: Yeah. And it can feel very scary for sure. I think that's one of the reasons that we had kind of kept it separate for a while, because it feels like you might have to act on all of those pieces of feedback. But in the end, even if we can't act on their feedback or if we can't address it, I'd rather know it rather than keep it separate, both to create a culture of inclusivity but also just because I don't know what I don't know. I've only been here for a year. They talk with prospects 100% more than I do. I talk to no prospects. I only talk to customers who have usually been using us for a few years. So, they all have great perspectives, and we're lucky to have them when they join us.

Noelle Webster-Milam: All right. I have one cascading question into... That's such an amazing story. You got where you are over the past year. Kudos to y'all for the amazing growth and change that you've had happen at your organization. So, knowing where you are right now, what's the next big thing you're going to try going forward, and what might be your reason why?

Jaki Clark: I do want to put a giant caveat that I have not yet mentioned that the reason we were able to do that amount of change... Because you're right. It is a lot. It's a lot to pivot one thing that people were like, " Why does design matter?" Or not" Why does design matter?" but" You're people that make screens, right?" That does not happen without a really amazing team. I was expecting way more pushback than I got initially, and that I think is a result of both the customer- centered culture that Lessonly has created as a company. I was having account management and sales and customer experience be excited that we were having these conversations. I wouldn't expect they would care at all, and they were banging down my door, which I think that was ... I don't know how normal that is. I've never worked in a SaaS company before. But I just thought that was really fantastic. Then on the engineering and product management side, really, truly trust... I felt a very trusting relationship. It doesn't happen without that. And they had no reason to trust me. I was brand new. But they did anyway, and that earned a lot of trust heart marbles, as Brené Brown would say, for me. They were excellent partners. That cannot be understated enough that it did not happen without their partnership. For the future, I think there's a couple of things. We're kind of building out the product function in our organization, which is really exciting. So, to kind of hearken back to the thing Casey had mentioned, which is being a little bit more buttoned up on our metrics and execution side and really evaluating are we actually succeeding, because if not, should we keep doing this? Should we pivot? Then on the operational design side, I mentioned we are getting a design system started. We are building out. We're sort of in the process of doing a little bit of hiring on the design side and really starting to truly... We have baby giraffe legs, as far as our design system is concerned right now. It's very early, very wobbly, but we're getting there. On the operational design side, I would love a world in which we barely do wire frames and we do them almost maybe together, depending on the pairing, and then it's design and front- end engineering using a design system, using components or existing patterns to build it out really quickly together and have more of a conversation rather than a" It's my turn, then it's your turn, then it's my turn, then it's your turn." So, I think that's where I'd like to see us get to, both from a culture perspective, a culture of collaboration, as well as I think it's faster and better, because it literally does not matter what your sketch file looks like. It doesn't matter. It doesn't matter even a little bit. It's not real. It only matters what it looks like when you ship your code to your customers. So, I think that's what I'm really excited about on the operational side.

Noelle Webster-Milam: You're speaking my language, girl. Emoji heart eyes.

Casey Cumbow: I honestly don't know if I have anything different to add. The biggest thing that comes to mind for me is what I mentioned earlier about measuring success after we release something. What does success look like from a feature standpoint? How do we know... We introduced the concept of on- demand practice. What are those feedback loops? Are we intentionally gathering feedback from customers? Are we measuring how often X, Y, and Z is used? Setting some goals, which we do for the most part now, but also following up on those goals a month out, three months out, so that we know if we do need to sunset something or if we need better enablement. Also, I'd love to see us track even more from the enablement side. How confusing is this thing? How many questions do customers need to ask to get something set up or something working? Because those are all things that we're working on and we're improving, but we definitely have a ways to go there. So, really answering the question" What does success look like from different pieces of the product?" in addition to that increased collaboration. We've done so much there, and we are continuing to grow and improve. I just want to see us continue that.

Jaki Clark: Agreed. From another operational pieces, we're starting to do benchmarking, benchmark test every... We do it every six months. Our product hasn't changed significantly every quarter, but that's another thing I'm really excited about that can better help inform that sort of strategy. But when we think about the thing that Casey is mentioning, the stuff that I mentioned, it's not just about I think working faster because it's fun or working collaboratively because it's fun, but the reason I'm really excited about it and the reason I'm really excited about the future is because I think we'll be able to deliver measurable value much faster to our customers. We want to ship them the best things we can think of to make their business successful. That's what's fun about working at Lessonly is you have a direct impact on hundreds of companies. And if we're able to make their lives a little bit better by making their thousands of learners' lives better, that's really exciting, and we want to do that as fast as possible.

Zac Darnell: Okay. This has been a really awesome story. I want to mention we're six months into this pandemic in 2020. So, as I think about the last year and some change, maybe almost half of it has been, now that we've been working from home and you talk about coming together in a single office and having to actually help the teams work more together, I would imagine it's been challenging over the last six months. So, kudos to both of you and the rest of your teams, because that is impressive. I really look forward to hearing about 2021. 6 to 12 months from now we're going to have to have a followup conversation-

Jaki Clark: Yeah. For sure. Do a retro.

Zac Darnell: ...to hear about all of the cool things that you guys are doing soon. Yes. Jaki and Casey, thank you so much for joining us and sharing a bit of your journey.

Jaki Clark: Of course. It's my pleasure.

Casey Cumbow: Thank you.

Jaki Clark: This was so fun. It's always fun to get to talk about things after you're done with them. That's the fun and easy part. So, thank you for that gift.

Casey Cumbow: Absolutely.

Zac Darnell: We appreciate it. And we are definitely going to have a followup conversation next year.

Jaki Clark: For sure. No pressure, but we'll try to deliver.