Josh Bottomley is CEO of Dunnhumby (UK), a global leader in customer data science. Josh has led digital transformation initiatives at media and finance businesses. After overseeing customer data-focused traditional print businesses, Josh gained invaluable strategic experience early in the digitalization of organizations’ income streams and operations. Josh shares his insights about how he aligned multiple internal groups as new tech-enabled opportunities cut across business units. He explains the importance of working frameworks and freedom for employees and how to view any roadblocks.     KEY TAKEAWAYS   [02:46] From childhood, Josh was interested in what will eventually be called systems thinking.   [03:52] Joining the Financial Times during the internet’s early days, Josh’s job takes an unexpected turn.   [04:47] How the internet changes the way a newspaper needs to operate.   [05:51] Josh tries to recruit for jobs and titles that don’t exist yet.   [06:46] The importance of details in marketing.   [09:43] Digital transformation isn’t easy—how Josh succeeds by talking to customers.   [12:54] Using YouTube as a Trojan Horse to move parts of advertising budgets from TV to the Internet.   [15:45] How Josh finds an innovative way to create alignment in teams and mindsets.   [17:38] Digital integration is done cautiously across a company, working closely with customers.   [19:59] The perfect place to be is one step ahead of your customer, not three.   [21:58] What Josh took from Google to HSBC and every organization after.   [24:47] Why we now think more about systems and ecosystems to understand our world and business.   [27:02] What Dunnhumby has been doing for over 30 years.   [29:20] How “nudges” help people get what they want.   [31:40] How to strike the right balance relating to employees’ need for freedom and structure.   [35:05] Clarity about expectations and sustaining individual motivation are key to empower employees.   [37:54] Having a sense of purpose and nurturing it in others helps internal mobility, Josh explains.   [39:40] IMMEDIATE ACTION TIP: Pick a theme, a sense of purpose. Leadership is a journey. You may or may not get to your destination. Rather than getting frustrated, be curious about the silly stuff that gets in the way — see them as roadblocks to overcome as you progress. Life is an obstacle course, not a sprint.   [42:21] Gen AI may be leveling blue and white-collar work--the impact has yet to be estimated.     RESOURCES   Josh Bottomley on LinkedIn dunnhumby.com     QUOTES (edited)   “We would spend $200 million a year on direct marketing and get a response rate of 2%. If we could get the rate to 3%, we would be getting 50% more customers for our money because one person in a hundred is making a different decision. So the lesson was, I might operate in this business at a level of detail such that one person in a hundred makes a different decision.”   “The perfect place in the business is one step ahead of your customers, not three.”   “Get curious about what’s getting in the way. And once you know what’s getting in the way, you can usually find a way to fix it.”   “Shoppers are not totally rational. That’s why I love businesses where the data and the tech result in some form of human decision.”   “I'm so impressed by younger generations because I think life is much harder. The default career options aren’t there. I think it’s much harder coming into the workforce now than it was when I was at that stage.”