What does a Chief Product and Technology Officer want you to do to understand you customers better, including how to effectively use AI. For Simone Basso, Chief Product and Technology Officer at WeRoad, understanding customers is about more than data and dashboards. It's about observing how people actually behave when they are making one of the most emotional and complex purchases of their year, their vacation. Q: How does WeRoad use AI today? We use a wide range of AI tools across the company, from marketing to product. Our teams experiment with creative and automation platforms such as Midjourney, and we have built an in-house AI stack that powers semantic search to help travelers find experiences in a more natural, intuitive way. Q: What have you learned from watching how people interact with your product? Our business is complex. From the moment someone lands on our website to the moment they book a trip, it is often a three-month journey. There is a lot of discovery, comparing, and saving options. Since travel is a deeply emotional purchase, it is essential to see how people browse, where they click, and what they do not understand. You cannot see that only from funnels and dashboards. Q: What role should humans still play as product analytics and AI tools evolve? Ideally, a tool could analyze behavior and tell me exactly where the anomalies are, the three things that need attention. That would be incredible. But for now, every tool is still far from that. Until then, it is up to humans to connect the dots, understand the context, and make sense of the story behind the numbers. Q: Where do you find product inspiration? Podcasts and YouTube. One of my favorites is Lenny Rachitsky (Lenny's podcast), which is always top of mind. Simone’s perspective is a reminder that great product leadership means blending data, observation, and empathy. Real insight comes from watching what people do, not just reading what the numbers say.
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Most marketing teams are using AI like it’s a copy assistant. That’s the smallest part of what it can do. As Chaenara O'Brien, Principal Strategist at Thought Bakery, puts it, AI’s real power is in helping you think and operate differently. Marketing teams today are being asked to do more with less: fewer people, smaller budgets, bigger goals. And that means our time and energy have to move toward deep work, the kind that builds real leverage. Here’s Shay’s take: “Marketers today need to become a bit of product builders.” She’s right. The next generation of marketers won’t just write briefs or launch campaigns. They’ll build internal systems, automations, data flows, and “central intelligence layers” that make creativity scalable. AI isn’t replacing the marketer. It’s pushing us to become architects of our own marketing engines. 🎧 Full conversation with Alec Cheung, Barb VanSomeren, and Chaenara O'Brien now live on The Marketing Share Podcast. Links in the comments. #MarketingLeadership #AIinMarketing #GoToMarketStrategy #MarketingOps #TheMarketingShare
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Chaenara O'Brien articulates what many CMOs are feeling. Greater shift toward orchestration and deep work. Marketing, product, sales, and I'll add customer experience need to be linked closer than ever - one commercial motion. The Marketing Share Podcast
Most marketing teams are using AI like it’s a copy assistant. That’s the smallest part of what it can do. As Chaenara O'Brien, Principal Strategist at Thought Bakery, puts it, AI’s real power is in helping you think and operate differently. Marketing teams today are being asked to do more with less: fewer people, smaller budgets, bigger goals. And that means our time and energy have to move toward deep work, the kind that builds real leverage. Here’s Shay’s take: “Marketers today need to become a bit of product builders.” She’s right. The next generation of marketers won’t just write briefs or launch campaigns. They’ll build internal systems, automations, data flows, and “central intelligence layers” that make creativity scalable. AI isn’t replacing the marketer. It’s pushing us to become architects of our own marketing engines. 🎧 Full conversation with Alec Cheung, Barb VanSomeren, and Chaenara O'Brien now live on The Marketing Share Podcast. Links in the comments. #MarketingLeadership #AIinMarketing #GoToMarketStrategy #MarketingOps #TheMarketingShare
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AI video explainer quality just got noticeably better. I've been using NotebookLM to create podcast versions (with AI hosts) of my newsletters for months. I've also been testing their video feature, a slideshow walkthrough with narration. With the enhancements, I'm now including an 8-min AI explainer video below alongside the 12-min AI podcast for my latest newsletter on how AI is reorganizing GTM teams around customers, not departments. Here's what stood out: ► It tied McKinsey's research to real case studies and made the Journey Teams model feel practical, not theoretical. ► The graphics explained the frameworks clearly and were visually appealing. ► It focused on the most important point: you don't have to evolve your organization overnight. Start with one painful workflow, fix that handoff, build from there. Most leaders need to hear that third one. Org transformation sounds overwhelming. The video made it feel doable by showing the crawl-walk-run approach. Start small, prove it works, build momentum. I still reviewed every second for accuracy. AI is good at pulling information together but can't replace knowing what GTM leaders actually need to hear. Now I have another format to reach different learning styles and time constraints. Links in comments for the video (8 min), podcast (12 min), or full written newsletter with frameworks and case studies. Pick the format that fits how you actually learn.
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🚧 The biggest barrier to future-proof content isn’t lack of skill — it’s clinging to old habits. I challenge teams to rethink what “good” content means. Today, it’s all about utility, clarity, and adaptability for diverse AI consumption models. Question traditional metrics. Embrace continuous learning in AI content strategy. Are you innovating — or resisting the inevitable? The mindset shift you need to thrive is here: https://lnkd.in/eTmTCKDw Is your content strategy agile enough for the AI leap? 🤸♂️🚀 #ContentInnovation #MindsetShift #DigitalAgility #FutureOfWork #Leadership
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I’ve been in countless rooms, podcasts, and webinars where the conversation about AI in marketing is all about data, funnels, and ROI. The energy is all masculine: logical, structured, and driving for efficiency. And it’s powerful. But it's only half the story. What's often missing is the feminine 🫅 energy: the intuition, the empathy, the ability to truly connect with another human being. And in a world where consumers are bombarded with over 300 ads a day, that connection is what makes a brand memorable. We're building AI systems with a startling lack of diversity—78% of AI employees are male. This imbalance shapes the very tools we use, leading to a marketing landscape that feels cold and impersonal. It's time for a new, Human-First Playbook 🏃♀️➡️ 🏃 . One that marries the analytical power of AI with the creative, nurturing, and intuitive aspects of feminine energy. It’s about using technology to amplify our humanity, not erase it. This is how we move from B2B or B2C to H2H: Human-to-Human 😊 marketing. If you’re a founder or company rethinking your marketing and ready to build a more human brand, I’m offering two free 20-minute audits this month. DM me to connect. #HumanToHuman #MarketingStrategy #AI #FeminineLeadership #BrandBuilding
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🎙️ Season 2 of AI, I’ve Got Questions is here! This season, I’m talking with CMOs who are leading through one of the most exciting and uncertain times in marketing. AI is changing everything, and we know we should be using it to move faster and get smarter, but there’s no blueprint, no best practices, and no one right way to do it! That’s what makes my first guest, Ashley Brucker Stepien, CMO at Hex, so inspiring. Ashley has led marketing at some of the most respected brands in tech including Figma, Dropbox, and Asana. She believes this is the best time to be a marketer and she’s truly attacking the AI opportunity. In this episode, we talk about how her team is embracing AI in both practical and bold ways. She shares how her team identified where AI could make the biggest impact, and a dramatic shift in how her team is structured to move faster and think more broadly. Ashley’s energy and optimism are contagious, and her approach is a great reminder that the CMOs who lean in and experiment will be the ones who win. 🎧 Listen at the link in the comments And don't forget follow AI, I’ve Got Questions for more conversations with marketing leaders who are figuring out what great looks like in the age of AI. We've got more amazing guests coming up!
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This was a good time- we talked covered A LOT of ground. I've recently seen some real AI skepticism from my fellow marketers on here. Don't listen to this episode if you want skepticism. I'm all in on AI and this chat will tell you why... Some of the things we cover... 1. Org Structures- At Hex we're really challenging everything from workflows to org structures so the team can work smarter, not harder. My takes in this discussion with Stacey may seem far out but I think marketers will be oriented in problem-solving versus functional specialization in the not too near future. Or if you're at Hex, now. 🙂 2. AI Strategies- There are two uses for AI: things that make your life easier and things that make you smarter. Most people have started to tap into the "make your life easier" camp. But the real fun stuff with AI is what makes you smarter. 3. Build vs buy - The build vs. buy convo is a VERY interesting one right now. The AI explosion has, in equal parts, given us the ability to build more than we could have imagined as well as a slew of remarkable AI solutions that are game changers. TLDR from me? If you've built a disruptive and problem-solving tool that has AI natively integrated throughout, I'm all ears. If you've built purely an AI tool or worse, a tool with AI bolted on, I'm skeptical all day. The line between the two may seem blurry but the real ones know. (Would love spicy takes on this one from y'all.) Thank you for having me Stacey Epstein! (Oh and the genius I mention in this chat is Bryanna Clancy- she's 10x smarter than me. That's the secret- hire people smarter than you.)
🎙️ Season 2 of AI, I’ve Got Questions is here! This season, I’m talking with CMOs who are leading through one of the most exciting and uncertain times in marketing. AI is changing everything, and we know we should be using it to move faster and get smarter, but there’s no blueprint, no best practices, and no one right way to do it! That’s what makes my first guest, Ashley Brucker Stepien, CMO at Hex, so inspiring. Ashley has led marketing at some of the most respected brands in tech including Figma, Dropbox, and Asana. She believes this is the best time to be a marketer and she’s truly attacking the AI opportunity. In this episode, we talk about how her team is embracing AI in both practical and bold ways. She shares how her team identified where AI could make the biggest impact, and a dramatic shift in how her team is structured to move faster and think more broadly. Ashley’s energy and optimism are contagious, and her approach is a great reminder that the CMOs who lean in and experiment will be the ones who win. 🎧 Listen at the link in the comments And don't forget follow AI, I’ve Got Questions for more conversations with marketing leaders who are figuring out what great looks like in the age of AI. We've got more amazing guests coming up!
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𝗛𝗮𝗿𝗻𝗲𝘀𝘀𝗶𝗻𝗴 𝗔𝗜 𝗳𝗼𝗿 𝗠𝗮𝗿𝗸𝗲𝘁𝗶𝗻𝗴 𝗦𝘂𝗰𝗰𝗲𝘀𝘀: 𝗜𝗻𝘀𝗶𝗴𝗵𝘁𝘀 𝗳𝗿𝗼𝗺 𝗳𝗼𝗿𝗺𝗲𝗿 𝗛𝗲𝗮𝗱 𝗼𝗳 𝗔𝗺𝗮𝘇𝗼𝗻 𝗧𝗲𝗰𝗵𝗻𝗼𝗹𝗼𝗴𝘆 𝗦𝗲𝗿𝘃𝗶𝗰𝗲𝘀 (𝗔𝗧𝗦) In a future Culture by Numbers podcast, I sat down with Matthew Dwyer, CEO of Impact Lab AI, to discuss how marketers can effectively leverage AI within Amazon's advertising ecosystem. He highlights the importance of governance to align with strategy. As AI tools increasingly automate creative media execution, the question arises: where do humans add value? Dwyer emphasizes that while AI is a powerful tool, it is not a standalone solution. He states, "AI is a tool, not a solution," highlighting that human creativity and strategic thinking are essential in guiding AI's application. Dwyer points out that data serves as the fuel for AI, particularly within Amazon's ecosystem, which is rich in consumer insights. Brands can use this data to refine their strategies and achieve better results. However, the challenge often lies in navigating the overwhelming amount of data available. To combat this, Dwyer advocates a focused approach, advocating a "data diet" to extract meaningful insights without becoming bogged down by Big Data. Core Principles of Impact Lab AI: Dwyer outlines several core tenets that guide the mission of The Impact Lab: 1. 𝗗𝗲𝗽𝘁𝗵 𝗢𝘃𝗲𝗿 𝗕𝗿𝗲𝗮𝗱𝘁𝗵: Concentrating solely on Amazon's advertising and AWS stack for specialized expertise that drives business impact. 2. 𝗕𝗿𝗶𝗱𝗴𝗶𝗻𝗴 𝗠𝗲𝗱𝗶𝗮 𝗮𝗻𝗱 𝗧𝗲𝗰𝗵𝗻𝗼𝗹𝗼𝗴𝘆: There are significant challenges between media-focused and technology-focused partners, and filling this void is necessary. 3. 𝗜𝗺𝗽𝗮𝗰𝘁 𝗢𝘃𝗲𝗿 𝗔𝗰𝘁𝗶𝘃𝗶𝘁𝘆: Unlike traditional consulting models that emphasize busy-work, prioritize tangible business results, rather than sheer activity levels. Dwyer candidly discusses the challenges brands face when incorporating AI into workflows. He emphasizes the importance of starting small and iterating rather than attempting to implement large-scale changes all at once. By focusing on a minimum viable product (MVP), brands can experiment and learn from initial implementations before scaling up. #podcast #techpodcast #media #technology #consulting #advice #AI #thinkbig #startsmall #advertising #adtech
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Everyone’s racing to “do more with less,” then wondering why everything sounds the same. Budgets shrink. Headcount drops. The AI mandate arrives like a memo from Mount Olympus: use it, ship faster, cut costs. "Make it work." Here’s the twist — AI isn’t your edge. Your point of view is. If your story’s bland, the tech just scales blandness. In this episode, Jason Lankow and I sat down with Column Five's very own AI Strategist, Julien Pallière, for a necessary reality check on what it takes to actually build AI workflows for content creation. We unpack why “just add AI” is a lazy brief, how AEO is quietly disintermediating brands, and why volume is typically the enemy. We also cover: - Using a sharp POV as a wedge, and then building a repeatable, AI-powered content engine to serve as a lever. - Personalization That Actually Personalizes: Using CRM, 6sense, and LinkedIn signals to adapt copy by persona in real time. - Where AI Belongs (and Doesn’t): Mapping workflows, targeting structured/repeatable steps, and avoiding fragile creative processes. - And much more. This episode was a ton of fun to produce and full of practical info - a big thank you to Julien for joining us! (Links to the episode in the comment below)
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The best AI teams are built on habits. Kieran Flanagan, SVP Marketing, AI & GTM at HubSpot, shares the 3 practices every team needs to become fluent in AI: 🟢 Prompting as a skill. Everyone should know how to translate intent into high-quality AI output. 🟢 Shared inspiration. Create open Slack channels where teammates post what’s working, real-time learning compounds fast. 🟢 Mini hackathons. Bring GTM, marketing, and sales together to prototype AI workflows that actually move the needle. The companies that learn AI together will out-execute everyone else. Watch the full episode on YouTube (link in comments 👇)
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