Giant Robots Smashing Into Other Giant Robots

459: Adobe Express with Kasha Stewart

January 26th, 2023

Kasha Stewart is the Director of Growth Engagement at Adobe Express.

Victoria talks to Kasha about finding advocates that encourage her to chase problems, getting more women into product development and why it's essential to bring different perspectives into this area, and ways to bring connection between the end users and customers, engineering teams, and the rest of the organization to the business.

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VICTORIA: This is the Giant Robots Smashing Into Other Giant Robots Podcast, where we explore the design, development, and business of great products. I'm your host, Victoria Guido and with us today is Kasha Stewart, Director of Growth Engagement at Adobe Express. Kasha, thank you for joining us.

KASHA: Well, thank you for having me.

VICTORIA: Well, I thought I'd start off by asking you to tell me a little bit more about your background and how you found your way to product from starting out in film and video production.

KASHA: I originally started...I have a fine arts background and did a lot of digital story narrative, post-production. Back in the day (I'm going to date myself.), you had to was a very manual process of chroma keying and removing backgrounds, or refining someone's skin, or some type of background. That was where I kind was my bread and butter. I really loved it. It was creative.

Then in 2008, 2009, the housing market crashed, and the recession happened. And I thought, you know, I'm not a homeowner. What does it have to do with me? I'm taking these freelance jobs. I had just finished my grad program. And then all the jobs kind of disappeared. And I was thinking; here I was; I had gone to grad school. I had a really specific skill set. And then everything just poofed overnight, disappeared. And I thought, okay, well, what's more stable? Like, what could I do to secure a little bit more stability in my job, career?

So I started applying for jobs in all these very different tech, like, they wanted people to be what we used to call a preditor, like, a producer and editor, someone that knew how to do this but also knew how to like FTP massive asset files and also knew how to flag something for when things were going wrong. And so I thought, okay, well, let me just apply for one of these. I have some of the skills. I tick the box on some of the requirements.

And there was a was actually on Craigslist. I actually didn't even know if it was a real job or if it was a scam situation, but I applied. It had a very unusual title; I think it was content distribution editor. And I thought, okay, well, this is interesting. And it was for And this is about 2010. I applied. They called me. I thought, okay, why is ABC on Craigslist? But never mind, it was a legitimate job.

And I got into what we call content distribution, so understanding content management systems. And I would be the last person that would actually process the content that would then be delivered to Hulu platforms,, many different affiliates. There were also Verizon mobile deals at this time, where the cell phone carriers had their own television networks that they tried to stand up.

In that process, I started to really learn about licensing, how content is distributed, meta-tagging, and then also the architecture of a CMS. And I just for the life of me couldn't understand why this was built this way. It was a very cumbersome tool. And like clockwork, around 11:00 p.m. at night, it would crash. And if you hadn't saved your metadata on a notepad or in a spreadsheet, you're basically starting over from scratch.

And I remember asking all these questions, and they were like, "Well, it's proprietary software, and it was built in Seattle." And I was like, "Yeah, but did they ever talk to the, you know..." I didn't know the terminology like end user at the time. But they never talked to any of us that were part of this small team that had this really pivotal role of publishing the content.

And I remember asking all these questions. I had a supervisor at the time. And he jokingly said, "Well, you should go into product management since you love to ask questions." I didn't even know what product management was. I was like, well, I'm on a producer's track; that's my goal. I have this film and narrative background. And a role came up internally, and it was for a product specialist. I would say I needed a little bit of convincing to apply.

I had some advocates in HR that saw this role and thought I would be perfect for it. And I was like, I don't know, it has all this data analytics. And what does this have to do with people and storytelling? And they were like, "We think you should apply for it." And I made the transition, which is rare sometimes in corporate and internal transitions. But I did make the transition, and I became a product specialist.

And I kind of dived deep in into understanding consumer products from a front-end experience. So before, it was more from a distribution and back end. And now it was really focusing on the UX flow, the UI. What are the targets? And how do we position the content? And then, what are our consumers saying about the content? So I did open up a whole new world for me.

I went ahead, and I made plenty of mistakes. There were times that I was like, I don't know if I'm for this if this is right for me. And people definitely weren't shy then. They would tell me, "You don't look like a product manager." Or "You don't have that background of CS or data and analytics person." And I totally didn't, and I never sold myself as a false representation. But what I did have was I had this really strong inclination of really understanding from the consumer perspective.

I always took it back to even in my own circle. And I think I'm an early adopter. I love technology. But I also have friends that are still using Yahoo or Hotmail. And I'd be like, "Oh no, you got to try Gmail, or what about Gchat? This thing came out. You have to check it out." And I would think...back when I was building out these products, and this was, to level set, this is around the time of Web 2.0. I would think, oh, well, how would my friend in New York use this? Or how would my mom find her content? Or, how would my brother...

And I think sometimes we get very seduced when you're building something, especially as a product manager, that everything is from your lens and from your perspective. And the data and then also the feedback was telling us that we weren't really hitting it where consumers were. They weren't able to find the content as easily as we hoped.

And from there, I jumped into kind of entertainment streaming platforms, building out architecture, CMS, and then eventually transitioning into growth-led roles and then leadership roles later in my career. And so I've had the pleasure of working for startups like Beachbody, which was a fitness company big in the fitness space but smaller on the digital perspective, all the way to going back to Disney leading a team at Movies Anywhere. And now, I'm leading a growth team at Adobe.

VICTORIA: Wow, thank you so much. That's so interesting. And we have a couple of different tracks we could get into here. One thing I want to note that I thought was interesting is when you got into your new role, what really kind of presented itself to you is that you identified a problem in the UX. Like, you kind of lateral moved, and then you found this problem, then you had advocates who pushed you to go in that direction. And so, if you have advice for people who are looking to make that transition, how do you find those advocates that encourage you to chase the problems that you find?

KASHA: Oh, that's a great question. People ask me this frequently because I think on paper, it is hard. And no one's going to find you in your cubicle...or now a lot of us are working remotely in our houses. So you have to be your best cheerleader and campaign manager. I also think, like, what is it that is on your top three lists? In product, we have nice-to-have, must-haves, and then we kind of prioritize or stack rank our work backwards from that.

So I ask people, "What's the most important thing for your next role?" And then those are the things that you need to either lean in and start to amplify that you're already doing and how you would make a great candidate. I think internal candidates do have an advantage because they know the culture, or they may know the players, or they may see something from a different perspective, but they know what the company's challenges are.

So I would start by first talking to your manager, and you can have a great manager or not-so-great manager, but start there. Show them that, you know, I'm on this track plan, but I really want to be here. Are there things that I can do in my current role that would support that transition? Are there people that you can recommend? And sometimes, you can get traction with your manager, but if you can't, then start to search within your network.

And if there's a product manager who's maybe in your org or actually would be maybe at the same leveling or someone new, start to explain to them, "Hey, I would love to set up a coffee chat, a 15-minute informational just to hear how you did it or what's your perspective?" And constantly, as you're taking notes...people usually like it when they get an opportunity to share their story or talk about themselves. And as you take notes, "Ah, I am actually looking to transition to that. Do you have any advice for me? If you had something in an open role, what would you want from that candidate?"

And so you're constantly planting those seeds of like, I am this candidate, here's why. And product managers and, I think, also hiring managers, we have a room full of distractions. But if something's laid out to me in concise language and it's showing results of like, oh, well, I did this on the content management side, and I think this would be transferable, and here's why. And you don't have to be long-winded. I'm not into people writing dissertations and producing 20-page decks. I don't always have the time to read that, as lovely as it sounds.

Drive in on your skills. How are they relatable or transferable? And then, what are the goals that you've been able to achieve in your current role? And what are you looking to do in your next role? And I think if you start to place yourself there...and definitely get out and start talking to people in your employee resource groups.

And then also, internally, there's always, at some companies, there are HR or employee resource groups that will have at least a blog post on how to transition within the company, and if they don't, search out those people. And it's not an overnight process. I've seen people where it's been a flip of the switch, and they're on a rocket. And I've seen other people where it's taken time, but they've built those rapports with people that started to get to know them outside of their current role.

VICTORIA: That makes a lot of sense. And you're also involved in many professional networks. And so, do you also get a benefit for your career growth from that?

KASHA: Yes. I feel like I never stop learning. As much as there's always something new coming out, I mean like now I'm into the chatbots and AI. And I'm like, okay, here's another thing I got to learn. Let me [laughs] add this to my to-do list. So I never want to take that for granted.

So I feel like the communities kind of keep me, you know, it's a temperature check of what's going on, either from a challenge perspective or what type of new technologies people are integrating into their existing platforms, and how it's actually growing or benefiting them, whether it's from a machine learning and building out recommendation engines that have saved time, and then actually gets smarter. And we're building out algorithms all the way to, you know, what would it be like to have AI enhancements on an existing platform and still help drive that high-value consumer experience?

So I don't take for granted. I also recommend people that, even if you're not in product to, join product communities so that you start to hear the language and you start to see how product managers think and how hiring and leadership think. And LinkedIn is a great resource. I belong to Women in Product, Black Product Managers. There's a slew of Tech Ladies. And I'm always kind of looking.

There are newsletters that I love, Lenny's Newsletter. And I'm always like, oh, that's a nice one. Let me take that away for my team, or, oh, I didn't actually see that. I didn't think about that. I didn't see that playing out with NFTs in that way; hmm, really interesting. Or that TikTok is taking over search. And now I'm like, okay, how can my product that I'm growing from an engagement standpoint also have really strong representation on TikTok in a way that's authentic and users can find us, and we can continue to engage with users that way?

Start small. Find the right community that works for you. There's also Product-Led Growth, Product Alliances. There are so many of them. And I think you just start to kind of join them if you can. Some of them are free, some of them have dues. And they're really worth it. It's a value add. And you never know who's going to be posting in these Slack community groups too. You might see something where they're okay with associate level or okay with someone transitioning, or looking to help someone transition.

And I often mentor and direct some of my mentees in that direction so that they don't feel like they're in the passenger seat of their career and waiting for something to happen. You have to be active in this pursuit. And you also have to be a driver in it.

VICTORIA: Right. I felt that myself in my career. I felt like my network was my number one source of learning like you said. And also, when you're considering a career change, sometimes you don't even know what else is out there or what other types of jobs are out there. [laughs] I love what you said about that. And you also mentioned Women in Product and Black Women in Product. How can we promote those groups more [laughs] as we get more women in product? And why is it important to bring a different perspective into product?

KASHA: Yeah, that's a great question. I mean, I think podcasts like this, you know, letting people know. And then also, when I do a post on LinkedIn, I do the hashtags of all the groups that either I belong to, or I might tag them. One thing that I do when I do start to mentor someone I say "Be active in the community, share your voice. You're going to start to get comfortable."

Product managers have's not a career for the weak, I'll say that. [laughs] And you have to have an opinion, so start small and start promoting yourself in those groups or hearing what people are saying. And even if my company is hiring or someone else, another hiring manager, and it has a post, I'll say, "Oh, did you think about posting this or adding this hashtag to this? This would definitely help give you a different type of candidate and also get more traffic."

And it's important to me because if I think about the world population and how we're changing, and who's showing up, you want that representation of the people that are working on it. They're going to be thinking about it from a different lens that I didn't even realize that that was an issue or oh, wow, we need to really tap into that. Or actually, we should promote this in a different way because we're going to cast a wider net, or we're going to cast a really specific net. With this demo, it can grow by 10x. Versus us thinking very generally and saying, "Well, we're happy with a 2x growth."

So that's why it's important to me. I'm also always balancing, like, do I have enough representation of women? And do I have enough representation of men on the team too? I don't want to go one side too far and then I'm out of balance and I'm just hiring the same people that are like me. It is kind of challenging sometimes because I have to think about what does the team need? What is the team dynamics missing? And who is that person that can bring in or usher in that different perspective? And then also work cohesively with the existing team.

And so that's a lot of balancing act that I do in my current role and really thinking about okay, well, we're serving small businesses. We're serving social entrepreneurs. Has anybody ever done that? We can be very kind of elitist in tech, especially in product of, like, well, I do it this way. I've [laughs] got Discord, and I have all the NFTs that I've ever wanted to collect. And I can hear and listen to all that, and I can geek out.

But then I'm like, if I go back to my friends, they'll be, "Kasha, what are you talking about? Can you speak English to us?" [laughs] And they'll be like, "Can you please calm down?" And I'm like, "Oh, but there's this thing." And then I'm like, well, maybe I need to have someone who is not like me because they're going to be thinking of that person who really just has a simple task they're trying to solve for. They have a limited amount of time, and they also have limited patience. They're not in a place where they want to learn and go on YouTube and watch a tutorial.

They're really just, you know, "Hey, I need to get this birthday card or this invitation out for my kids. And this was a free product that I saw from SEO results, and I'm here." And that's the value in finding that person and then carrying them through a journey. Me, I'm going to be picky. I'm going to probably research. I'm going to look at reviews. I'm going to look at two other competitors that I'm going to start to line up. [laughter] And then you've lost me by that point. You want to get that person, and you want to make it a frictionless experience.

So I do encourage, when I'm building teams, to think about the dynamics, always going for people that are, you know, want to be there and that are really dedicated to the product but also bring a different perspective than I did. And I come from an untraditional background in tech, so I think that's probably why I'm so conscious of this and how we can make these changes. And I think, historically, or the data proves that diverse teams often excel faster and better than traditional teams.

VICTORIA: Right. And teams that are diverse and are in an inclusive environment where they feel like they can bring their authentic selves.

KASHA: Correct. Yeah, it's one thing to have diversity, but then it's also another, you know, the counterbalance of inclusion. And how do you set people up for success that have different backgrounds? And I have a great strong team of rock stars, as I say, but they all are different. They all need different things. They all have different kinds of needs from a coaching or leadership perspective. Some I'm more hands-on, others I'm hands-off. But as a leader, it's being perceptive of that and saying, okay, well, this person likes to run their own ship. I'm going to be here on the sidelines. And this person I'm going to be out front. I'm going to be walking with them side by side.

I don't know why I have all these sports analogies because I was terrible at sports in junior high, in high school. But I always feel like I'm this coach out here with a whistle and a clipboard. And I'm telling them I'm like, okay, I'm going to set this person up. This person is going to happen here. And that's how I look at it from a growth perspective.

When I'm really assessing the roadmap and the backlog and what's going to be our impact, I'm also thinking about, well, how is everybody working cohesively? And is there a way that we can have shared experiences so that that way, oh, we learned from such and such an experiment, and that's going to influence the other half of my team? Or, actually, I'm going to have them focus, or I know that we're going to have too many mobile tests at the end of Q2 because the monetization team is also trying to test something very similar. So it's a constant juggling act in my role.

VICTORIA: Right. I very much relate to that. I was a competitive rock climbing coach a few years ago on top of my full-time job.

KASHA: Oooh.

VICTORIA: And my kids would ask me if I was also a motivational speaker [laughs] because I was always pumping people up while they're climbing. So yeah, I find it fascinating how you think about the needs of your team and your own growth from an individual contributor into a leader. And how do you coach people in your team along that path, like making that transition from being really strong in product to managing a team of product people?

KASHA: Oh, that's a great question. And I love that you're like a rock climbing...I love that. I'm like, [laughs] what we call thumbs. I would just be looking; I mean, just thinking about rock climbing, my hands are probably getting sweaty right now. [laughs]

And for my team, I do have people that they're getting to a senior PM level, and they're like, "What's next?" And I really like to do an assessment of, like, "Well, what do you think is next? And what is really going to help your career growth?" And some of them are like, "Well, I want to do leadership. I want to do this." And I ask, just like I ask in any product question, "What's the why behind that? Is it a financial contribution? Is it a recognition? Or is it that you are really invested in people development?"

Because one thing I do like to preference, especially people that are in early or mid-level careers, is that managing a product versus managing people are two different skill sets. And I didn't even understand that when I started to get into management; I kind of fell into it. I had a leader that exited the company, and it was like, "Oh, gosh, what will we do next?" And I was just like, "I think we should still continue to pursue the roadmap [laughs] is what I would think to do first."

So one of the things I do say is that your work is going to change. I don't PM, and I'm not regularly with the engineering team on a day-to-day basis. And so I will say to the team that first, at certain points, you can balance it. You'll have both where you might own still part of the portfolio, but then you have maybe one or two direct parts.

But as you start to grow, you will start to transition out of the day-to-day or building individual features or initiatives. And I do ask my PMS, are they ready for that? And if they check all the boxes and say that they have a strong why, then I start off by, okay, well, let's see if our team is eligible for an internship. We're going to open up an internship this summer, and instead of this intern reporting to me, they're going to report to you.

What's your onboarding plan? What's your growth strategy for this person? And then, what do you want this person to accomplish at the end of the internship? And it's a baby step for them to kind of get their feet wet on what is it like to lead someone? And then also, what are the challenges? There's always a perfect storm where things go great.

But what about the times when things are not going great, and how do you communicate with that person? What are the nudges that they need to give for them to either redirect them, or what are the things that you need to do to kind of show them the happy path to success? So those are where I start. We have international teams and people onboarding. I work for a huge company, so there are more opportunities there.

But then I will also say if someone wants to drive and be in a leadership role, what are the mentoring opportunities within the company? So, how would you mentor somebody? And what would be your advice? How do you set up a weekly cadence? What are your expectations of this? How should they measure success and goals? All these are things that are going to be transferable when that opportunity comes up.

And then also, too, what is the right situation? Is it a mix of where I'm 50% IC and then I'm, you know, this other 40%-50% of people management? I encourage them to look at opportunities internally, even if I'm at the sacrifice of losing what I call one of my rock stars. I know that it's inevitable for people to grow. And I never want to be the person that held someone back out of jealousy, or fear, or my own insecurities.

And I do have a strong network that when I post something, I get so many candidates. It's almost to the sense of like, wow, this person is greater. Wow, this, they went to Stanford, and they did this, and now they're transitioning. And I'm like, oh my gosh, they want to work with me. And so that's always very exciting. So I never want to get so trapped in the ideology that the team is only great with these people.

I'm like; the team starts with me and my leadership. So I need to be able to build a team. I need to be able to grow a team. And sometimes, you might have a great talent pool, and other times you don't, and then what do you do in those? I mean, that's what leadership really is. It's not always when you have everybody applying for your job, and you have all this funding, and your P&Ls are going incredible.

It's those times where they come back to you and say, "Yeah, we're not going to get that done this sprint, so you'll just have to figure it out." Or someone's resigning that you didn't see coming. And then you're like, okay, I might have to roll up my sleeves and take over their part of the roadmap just as a stopgap till I have someone. And that's the things that can make or break your leadership.

VICTORIA: Yeah, it's easy when everything is going great. [laughter]

KASHA: Yes. Don't we love that? [laughter]

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VICTORIA: You mentioned a few times, switching more into your approach to product management about the experiments that you run. Sometimes those go great, and sometimes they don't go so great. So can you tell me about a time you ran an experiment, and the results were really different than what you expected, and what did you do from that?

KASHA: Oh gosh, yeah. There are so many. I'm trying to think of what's the best example. Gosh, I'm like, do I go for mobile? No, web. [laughs] Well, I think in growth, a part of your experiment should fail because if they're not failing, that also means to me you're not taking enough risk. And you're taking things that you already know, in some ways, are like low-hanging fruit, and you're very comfortable in it.

And I do encourage my team to take a big risk of how do we start to find something? We recently had something to help users on the AI side. It was a really unique feature. A user uploads an image, and AI automatically spits out templates with this user-generated content. And we were so excited. We were watching the demos, I felt like on replay, you know, as we got out the meaning.

It didn't necessarily do what we thought it would do. And so then we had to take a pause, like, what happened? And one of the things that we learned from the test is that people just didn't understand what they were supposed to do. They didn't understand the process of their workflow. And they also weren't engaged with what the results came back.

So I think that's one thing that, you know, I know there's a lot of chatter in the space about AI taking over and where are we going to be. And I still think we need to have that human perspective, that person that is like, hey, these search results are really not what the consumer is looking for. And yes, it solved a requirement of picture upload output, but the output is not matching what the consumer's needs were. It didn't solve their problem. And we have to constantly continue to filter and refine the algorithm.

So our first output back was not great. But what we learned is that we have to have more variety of the type of output of content and that we also have to do more hand-holding. As much as we think that people are going to dive right in because it's in the press, and it's in TechCrunch and on Verge, that is not our general population.

I can talk to my girlfriend; she's a doctor. And she's like, "Hey, I'm just really trying to do this for my local women physicians network." All this other stuff, she's like, "It's kind of overwhelming to me." And I didn't even see that. I was just like, "Aren't you excited that you have five options? She's like, "No, I just kind of needed the one thing with the squiggly backgrounds [laughs] and the template that I could alter." She's like, "These don't actually really speak to me."

And so we had to come back and re-define the algorithm and also think about less choices for people; as much as we were like, we can randomize it; we can output more types of templates. It's really about finding the cues that the user is giving us to find that right match, and it's not something that I think we're going to get...and knowing from the test, we're not going to get on the first try. We're going to continue to test this, and that's what's going to make it better because we stress-test it.

I mean, in growth, sometimes, I tell my team, like, don't get our hopes up, our hearts set into it because we can spend a lot of time in crafting the experiment and doing the 50% and then the other 50% control and variants, and then when it comes back, they're just not excited, or the consumer just didn't really gravitate or attach to it.

And so then we have to stop, and I think, okay, there's a lesson here. Is it the education? Is it the guidance? Isn't the language that we use? You'd be surprised how one word can throw off someone's context. And they're turned off, or they don't want to do it. Or they like, "Oh, this is kind of cool. Oh, I didn't realize that this was a free service." Or, "Oh, I didn't realize that I could save this, and it's removing the background for me. And then now I have all these options."

Growth is a hard challenge. I mean, we move so fast, which is what I love, but then we're always kind of looking at the data and having to constantly pivot and transition based off of our previous tests. [laughs] Now I'm thinking about a time when I was at Beachbody, and I was so excited because I got to do native app development on mobile platforms, and I'd never done that before.

We were all excited. We had an iOS product that was really strong. And, of course, many of the people that worked in the office were all iOS users. So they weren't even thinking about Android. And we had just missed the mark as a company not really focusing on building out a great Android native app experience. And we were just kind of relying on the mobile web experience.

And I remember thinking like, oh, okay, well, you have something. And then I went into a Facebook community group, and I just saw all the complaints. I saw all the people's frustrations. I saw also all these user-generated hacks. People were sharing what to do when your video stops. And I just was like, oh my gosh, we need to get on this.

And so from that experience, I was able to champion and be one of the people that was like, hey, we need to help drive this. On Android, we need to really, like, this is really a problem. We could set ourselves up for success. And then we can also grow in other markets outside of the U.S. And I remember looking at the first designs, and they were all done by our creators' team, which were iOS users.

So even in that situation, I think of that as more of growth internally versus putting something out user-facing to the consumer. It still was a challenge. Like, how do I influence? How do I show that this is not the right path? How do I show that, hey, we're not using material design or best practices, and this is going to hurt us in the long run? Because people that are on these platforms on Android they're used to seeing things in this manner. And we're presenting it to them in another way, and then now we're wondering why they're confused.

VICTORIA: Right, right. And you mentioned a couple of different tactics to connect to that consumer voice. What other ways do you try to bring that connection between the end user and the customer, to the engineering teams, to the rest of the organization, to the business?

KASHA: I'm very privileged in my organization. We have a really strong user research team as well. As we're doing our experiments, depending on how large or how much time we'll invest into an experiment, we will do a prototype kind of test in a smaller pool, let's say, before we go out to A/B test or have a controlled and variant situation.

And sometimes those are the little things that I can take back, a video, or likes, comments, and send it. I don't even need to wait for it to be polished into a presentation or to a Confluence page, or even in Jira. And I can say to my counterpart, "Hey, Ganesh, do you see this? This is what I'm trying to solve for." And then it's like that aha moment. And I can say, and, you know, and engineers are always delightful. And they'll say, "Well, that's only one data point." And I'm like, "Yes, but it is a significant point. And I think if we tested this more, we will see more people are struggling with this." And how can we change that? What are their solutions?

And I'm really big on collaboration. Product owns kind of the deliverables and the path and is accountable for the results. But this is a joint effort between design, between data and analytics, and engineering. So early on, I present the problem. This is the why; here's kind of our best path. But what do you think?

And that to me and my career has always yielded such a higher result instead of coming from an authoritative or dictatorship of, "Well, this is the way that I've envisioned it. Here's my mocks, here are my wires, and this is why," and then kind of leaving it out to pasture or throwing it over the fence and saying, "Okay, and I need it in a week and a half."

And I've been on both sides of different product teams, and different engineering teams work differently. But I have found that when you get people to buy in, to care, and then also give them that consumer value of that person is frustrated; I mean, that's what was the trigger for me when I went into the Facebook groups. I really didn't have the biggest inclination that we were having such a problem on Android. I was an iOS user. I was happy with the product; I could get my workouts in, or I could find what I was looking for. And then, when I did that, I started screenshotting. And then, I started to share this out in the Slack channel.

And then there are also we have so many things where you can have bots that will record the feedback if someone says something in the App Store. That's one way to kind of bring it up to people. And then, if you don't have the funding or have an in-house user research, there's always That is one way that you can start. Even if you work with design, and you guys are a small team, "Hey, I am so committed to this working. But I really would love to run a test."

And then also running a survey after people test or even in product, you know, what did they think about the experience? And if you can't even get that, you can always do thumbs up, thumbs down. [laughs] You can always do is this a four-star experience or a five-star? Would you like to tell us more?

I would say that sometimes we have blindness to surveys and to people asking for our opinions because you just want to get to that thing. But that small sampling of people that do respond, I think, is a way for you to kind of, if you're not sure, think about this directionally. I was leaning more towards this, but, wow, this user research came back, and I think people are going to really appreciate having this extra step.

Which is something like an oxymoron for me because I'm always thinking about, well, what's the easiest path? Or what's the least path of resistance to getting the user into the experience? And then sometimes you're dropping them into a whole new what we call canvas or experience, and they have no idea what to do.

VICTORIA: I liked the way you described your approach or how not to do it was like, just throw things over a wall [laughs] and say, "This is the way."

KASHA: [laughs] Yes.

VICTORIA: One of my questions that I like to ask people who have design and product backgrounds is just what does product design have to do with DevOps?

KASHA: Yeah, so everybody has to have a starting point. And a lot of times, I was definitely a product manager when I was more in the day-to-day, and I see my mind, I like to figure things out on my own. And that way, I like to come with this pretty package of, like, I thought of all the different angles. I thought of the best use case and the worst use case.

And as much as that was delightful for me, I noticed that the people in engineering would kind of check a box too, and they'd be like, okay, done. And then we might get to a certain point, and they would be like, "Oh, well..." one time when I was building something for Beachbody, and, again, it was on Android, and it was the search. And I didn't think anything of it. I was just like, oh yeah, top result, then stack rank alphabetically.

And then I hadn't thought about new content. And I remember thinking, like, why didn't my engineer say this? Because this is something that we do on iOS. And they said, "Well, you never asked us." [laughs] And I was there, you know, "But you work on the product too." And they're like, "Oh yeah, but you run the show. So this is what you wanted, so this is what I coded."

And I just remember feeling like I had egg on my face in a meeting because now we had all this new content coming out, and the search results weren't accommodating for new content. They were accommodating for the existing metadata. And I just remember thinking like, never again. And from a DevOps perspective, I think of there's a lot of change in the industry where we also have product ops people as well.

And I think of it as additional layering; it can be good and bad. I think there are positives and advantages. I think there are always growing points. And I think you have to give what is the ultimate goal? Like, if you do have a DevOps team, are they also early in the iteration? Are they part of the brainstorms? That's how I run my small pod. We have design, analytics, and engineering part of our early brainstorms.

So instead of us kind of holding our ideas in a huddle, we will kind of tee up, let's say, our top five and say, "Hey, directionally, this is the direction that we're going." And we're framing it to the problems that are most important for us to solve. So we don't turn it into a hackathon where people are trying to build a spaceship in a brainstorm. That's not the goal.

The goal is that, hey, we have these particular problems. This is the direction that we want to go in, and this is how we carry it through. And then, what do you guys think? And then we're in a Miro board in real-time. And we put the timer on and then get everybody's opinions. And some product groups I've seen where product team doesn't actually talk to the engineering. They just talk to the technical PM, which then translates out what the actual specs and requirements are.

I haven't been part of that type of org yet in my career. I have been traditionally where it's a one-to-one ratio where if there's a product manager, there's going to be a data and analytics analyst assigned to them. There's going to be an engineer assigned to them. There's also going to be a designer. And that's been my sweet spot. And I've had a lot of gains and tractions for that.

In my mind, ideas can come from anywhere. It doesn't have to start with product, but product is going to be the leader. And I don't want to think of it as a gatekeeping situation. But we're the ones that are going to drive it through with our own cross-functional teams as a partnership. So I hope that answers the question about DevOps; I'm not sure. Sometimes I can get into a little bit of a tangent [laughs] and start talking about my own experience.

VICTORIA: I love talking about it because some product, people will say nothing. [laughter]

KASHA: Oh really?

VICTORIA: And I'm like, no, you're supposed to talk to people. Bring everybody in, and that's the whole philosophy of it. And I like that you mentioned product ops and design ops as well, thinking about how you can automate the process of what you're doing or how the information flows across your team. I'm sure with your designs and end product, and everything is more on the product ops side.

KASHA: And I think having an ops, you know, it does have like one central point of contact. So if you want to think about alleviating steps, or reducing the white noise, or the friction that you may have in the organization, you have one kind of point of contact. And that person will own it, and they'll almost become a mini pod and then distribute the information, which is definitely like a gain and a positive.

I just wonder on the reverse side, though, how does that engineer or how does that designer then surface, "Hey, what about this?" Or "I think this is a better way," or "Actually, we tested this two years ago, and the results weren't great." And so that's the only thing where how does that two way-communication go back and forth when you have ops?

I think ops definitely gives more structure. You're definitely in a high performance. Everybody knows what their marching orders are. We know who's on first. And we also know from an accountability and an escalation process where all these pieces are working together. So I can see the benefits to it. I'm not opposed to it. I just want to make sure that the people that are actually building the product also have time to have a say and have an opinion.

And whether that helps change me, I want to at least hear the feedback first. And then as a product leader and as a product manager, it's up to that person to make the decision of, like, okay, you know what? I've thought about this looking at the data, or this person raised a really significant point that I hadn't considered. I do think that we need to think about this and focus. That's the advantage for me, I feel like, of having that bottoms-up approach to development and then running your teams.

VICTORIA: I think that makes sense. And you're right; I think it can be successful. But I think there's a good warning there about...and people do this with DevOps teams as well where they create a DevOps team and then put them in a silo, right? [laughs]

KASHA: Yeah.

VICTORIA: And that's kind of missing the point about the whole thing. It's like we want to power these people.

KASHA: Yeah, everything new is old again. I remember when I didn't even talk to an engineer. And I remember...and this was early in my product when I had the product specialist. I would be at my cube writing requirements. I thought they were great. And then we switched to an agile format, and I remember going into a meeting thinking, okay, we're just going to go over the stuff that's next. And they had all these questions for me, and it terrified me. [laughter]

Because it made me think, like, maybe I don't know what I'm talking about or, yeah, I didn't think about the error messaging. Oh, okay, yeah, what happens if someone loses internet connection during that session and they've started the process? Oh, I don't know. What should happen? [laughs] And so there were all these kinds of questions.

But before, I would just process my requirements, put it in a Jira ticket. And then you might get some Jira comments, but there wasn't this back-and-forth in real-time. And then, I had to really step up and write my requirements better. Because at that point, I had just had like, oh, this happens in check one. This happens at step two. And then step three, the end. That was my own kind of naive perspective at the time when I was writing requirements.

And I didn't know that the engineers had all these questions because we had that layer of...they didn't call it a DevOps person. I think they called it, you know, an engineering lead where he would just take the tickets, and then they were doing their own sub tickets to make it make sense. And so then, when we started to transition into more of an agile and rating things and giving value to them, I really had to change.

And it helped me grow. And it was definitely uncomfortable. But it definitely pushed me into thinking, okay, someone's reading this. They're an engineer. They're not thinking about this. How can I get as clear as possible but also still think about the consumer or the persona that I'm thinking about that is trying to solve this problem?

VICTORIA: That makes sense. It reminds me of one of my first jobs actually was in Washington, D.C., which you went to undergrad there. I would actually pass by Howard University on the bus every day to work. [laughs]

KASHA: Oh wow. [laughs]

VICTORIA: I wonder, are you familiar with BisonHacks and their annual hackathon that they have there? I know you're from the film department. But the computer science does a hackathon there every year.

KASHA: I am not familiar with that specific one. But I participated; I mean, we have some at Adobe. We have our regular hackathons internally. But I would love to hear more about the one that you're describing. It sounds pretty fascinating. Do they have an ultimate goal? Are they building from an existing product, or is this something new?

VICTORIA: I think it's something new. So I believe that they come together to create solutions to help improve the livelihood of the DMV community.

KASHA: Oh wow.

VICTORIA: So I think every year they make it a different purpose.

KASHA: Okay, I got it.

VICTORIA: But they interact with students and do different projects. And it's a super fun organization. So, yeah, I'll send you a link. We'll share it in the show notes as well. [laughs]

KASHA: Yeah. I love it. I love it. This podcast I'm already growing [laughter] in the short time we've talked, so I love that.

VICTORIA: And we're coming to the end of our time here. I have one final question before I ask you if you have any other final takeaways. [laughs] But what are you most excited about on the roadmap for Adobe Express that you have coming?

KASHA: Well, I'm excited...gosh, what can I share? [laughs] I'm like, I see legal tapping me on the shoulder. [laughs] I'm excited that we are making so many improvements to really simplify the experience and that we're also diversifying our use cases of the types of people that will be coming to the platform.

So when I say that, let's say we've been focused on what we call the social creator, or the small business owner, or hustler, I really want to lean more into that and expand that. We also have more of what we call our pro users coming to Adobe Express. So if you think of someone that's a professional graphic designer that may need something where they need to have a collaborator, we're enhancing that process.

And then also, I'm most excited coming into 2023 is that Adobe's Express is going to be what we think of as the doorway to all the Adobe ecosystem. So whether you start with Express on a small scale and building out a template, you can really grow with this product. And whether you use it for your everyday either social needs or even in your everyday work or marketing, you can start to have people come to the platform and collaborate on it.

We have so many exciting things that it's interesting because my team is focused on activation and repeat engagement, and how do those two worlds kind of marry each other? Getting the user in from having them on a first great day one experience and then carrying them through for when they return.

And one thing that I'm excited for is that we've had this recent pivot, and this came out of user research. We don't have to wait for the user to leave the platform to remind them of all the great things that we can do. And I'm really excited about having machine learning capabilities on the platform; where, if your next step is this, what's the next best available action? And then how does that help enhance not only your experience of the product but then also starting to plant those seeds of you can schedule this in advance or creating this type of content once a week will drive exponentially your growth on your platform?

And that, to me, is making us stronger and really looking at it not only from I want the consumer to do these series of high-value actions, but I really want to see them grow on their own personal platform level. And here's a tool that can help you do everything that you need to.

And whether you're someone that posts once a week, or whether you're someone in an office that is collaborating for a marketing meeting, or if you're a professional that has something that, you know, I just really want to use a template. I have an aesthetic. I know how to use Photoshop. I know how to use Illustrator. But let me put this in Express. I can send it to the client. They can make comments, and then they can also feel like they're part of the creative process.

That makes me happy because I was this fine arts major. It feels like 100 years ago. [laughs] And I remember thinking like, oh wow, I love these products. They're expensive, or saving up for them. And then now there are so many different plans. There are so many different ways. And I would have loved an opportunity to have a free product that allowed me to just start to understand my own type of style and capabilities without having this feeling that I have to be a designer and that everything has to be perfect. So I'm excited for that.

We have so much growth planned, new, exciting ways on the platform. And, also, you'll see some new looks. I can't share too much more than that. [laughter] So I hope the little bit of tidbit doesn't get me in trouble. But sometimes you got to break some rules. You got to break some eggs to make an omelet.


VICTORIA: Any other final thoughts for our listeners today?

KASHA: I would love for, you know, to give me feedback. I always love doing these. I'm active on LinkedIn. You can find me at Kasha Stewart. Shoot me a note. I get a healthy amount of mail, but I promise I will reply back to you if you have questions and what your biggest challenges are. Check out Adobe Express. It's free, by the way.

And continue to, you know; I just remember being this, like, early in my career and having these questions, and at different points, I was afraid to ask questions because I was like, I don't want to sound silly. Or maybe I'm not understanding that, or, you know, maybe I should have been a CS major. And I say to people now, like, you have to have a starting point. You never know what is next on the horizon. Or that everybody had been thinking about that and they were just waiting for the person to raise their hand. That's one of the things that I always want to encourage people and to check out these products, communities.

And thank you to this podcast for allowing me to share my journey and my story. It's always a pleasure. I learned something, and I'm like, oh yeah, I did actually do that. But that was a while ago that; I might forget. So it's good. It's like having my own little mini retro. So I thank you for inviting me here and to, you know, share my journey.

VICTORIA: Well, thank you. That's a very powerful message, and I appreciate you coming on today to share it with us.

You can subscribe to the show and find notes along with a complete transcript for this episode at If you have questions or comments, email us at You can find me on Twitter @victori_ousg.

This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore.

Thank you for listening. We'll see you next time.

ANNOUNCER: This podcast is brought to you by thoughtbot, your expert strategy, design, development, and product management partner. We bring digital products from idea to success and teach you how because we care. Learn more at

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