The Campaign | A Marketing Podcast by 97th Floor

What does it take to build groundbreaking companies across three decades of tech evolution? Daniel Nissan, founder of Structured (formerly Structured Web), made the first internet phone call in 1993, launched the first nationwide grocery delivery service before Amazon, and is now rebuilding his 26-year-old platform from for the AI era. In this episode, Daniel shares hard-won lessons from the frontlines of innovation—from cold-emailing the CEO of FedEx to secure a nationwide delivery partnership, to navigating two major market crashes, to recognizing when "bolting on" AI isn't enough. Key takeaways for marketing leaders: Why "AI-first" requires a complete rebuild: Learn the difference between bolting on AI features versus architecting for conversational interfaces from the ground up Timing the market: Daniel's framework for knowing when to jump on emerging technology (even when it feels too early) Building conviction in your team: How to rally skeptical teams around radical platform changes and get them to believe the impossible is possible Daniel also reveals his prediction for when AI will finally be able to generate human-approved marketing content at scale—and why the real transformation comes when AI moves from generative to agentic. If you're a marketing leader wondering how to think about AI beyond the hype, this conversation offers a rare perspective from someone who's successfully navigated multiple technology revolutions. Resources: See what Daniel’s up to at https://structured.ai/. Find Daniel Nissan on LinkedIn: https://www.linkedin.com/in/danielnissan/ Connect with Paxton on LinkedIn: https://www.linkedin.com/in/paxtongray/ Looking for an agency that'll be worth the investment? 97th Floor creates custom, audience-first campaigns that drive pipeline and conversions. Get started here: https://97thfloor.com/lets-talk/. About Daniel Nissan: Daniel founded Structured in 1999 and leads the company’s strategic vision across marketing, engineering, and product development efforts. From 1996 to 1999, Daniel was the President and CEO of NetGrocer, which he led to be a highly recognized and established leader in the field of eCommerce. He served as a Vice President of Marketing for VocalTec Communications, Ltd. (VOCL) from 1993 to 1996. Part of the original VocalTec group that created the Internet Phone, Daniel was responsible for its breakthrough product concept, marketing, and strategy development. Timestamps: 04:27 - Why join a "stupid idea" startup 05:03 - Making the first VoIP call 51:20 - Traditional platforms vs AI conversation 52:38 - Agentic AI timeline 55:10 - Getting teams to believe 57:50 - The lamplighter analogy

Most B2B marketers are stuck playing it safe, following "best practices" that guarantee mediocre results. Udi Ledergor, former CMO of Gong and author of Courageous Marketing, has spent his career doing the opposite—running Super Bowl ads for 5% of the expected cost, getting Times Square billboards for $500, and building a marketing machine that made Gong impossible to ignore. In this conversation, Udi breaks down the exact six-step formula he's used repeatedly to make companies appear years ahead of where they actually are—and why this matters more than ever for early-stage companies trying to cross the chasm to enterprise buyers. Key takeaways for B2B marketers: The six-step formula for punching above your weight: How to leverage iconic advertising mediums (Times Square, Wall Street Journal, Super Bowl) for a fraction of what you'd expect—then amplify that investment through your owned channels and employee networks Getting experimental budgets approved: Why every marketing budget should have a 10% line item for "marketing experiments" and the two arguments that get it past skeptical CFOs every time Attribution without obsession: How Udi used Gong's own platform to track that 452 sales conversations mentioned their Super Bowl ad—and why you shouldn't let attribution fears stop bold campaigns Sales as your secret creative weapon: Why Gong's best content marketers were former salespeople, not traditional marketers, and how to tap into your sales team's market knowledge AI for creativity (the right way): Kyle Lacy's framework for using ChatGPT in brainstorming—get 10 ideas, table them all, then create something original Udi also addresses when it's time to move on from a company that won't let you be courageous, how to vet product-market fit before joining a startup, and why the "medium is the message" principle is more powerful than ever in an era of digital dashboards. If you're tired of blending in with every other B2B company and want permission (plus a playbook) to do something bold, this episode is your rallying cry. Resources: Get your copy of Courageous Marketing: The B2B Marketer’s Playbook for Career Success here: https://www.amazon.com/dp/B0F22HWR3C See what Gong can do for your business: https://www.gong.io/ Follow Udi on LinkedIn: https://www.linkedin.com/in/udiledergor/ Connect with Paxton on LinkedIn: https://www.linkedin.com/in/paxtongray/ Looking for an agency that'll be worth the investment? 97th Floor creates custom, audience-first campaigns that drive pipeline and conversions. Get started here: https://97thfloor.com/lets-talk/. About Udi Ledergor: Udi Ledergor, a five-time B2B marketing leader, served as CMO during Gong’s rise from new SaaS startup to industry dominance. By building a playful, human-centric brand with a lighthearted tone, he captured buyers’ attention and dollars and turned them into raving fans. He later led the creation of the revenue intelligence category, which helped Gong go from zero to hundreds of millions in revenue, earning major industry awards and achieving a multi-billion-dollar valuation. Over his 20-year career, Udi has led marketing teams at successful companies, advised startups, served as a board member and angel investor, and mentored hundreds of marketers. His work reveals how courage and creativity can build iconic brands, connect with audiences, and drive measurable results. Timestamps...

Most early-stage startups fail at the same place: they can't figure out marketing. Sterling Snow, former CMO at Divvy (acquired for $2.5B), has cracked the code on what actually works when you're searching for your first scalable channel—and it's not what the playbooks tell you. Sterling calls it "the haystack phase"—that brutal early period where you're testing everything, burning through budget, and desperately searching for the needle of a channel that actually works. Most marketers try to be "data-driven" during this phase, which Sterling argues is impossible when you have no data yet. In this tactical conversation, Sterling shares the unconventional approaches that took Divvy from zero to acquisition and what he's building at Redo with AI-powered personalization at scale. Key takeaways for marketing leaders: The haystack phase framework: Why activity (not analysis) is what matters when searching for your first scalable channel. Creating proprietary lead flow: The newsletter sponsorship story that became Divvy's #1 channel for years (before everyone else figured it out). Comp marketers on revenue: Sterling's controversial take on why marketing should be paid one level deeper in the funnel. Zigging when everyone zags: Why Sterling believes the rise of AI search means doubling down on high-touch, human interactions (micro-events, partnerships, in-person)—the exact opposite of what most marketers are doing. Sterling also addresses what he looks for when hiring "haystack phase" marketers (hint: it's the 14-year-old who 5x'd his lawn mowing business through guerrilla tactics), why he believes freemium can work if you're creative enough to monetize usage, and how marketing team composition needs to shift from "button-pushers" to strategists and orchestrators. If you're tired of being told to follow best practices that produce mediocre results, this episode is a masterclass in finding alpha where others aren't looking. Resources: See what Sterling is building at https://redo.com/en Connect with Sterling on LinkedIn: https://www.linkedin.com/in/sterling-snow-051baab5/ Connect with Paxton on LinkedIn: https://www.linkedin.com/in/paxtongray/ Looking for an agency that'll be worth the investment? 97th Floor creates custom, audience-first campaigns that drive pipeline and conversions. Get started here: https://97thfloor.com/lets-talk/. About Sterling Snow: Sterling Snow is the CEO and Co-founder of Redo, a customer experience platform for online brands. He's a member of Utah's oldest and largest early-stage venture firm. He was a former Senior VP or Revenue at BILL, a former Chief Revenue Officer at Divvy, and a former Marketing and Sales Director at LogMeln. Sterling is also an angel investor mainly in the seed and Series A rounds His investment portfolio includes Kaedim (AI for 2D and 3D image modeling) and Trinsic (full-stack identity platform). Timestamps: 00:41 - The haystack phase: activity beats strategy 04:07 - Creating proprietary channels vs. following playbooks 05:25 - The $1,000 newsletter ad that changed everything 26:23 - Why SDRs are becoming extinct 28:42 - Making freemium actually profitable

The Apple-Gemini announcement changed everything—but not in the way most people think. Eli Schwartz, author of Product-Led SEO, explains why this partnership doesn't signal the death of SEO but rather Google's complete dominance over search for the foreseeable future. In this wide-ranging conversation, Eli challenges nearly every assumption marketers hold about SEO in 2026. From why your thin content strategy is obsolete to why some multi-billion dollar companies shouldn't spend a dime on SEO (while others should spend freely), Eli offers a refreshingly honest take on what's actually changing versus what's just hype. Key takeaways for marketers: The expanding definition of SEO: Why your smart alarm clock, car dashboard, and eventually your pillow will all be search surfaces you need to optimize for The 2020 vs. 2026 playbook: Why generic listicles ("top winter vacations") are dead, and personal, emotional, middle-of-funnel content is where SEO belongs now The pizza shop principle: How online and offline worlds are finally aligning—you wouldn't walk into a diner for the best pizza, so why try to rank for everything online? Bottom-line goals vs. mushy emotional goals: The two types of SEO objectives every company has (including making sure the CEO sees you rank when they Google on the way to work) Who shouldn't invest in SEO: The framework for deciding if your company should spend money on SEO (hint: if you're Boeing selling F-35s, the answer is complicated) Resources: Sign up for Eli’s newsletter at productledSEO.com Connect with Eli Schwartz on LinkedIn: https://www.linkedin.com/in/schwartze/ Connect with Paxton on LinkedIn: https://www.linkedin.com/in/paxtongray/ Looking for an agency that'll be worth the investment? 97th Floor creates custom, audience-first campaigns that drive pipeline and conversions. Get started here: https://97thfloor.com/lets-talk/. About Eli Schwartz: Eli Schwartz is an SEO expert and consultant with over a decade of experience driving SEO and growth programs for B2B and B2C companies. Eli’s clients have included WordPress, Shutterstock, BlueNile, and Zendesk, all of which he has helped build Global SEO strategies to increase organic conversions at scale. He is the author of the book Product Led SEO. Timestamps: 02:03 - SEO is everywhere 03:58 - Why Google won 11:22 - How to invest in SEO in 2026 13:45 - The content playbook shift 19:36 - When NOT to invest in SEO 26:56 - LLM visibility is brand budget

With AI making it easier than ever to launch startups, B2B SaaS companies are facing an unprecedented wave of competition. Bill Macaitis, former CMO of Slack and Zendesk, shares exactly what marketers need to do in 2026 to not just survive—but dominate. Bill brings decades of experience taking companies from startup to IPO, and his perspective on what's coming is both sobering and energizing. The old B2B playbook of white papers, analyst relations, and enterprise sales cycles isn't going to cut it anymore. The companies that win will be the ones bold enough to rebuild their entire go-to-market strategy. Key takeaways for B2B SaaS marketers: Why brand is your competitive moat: How to measure brand metrics (aided recall, sentiment, share of voice) and prove ROI to skeptical boards—including the hidden impact on deal velocity, deal size, and churn Put your marketing where the eyeballs actually are: Why B2B marketers need to stop hiding behind "serious" channels and start creating content on TikTok, YouTube, and Instagram (with tactical examples) The pricing revolution: Why per-user pricing is dying and how to transition to usage-based, outcome-based, or token-based models before your competitors do it first Product-led sales for mid-market: How to combine freemium with enterprise upsells by differentiating on compliance features (not functionality) to mine product-qualified leads Bill also addresses the fear many B2B marketers have about being "too consumer-like" with their marketing, explaining why that risk-averse thinking is exactly what will make you invisible in an overcrowded market. If you're planning your 2026 strategy and wondering whether to play it safe or go bold, this episode makes a compelling case for the latter. Resources: Follow Bill’s YouTube Channel SaaS CMO Pro: https://www.youtube.com/@SaaSCMOPro Find Bill Macaitis on LinkedIn: https://www.linkedin.com/in/bmacaitis/ Connect with Paxton on LinkedIn: https://www.linkedin.com/in/paxtongray/ Looking for an agency that'll be worth the investment? 97th Floor creates custom, audience-first campaigns that drive pipeline and conversions. Get started here: https://97thfloor.com/lets-talk/. About Bill Macaitis: Bill Macaitis has led marketing and growth for the three of the fastest ever growing SaaS companies. At Slack he served as the CRO leading up the marketing, sales, success and support teams. Before that he served as the CMO of Zendesk taking the company through a successful IPO. Before that he served as SVP of Marketing for Salesforce where he helped grow revenues to $3B. Currently, Bill serves as board advisor and independent board member to aspiring unicorns and decacorns. Timestamps: 01:48 - Brand is your only real moat 08:58 - Move B2B marketing to social + video 12:53 - Stop being boring; buyers are people 18:01 - SEO is dying; shift to AIO 21:32 - Use AI imagery when it improves UX 28:34 - Product-led sales makes deals easier

While everyone's talking about AI, very few are actually making it work. Marie Haynes, renowned SEO expert and AI experimentalist, is one of the rare practitioners who's gone beyond the hype—building 50+ custom AI tools (gems), testing workflows daily, and learning what actually ships versus what crashes and burns. In this candid conversation, Marie shares the unglamorous reality of AI implementation: the deleted emails, the abandoned projects, the hours of frustration—and why pushing through that wall is the only way to gain an unfair advantage. Key takeaways for marketing leaders: The 5% rule: Why most AI projects fail and what separates the builders who succeed from those who give up after the first failure User signals over algorithm optimization: Why understanding vector search can actually hurt your SEO if you're not paying attention to engagement metrics The code-without-coding revolution: How Marie went from zero programming knowledge to building custom tools in weeks (and why every marketer should learn to "vibe code") Agents vs. gems: What's actually ready for production right now versus what's still 6-12 months away from being reliable Marie also addresses the elephant in the room: Is the AI bubble real? With Gartner predicting 40% of current AI projects will be canceled by 2027, she shares why she's betting her investment portfolio entirely on AI companies—and what signals she's watching from industry leaders like Zuckerberg and Musk. If you're exhausted by AI hype but still believe there's something real underneath, this episode cuts through the noise with hard-earned lessons from someone actually building in the trenches. Resources: Learn about Marie’s work and join her community at https://www.mariehaynes.com/ Google’s Python Class: https://developers.google.com/edu/python Google’s Agent Development Kit: https://google.github.io/adk-docs/ Connect with Marie on LinkedIn: https://www.linkedin.com/in/marie-haynes Connect with Paxton on LinkedIn: https://www.linkedin.com/in/paxtongray/ Looking for an agency that'll be worth the investment? 97th Floor creates custom, audience-first campaigns that drive pipeline and conversions. Get started here: https://97thfloor.com/lets-talk/. About Marie Haynes: Marie Haynes is a leading expert in AI and Search. She helps her clients prepare for agentic search, surfacing more often in LLM tools like ChatGPT and using AI in their workflows.Timestamps: 01:26 - Working on AI agents and Google's development course 04:34 - AI overviews change every 2 days 06:10 - Industry missing user interaction signals 41:11 - AI creating work-free future 43:51 - Tips: Use LLMs daily, learn to code