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Crafting thriving organizations through human-centric excellence

Fail Faster

Episode 430


37 minutes

Ryan Spanswick is a relentless servant leader that has spent the last 18 years leading and designing in enterprise organizations like SiriusXM, Starbucks, and IBM.

He truly believes that investing in the health and success of people creates the highest quality work and builds design organizations that thrive and endure. He enjoys the challenge of creating impactful and intuitive user experiences that drive significant value for the business.

Podcast transcript

Khushboo: Hi, Ryan. Happy Friday, first of all, and thank you for being here today with us on the Fail Faster podcast. How are you? 

Ryan: I’m great. Thank you. And thank you for having me. 

Khushboo: Yeah, yeah, I am super excited to be talking to you and do like one of my last podcasts for the day because I’m in Florida and I can’t wait to just go to the beach and relax. 

Ryan: Sounds amazing. 

Khushboo: Awesome. So let’s get started here. Why don’t you share your background? Like where were you born and raised? What was childhood like? And what are your family dynamics so that our listeners know a little more about you than they know from your bio today? 

Ryan: Sure, thank you. Well, today I am in transit from moving from Austin, Texas, where we’ve been for the last six years, back to Seattle, with my wife and two kids. I’ve got two teenagers. So exciting time, we’re going to be downtown Seattle, very different dynamic from the suburbs that we’ve been in for the last 10 years or so. So we’re really looking forward to that. But I grew up in Colorado, particularly in Colorado Springs. 

My mom and dad are both very accomplished, very ambitious folks who I learned a lot from and got a lot of my drive from over the years. My dad was a police officer for 35 years. Now he works security and he works as a mortuary assistant driving the hearse and doing some funerals. So we joke around that he was a first responder for many years, and now he’s a last responder. But he’s a big hero of mine. And I get a lot of my drive. And honestly, the way that I lead teams comes from both him and my mom. 

My mom was a school teacher or public school teacher for many years before she transitioned into the IT organization for the same school district. And by the time she retired, she was leading that IT department. She had multiple master’s degrees. She in her spare time was helping principals get their certificates. So she was teaching at the local school, community college to help aspiring principals for high schools and below to get that certificate and move into schools. 

And then after she retired, she kept working. She was working as a senior project manager for Pearson, which is a digital education technology company that partners with a lot of school districts. And then I have one brother and one sister, they’re both older. So I’m the baby. My older sister, who’s the oldest, was kind of a gold star. She is still very much a mentor of mine in my career. 

She went to Wharton, she got two master’s degrees from Wharton, she worked at Apple for a very long time. And now she is the head of retail for North America for Chanel. So she is somebody that I speak to regularly when I’m looking for advice on leadership challenges, or just for inspiration on how I can grow as a professional, how I can help my teams grow. And my brother is by day, he works for a school district in admissions and data. But by night, he is actually a very successful black metal band frontman, singer, guitarist. 

I think he’s got six or seven tours that he’s going on this year, all across the world. He was just recently in Columbia, I think he’s going to be in Texas this weekend. And then he was in Europe just a few weeks ago. So a very ambitious family, very high performing, intelligent people that have inspired me over the years into the positions and career tracks that I’ve gone into. So it’s a wonderful and challenging group to be a part of. 

Khushboo: Awesome. That’s interesting. That’s exciting. Now, just just quick question, like when you were growing up, and at what point you realize that this is what you want to do, and this is what you love. So how did technology come up in your career? Like, what were your career paths? And how did you land up being in technology? So what was the inspiration? And what led you to be in technology? 

Ryan: Yeah, so I really started my path as more of a fine artist, typically, and particularly drawing comic books, doing paintings and sculptures all through high school, I was really interested in the different facets of art, but I really wanted to get into special effects for the movies. And so I decided to go to art school. I was working on my portfolio for my junior and senior year to try and get into art school. I ended up going to the Art Institute of Colorado for an animation degree. 

And that was going to be kind of half and half where I was learning a traditional cell animation, which is the hand drawing that you see in classic Disney movies, as well as the 3d animation for, you know, creating special effects for something like Jurassic Park, Star Wars, and so on. And I was really interested in the latter, particularly, so invested really heavily there on how could I learn 3d programs and, and really get into it. I’ve always been a huge movie buff, and tech nerd, and gamer. 

So I’ve been into video games for a very long time. And when I got there, when I got to the Art Institute, I went for somewhere between three and six months before I started to realize that the open positions for digital animators like that in the movie industry were rare and really competitive. And I was seeing this huge, huge landscape of all of these people that wanted to do the same thing I wanted to do. 

And so I started to take stock of what was the reality of how successful I could be in that particular field. And was there anything else that interested me and one of my best friends at the time who had gone to school all the way from kindergarten through college with was also there studying with a focus on graphic design. And so I started talking to him about graphic design, and it really got its hooks into me the way in which you can really manipulate typography, color theory, and especially designing logos, designing logos was something that really interested me. And I put a lot of time into over the years that I was studying there. So that kind of got me into this, this route that led me down this really long path to where I’m at today was really the switching from animation to graphic design focus. 

After I graduated, I had my first job at a small boutique agency where I was a print designer. And within six months, my boss, and there were only four of us, was a web designer. And he said, he didn’t have enough print work to keep me busy. But he was overwhelmed with website design and flash animations, and asked me if I’d be interested in learning that. And so I was like, absolutely. I love learning. 

And now, you know, 20 years later, I realize I am, you know, I thirst for growth at all times. So even the idea of getting to learn a new skill from somebody who has mastered the craft was just so enticing. And so I jumped right on it. And he taught me HTML and CSS and how to build websites and animating and flash and then coding and flash. And that launched me into the next several years of my career, I really focused on web design and flash development. And I got a lot of certificates in flash development, because the technology side of that coding and what you could do with the dynamic coding was just so interesting. 

And of course, Apple then announced that they weren’t going to support flash on the iPhone. And so I was like, Oh, no, I had to pivot. But that was right around the time of responsive design and HTML five and CSS three. And, you know, with each of these kind of big moments in my career, I pivoted into an area that was tangential, but still really interesting. So I was a front end developer for a while, then I went into UX design, and then into design leadership. 

That kind of led me, you know, through, through all of these companies that I’ve worked for in positions that I’ve been in, and I’ve, you know, had a great breadth of experience across a lot of different facets of design. Yeah, that has been really fueled by my love of technology, my love of design. And as I got older and better, you know, within the spaces that I was in, really the focus on people and growing people is what really started to inspire me in the direction of leadership. 

Khushboo: Yeah, yeah, that’s amazing. And while we’re talking about your experience here, and like you started from graphic and web designer space and role in 2005, to fast forwarded to today, like where you’re like, senior director experience design, design at SiriusXM. So now, if you have to sit down, look back from where you started to where you are today, like, what would be your one or two biggest achievements? I know, it’s a big career that you’ve built and kudos. But then if you have to just point out like one or two examples of your successes, your proudest moments, what would those be? 

Ryan: That’s a great question. And it’s funny, because I think something that I’ve been coaching the people on my team and leaders that I work with is on this idea of keeping a career journal. And it’s because we’re good at helping to recognize other people for the things that they’re doing. But sometimes we forget the amazing things that we did. And looking back and retroactively trying to figure out like, what were all the things that I delivered this year, last year in the last 10 years, to say what were some of my big successes, it can be harder to be retroactive, you know, about those things and find find the good ones to cherry pick. 

So now I’m starting to keep this career journal when I have good wins or things that I’m proud of, or things that I don’t want to do again, you know, putting them in this so that it’s easier to look back and reflect. But as I was thinking about this, there were a couple of things that really stood out to me. One was during my time at Starbucks, the first year that I was there as a front end developer, doing a lot of coding, and I realized it was kind of a bit of a mistake for me to move so far away from the creative side of my career. 

And so I repositioned into a UX role within the HR department on the learning team. And it was a jack of all trades role, you know, where I was doing design project management, actual coding implementation for the Starbucks learning platform. And at that point, this was 2014 or 2015 timeframe, everybody in the stores, all the baristas, all the store managers, the district managers, they were all still being trained out of paper binders. And when I joined that team, that concept just blew my mind, because, you know, I’m inside the corporate headquarters, and there’s this huge technology department, fantastic team of creative designers, we’re doing all of this cutting edge work on the app and on the website. And yet our store employees are learning out of these giant archaic binders. 

So getting to not only from the ground up build that digital learning platform that was rolled out to all the stores nationwide, as well as to the district and store managers, but also building out that team. So hiring, you know, and bringing on a graphic designer, having another coder come on, so that I could really focus more on the user experience and the user research side of things, helping to shape the manager role that ended up being over the top of us. 

Then actually getting to kind of dip my toes in the water of my first leadership role, having the graphic designer reporting to me directly, all of those were just, you know, such a formative moment for me, as well as a huge win of rolling out this digital platform for all these stores. It came with some really interesting challenges. Like one thing we hadn’t thought of is every store only has one computer and the store manager uses that for inventory. 

So what do you do when you need a new barista to take four hours of training, but the store manager needs the computer to be able to do inventory. So we ended up getting approval to get extra devices and all the stores, which was no small feat. It was a four year huge undertaking. And it was such a success. It was a huge moment for me, both as a designer, a creative professional, but also as a leader and getting to really start to take my first steps into leading other creative professionals. So that’s one of my biggest wins, I would say. 

But honestly, looking back over the last 10 years, even 20 years, my most proud moments are usually tied to the people that I’m coaching and mentoring. So most recently, a leader who was on my team in my previous role at Ascension Healthcare had aspirations of leadership. She was a manager on my team that I hired into that role after I first started there. But after I left, we were doing a lot of coaching and mentorship conversations as she pursued that next level taking on a director role owning more of the portfolio, really showing her capability and confidence with the executive leadership. 

When she got that role, after I had moved on to SiriusXM, and took over a lot of the responsibilities that I had in that previous role, it was just such a moment of pride for me, you know, and it’s, it’s all her, you know, she did all the work, I was just so glad to get to be a small part of her journey. Those are the moments over the last 10-20 years that really brought the most pride for me. 

Khushboo: Wow, that’s amazing. And while again, we’re talking about the wins and the successes, and we also have to think about your most epic failures. So we’ve all failed, right? We’ve all failed. And so what are your most epic failures that you want to share today? And also that journey of bouncing back from that failure? 

Ryan: Absolutely, yes. We wouldn’t be where we’re at without failing and learning and growing and overcoming some of these challenges. But I have one go to that is, for me, a cautionary tale for all new and aspiring leaders that I work with. And it is when I took my first manager title role, which was at Blackboard Education, working on their design team, I moved into a design manager role. And I was so happy to finally, you know, take that formal step, have that formal title really be seen and invested in as a leader. 

But it also came with some ego that I wasn’t anticipating. And so at one point, I had a designer on my team who was a senior or lead designer, I can’t remember at this point, but they were having challenges with another designer, one of the staff designers on another team. And it was just a personal dispute, they were really struggling to even work together. And it was becoming a problem because they were on the same project together. So me being the very confident new manager, I stepped in to help remediate the situation. 

And what I did was I talked with each of them individually. And in those conversations, thinking I knew everything there was to know, I guess at that point was trying to help the one person understand the other person’s point of view and what they were trying to say, which was the biggest, the big mistake that I was making was trying to speak for them or trying to interpret what they were saying in order to, to relieve some tension or solve some problems. And so I talked with the other designer, and I ended up making him more mad because he, you know, at that time, they were like, well, if that’s what they’re trying to say, then you know, that makes me more mad for you know, whatever reason. 

So I’m, at this point, very clearly not communicating well and misunderstanding what people are saying and interpreting it wrong. And so then I go back to my designer and do the same thing. And then I go back to the other designer and do the same thing. I did this two or three times, and I ended up escalating their fight with each other when they weren’t even talking to each other, you know, so I’m making things worse and putting words in people’s mouth and ideas in people’s heads that weren’t actually reflective of reality. 

And so then they were even more angry with each other and the problem was worse. And my VP had to step in and help, you know, remediate the situation. And in the process, I learned some really valuable, you know, lessons around one, just because you have a title, just because you’re a manager or people manager, whatever title that you get, it doesn’t actually mean you know what you’re doing. Yeah. In fact, I’ve learned over the years, I’ve started to think of different roles and promotions as you are now an entry level of that. So I was an entry level manager. And I had a lot to learn before I could even say that I was a seasoned manager that could be looking at senior managers. So really understanding that just because you have the title, you doesn’t mean you know what you’re doing. 

Yeah. So don’t speak for other people, you know, there are ways to deal with challenging conversations and conflict without trying to help people understand what somebody else is saying, because you don’t really know you are not that person, and you shouldn’t be speaking for them. So in the end, I think six months or so later, one of those people ended up leaving, they never really had a good relationship past that. And that was a huge, huge failure for me. But it was also one of my biggest learning moments as a leader, and really shifted the tide for me and how I addressed challenging situations of all kinds and became much more empathetic and thoughtful and deliberate in my approach to things. 

Khushboo: Yeah, I mean, and I 100%, or I would say 1000% agree with you on this title. And this job title inflation is such a massive problem. You know, so many people just have this, like, like you were saying, manager, director VP titles, but with actually close to no real skill or experience to manage, direct and also sometimes run that stuff that comes with heavy duty titles, you know, this is like vanity at best. So yes, this is the trend. This is the trend. But I really hope this changes and these titles are just more apt and accurate and people like who come with all the knowledge and expertise get more visibility. 

Ryan: Yes. Yeah. And that’s that, you know, kind of strikes a couple of things for me. One is we are both in the design field in general, but especially in design leadership, it’s still very new. Yeah, you know, so we saw this with front end development, we saw this with, you know, early web design roles, with a lot of engineering roles where titles were inflated, there was a lot of different things going on, it took 10 years, 15 years for things to actually start to hone back into a more appropriate range and set of titles and expectations as you were interviewing or, you know, working with people across the industry. 

And I still think that there’s some room to grow there. But yeah, I see this all over the place. We’ll have people who are design managers who are really designers that are given direct reports, but not really given the space to learn and grow as a leader. It’s more of a player coach title, heavy emphasis on players, and not necessarily setting them up for success long term as a leader. Or I’ve seen organizations where you have a senior director who reports to a senior director, a director reports to them, another director reports that person, you know, you’ve got one and two people reporting to each other up this very long daisy chain. 

And then when you ask them what they’re doing, the director is like, Oh, well, I’m actually just design, you know, but the way our titles work here, the way the pay works to be able to, you know, and I’ve been here for 10 years, and, and we acquired another company, there’s all these different factors that kind of run into that. But it leads to this weird title misalignment and title inflation within the design industry, but especially in design leadership right now. I think it’ll take us a few years to kind of get our feet under us and really solidify that. 

Khushboo: Absolutely. Yeah, you hit the nail just right. Now moving on to like your experience in the experience design space. Now, this is a rapid evolution of technology and user preferences, right? So how do you ensure that your platform’s advertising and creator experience stays relevant and keeps pace with the changing landscape? 

Ryan: That’s a great question. And it really, you know, it’s, it’s something that everybody has to really take, take a part of the responsibility for making sure that that happens. So as a senior director, you know, I have a team of about 1415 people right now, that includes a couple of people leaders, as well as a lot of designers. So, you know, it’s, it’s on me and the other senior leadership to help look for and define the strategy of what we’re going to be doing, you know, in the next year, two years, five years, you know, for Sirius XM, you know, we’ve got the in car satellite radio component of our business. 

We also have the streaming side of our business. We own Pandora, we own Stitcher, which is being sunset this year, we own Simplecast, which is a podcast publishing platform, and a lot of ad technology, as well as all the tools that support those, such as the the creator side that my team owns is the tool for Pandora, where artists can go and upload their music and track usage and, and spins across the platform to see how they’re doing and kind of leverage that for their marketing and increasing their growth and awareness. 

All of those things kind of hit a lot of different areas of super bleeding edge versus really antiquated, you know, so you have current listening experiences within Pandora or Stitcher, where we have to stay hyper relevant against competitors, especially, you know, the big players like Spotify, Amazon, Apple, so making sure that our design, our experience, you know, the the engagement with our users, and keeping up with the current trends through the different tech companies is helping to fuel what are we spotting as opportunities and really pushing out into these products and experiences. 

Then we have to take that back and kind of roll it backwards into our internal tools and our creator experiences, these platforms that have been around for 1015 years that are not customer facing, you know, one good example of that, which a lot of people who love Pandora will know it is powered by something called the music genome project, which is this fantastic recommendation engine, you know, that really, if you hit, you know, thumbs up, thumbs down, if you start a station from a particular artist, you’re going to get a great listening experience for a really long time, often without having to skip, you know, without having to change stations, it’s just amazing. 

Well, there is a very robust internal tool for programmers. And by that, I mean, music programmers, curators, the people who are finding artists, making, you know, connections between things that are rock and roll things that are punk rock, you know, there’s a tool for that, where artists are getting their music analyzed. And these professionals along with some of our automated systems are doing things to help drive tags that are used internally that help the system to bring up the next song that will make the most sense based on your preferences. So designing for this tool that’s been around since you know, the inception of the Pandora company that has, you know, has had its updates over time, but without a customer facing experience, there can be less emphasis or driver prioritization from the organization to update that and create really good experiences. 

So often it is up to the design team that is on those programs and the engineers who are working on it to just make sure that we’re doing that and try to bring it, you know, as close to parity with the style and trends of our consumer-facing apps as possible. So I kind of took a long circuitous route there to bring it back. I’m looking at the strategy along with my senior and other senior leaders at what we’re trying to do within our different product throughout the year, and then working with the leaders on my team to say, here’s what’s coming. 

Here’s what we’re seeing from competitors, what can we do not only to stay relevant in those spaces, but what are you all seeing within the design industry, new trends, working with, you know, new add ons and figma or new styles of, of delivering files to development, different ways of setting up design systems, you know, so I will look for some of those things. But a lot of it is, how do I inspire the people on my team to take that work on as well, and so on, you know, they take it to their teams, and it is a group effort to really make sure that we’re using all of the brain capacity that we have at our disposal to really shine. 

And then from there, like, how about user feedback? And so how does your user feedback and data play a role in shaping the advertising and creator experience? So for example, what methods do you use to gather and analyze user insights from that? That’s a great question. And some of that I have direct insight into, but we do have separate teams that are responsible for a lot of this. So we have, we do have a data and analytics team that is working with engineering, working with design and our research team. But we do have an internal research team headed up by the wonderful Devani Patel, who is one of my peers. And she has a couple of people assigned to our portfolio. 

So we work with two wonderful researchers who, you know, we have a very large portfolio. So you know, always research tends to be the one that you want the most head counting investment, but usually you have to work with a couple of people across a lot of work streams, and they do an amazing job. But they help us to do things like engage with artists around what they are looking for? What are they getting out of tools like Spotify for artists? What are they looking for in our Pandora AMP tool that can help them be more successful? 

You know, where are we missing some of the things that they’re like, you know, I’m trying to do this tour, this kind of release, and I like the data that I’m seeing from this platform, but it’s not helping me do X, you know, really digging in with them to understand where those gaps are that we can get new features and priorities on the roadmap. They’re also creating things like personas, or really more user archetypes. 

We don’t delve too deep into really the more traditional marketing style of personas. But you know, what are the major user types that we are creating for giving an example, we’ve got in the simple cast podcast publishing side, we have one user type that is really around newer podcasters, they’re trying to grow their audience, they’re just starting to get traction, what tools do they need, we’ve got one user segment that is for more professional, they already have a good audience. 

And now they’re trying to figure out how best to monetize and scale. And then of course, the enterprise layer. So the research team works directly with us on on doing those studies, synthesizing that data, the design team has a heavy hand in supporting. So you know, when you have two researchers and 14 designers across, I think we have a total of about 12 products in my portfolio, that’s a lot of ground to cover. So the research team is is fantastic at, you know, setting up especially in the generative phase, doing a lot of support, but also setting the designers up so that they can do some of the more evaluative work, you know, doing usability testing and concept validation types of activities, either in the middle or on the back end, and then working with those researchers to try and synthesize and get good readouts and shareouts that can help impact and influence our roadmap. So yeah, we’re doing a lot of great stuff in that area right now. But it’s, it can be a bit scrappy. 

Khushboo: Yeah, yeah, I totally get you. And you meant you mentioned, like working with different teams and collaborating. So like, you know, we know, like collaboration often plays a crucial role in the design processes, especially. So can you describe like how your team collaborates with like other departments to bring out an exceptional user experience? 

Ryan: Absolutely. Great question. So we are working with a lot of different departments and stakeholders, you know, because we have pseudo consumer facing with our artist tools, we have internal facing tools like the music genome project tool, we have advertiser facing tools and podcaster facing tools that where they can see stuff coming from the advertising space and advertisers can see what’s available podcast. So we have a lot of different areas that my team touches. 

So from a leadership level, we are engaging with obviously product and engineering leaders, but also go to market strategy, data, and sometimes even public relations, customer support to make sure that we are really ringing all the bells and ensuring, you know, quality experiences. A good example of that is, we are currently working on an accessibility initiative, which I’m spearheading across the company. And one of those things will be around the ways that people who are looking for improvements on accessibility can reach out to our company. So we have to be working with customer support on how do they reach out? Do we have an email like accessibility at SiriusXM.com? 

If somebody reaches out, what is our, you know, our internal resolution structure so that who gets pinged, who owns it, where does it go to, to get communicated back to get resolved. So we touch a lot of different areas. And then within the designer, you know, the designers that are on the team, they are working with the product managers, the engineers and the users to not only, you know, try and tackle these things that come on the roadmap, but to influence what that roadmap looks like, you know, so right now, we’ve got one team that’s working on some stuff for our Simplecast platform. 

And they’re doing a lot of generative research and concepts based off of some high confidence feature areas that the product team wants to work on. So as the product team starts to get their hands around, all right, now it’s time to start executing on this and figuring out what delivery deadlines and engineering scope looks like. We’re coming to the table with really well executed points of view and concepts, not only for them to take forward, but also for them to consider of what should come next. And why is this experience for this user going to be the thing that we should focus on? And how does it positively benefit, you know, the outcomes that we want as a business on the back end during release? 

Khushboo: Yeah, this is great. And while we’re talking about this, like making sure how the customer journey is spot on and like how you’re ensuring it, the end users are benefiting with the platform. So if you have to tell me something like that you and your team are focused on, for example, what would have to happen as a result of your or your team’s efforts for the whole organization to go like this would take us to another level. 

Ryan: That’s a very apropos question right now, because we, you know, owning these creator experiences and creators is broader than just music musicians and artists. You know, it’s it’s people who are curating playlists. It is podcast creators, you know, the internal and external programmers, there are people that curate playlists on Pandora who don’t work for Pandora for SiriusXM that are very popular and have huge following. So there’s a lot of different areas that fall into this, this creator space. 

But one of the big concepts that we are driving and getting across and reshaping mindsets within our organization is the value of providing really good experiences for these creators to enable them to upload easily great content. And the more fantastic content that we have at our fingertips, the more we’re going to draw listeners in on the consumer facing side, which is only going to drive more revenue from, you know, a subscription model from the free ad based models from our advertising side of the organization. 

Right now, you know, there’s a lot that we can do to improve that side. But really changing that mindset from yes, they’re important, but let’s make sure our consumer experiences are great. Of course we should, you know, that is super important that our consumer experience is great. But when you look at some of our competitors and how much they are really investing in the success of artists, you can see how that turns on to the other side of the coin where they are getting really great content that draws listeners in. 

So that’s the big thing that we’re pushing for this, this concept in 2023 2024. And we’ve made huge strides, especially on the Pandora AMP experience for artists just this year, but really showing those artists that we are dedicated and truly invested in helping them succeed, that is going to organically drive more engagement from them, more content creation, more things uploaded, more listening from listeners, which all comes back around to success for our business and more revenue. 

Khushboo: Wow, wow, this is very interesting. And we I mean, this has been an overall amazing conversation. And I definitely want to do another podcast, you know, like, I’m like, the time just flew by. But thank you so much, Ryan, once again, for coming here and sharing all these amazing journeys and insights. And also intels. I think this will really help our listeners to navigate some of the situations. Thank you. So Ryan, before I let you go, if people want to reach out to you and know more about the exciting and cool stuff that you are doing, where can they find you online? 

Ryan: Yeah, thank you. Best place to reach me online is through LinkedIn. I’m there pretty regularly. Just the normal LinkedIn string slash Ryan Stanwyck is the best place to reach out to me. I do a lot of growth and mentorship conversations with the aspiring and established leaders in the design community. Or if you’re a part of AIGA, or even the InVision Design Leadership Forum, you can find me there. But the easiest way to reach out to me is through LinkedIn. 

Khushboo: All right, thank you once again, and enjoy the weekend ahead. 

Ryan: Thank you so much for having me on your show. I really enjoyed this. 

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