3245: How Trello is Tackling Task Overload with AI and Design Thinking
Release Date: 04/16/2025
Tech Talks Daily
What if the biggest breakthrough in weight management is not a new diet, but finally seeing how your body responds in real time? That question sat at the center of my conversation with Sharam Fouladgar-Mercer, CEO and co-founder of Signos, a continuous glucose monitoring (CGM) and AI-powered health platform built to help people manage weight by understanding their metabolism. January is when motivation is high and the wellness noise is loud, but it is also when a lot of people realize how hard it is to stick with generic advice that does not fit real life. This episode is about why...
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What if your website could spot its own problems, fix them, and quietly make more money while you focus on building your business? That question sat at the heart of my conversation with Aviv Frenkel, co-founder and CEO of Moonshot AI, and it speaks to a frustration almost every founder and digital leader recognizes. Traffic is expensive, attention is fragile, and even small issues in design or flow can quietly drain revenue for months before anyone notices. Traditional optimization often means long cycles, internal debates, and teams juggling analytics, design tools, and testing platforms...
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What happens when decades of supply chain planning collide with AI, volatility, and a world that no longer moves at a predictable pace? That question sat at the heart of my conversation with Piet Buyck, a serial entrepreneur whose career spans early optimization engines, cloud-era planning systems, and now AI-driven decision environments. Speaking from Antwerp just days before the holidays, Piet brought a calm, grounded perspective shaped by years inside organizations operating under real commercial pressure. His journey includes building Garvis, an AI-native planning platform later acquired...
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Today's episode is a conversation with Bret Kinsella, recorded while he was in Las Vegas for CES and preparing to step onto the AI stage. Bret brings a rare combination of long-term perspective and hands-on experience. As General Manager of Fuel iX at TELUS Digital, he operates generative AI systems at a scale most enterprises never see, processing trillions of tokens and delivering measurable business outcomes for global organizations. That vantage point gives him a clear view of both the promise of generative AI and the uncomfortable truths many teams are still avoiding. Together, we...
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What does it actually take to move beyond AI pilots and turn enterprise ambition into real productivity gains? That question sat at the center of my conversation with Olivia Nottebohm, Chief Operating Officer at Box, and it is one that every boardroom seems to be wrestling with right now. AI conversations have matured quickly. The early excitement has given way to harder questions about return, trust, and what changes when software stops assisting work and starts acting inside it. Olivia brings a rare vantage point to that discussion, shaped by leadership roles at Google, Dropbox, Notion, and...
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What happens when the systems we rely on every day start producing more signals than humans can realistically process, and how do IT leaders decide what actually matters anymore? In this episode of Tech Talks Daily, I sit down with Garth Fort, Chief Product Officer at LogicMonitor, to unpack why traditional monitoring models are reaching their limits and why AI native observability is starting to feel less like a future idea and more like a present day requirement. Modern enterprise IT now spans legacy data centers, multiple public clouds, and thousands of services layered on top. That...
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Are we asking ourselves an honest question about who really owns automation inside a business anymore? In my conversation with Darin Patterson, Vice President of Market Strategy at Make, we explore what happens when speed becomes the default requirement, but visibility and structure fail to keep up. Make has become one of the breakout platforms for teams that want to build automated workflows without writing code, and now, with AI agents joining the mix, the stakes feel even higher. Darin talks candidly about the tension between empowerment and chaos, especially in organizations that...
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Was 2025 the year the games industry finally stopped talking about direct-to-consumer and started treating it as the default way to do business? In this episode of Tech Talks Daily, I’m joined by Chris Hewish, President at Xsolla, for a wide-ranging conversation about how regulation, platform pressure, and shifting player expectations have pushed D2C from the margins into the mainstream. As court rulings, the Digital Markets Act, and high-profile battles like Epic versus Apple continue to reshape the industry, developers are gaining more leverage, but also more responsibility, over how they...
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In this episode of Tech Talks Daily, I’m joined by Kiren Sekar, Chief Product Officer at Samsara, to unpack how AI is finally showing up where it matters most, in the frontline operations that keep the global economy moving. From logistics and construction to manufacturing and field services, these industries represent a huge share of global GDP, yet for years they have been left behind by modern software. Kiren explains why that gap existed, and why the timing is finally right to close it. We talk about Samsara’s full-stack approach that blends hardware, software, and AI to turn...
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What if airlines stopped thinking in terms of seats and schedules and started designing for the entire journey instead? In this episode of Tech Talks Daily, I’m joined by Somit Goyal, CEO of IBS Software, to talk about how travel technology is being rebuilt at its foundations. Since we last spoke, AI has moved from experimentation into everyday operations, and that shift is forcing airlines to rethink everything from retailing and loyalty to disruption management and customer trust. Somit shares why AI can no longer sit on the edge of systems as a feature, and why it now has to be...
info_outlineWhat happens when one of the world’s most loved productivity tools decides to reinvent itself for the age of AI? At Team 25 in Anaheim, I sat down with Gaurav Kataria, Head of Product for Trello at Atlassian, to unpack the biggest release in Trello’s history and what it means for individuals and teams navigating the chaos of modern work.
Gaurav describes the new Trello as “an AI-powered to-do list,” built not to replace project management tools like Jira but to complement them—especially for those personal tasks, scattered action items, and mental notes that get lost in a sea of email, Slack messages, and SaaS app notifications. With half a million users opting into the beta within 48 hours of launch, it's clear that the new direction is resonating.
In our conversation, we explore how Atlassian is using AI to enhance, not overwhelm, individual productivity—by capturing inputs from everywhere, organizing them intelligently, and helping users block time visually with integrations into Google and Microsoft calendars. This isn’t about automating your life; it’s about giving you clarity and control without friction.
We also talk about how Trello remains deeply personal. From list colors to card covers and mobile widgets, the design philosophy centers on reducing cognitive load and sparking focus. Trello isn’t trying to be a super app. It’s trying to be the app that respects your mental model, works the way your brain works, and empowers you to get meaningful work done on your own terms.
If you’re overwhelmed by task sprawl or skeptical of AI’s growing role in daily workflows, this episode offers a grounded look at what thoughtful, user-centered innovation looks like in action. How do you strike the balance between simplicity, automation, and human creativity? Let’s explore that together.