Brenan Klain

🌶️ Hot Takes 🌶️ Gen Z didn’t kill the 9-to-5. They just exposed how outdated it is. There’s a common narrative that Gen Z is “anti-work” or “too soft” for corporate life. But the reality is far simpler. They didn’t break the system , they just stopped pretending it still works. The traditional 9-to-5 model was built for a different time. It made sense when work was physical, communication was synchronous, and showing up was half the job. But today, most roles are digital, output-focused, and flexible by design. Yet we’re still clinging to clock-in-clock-out logic that doesn’t reflect how people actually work best. Gen Z is not rejecting structure. They’re rejecting performative structure. The kind where being online at 9 AM sharp matters more than what you actually delivered. The kind where sitting at your desk until 6 PM signals dedication, even if the work was done by 3. They want ownership, autonomy, and purpose , not micromanagement disguised as tradition. They’re willing to work hard, but not willing to perform burnout to prove it. It’s not a lack of work ethic. It’s a refusal to inherit broken systems just because that’s how it’s always been done. Maybe it’s not Gen Z we should be questioning. Maybe it’s the system that needs an update. What do you think? Is the 9-to-5 still relevant in the way we work today? #HotTakes #FutureOfWork #GenZAtWork #WorkCultureReboot

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If your analytics reporting includes branded search with "Google search traffic" you're doing it wrong. Why? Because it'll bias your execs to think they can/should invest more in search marketing rather than brand/social/content/other channels -- the ones that *ACTUALLY* drove the demand for those branded Google searches.

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Agencies that only know how to “run accounts” are going extinct. Tech is catching up fast, but the future isn’t agencies vs. tech. It’s agencies with tech. They will converge. The smartest operators I know are already blending strategy, creative, and data. They’re building systems that make human decisions more accurate, not replacing humans. The agency of the future won’t be a service. It’ll be a strategic engine powered by tech.

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There’s a new wave of AI-first startups (see: Jimmy Ren’s AI market map) rethinking how programmatic media gets activated. One of the most impressive is SWYM.ai - an Aperiam portfolio company led by Ravi Patel - and one of the fastest-growing. On this week’s Open Market, Joe and I sat down with Ravi to talk about how SWYM is attacking some of ad tech’s biggest inefficiencies. We covered: - How SWYM automates curation, decisioning, and optimization across DSPs and SSPs - The evolution from tools to intelligence in ad tech - Why SWYM isn’t middleware - it’s a new layer entirely - Ravi’s path from PwC to building a breakout startup in a crowded space As an added bonus, we workshopped some of SWYM's market messaging in real time. One of my favorite conversations yet. Episode link in comments.

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Building a 0-1 product is hard enough. Getting it to $20M ARR is even harder. Sunsetting it despite this success, is the hardest. In this episode, Stacey Feero (Director of Product @AgencyAnalytics) shares how she built, iterated on and ultimately sunset a product that many would consider a success. She gives practical advice throughout this journey, especially on how to match user mental models with the product you’re building. Give it a listen now: Spotify: https://lnkd.in/emBVE2hp Youtube: https://lnkd.in/eHf_KcUa Apple: https://lnkd.in/ek9GhriY

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Why most founders get agents wrong They think agents are plug-and-play. But the truth is: Agents aren’t just LLMs wrapped in frameworks. They’re systems. And systems always break without structure. The part nobody talks about, Planning. Skip that, and the crash is guaranteed. What actually makes agents work is simple, but never easy. You need guardrails that keep them in bounds. You need scope that makes them useful. You need decisions that shape their behavior. And all of that only comes alive through a process. When you approach agent-building step by step planning, designing, developing, testing,  Deploying, maintaining, something shifts. The chaos fades. The dead demos stop. What looked like magic starts looking like engineering. Miss the process, and everything downstream breaks. Follow it, and you stop burning time, trust, and credibility. Because at the end of the day, agents aren’t hacks. They’re systems. And systems need care. Found this useful? Hit the 🔔 icon in my profile. Get notified of my next post. Repost it to help 1 new person. ♻️

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"We need a website refresh." Those words strike fear into many SaaS leaders' hearts. It feels tactical. Expensive. A vanity project. But here's what I've learned working with multiple established B2B SaaS companies: What looks like a website problem is almost always a MESSAGING problem. We faced this exact challenge at one SaaS company. We started immediately on refining our ICP and building a compelling strategic narrative and then quickly rolled out the new message to a newly redesigned site. Our website redesign was a bold move—we chose the most creative concept presented by the agency that positioned us unlike anyone else in our space. Our employees loved it, prospects found it intriguing, and it initially achieved our goal: standing out in a crowded field with much bigger but more boring companies. But after being in-market for a while with this "clever" site built on our initial strategic narrative, the data told a different story. Our demo-to-opportunity conversion was lower than expected. Prospects arrived at sales meetings confused about what we actually did. 😬 Instead of defaulting to another website redesign, we did something powerful: we listened to customers, brainstormed with frontline client teams, and studied newly available data. Here's what that looked like: • Analyzed 12+ months of sales calls to identify how prospects described their challenges • Interviewed customers about how they actually use our solution (not how we thought they did) • Examined usage data to find the most-used features and five-year retention and upsell data to see which customers appeared to be getting the most value • Gathered customer-facing teams to understand what customers told us were the most compelling reasons they bought and continue renewing • Conducted competitive analysis to clarify our unique value • Led an executive offsite dissecting our most successful customer relationships, SWOT and competitor SWOT The result? A tighter strategic narrative and messaging framework that spoke more directly to customer pain points—a significant evolution from our first attempt a year earlier. Then, for our second website iteration, we partnered with Anthony Pierri 🎸 at FletchPMM (the GOAT of home page messaging) and built an entirely new homepage grounded in this research-backed story. When we launched this new customer-driven site: ▶️ Demo-to-pipeline conversion improved by 50%+ ▶️ We maintained the same inbound pipeline even after CUTTING ad spend by half ▶️ Sales cycles shortened as prospects arrived better qualified The hard truth for every SaaS leader: Your intuition about your market is probably wrong. The way you talk about your solution likely misses the mark. The fix isn't just a creative redesign. It's taking a humble step back, doing systematic customer research and having the courage to rebuild your story from scratch—even if that means scrapping work that seemed innovative when launched.

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Shopify IS Becoming the Product Layer of the Internet Kurt Elster recent post about Shopify's quiet infrastructure play got me thinking about what this really means for agentic commerce. The MCP piece everyone's missing: Model Context Protocol isn't just another API integration. It's the plumbing that makes AI agents actual shopping partners, not glorified search boxes. Here's what changes: AI agents become your sales team They don't just answer questions - they understand context, remember preferences, and can complete transactions across any MCP-connected store. Maybe the most exciting thing is for B2B - Is Shopify ready for this? Every touchpoint becomes transactional Your customers' AI assistant can now shop your catalog while they're researching on Perplexity, planning in Claude, or working in any MCP-enabled app. Commerce becomes invisible infrastructure Just like Kurt said - Shopify isn't just a platform anymore. It's the product graph that powers AI-driven purchasing decisions across the internet. The shift that matters: We're moving from "visit my store" to "my products exist wherever customers think to look for them." Your brand presence becomes less about your website design and more about how well your product data performs in AI-mediated discovery and purchase flows. Humans are always involved - but now they're involved through conversations with AI that can actually complete transactions. The question keeping me up at night: Are we ready for commerce that happens in AI conversations instead of shopping carts? Because ready or not, that's what Shopify just made possible.

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From Acquisition to LTV: Why the Smartest eComm Apps Are Playing the Long Game. 🚀 Having led growth at mobile-first startups and scaled revenue past $100M, I’ve seen the playbook evolve — and the latest AppsFlyer eCommerce App Marketing Report makes it crystal clear: growth today is fueled by retention, not just acquisition. • Remarketing budgets rose 29% YoY in 2025, with iOS up 42% and Android 16%. • China-based apps, already dominant in iOS UA, ramped up remarketing globally. • But the real shift? Owned channels now outperform paid media for both conversions and retention. 🔥The old playbook — pouring budget into paid UA and hoping for retention — is broken. Today’s leading eComm brands are aligning around one goal: maximize long-term LTV through smarter user journeys. That starts by acquiring high-value users early with intelligent bidding tools like tROAS and app-conversion bidding — and keeping them engaged with AI-powered personalization, loyalty offers, and seamless web-to-app experiences. As Lee Jones from Google puts it: “Leading eCommerce brands are using intelligent bidding to find high-value users early, knowing they’ll drive stronger retention and order value.” Winning teams are asking: • What signals from the first session predict high-value behavior? • How do we unify KPIs across web and app to align teams and journeys? • How can AI optimize not just acquisition—but re-engagement and loyalty too? 📊 Standout stat: iOS users convert 1.3 days faster than Android, with a 39% higher first-time purchase rate and 68% stronger re-purchase performance — reaching that critical second conversion faster and proving the power of loyalty-driven growth. 💡 adidas saw 2.4X higher ROAS from app users compared to mobile web. This shows what happens when retention becomes the strategy, not the afterthought. Mobile apps are key to long-term retention, with app users delivering higher order values and stronger brand loyalty than web users. To succeed in today’s landscape, growth must be: • Predictive, not reactive • Product-led, not channel-led • Focused on lifetime relationships, not just installs The long game belongs to companies that align data, product, and performance marketing from day one. That’s where real LTV is won. 👉 Want more insights? Read the full AppsFlyer eCommerce report here: https://shorturl.at/GSxwv #LTV #Retention #Growth #Marketing #MobileMarketing #ProductLedGrowth #AI #eCommerceStrategy #Sponsored AppsFlyer

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Does color actually matter for conversions? GoFundMe recently posted about a 2.2% CTR lift when they tested new button colors. Interestingly, the lift came from people clicking to share, while the donate button showed no statistically significant difference. We tracked that A/B test at DoWhatWorks and saw it beat the control. I’ve also heard similar stories from my friends at Adobe, where changes to button color led to a 3–4% lift in click-through rates. This led me to dig deeper into our own data.   Is it the color itself? Is it the contrast between colors? What’s really making the impact? Here’s what I’ve found: 1) High contrast between dual CTAs leads to more overall clicks. In tests comparing two similarly shaded buttons (primary and secondary) versus versions with greater contrast, the higher-contrast versions almost always win. Conversations with CRO and website testing teams consistently confirm that higher contrast drives measurable lifts in total clicks. 2) Consistent and memorable color schemes create brand recall. That yellow-green CTA instantly makes us think of Ramp. Those shades of purple? Mutiny. If you’re not following Riley Hennigh 🏴, he’s a brilliant designer with great insights on how brands leverage color and the nuances involved. Historically, lots of marketing pyschology has talked about how “X color beats Y” or how iconic brands use emotionally resonant colors. I’m not so sure about that. It seems less about choosing a specific color (blue vs. orange) and more about the consistent use of color, contrast, and possibly even the saturation or execution of that color. For example, GoFundMe recently moved away from orange in favor of their green palette, but HubSpot has strong brand recognition with orange, and their orange feels more professional than GoFundMe’s. No doubt a designer could explain why. What’s been your experience testing color on CTAs? Have you seen measurable lifts?

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Everyone’s shipping AI features. Few are actually solving problems. What I learned from launching Code Layers in Figma Sites last summer is that you have to be very intentional with your AI launches. Founders and GTM teams often skip the obvious question: 👉 Is this AI feature actually removing a pain point for your users? #ProductMarketing #AI #Startup #GTM

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