Build Marketing Around Proof, Not Pitches with Lena Waters

Lena Waters is a marketing executive and advisor who specializes in the inflection point where product-led growth meets enterprise scale. She has built and led global marketing teams across growth, demand, and brand at companies including Grammarly, DocuSign, Responses, and Lookout, and most recently served as CMO at Notion. Across those roles, she's operated both enterprise and product-led growth motions and developed a point of view on how the two can reinforce each other rather than compete. Lena joins Jon Miller and Sydney Sloan to share her controversial take: stop trying to persuade your buyers and start giving them proof instead. In this episode, she breaks down why she'd rather put a marketing dollar into product experience than a brand campaign, and how that thinking took her from DocuSign to Grammarly to running go-to-market at Notion. Lena walks through how she merged product-led growth with enterprise sales without treating them as competing motions, why she thinks MQLs are measuring the wrong thing, and the three blunt questions every CMO should ask their CEO before taking the job. We also get into why she thinks the AI-native marketing team problem isn't a talent problem at all. Jump Into the Conversation: (00:00) Where PLG meets enterprise scale (01:40) The CMO who resisted becoming a CMO (03:51) Selling the pony: An origin story in positioning (07:54) What "strategic" actually means in the AI era (10:06) Repositioning Notion from note-taking to context platform (12:44) MQL vs. MQA and letting the data kill the old metric (15:00) When brand spend is just rented attention (20:47) Community compounds, awareness evaporates (23:14) How Notion measured a narrative change (25:51) Three questions every CMO should ask their CEO (33:13) The AI-native team is a permissions problem, not a talent problem (36:24)Why speed beats consensus Key Takeaways Replace persuasion with proof.  Lena argues that much of traditional B2B marketing has been designed to persuade prospects before they have meaningful experience with the product. MQLs often measure whether someone consumed a whitepaper, webinar, guide, or event and then translate that behavior into assumed buying intent. Product experience provides a different signal: someone has used the product, experienced its impact, and potentially built a dependency on it. The strategic question becomes how much value you can let customers experience before asking them to buy. PLG and enterprise don't have to be competing motions. Lena's experience owning both enterprise and product-led targets changed how she thought about growth. Individual product users can build durable brand affinity, while small teams and developers can become a front door to the enterprise pipeline. She doesn't argue that every company needs a traditional PLG model. Instead, she asks how wide a company can open its front door—through a free experience, API access, a usage-based tier, hands-on proof of concept, or another way for customers to experience value before the contract.  Build brand assets that compound. Lena distinguishes between attention that disappears when spending stops and evidence that keeps working for the company. Community, original research, customer advocacy, and the stories customers tell about a product can create value long after the initial investment. Rather than asking a CFO to simply “fund brand,” her approach is to show how those assets keep returning value and use a combination of quantitative and anecdotal evidence to demonstrate whether the company's narrative is actually changing. AI-native marketing starts with permission, not the org chart. Lena pushes back on the idea that AI transformation is primarily a talent problem. Before debating new roles or hiring more generalists, she asks whether marketers actually have access to the CRM and product data they need to execute. She also argues for moving away from teams organized around individual channels and toward one shared department outcome. AI can dramatically increase production, but that advantage disappears if the company keeps the same slow approval structures around the work. Standout Quote “If you can help somebody experience the product before they buy and they already know what you are before they arrive, then the funnel stops doing the persuading that we've been trying to do all this time. And the product and your company reputation do it first.” — Lena Waters Guest Links LinkedIn: https://www.linkedin.com/in/lenawaters/  Mentioned in this Episode Scott Olrich: https://www.linkedin.com/in/scottolrich/  More from The B2B CMO Project Website: https://www.b2bcmoproject.com/ LinkedIn: https://www.linkedin.com/company/b2bcmoproject/ Jon Miller: https://www.linkedin.com/in/jonmiller2/ Sydney Sloan: https://www.linkedin.com/in/sydsloan/ More Episodes: https://www.b2bcmoproject.com/podcast