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When I was an engineer at Stripe circa 2017, I pitched a machine learning system that would cut our support headcount in half. I thought I was solving the biggest cost to the company: people. After all, isnt that the point of automation? The head of supports response caught me off guard: Congratulations. Youve automated the easy part. I realized the real problem was the workflow. Agents were toggling between 10 different tools. Institutional knowledge was stuck in silos. Work was being routed manually, without any visibility into patterns or bottlenecks. The biggest cost wasnt people. It was the broken process. Cutting labor costs in the name of AI has often proven to be a losing proposition. Take Klarna, for example: in early 2024, their OpenAIpowered assistant took on the workload of nearly 700 support agents, but that bet didnt stick. By mid2025, the company began rehiring human agents, acknowledging that customers still want empathy, and that AI needs human oversight to deliver quality service. The companies actually moving the ball forward on AI arent fear mongering about its potential or laying off entire teams. Theyre rethinking how work gets done. Theyre investing in programs and structures to accelerate learning and experimentation, helping employees evolve and drive efficiency alongside the technology. Its the combination of humans and AI that unlocks AIs full potentialnot AI-only at all costs, which only serves to sow reticence among the very people we need to move it forward. Heres how they think about using AI to unlock real gains. Design for orchestration When companies view AI through the lens of headcount reduction, they end up chasing automation for its own sake. But automating without connecting systems, roles, and feedback loops just accelerates the mess. Its like building an assembly line where the sections dont fit together. The most effective teams dont treat AI as a stand-alone fix. They treat it as one part of a larger machine: human judgment, internal tools, data flows, and real-time decision loops. The goal isnt fewer people. Its better flow. At Stripe, I once built a model to auto-answer simple support queries. Automation wasnt the most valuable part. The most useful outcome turned out to be refreshing the categorization of support issues and documentation, which had gotten outdated and too broad. For example, we identified that chargeback fee questions should be treated differently from chargeback evidence questions, which had previously been grouped together. This freed people up to develop training, build the right internal tools, and organize product feedback. Build on top of clean documentation Fear of job loss often drives leaders to chase AI quick wins: Can we automate answers tomorrow? But AI cant answer questions no one has documented properly. Knowledge usually lives in chat threads, outdated docs, or in one persons head. And thats where adoption efforts stall. High-functioning, AI-forward teams treat internal knowledge as a product. They document how decisions are made. They build systems where humans feed lessons back in. And they make it easy for AI (or anyone) to access and apply that context reliably. One company in Latin Americas online food-delivery sector offers a useful example. When AI chat support went sideways, the team first centralized their standard operating procedures and mapped gaps with product managers. According to their product manager, many policies didnt exist or were outdated, with no overarching process to keep documentation fresh after product changes. That unlocked clarity and consistency before any AI was involved, and enabled faster automation once the AI effort got underway. My most frequently given advice for companies to accelerate their AI initiatives is to write things down, keep them up to date, then use AI to surface patterns and speed up decisions. AI isnt magic: Its infrastructure When leaders frame AI as a shortcut to job cuts, they set themselves up for disappointment. The teams seeing real impact take a very different approach: they treat it like plumbing. They connect it to their systems for scheduling, analytics, forecasting, and decision-making, and they generally measure outcomes, not vibes. They also dont overcommit. They test. Adjust. Roll back. The smartest operators dont ask, What can we automate? They ask, Whats breaking right now, and could AI help? One payroll provider with over five million users illustrates the point well. Instead of ripping out their call center, they built a dial to A/B test between an AI voice agent and the classic press 2 for billing interactive voice response. They measured resolution rates, sampled calls, and tested continuously. By plugging AI into existing systems for telephone and quality management, they were able to target specific workflows for automation, such as troubleshooting common reasons for delayed payments. AI isnt going to transform your workforce overnight. The best leaders know how to measure success, build systems around those learnings, and roll out changes rigorously. Done right, AI can help you build a workforce thats more resilient and less dependent on heroics, not by chasing headcount cuts, but by integrating AI thoughtfully into the messy reality of operations. In this way, organizations can bring employees along for the journey, ensuring AI becomes a tool people want to use and ultimately adopt. The conversation we should be having isnt about which jobs vanish, but about how we redesign systems so humans and AI can work together at their best. Thats where real innovation happens and where the gains compound.
Category:
E-Commerce
ABC has suspended Jimmy Kimmels late-night show indefinitely after comments that he made about conservative activist Charlie Kirk’s killing led a group of ABC-affiliated stations to say it would not air the show. Kimmel, the veteran late-night comic, made several comments about the reaction to Kirk’s assassination on his show on September 15 and 16. He said that many in MAGA land are working very hard to capitalize on the murder of Charlie Kirk. ABC, which has aired Kimmel’s late-night show since 2003, moved swiftly after Nexstar Communications Group said it would pull the show starting Wednesday. Kimmel’s comments about Kirk’s death are offensive and insensitive at a critical time in our national political discourse, said Andrew Alford, president of Nexstar’s broadcasting division. Nexstar operates 23 ABC affiliates. There was no immediate comment from Kimmel. President Donald Trump celebrated ABC’s move on the social media site Truth Social, writing: Congratulations to ABC for finally having the courage to do what had to be done. He also targeted two other late-night hosts, Jimmy Fallon and Seth Meyers, and said they should be canceled too, calling them two total losers. Kimmels contract is up at the end of next season, which ends in May 2026. After ABCs announcement, White House deputy chief of staff Taylor Budowich posted on X: Welcome to Consequence Culture. Normal, common sense Americans are no longer taking the b- and companies like ABC are finally willing to do the right and reasonable thing.” In his monologue on September 15, Kimmel said, We hit some new lows over the weekend with the MAGA gang desperately trying to characterize this kid who murdered Charlie Kirk as anything other than one of them and doing everything they can to score political points from it. Kimmel said that Trump’s response to Kirk’s death is not how an adult grieves the murder of someone he called a friend. This is how a 4-year-old mourns a goldfish, okay? He also said that FBI chief Kash Patel has handled the investigation into the murder like a kid who didn’t read the book, BS’ing his way through an oral report. He returned to the topic the following night, mocking Vice President JD Vance’s performance as guest host for Kirk’s podcast. He said Trump was fanning the flames by attacking people on the left. Which is it, are they a bunch of sissy pickleball players because they’re too scared to be hit by tennis balls, or a well-organized deadly team of commandos, because they can’t be both of those things. Authorities say Tyler Robinson, 22, who is charged with killing Kirk, grew up in a conservative household in southern Utah but was enmeshed in leftist ideology. His parents told investigators he had turned politically left and pro-LGBTQ rights in the last year. Utah records show he was registered as a voter, but not affiliated with either political party. His voter status is inactive, meaning he did not vote in two regular general elections. He told his transgender partner that he targeted Kirk because he had enough of his hatred. Kimmel, like CBS late-night host Stephen Colbert, has consistently been critical of Trump and many of his policies on his ABC show. CBS said this past summer that it was canceling Colbert’s show at the end of this season for financial reasons, although some critics have wondered if his stance on Trump played a role. By David Bauder, AP Media Writer
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E-Commerce
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
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