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The Target brandonce one of the most enviable in retailis in tatters. The 50-year-old company is battling rising prices, disorganized and sometimes understocked stores, and a consumer boycott over its sudden retreat from DEI under the Trump Administration. That’s why Target raised eyebrows when it announced that Michael Fiddelkewho has been at the company for two decades, most recently as COOis taking the top job, replacing current CEO Brian Cornell in February. Some analysts have questioned the decision to promote an insider, instead of finding an external candidate with fresh ideas. Indeed, when Fiddelke articulated his strategy for helping Target bounce back during the company’s earnings call this week, it didn’t sound like a bold new direction. Instead, he’s focused on reviving the retailer’s design-forward private labels and updating back-end technology to make operations run more smoothly. I’ve reported on both the early success of Target’s private-brand strategy and the company’s more recent troublesincluding the boycott. It’s clear that Target will need to make bigger changes to recover its former glory. Here are three things Fiddelke must do to save Target from further decline. Showcase Design, But Make It Affordable For more than two decades, Target has differentiated itself from other retailers with its focus on good design. It collaborated with high-end designers like Alexander McQueen and Rodarte to create affordable versions of their products. It also has a $31 billion portfolio of trendy private labels that mimic more expensive brands on the market. But over the past three years, as America has experienced inflation, many consumers are tightening their belts. With less money for discretionary purchases, they’re limiting their spending to essentials. Michael Fiddelke [Source Photo: Target] This is partly why Walmart has thrived in recent years, according to analysts. Walmart has remained focused on keeping its prices as low as possible, allowing it to hold onto low-income consumers and also attracting wealthier ones. “Even households that makes more than $100,000 are looking to save money,” says Mickey Chadha, Moody’s retail analyst. “They’re gravitating towards the Walmarts of the world.” Fiddelke has said it is imperative for Target to focus on its merchandising strategy and return to its “style and design North Star,” especially for its own brands. But he will have the difficult task of creating well-designed products at prices that will appeal to budget-constrained consumers. Given that Target manufactures most of its merchandise overseas, Trump’s tariffs will make this even harder, even if the company has been trying to diversify countries of production. And these days, Target isn’t the only retailer focused on good design. Walmart has been investing in creating its own well-designed private labels, from its premium food brand Bettergoods to its clothing brands designed by Brandon Maxwell. With these brands, Walmart is creating a flywheel: Shoppers come to it for low-priced basicsespecially groceriesbut leave with a more expensive purchase. For Target, the opposite is true: Its promise of style and newness at an affordable price, as chief commercial officer Richard Gomez described it on the earnings call, are what drive people to shop there. Target is not going to beat Walmart on groceries: Food and beverage makes up 65% of Walmart’s sales, compared to only 22% of Target’s. So Target needs to find a way to signal that its discretionary items are affordable and worth a store visit. Just as important: It would do well to bring even more of its style sensibility to essentials. Fix The Shopping Experience “There are some forever truths in retail,” Fiddelke noted on Target’s March earnings call. The first, he said, “Retail is about product, and the best product at the best value wins.” The second: “Experience is critical.” Over the past three years, the shopping experience at Target has gone downhill. In May, Fast Company spoke with Target employees about how stores were understaffed, resulting in messy shelves and long checkout lines. On Reddit, customers vented about how inventory was often misplaced and products were out of stock. The stores are disorganized, product is never where its supposed to be, and Ive seen expired product on shelveswhich is the worst thing you can do as a retailerand theres no one you can even complain to, Sucharita Kodali, principal analyst at Forrester, told me earlier this year. These are serious executional problems. Fiddelke has been COO since February 2024, so many of these slips in service have occurred under his watch. But on his call with investors this week, he said he is committed to improving the in-store shopping experience so it feels “elevated and joyful.” One way he will do this is to invest in new technologies, which will presumably include better inventory management systems. But Kodali points out that much of the store experience depends on employees. She says that Target needs to hire enough staff, and create a positive culture, so that team members are motivated to keep shelves clean and organized. And most importantly, Target’s leadership needs to be willing to receive feedback from in-store staff about what is actually happening on the ground and what they can do to fix it. “Target won’t succeed if it has a top-down culture,” says Kodali. “They need to listen to people at the grassroots level, because that is where the problemsare.” In his recent earnings call, Fiddelke sidestepped the question of whether hed add more staff to stores. But he did outline a plan to designate certain stores as fulfillment centers for digital orders, while letting other stores off the hook for digital orders so that they can focus on the in-store experience. The company is already testing the strategy in Chicago, and plans to roll it out to 30 to 40 more markets by the end of the year. The apparent goal here is to take pressure off store employees, but it’s unclear whether it will work. Establish Target’s Values Consumers are confused about what Target represents. For years, the company aligned itself with progressive values, which made it popular among liberal-leaning consumers. This was a smart strategy because the majority of Target’s stores are located in cities, where the population tends to lean left. But over the past year, the company has backed away from its DEI commitments, leaving many consumers to question what the brand stands for. Cornell helped craft Target’s image as an inclusive company. He spearheaded Target’s first Pride product collection in 2015 and announced a trans-inclusive bathroom policy. Cornell also spoke about how profoundly George Floyd’s murderwhich took place near Target’s Minnesota headquartersaffected him. He launched a range of DEI policies, from spending $2 billion in Black-owned businesses to increasing its Black workforce. But in January, Target reversed many of these policies, which angered Black consumers. “It felt like a betrayal,” says Marcus Collins, a marketing professor at the University of Michigan and author of For the Culture. Civil rights leaders like Jamal Bryant and Al Sharpton launched a nationwide boycott of Target stores, which led to months of declining foot traffic. The appointment of an insider like Fiddelke wont do much to quell the backlash unless he steps up and speaks directly about the boycott. If Fiddelke is to win consumers back, he needs to clearly identify what Target stands for and communicate this message to consumers. Consumers now have many alternatives to Target. They can shop at Walmart, which has stayed laser focused on its commitment to offering the lowest prices. Or they can shop at CostCo, which has chosen not to back down on DEI. Consumers need a reason to choose Target, and Fiddelke needs to figure out what that is.
Category:
E-Commerce
On August 21, the self-described leading multi-platform sports entertainment brand began allowing consumers to subscribe directly through a service called . . . ESPN. Unlike ESPN+, which launched in 2018, the new streaming service provides access to the networks full range of content and coverage. The various pricing and bundling subtleties would take too long to describe here, but the direct-to-consumer version of ESPN costs around $30 a month and is mainly targeted at the 60 million-plus households that are not accessing ESPN in the traditional ways today, says ESPN chairman James Jimmy Pitaro, a former lawyer whos been running ESPN for more than seven years. He will need those households, plus as many future cord-cutters as possible. Over the past decade, ESPN has lost more than 25 million cable subscribers (each worth about $10 a month in carriage fees the network collects from cable providers). And more are disappearing every day. I recently sat down with Pitaro at his Westport, Connecticut, home, an airy place with a Beatles bathroom (the walls are covered with photos of the Fab Four), a basketball hoop in the driveway, and a mixed-breed rescue dog named Jeter. We spent the bulk of the interview talking about the DTC service but also covered his relationship with Disney CEO Bob Iger and the growing importance of gambling to ESPNs business. A few weeks later, following news of ESPNs big deal with the NFL, we had an email exchange about his vision of where the NFL Network and RedZone will fit into ESPNs expanded portfolio. This interview has been edited and condensed. Following the fans: Jimmy Pitaro is betting big on the new ESPN app. [Photo: Mackenzie Stroh] Your job is to make big bets that take years to plan. Youre doing long-term rights deals and building the product at a time when consumer behavior and technology are moving so quickly that its hard to predict the next year, much less the next decade. How do you manage that? That question is incredibly relevant to ESPN today. We are navigating through some storms here, and the biggest is cord-cutting. My challenge has been protecting that traditional ecosystemcable and satellite televisionbut also setting ourselves up for a direct-to-consumer future. We launched ESPN+ in 2018, and over the past seven-plus years, weve been very strategic, very thoughtful, about how much we move over from traditional television to direct-to-consumer, how much we simulcast on both, and how much we acquire specifically for direct-to-consumer. Weve also been very focused on the trends and where customers, especially younger people, are spending their time, right? And every week, every month, we see reports from our strategy team that have led us to this moment: our full direct-to-consumer launch. We will make all of our channels available direct-to-consumer, not just that subset of content that we put up on ESPN+. But we will continue to run these parallel paths. If youre happy with your traditional cable or satellite subscription, were going to be there for you. If you are currently on the sidelines, meaning you do not have a cable or satellite subscription and are therefore unable to access all of ESPN . . . were [now] going to be there for you as well. What elements of your previous jobs at Yahoo and Disney are most relevant to the challenges you face at ESPN? Well, I started as a lawyer. I was a litigator for many years in New York, and I learned a ton practicing law. Probably most important was my experience on the dealmaking side. At ESPN, I spend more than 50% of my time on dealmaking, on partnerships with the leagues, partnerships with the [college] conferences. I had done a bunch of deals as a lawyer [for Yahoo] for the guy who was running Yahoo Media Group, and the job opened up to run Yahoo Sports, and they were looking for a dealmaking guy. I went from managing a very small team to managing a very large team, including hundreds and hundreds of engineers. Im not an engineer, dont know how to write code, but the challenge of taking on tech responsibility and immersing myself in tech was very helpful to me today as we think about going all in on direct-to-consumer. Iger is a big sports fan. Has that helped you in your job? We talk or text seven days a week, not just about business but also about our families, and yeah, we share our fandom and our passion for the Yankees and the Knicks. Bob happens to be a Green Bay Packers fan, so we do not share that. Im a Giants and Rangers fan. But we speak daily about sports. We also have a relatively new CFO at Disney, Hugh Johnston, whos a huge sports fan and knows a ton about the sports industry. Im fortunate to be surrounded by colleagues who care deeply and a boss who cares deeply about what were doing at ESPN. Lets talk just a little bit about your leadership philosophy: Discuss, Debate, Decide, Align. I dont know if I can take credit for that, but I can tell you I have really embraced the idea of getting our executives together and presenting topicssome of which are quite polarizing, quite hairyand debating. All of my direct reports know that they can challenge me. We try to decide as a team. I learned more from team sports than I did from undergrad and law school combined. We meet as a leadership team every week, and its my job to create the agenda for the meeting and to try to tackle the most material issues. Well go around and well debate, well disagree, and then we decide as a team. And for the most part, were able to do that. There are times when we cant, and then Ill decide, and then the expectation is that we all align. Otherwise, it all kind of craters. It falls apart. Whats an example of a debate that was particularly polarizing, where there was no obvious right answer? The foundation of ESPN is live games. And because live games are so important, we spend a huge amount of time talking about whats out there that we might want to go after, what we currently have and do we want to renew, extend, or do we want to exit. For example, with Major League Baseball, we had a contractual right to opt out [at the end of 2025]. And so we actually all decided together as a team that it made the most business sense to execute that, to opt out. But there are other examples of rightsleague rights, conference rightsthat are either with us today or becoming available, where te team has not been united. But look, its very expensive. And theres more competition today than there has ever been, and it is harder today to value these rights than it was when it was just linear television. How do you look at the entrance of the streamers into live sports? Well, first off, I think having someone like Netflix, Amazon, YouTube investing in growing leagues and growing sports is good for us. Its a rising tide. What Amazon has done with Thursday Night Football is great for the NFL, and Id argue its great for ESPN and the Walt Disney Company, because [having] more people, including younger people, watching Thursday Night Football means more people are going to watch Monday Night Football. On the bad-news side, yeah, its more competitive there, and prices are going up because there are more interested parties. I can only give you my perspective on their priorities, but what Ive seen, especially over the past year, is the same amount of discipline that weve demonstrated [in valuing rights]. They are modeling these rights out, and I dont think that any of them are going to do a deal that puts them in the red. Theyre only going to do something that is profitable for them. Which is good for you. Correct, correct. Of course. Sports betting is a huge part of the sports business and sports media, and ESPN is no exception. What is your vision for the role of gambling in the future of the company? My job is to provide clarity in terms of our mission and our business priorities. Our mission is to serve the sports fan anytime, anywhere. The sports fan today views sports bettingnot every sports fan, but for the most partas a part of the fan experience. And so we decided, as a leadership team at the Walt Disney Company several years ago, that we needed to be present. So we took a step back and looked at the value of our brand. And we know that our brand conveys trust to the sports fan. We know that we are the place of record for sports fans. When something happens in sports, people turn to ESPN, and so theres a great deal of responsibility there. But again, if you look at the sports fan experience today, if were going to deliver on our mission and were going to serve the sports fan responsibly, we needed to do more, and so we started to speak with several online sports books, and we ultimately decided to partner with Penn Entertainment. We did essentially a brand licensing deal to start. The book is now called ESPN Bet, and were looking at this as still being early days. Really the first inning here. When we launch the enhanced ESPN app, youre going to see significant betting integration. Now, its our responsibility to make sure that were doing this in a responsible way, and a lot of this will be driven by personalization. Youre going to see more betting integration if you are a sports bettor and if you have linked your ESPN account with your ESPN Bet account. We will, of course, have that information and be able to personalize the experience for you. Do you believe there is tension here? People need to believe that these games have competitive integrity. News just broke [in late June] that former Detroit Pistons guard Malik Beasley is under investigation due to unusually heavy betting on his personal stats during some games in the 2023-2024 season. Do you worry about gambling undermining the publics trust in the games, either due to a big 1919 World Series-type scandal or things like the Beasley news? Look, obviously Im aware of the incidents. I will tell you that my interpretation is that the system is working. We have been able to identify the problems. Meaning the tech can spot irregular betting patterns that indicate corruption? Yeah, exactly. I want to add: Were investing in this space [for other reasons too]. Yes, its a part of the sports fan experience, especially for younger people today. But also, if you place a bet on a sport, youre more likely to watch it, right? So sports betting is actually driving the business because its driving audience engagement, its driving ratings, its driving corresponding ad sales and sponsorship. So yes, theres the sports betting side of it. Were getting paid [$2 billion in cash and stock over 10 years] by Penn Entertainment to use our brand, but also, the more people bet on sports, the more engaged they are with our linear programming, our direct-to-consumer offering. Now, I dont want that to sound callous. We have to be responsible, and we need the technology. Penn has the technology, in terms of identifying problem bettors and cutting them off. We do public service announcements. Were doing, I think, what we can to be responsible here. Penn Entertainments market share is still very small, 2% to 3%, and it hasnt really grown. DraftKings and FanDuel occupy the top slots, periodically trading positions as No.1 and No.2, with a combined market share of about 70%. Does that concern you? Are you disappointed that Penn hasnt been able to carve out a larger share? Its the first inning. I said it before. We are very early. We need some time to launch this enhanced app with the full betting integration. I think well be in a better position in a years time. Talk to me a little bit about how you see the future of women’s sports, which has exploded in popularity in recent years. Women’s sports is not a new priority at ESPN, and this long predates me. We’ve been investing in women’s sports for decades. The momentum today, with so many of our competitors embracing women’s sportsit’s great for the industry. We are going to continue to make these investments. We will continue to acquire rights. We recently closed our WNBA deal that starts next season. It’s a new 11-year deal. We reached an agreement with the NWSL [National Womens Soccer League], and we would love to talk to the NWSL about expanding that partnership. We are massively invested in women’s college sports. Its not just the games, it’s the studio programming. We have a new [women-led studio] show called Vibe Check. Were investing in female talent, investing in a fantasy game for the WNBA, investing in covering women’s sports on social. Identifying more and better time slots on ABC and ESPN for women’s sports has been a priority, and you’ve seen us continue to lean in there. These investments are a huge morale boost. Our employees love working on women’s sports, and take so much pride in advancing these leagues and advancing these games. I would be remiss if I didnt ask if you will support the presidential campaign of Stephen A. Smith. I actually have not talked to Stephen A. Smith about any of that. We just got our deal done with Stephen, and I’m thrilled with it. He is in a very good place himself with the deal. There is no harder working person in the sports media business than Stephen. I’ve never once called him and asked him to do something where he hasn’t immediately said yes. We are very fortunate to have him on our side. We know that people tune in to First Take specifically for Stephen. That matters in terms of our desire to grow our audience, and it matters in terms of our ability to secure advertisers and secure sponsorship. Stephen is a huge part of our future. Youve got a few years here, but Im curious if you’ve had any early thoughts on the 50th anniversary, in 2029, and what you migh do to honor that occasion. I was fortunate to be here for the 40th anniversary, and we had many of the legends at ESPN, some of whom don’t work at ESPN anymore, like Mike Tirico and Robin Roberts, come back to Bristol, and sat on a stage and talked about their experience. And Ive got to tell you, as a sports fan, I got chills sitting there listening to them. It’s still one of my proudest moments at ESPN. Fast-forward to our 50-year anniversary, and I would like to do something very similar. It was such a huge success, and I just remember looking out into the audience and seeing hundreds of ESPN employees smiling and taking so much pride in what we’ve accomplished together and hearing firsthand from these legends. This time maybe we’ll broadcast it. It would probably warrant air time. You mentioned that you and your leadership team spend a lot of time debating sports rights. How would you characterize the level of agreement or disagreement around the NFL deal involving NFL Network and RedZone? Everyone was on board with the idea of being able to include the NFL Network and all of the games and other NFL content in ESPN direct-to-consumer, as it will give fans another way to engage with the network and, at the same time, fuel our overall business. Bottom line, were making more content from the most popular league in America easier for fans to access. The NFL will own 10% of ESPN. ESPN covers the NFL intensively, and covering ownership presents ethical issues. Does this concern you? Were not concerned. The NFL has never asked us to change our approach to coveragenor would we. Objective and fair reporting is core to our DNA. That applies not just to the NFL but to all our league partners. They understand that, and its not going to change. Your name comes up often as a potential successor to Iger as CEO of Disney. Youve downplayed it, sayingIm paraphrasingthat youre happy at ESPN. Have you officially told the board that youre not interested? What I have said is I am in my dream job. Im a huge sports fan. I spent years competing as an athlete. Then I ran Yahoo Sports. I spent years competing against ESPN. Then I spent years at the Disney leadership table, reporting directly to Bob Iger, getting my annual review, and always finishing that conversation with, Hey, maybe someday Ill end up at ESPN, or Bob saying, Maybe someday youll end up at ESPN. Weve worked very hard over the past few years, building out this direct-to-consumer strategy, this parallel-path strategy. One of the things that Ive said to our leadership team at ESPN and to the team at Disney is we cant look at this launch as a movie opening. The product is going to get better regularly, and so were not going to judge ourselves based on either the number of people that subscribe to ESPN over the first weekend or the first couple of weeks, or even the first couple of months. And were not going to evaluate the product that way either. Thats a long way of saying that I am incredibly motivated by my current job. I love my job, and this is the job that Ive always wanted for as long as I can remember.
Category:
E-Commerce
Every CEO knows the feeling of promised features taking months longer than expected, simple changes breaking unrelated systems, and top engineers fighting fires more than they build the future. Welcome to technical debt: the detritus of yesterday’s innovation that increasingly blocks progress today. The crucial reality is that tech debt isn’t an “IT issue”it’s a business strategy problem that directly impacts your bottom line, competitive positioning, and organizational resilience. Left unmanaged, tech debt will quietly erode your margins, reduce your velocity, increase your fragility, and throttle your growth. The Executive Blind Spot When your product team promises a “quick” integration with a new partner, but it takes six months because legacy systems can’t handle the load, or customer support tickets spike after rushed features create cascading bugsthose aren’t engineering failures, they’re consequences of business decisions. The most successful companies understand that technical debt operates like financial debt. A little tech debt can accelerate growth, but unmanaged, it becomes a compounding burden that eventually consumes more resources than it creates value. Unlike corporate financial debt obtained on favorable terms, you’ll pay high, fast-compounding credit-card interest rates on every tech debt decision you accept. Why Engineering Teams Stay Silent Each of your engineering teams generally knows where their tech debt burdens are in the features they control. They live with the daily friction of working around brittle systems, patching crumbling infrastructure, and building new features on shaky foundations. But they rarely surface these challenges in terms that executives can act upon. The problem isn’t unwillingness; it’s translation. Engineers speak in systems and code quality, while executives speak in velocity and competitive advantage. When an engineer says, “We need to refactor the authentication service,” an executive hears, “I want an expensive delay with no visible bottom-line benefit.” This communication gap creates a vicious cycle in which engineers grow frustrated that leadership doesn’t understand their constraints, while executives grow frustrated that engineering timelines seem unpredictable but constantly increase. Meanwhile, the technical debt compounds silently, aggravating both problems. The Hidden Mountain Range Most executives have been told they have “some technical debt,” but they consider it a manageable hill their engineers can traverse during slower periods. The reality is far more complex. In most companies, technical debt is a mountain range of interconnected challenges across teams, systems, and processes. Individually, each team manages its local challenges: the authentication team’s debt slows the mobile team’s development. The infrastructure team’s shortcuts create reliability issues, consuming the platform team’s capacity. Fragility causes outages, rollbacks, and time lost to solving proximate causes instead of root causes. These isolated struggles compound into an organizational burden that will remain invisible until measured systematically. Measuring What Matters High-performing executives have learned that, just as with any other business metric, technical debt must be measured, tracked, and managed through systematic and objective statistical gathering that translates technical realities into business impact. A comprehensive anonymous engineering survey provides CEOs with their first aggregated, organization-wide view of their tech debt burden, transforming individual team struggles into strategic intelligence. The survey should capture both technical specifics and business impact: How much time does each team spend on maintenance versus new features? Which systems create the most friction? What technical limitations block business objectives? The real value comes from expert analysis that translates findings into actionable metrics. Instead of “refactor the authentication service,” the business case becomes “investing $200K in authentication upgrades will reduce feature delivery time by 30% and eliminate $50K in monthly authentication-related outage costs.” The Strategic Transformation Once executives see their complete technical debt landscape, the conversation shifts fundamentally. Technical debt becomes a strategic business initiative with clear ROI and executive ownership. This happens because measurement shifts the conversation from IT to money. That rushed product launch that skipped proper testing? It’s creating $35K monthly in customer support overhead. The decision to delay infrastructure upgrades to hit quarterly targets? It’s costing $220K annually in reduced development velocity. Armed with this visibility, executives can make informed trade-offs: investing in technical debt reduction because the business case is clear, not because engineers are complaining. A Practical Framework For companies with fewer than 1,000 employees, building technical debt visibility doesn’t require a massive investment: Establish Baseline Measurement: Send all engineers a comprehensive anonymous survey focusing on time allocation, system reliability, known technical debt, and cross-team dependencies. Translate Technical Findings: Work with engineering leadership to translate technical debt into business impact metrics. Calculate the financial costs of delayed features, customer support overhead, and productivity losses. Identify High-Impact Opportunities: Focus on tech debt that affects multiple teams, blocks business initiatives, or creates recurring costs. Prioritize based on business impact, not technical complexity. Integrate into Business Planning: Make technical debt a standing agenda item in strategic discussions and factor ongoing costs into road map trade-offs. Winners Move Fast While Others Fight Fires Companies that master technical debt measurement move faster because they’re not constantly fighting technical friction. They scale more efficiently, attract top talent who want to work on well-maintained systems, and make better strategic decisions by understanding the actual cost of proposed technical trade-offs. Technical debt will always exist in fast-moving companies. The question isn’t whether you have itit’s whether you’re managing it strategically, or letting it manage you. Companies that win in the next decade will treat technical debt as a business discipline, investing in measurement and strategic management just as they do for financial debt.CEOs might be surprised at the resources high-performing companies spend managing this: Netflix, Spotify, AirBnB, Syngenta, and Booking.com devote as much as 20% of engineering time to managing technical debt. While youre not alone in facing this issue, solving it simply must be a strategic C-Level business focus.
Category:
E-Commerce
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