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In an age obsessed with the new and the next, creating sustained business success is an art form but a hard craft to master. The headlines tell the story. Starbucks is on its third CEO in five years. HBO changed its name, then changed it back again. Nike is slowly returning to form after three years of share decline. As an Innosight report wisely noted almost a decade ago, Half of S&P 500 companies are expected to be replaced over the next 10 years. So, when results falter, how do legacy brands transform? What separates those that rise again from those that fade away? To find out, we spoke to CMOs from a rare group of brands that have won the hearts of multiple generations. What follows is a distilled playbook plus sharp provocations to guide your own transformation. 1. Only the sharp survive The longer the legacy, the sharper a brand must be in consumers minds. But time blurs brand meaning. What starts as a clear idea becomes diluted by layers of well-intentioned additions until the brand loses its edge. As Jonathan Mildenhall, CMO of Rocket, a lender with 40 years of mortgage expertise, puts it: One of the hardest disciplines to practice is the company-wide skill of corporate editing. The truth is that over time and across markets, people add things on (new and new and new) but no one ever takes the time to sunset the old. Thats how brands become bloated and lose their focus. At Starbucks, CEO Brian Niccol famously cut 30% of menu items, not just for efficiency, but to get Back to Starbucks. The aim? Sharpen the brands identity by subtracting what no longer served. Question: What could your brand let go of to become sharper in peoples minds? 2. Drive a reappraisal, not a reinvention Reposition at your peril. Reinvention is risky; reappraisal is powerful. The most successful transformations we heard about began not by changing the brands fundamental role, but by finding contemporary ways to express its enduring truth. As PepsiCo CMO Mark Kirkham explains, Change the how, but dont change the what. PepsiCos core benefits of instant refreshment, enjoyment, and fun havent changed. But with the return of the Pepsi Challenge, the brand tapped into deep memory structures to drive trials of Pepsis zero-sugar variants and create cultural reappraisal. At Calvin Klein, CMO Jonathan Bottomley revived the brands cultural resonance without moving it off. Strategic partnerships with figures like Jungkook and Jeremy Allen White brought the brands key products and advertising iconography to a new generation. As Bottomley says: The path to getting the brand back on top was to make that iconic impact on culture feel very contemporary. Question: What cultural communities could viscerally connect with your brands core equities to drive a reappraisal? 3. History offers a map to the future, aka there is gold in the well Treated with intention, legacy isnt baggage; its a strategic advantage. A brands past is a pattern-recognition engine, a repository of whats worked and what hasnt. When Jonathan Mildenhall took over as Coca-Colas VP of global advertising, his first move was to dive into the archive. Ninety percent of the headwinds that Coca-Cola was facing had been dealt with in the past, by the brilliant marketers that had come before, he explains. That insight led to the Open Happiness campaign, which reignited the brands connection with a new generation. At Bacardi, CMO Ned Duggan followed a similar path. By revisiting past activations and aligning them with contemporary culture, he found fresher versions of what had already succeeded. There are very few new ideas on old brands that someone hasnt thought of, says Duggan. You can either find the ones that worked and make them fresh or roll the dice. Question: When was the last time you went back to the well to find your brand gold? 4. Transformation is an inside job. Brands dont transform by changing ads. They transform by changing organizations. Legacy brands often chase external reinvention through new logos and campaigns, before aligning internally. But if the brand evolution doesnt live inside the business, impacting culture and commercial planning, then it wont land outside it. The key is to make the brand genuinely valuable for other leaders and the challenges they are facing. At the BBC, Chief Brand Officer Charl Bassil views brand as a key internal decision-making tool: The brand is a key lens through which to arbitrage decisions. It speeds up execution by resolving internal tensions. At Bacardi, the brand mind map became a daily reference point. Duggan recalls: It guided everything. We looked at it every day. Internal clarity built external coherence. Question: How can you give your brand an influential role in decision making across your business? 5. Customers give you courage Transforming a legacy business means facing internal resistance. Every step forward comes with tension. What to keep, what to change. Its a tightrope walk. Every year Im told you cant do that, it will hurt TIMEs brand, says TIME Inc. Editor-in-Chief Sam Jacobs. Yet we have to take risks in informed ways and that does make a lot of people anxious. That anxiety is normal. Informed risk is non-negotiable. But bringing in customer voices can turn hesitation into momentum. At Visa, former CMO Lynne Biggar led a sweeping listening tour. She and her team spoke directly with thousands of people. We didnt sit in our offices and get a research company to do it all, she says. They talked to customers and noncustomers. Small business owners. Government officials. These voices became a North Star. They gave clarity. They inspired confidence. And they helped Visa elevate its brand across consumer payments, B2B money movement and new payment flows while imbuing a broader purpose. Customer insight didnt just inform the work. It gave the team the courage to act. And the organization the confidence to follow. Question: Are you listening widely enough to act bravely? 6. Soft power builds lasting change Startups run on founder energy. Legacy brands require a different mode of leadership. Transforming an iconic brand isnt about charging in. Its about building coalitions, editing wisely and earning trust. You need to come in ready to edit, not to conquer, says Duggan. When youre trying to evolve an organization of tens of thousands, many of whom have devoted decades to the very things youre now seeking to change, its not brute force that prevails, but the uniting influence of soft power. p>Charl Bassil sums it up: This is not the job for heroes. It is a job for team-builders and translatorsbut the pleasure of breathing new life into something that you find meaning in, and that you love, makes the job that much more fulfilling and meaningful. Question: Are you building an internal culture that can sustain transformation? Or one that depends on your personal energy? Transformation is not a one-off fireworkit is a constant campfire Icons need to feel owned and distinctive, but they also need to be constantly updated, says Calvin Kleins Bottomley, reflecting on what it takes to stay on top in the world of fashion. Its perfectly phrased advice for all brand icons, whether in fashion, food, finance, or beyond. Icons are in constant motion. For the CMOs of tomorrows icons, the transformation work is never done. Many companies can create a single pop of cultural relevance through a one-off campaign. The difference with the great stay-ups is that they inspire the entire organization. True transformation means tending a constant campfire. It means building and sustaining momentum, not relying on occasional big fireworks. Because staying on top means never standing still. Neil Barrie is global CEO and cofounder and Sara Tate is transformation partner at 21st Century Brand.
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E-Commerce
Although there are now 55 female CEOs among the top 500 U.S. companies, female representation is still only 11%. A recent McKinsey & Co. article, The Inner Game of Women CEOs, explores how women who reach the top navigate the mental, emotional, and relational polarities of leadership. How do they maintain confidence and humility while asserting their bold vision and operational grit without self-erasure? Women often lead differently because they have to. Their leadership isnt just a matter of style or preferenceits survival. And that reality doesnt just shape how women show up as CEOs; it reshapes how they communicate, both internally and externally. Female leaders face a double bind Female leaders are consistently caught in what sociologists call the double bind. They are penalized for being too assertive while also dismissed for not being assertive enough. According to McKinsey, women are more than twice as likely as men to be described as overly ambitious, even as they are equally as likely to be described as lacking ambition. Similarly, a Textio report on job feedback shows women receive 22% more feedback on their personality than men and 30% more exaggerated feedback than men. The gap is even greater for BIPOC women. For a female CEO, communication is not just a leadership tool; its a tightrope to walk. Every sentence, keynote, or town hall must project vision and conviction, but not aggression; authenticity, but not overexposure; strength, but not dominance. Sound familiar? Revisit America Ferreras epic monologue in the Barbie movie. Its a balancing act few men are forced to consider, much less master. Visibility versus relatability In high-stakes leadership, communication isnt about charisma; its about trust. Women CEOs often default to a relational, purpose-driven approach in their messaging, using we more than I, contextualizing decisions with values, and inviting dialogue over top-down decree. This isnt weakness. Its often a strategic choice to preempt bias and build credibility. But theres a risk. A too-collaborative tone can undercut authority in the eyes of boards or investors still primed for the Hero Archetype. On the other hand, an assertive female executive can be misinterpreted as cold or arrogant. This paradox means women CEOs must become highly intentional communicators, code-switching not just between audiences, but between their identities. Culture setting through language The best women CEOs use communication not just to lead, but to recalibrate expectations of what leadership looks and feels like. They narrate change. They humanize decisions. They model curiosity as a strength. And often, they do the extra work of translating their leadership moves, explaining not just what decisions they made, but why. This transparency builds alignment and trust but also requires time and emotional labor that their male peers are rarely asked to invest. Internally, this may require women CEOs to spend time: Holding stakeholder briefings that address business outcomes and cultural implications. Articulating a clear vision with space for feedback and co-creation. Saying I dont have all the answers, not as a sign of weakness, but as an indication of leadership maturity. Male CEOs are rarely expected to take these extra steps. Redefining the CEO voice Platforms like LinkedIn, Substack, and executive podcasts create room for women CEOs to tell their own stories on their own terms. This is crucial. While many still face biased gatekeeping in traditional media, digital platforms offer more nuance, depth, and control. We see the most effective women leaders using communications to: Elevate purpose over personal brand. Lean into values without becoming tokenized. Speak candidly about failure, ambiguity, or systemic change. Done right, this kind of external communication doesnt just enhance reputation; it redefines what executive presence looks like in the public arena. The Takeaway The leadership playbook is different for women than men because the expectations and penalties are different. The best women CEOs have developed an inner game of resilience, clarity, and purpose, not because they wanted to, but because they had to. What the McKinsey article illuminates, and what we must continue to say out loud, is this: Women are not thriving despite their different approach, theyre thriving because of it. And how they communicateas translators, narrators, and meaning-makersis central to their success. As more women take the helm, lets not ask them to conform to outdated norms. Lets rewrite the norms, starting with how we define strong leadership and how we choose to talk about it. Tyler Perry is co-CEO of Mission North.
Category:
E-Commerce
Millions of individuals and families across the U.S. are trapped in a vicious cycle. Financial concerns like inflation and housing costs are harming their mental health, and the rising cost of healthcareanother major concern for householdsis preventing them from getting the care they need. That makes all of their health problems worse, and the cycle keeps spinning faster and faster. That was the key insight from our recent survey on mental and financial health we conducted with Talker Research. About 70% of U.S. adults said their financial anxiety is at an all-time high, and 20% reported a decline in their mental health over the past year. If that weren’t alarming enough, roughly 30% of people said their mental health had been negatively impacted by the cost of healthcare, or by the difficulty of accessing healthcare for themselves or a loved one. Most discouraging, despite the evident need, only 14% of people were currently seeing a therapist or psychiatrist. The top reason people cited for not getting help? Affordability, by a wide margin. Mental health access barriers What is the biggest challenge preventing you from seeking professional care for mental health? Source: Included Health / Talker Research (2025) Costs are rising This tangle of financial anxiety, cost-related access barriers and deteriorating mental health are a crisis in the making for all of us. When people forgo needed care or medications due to costas 36% of Americans recently havetheir physical and mental health problems tend to get worse, which makes them more likely to end up in the emergency room or a hospital bed. This cycle is an especially acute problem in the commercial insurance market, which largely comprises employers providing health benefits to America’s workforce (158 million people). Thanks in part to surging hospital prices, per-capita healthcare spending has shot up faster in the commercial market than in Medicare or Medicaidand the cost trend is only getting steeper. Cumulative growth in per capita spending by insurance type since 2008 Source: KFF (2025) Employee benefits Rising costs are trickling down to individuals and families through higher premiums and copays, even though employers, to their credit, have absorbed most of the increases in recent years. In fact, in an effort to support their workforce and rein in costs, many employers have upped their investment in a wide range of health benefitsoften at little or no cost to employeesto close gaps in care and guide their people toward high-quality, cost-effective support. These benefits range from mental health apps, platforms for telehealth and chronic condition management, navigation services, and much, much more. While some of these offerings do help individuals get healthier and generate cost savings, it’s clear they haven’t done enough to reverse the broader affordability trend. How come? Engagement is one problem. Too few employees are aware of their benefits, enroll in them, or stick with them long enough to impact their health or financial outcomes. Employee engagement is always an uphill battle, and the lack of integration in healthcare only makes it harder. Mental, physical, and financial health can’t be addressed in isolation, as the recent survey findings show. But most tools and services arent connected, making it nearly impossible for individuals to experience a seamless journey that supports all of their healthcare needs. A bigger, related problem is the fee-for-service payment model. Engagement alonegetting people to use more serviceswont improve outcomes if the care isnt timely or high quality. In the commercial market, a shift toward value-based care and contracting is helping employers, employees, and healthcare partners align incentives to drive better clinical and financial results for everyone. What people really need, what theyre missing most, is personalized, all-in-one healthcare that provides integrated medical and mental health support, care coordination, benefits guidance, and help with billing and claims, all of it connected by empathetic humans who are looking out for the whole person. Mind, body, wallet. Taking care of any one of these dimensions of healthand bringing down costs for everyonerequires taking care of all three. Owen Tripp is cofounder and CEO of Included Health.
Category:
E-Commerce
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