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Leadership is not a straight line or a standard model; there are countless paths to the top. From Silicon Valley builders like Reed Hastings to steady hands like Warren Buffett, who had already led Berkshire Hathaway for decades before Netflix mailed its first DVD, the common thread is not a blueprint, but an ability to draw the best out of people. With two decades in the C-suite, Ive collected a handful of lessons that have shaped my leadership philosophy. I certainly dont pretend to have all the answers, and ultimately leadership is a journey, not a destination. But these five observations have helped me along the way. They serve as a useful guide in navigating the unpredictable terrain of leadership, and in my view, often separate tone-deaf leaders from those who really connect. 1. World-class products come from world-class people If there is one piece of wisdom I elevate above all else, it is that people matter most, every time. The flywheel of any successful company spins because of its people: Amazing people build innovative products and platforms; these drive healthy profits; healthy profits are reinvested in more amazing people. Embracing humility over hubris is key. Acknowledge your blind spots and recognize your limitations in knowledge and skill. Doing so gives you a clearer lens to find the right people and build teams that fill those gaps. At Twilio, my leadership has focused on nurturing a culture where teams are empowered to innovate boldly and embrace risk, especially during uncertain times. This approach has deepened my commitment to building teams that complement and challenge one another. 2. Absorb fear, lead the charge Fake it till you make it looks good on a bumper sticker, but it is a hollow mantra in the C-suite. Leadership is not about projecting false confidence; it is about absorbing the fears and insecurities of your team, even when you do not have all the answers. The balance is delicate: Project stability without slipping into manufactured bravado. Customers and employees are astute judges of authenticity, and they will see through a façade. As the late Kobe Bryant said, Confidence comes from preparation. There is no shortcut to the hard work of preparation, whether you are leading a basketball team or a boardroom. My 22 years at GE reinforced this lesson through constant rotation across roles: financial, cyber, legal, go-to-market, R&D. Just when I would get comfortable, I would be thrust into a new, ambiguous environment. That forced me to embrace vulnerability, cultivate curiosity, and build resilience to lead under uncertainty. Great leaders do not pretend to have all the answers, they prepare relentlessly to face the unknown. 3. Work-life balance is a myth The idea of work-life balance is often romanticized, but in my experience, it is a myth for those aiming to lead. Success demands more than a standard 40-hour workweek. It requires an unrelenting commitment to the craft of leadership, driven by curiosity and a willingness to step into discomfort. Effective leaders, whether technical experts or generalists, step beyond their core expertise to understand the full spectrum of their companys needs: customers, employees, and strategy. This agility, rooted in preparation, allows them to navigate uncharted waters and inspire others to do the same. 4. Customer obsession is a tired but true truism Companies may be powered by their people, but they orbit their customers. Customer obsession is a well-worn phrase, tossed around in earnings calls and interviews. Overused or not, its truth is undeniable. A core function of any CEO is to understand and solve customer pain points, not just today but for the future: three, five, 10 years down the line. That requires courage, foresight, and perseverance to weather short-term challenges to serve long-term gains. Last year, I met with the CEO of one of our biggest and longest-tenured customers. He told me we are not just a vendor, but one of three partners they rely on to succeed. That trust, earned through years of relationship-building and a deep understanding of their evolving business, is something we must re-earn every day. It is a reminder that customer obsession is not a buzzword, but a commitment. 5. Embrace failure: It is success that has not happened yet In his Dartmouth College 2024 commencement address, Roger Federer reflected on competition: In the 1,526 singles matches I played in my career, I won almost 80%…What percentage of points do you think I won in those matches? Only 54%…When you lose every second point on average, you learn not to dwell on every shot. His point is profound: Failure is inevitable, but success comes from winning just a little more than you lose, and moving forward without dwelling on setbacks. At Twilio, I foster a culture of permissible failure, one that values effort, encourages persistence, and rewards curiosity to push boundaries. Sometimes this leads to wins, other times it yields lessons. Both are invaluable. Leaders must create environments where teams feel safe to take risks, knowing that failure is not the end but a step toward success. THE PATH FORWARD There is no blueprint for great leadership. It is a personal journey shaped by observation, trial, error, and plenty of course corrections along the way. Traits like curiosity, resilience, and empathy, tend to shine through in those who lead well, but even then, no two paths or leaders look the same. Uncertainty has never been greater. That only amplifies the need for thoughtful, human-centered leadership. I encourage every leader, whether aspiring to the C-suite or not, to embrace curiosity, invest in people, obsess over customers, and create space for failure in the pursuit of something better. From my experience, a good CEO focuses on what their people need now to build a resilient company. A great CEO thinks beyond their tenure, laying the groundwork for others to build an even stronger enterprise. Still, I dont see leadership as a formula to master. Its a lifelong process, one that requires humility, openness to change, and, if Im honest, more than a little luck. The company and I are both works in progress, as it should be. Khozema Shipchandler is CEO of Twilio.
Category:
E-Commerce
Six months ago, I wrote about the need for marketing teams to develop computational thinking, data interpretation, and cross-cultural fluency. Today, I’m watching those concepts play out in real time. And Ive been seeing and hearing about which teams are actually making the transition versus those still talking about it. The difference is stark. The marketers who are succeeding arent just learning new skills; theyre fundamentally rewiring how they approach problems, make decisions, and execute campaigns. FROM COMPUTATIONAL THINKING TO SYSTEMS ARCHITECTURE Thinking like a programmer was just the beginning. Now, the most effective marketing leaders are thinking like systems architects. Theyre designing entire systems that can adapt, scale, and self-optimize on a recurring basis. Take personalization. A year ago, teams were excited about dynamic email content. Today, sophisticated players are building attribution models that connect a customer’s podcast listening habits to their in-store purchase behavior, then automatically adjusting creative messaging across seven different touchpoints in real time. This isnt about technological sophistication; it’s about systems thinking. It requires that marketing professionals visualize how every customer interaction feeds into a larger decision-making framework. Rather than just mapping customer journeys, theyre designing feedback loops. Its a bigger advancement than it sounds. All of this is playing out most clearly in retail media. The brands that are winning on Amazon, Walmart, and Target are going beyond optimizing individual campaigns. They’re building integrated systems where search performance informs creative testing, which influences inventory decisions, which shapes promotional strategy. And theyre doing it all simultaneously across multiple platforms. THE DEATH OF DASHBOARD MARKETING Marketing teams data interpretation programs have evolved from assumption challenging into something we can call signal detection. This is such an essential skill. The ability to spot meaningful patterns in noise before they become obvious to everyone else is something that has always separated market movers from those just keeping pace. McKinsey & Co. research on AI in the workplace reveals something crucial: While 94% of employees claim familiarity with AI tools, only 1% of companies have reached AI maturity. In marketing, this gap is even more pronounced. Teams are drowning in AI-generated insights but starving for strategic clarity. The solution isn’t better dashboards or more sophisticated analytics. It’s developing what military strategists call “battlefield awareness”the capacity to synthesize disparate information sources into actionable intelligence while conditions are constantly changing. CULTURAL FLUENCY AS COMPETITIVE MOAT Cross-cultural communication has become a differentiating capability. This is something that was once considered a nice-to-have. But here’s what’s changed: Its no longer about understanding different markets, its about understanding different information ecosystems. Gen Z consumers in Texas get their product information from TikTok and Discord. Gen X consumers in the same ZIP code rely on Google reviews and local Facebook groups. Millennials in New York City trust Instagram influencers. Meanwhile, their counterparts in Minneapolis might prefer podcast recommendations. The varying values of those media channels reflect the need to be more than culturally fluent. Marketing teams need to be informationally fluent. They understand not just what different audiences want to hear, but where they go to hear it, how they process it, and what formats they trust. THE INTEGRATION IMPERATIVE Here’s what I didn’t anticipate six months ago: how quickly these skills would need to work together. The best campaigns I’m seeing integrate computational thinking, signal detection, and cultural fluency into single execution frameworks. It matters that teams arent just good at one thing, but that theyre building hybrid capabilities that combine all three. Heres how I imagine a campaign that uses systems thinking to design a multi-platform attribution model by bringing all these disparate elements together. Signal detection can identify microtrends in consumer behavior, while cultural fluency can adapt messaging for over a dozen different audience segments. Its all managed through a single creative brief that gets updated in real-time based on performance data. This kind of integration is becoming table stakes. All clients are actively demanding less fragmentation within their agency setup. This demand is especially intense from mid-sized brands with tighter and tighter budgets over the last two years. They expect agencies to deliver fully-integrated and data-informed campaign creative as well as activation. Agencies like ours are winning these accounts for three simple reasons. One, a combined offering is now possible. Two, clients are calling out for greater efficiency on vendor cost. Lastly, better cross-trade data is here. And AI helps to decipher it more and more quickly every day. In the end, flexibility is the premium here. Specialized marketing teams are a luxury no one can afford. You need people who can toggle between strategic thinking and tactical execution, between data analysis and cultural interpretation, between human insight and technological optimization. THE NEW MARKETING OPERATING SYSTEM What were really talking about is the emergence of a new marketing operating system. Its one that treats adaptability as a core competency rather than a response to crisis. The most effective marketing leaders I know have stopped thinking about skills as things you learn once and then apply. Instead, they’ve built learning into their operational rhythm. They’re constantly experimenting with new tools, testing different approaches, and updating their frameworks based on what they discover. This isn’t about being early adopters or technology enthusiasts. It’s about recognizing that the pace of change has accelerated to the point where static expertise becomes obsolete faster than you can develop it. The marketing departments that will thrive in 2025, 2026, and in the years to come are those that have rebuilt themselves around continuous adaptation. Teams that view the reset not as a one-time event but as a permanent feature of how modern marketing works. The fundamentals haven’t just shifted. They’ve become fluid. The question isn’t what skills you need to learn, but how quickly you can learn to learn differenty. Tim Ringel is global CEO of Meet The People
Category:
E-Commerce
Forrester research found this year that only 58% of Fortune 500 chief marketing officers report directly to the CEO or sit in the C-suite. And CMO membership on boards is down more than 7% between 2023 and 2024. But in todays unpredictable cultural and political climate, we need marketing leaders at the table who can navigate complexity and change. I have always advocated for the inclusion of CMOs on company boards, on the grounds that CMOs bring a nuanced understanding of customer behavior and cultural context. In the past, Ive seen that the biggest challenge preventing broader representation of marketing leaders on board was the limited turnover of board seats. In this new reality, the question isnt just access to the boardroom, but how CMOs lead in complex times. That leadership in this moment can be broken down into three main ideas: practice discernment, prioritizing trust, and embracing breadth and depth. Lets discuss them in more depth. 1. Practice discernment Right now, its important to remember that not every cultural or political moment needs a branded response. Discernment means understanding timing, relevance, and deeply understanding your audience. CMOs can be leaders guiding internal debates on when not to engage publicly, just as much as when to act. Understanding that sometimes inaction is an action itself, is essential to public affairs leadership. More broadly, effective CMO engagement in public affairs is about knowing when and how to cut through the noise and maintain long-term strategic relevance. In my organization, weve developed response protocols that provide internal guidance on when a response is necessary. Our decision process on when and how we respond starts with the shared understanding of our organizations values. We discuss our values, our teams needs, and how recent news may impact them personally. From there we make decisions about how we respond internally, and if an external response is necessary. 2. Prioritize trust Trust is the cornerstone of any marketer’s role. CMOs should focus on long-term trust with staff, board members, and external audiences. It is here where marketing and communications alignment on trust is critical. CMOs who lead with clarity and consistency earn the trust that drives long-term success. 3. Embrace breadth and depth Especially right now, CMOs cant afford to specialize too narrowly. They must understand stakeholder engagement, public affairs, issues, and reputation management, among all the other pieces of their day-to-day work. This breadth, and the skills that come out of being an effective marketer, enable effective internal partnerships, especially with communications and government relations teams. This key idea makes the CMO indispensable at the leadership table. At my current organization, our stakeholders include staff, a broadly impacted patient community, healthcare providers, researchers, institutional and individual supporters. These stakeholders represent a myriad of backgrounds; socioeconomic, political, social, and geographical. That means we spend a lot of time thinking about the impact of our marketing campaigns as well as our communications and government relations strategies. MARKETING LEADERSHIP AS A NONPROFIT IMPERATIVE In the nonprofit world, the stakes for relevance, impact, and trust are even higher. With leaner budgets and heightened scrutiny, every message matters. CMOs in nonprofits must bridge fundraising, advocacy, and audience engagement, making them indispensable to long-term strategy and sustainability. Being a CMO is as much about strategy and strategic thinking as it is about any other piece of the job. Their proximity to audiences and grasp of evolving culture gives them a unique advantage, but only if they can lean in. As marketers and CMOs, we should work to reframe the role as a connector between brand, purpose, audience, and leadership. Simone Grapini-Goodman is chief marketing and digital officer of American Diabetes Association.
Category:
E-Commerce
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