Explore every episode of the podcast Best Story Wins

Everyone on your team can suddenly make content. That's not the win it sounds like, it's how a brand starts dissolving, one "good enough" post at a time.
Ross Crooks, co-founder of Column Five, has a fix that flips the whole production model: stop treating your brand team as the last line of defense and start treating the brand itself as the first input every tool reads. He argues the old system (brief, create, brand-team-approves, ship) is exactly what buckles under AI's volume, and that the brands pulling ahead aren't the ones making the most content. They're the ones encoding something their guidelines deck never captured.We also cover:

• Why moving your brand team from the end of the process to the beginning is the actual unlock
• The difference between "correct" content and "good" content and why AI only produces the first
• Taste and intelligence: the two things your brand guidelines never had, and how to encode them
• "Brand drift": how fine-looking content slowly pulls you off what made you distinct

Every designer you know is quietly panicking about the same thing: their Figma hours dropped from 90% of the week to 30%, and nobody told them what to do with the other 60%. Is that a crisis or a promotion?

Maria Irie runs brand at Chili Piper with a team of two — and she's spent the last year rebuilding her entire job around AI without losing what makes the brand feel human. She's mid-migration from Webflow to Claude, she's turned herself into a systems-builder instead of a one-pager machine, and she's got a theory about why the scrappiest, least "scalable" parts of marketing — the Ibiza offsites, the events, the stuff that doesn't show up in a report — are exactly what AI can't touch. This isn't a "prompt better" conversation. It's what happens when a whole discipline gets rewritten mid-career.

We also cover:

• Why Maria cut her Figma time from 90% to 30% — and what she's building instead
• The "too many windows" problem: what it actually costs your brain to run five AI tools at once
• Why a two-person brand team deliberately protects the stuff that doesn't scale — and bets the whole brand on it

Every AI tool you use was built to keep you happy, not to make you right. That's a problem when "happy" is also the fastest route to content nobody remembers.Sonja Silveira has run content teams at Meta, athenahealth, and now Cisco, and she's done with the idea that AI is either a job-killer or a magic answer box. Her real argument: these tools are optimized for engagement, not accuracy, which means the marketers using them need more suspicion, not less. She also names the thing most B2B brands won't say out loud — they all sound the same now, AI just sped up the slide into sameness, and the fix has nothing to do with the tools.We also cover:

• Why treating AI like "an answer machine" is the fastest way to lose your edge — and what to check before you trust a single stat it gives you
• The real reason beigefication isn't new, why it's "safe," and why safe is exactly what's killing your content
• Why almost every B2B brand that tries to become a media company hits the same wall — and what Cisco's Story Lab is doing differently

Twilio used to read like a company built for developers and nobody else. Then it found one word that made every audience feel like they belonged to the same tribe.Adam Morgan, VP of Brand and Creative at Twilio, spent three months finding that word  "builder" and watched it turn a stalled rebrand into what he calls lightning in a bottle. He explains why most companies chase logos and color palettes before they've earned the right to, and why brand resurgence isn't a reaction to AI fear — it's AI's actual byproduct. When everyone can generate a slick landing page for free, the thing AI can't fake becomes the whole game.We also cover:

• Why Adam built Twilio's entire rebrand around a single emotional truth he found at Hearst Castle — not a brand workshop
• The real reason AI is making brand storytelling more valuable, not less, and why "AI-resistant content" is the new differentiator
• Why locking creatives into rigid brand guidelines backfires, and what a "systems approach" looks like instead

Every brand team is being handed AI tools and told to do more with less. What they're not being told is that without taste and a real idea, the output is just sophisticated noise at scale.

Matt Scribner is a growth designer at Atlassian — a company whose brand touches tens of thousands of visitors a week — and he's been inside the AI-enabled design workflow longer than most. His take isn't a sales pitch for the tools or a doomsday headline about job loss. It's something more useful: an honest account of where AI actually helps, where it quietly fails, and why the designers who thrive won't be the ones who prompt the best.

We also cover:

• AI can get you to 60% — but if you couldn't get past 60% without it, you're not getting past it with it either
• We're heading toward a "singularity of design" where everything starts looking the same, and the only antidote is taste you built before the tools existed
• The Arts and Crafts movement followed the Industrial Revolution for a reason — and the same correction is coming for brand

Every quarter, someone asks you to prove the rebrand paid for itself in dollars. Bill Kenney's answer after 16 years: you're measuring the wrong thing, and the spreadsheet was never going to save you anyway.

Bill built Focus Lab into one of B2B's sharpest branding shops by owning a single vertical back when everyone warned him that niching down would scare off clients. He makes the case that brand ROI behaves like going to the gym — you don't step on the scale the morning after — and that the real opportunity for agencies isn't using AI to ship work faster, it's handing clients the tooling to run their own brand without you in the room. He also says the quiet part out loud about why a weekend in an AI tool will never replace what actually happens inside a 16-week rebrand: the second-guessing, the cold feet, the "can we sit on this another week."

We also cover:

• The Apple test for why feature parity just turned product differentiation into a branding problem, not an engineering one
• Why he shut down his own sub-agency after realizing clients "don't give a shit" how big or small your other clients are
• The one belief he died on for years — that a brand has to launch in a single perfect moment — and why he now thinks a slow, slightly messy rollout works fine
• The first-meeting question he asks every CEO that quietly decides whether the whole project survives

You're being outshouted. The average person now absorbs 5,000+ messages a day and reaches for their phone 205 times — and the industry's big answer was to staple "AI-powered" onto the homepage and call it a repositioning. That's not building a brand. It's a withdrawal from the one account you can't overdraw.

Amit Singh has spent three decades building brands at Adobe, American Express, Starbucks, and Nintendo — long enough to watch "dot-com" go from billboard flex to embarrassing relic, and he's convinced AI is headed the exact same way. His argument: the companies sprinting to rebrand as AI companies are mortgaging years of earned trust, while the question that actually decides whether you survive — why should you exist? — goes unanswered in most boardrooms. He maps where AI earns its seat at the table, where it quietly wrecks your creative without anyone noticing, and why the people declaring storytelling dead are reading the wrong scoreboard.

We also cover:

• A Meta study found AI-generated copy matches or beats humans on sub-$100 products — and consistently *loses* on anything pricier, where emotion does the selling. Most teams are pointing it at exactly the wrong work.
• Nintendo doesn't make video games. It makes smiles. Why your reason to exist is the North Star you build against — and the one thing you'll never put in an ad.
• 88% of marketers have adopted AI. Adoption was never trust — and Amit thinks the gap between the two is where the real risk is hiding.
• Long-form is quietly back: why a five-minute Adidas film outperforms your six-second TikTok precisely *because* attention has never been scarcer.

Most marketing teams are drowning in output and starving for meaning. The more they feed the machine, the more the machine becomes the creative director — and somewhere in the noise, the person on the other end of the content stopped mattering.

In this episode, Josh and Ross are joined by Julianne DeVincenzo, Head of Content Strategy, and Dan Reid, Creative Director — both at Optimizely — two people deep inside one of the most interesting rebrands happening in B2B right now. They make the case that the real threat of AI isn't job replacement — it's the slow erosion of judgment, taste, and the willingness to make someone uncomfortable. Julianne and Dan talk about how they're rebuilding Optimizely's content engine from the ground up, why they're turning their own marketers into subject matter experts and journalists, and where they're drawing the line between what AI can own and what stays irreducibly human.

We also cover:
•       Why the volume-as-strategy era is producing content that 'passes through people like water through a screen' — and how Optimizely is deliberately building against that.
•       How Dan is working directly with engineers to teach their own AI to honor brand — including the surprisingly simple feedback that blew a senior engineer's mind.
•       What happens when you empower employees to use AI and wake up to find your unreleased brand assets have already been fed into someone's personal workflow.

Every week, another round of tech layoffs gets explained away with the same two words: artificial intelligence. Meanwhile, the people making those calls have never once asked whether the cuts make strategic sense — or whether they're just making a number go up.

Mat Barnes has been building brands for 30 years, survived two back-to-back acquisitions, and now leads brand at IBM. He has opinions about all of it.In this episode, Josh and Ross sit down with Mathew Barnes — brand leader at HashiCorp, now IBM after two consecutive acquisitions — to pull apart what actually makes brand work at scale. Mat makes the case that AI will expose every creative who doesn't know what good looks like, and that clarity isn't a buzzword: it's the only thing that's ever made any brand matter.

We also cover:
•Why AI will 'expose the hell out of you' if you don't already know what great looks like — and what taste actually is when you can't fake it
•The one question every brand and creative team skips that causes every siloed, inconsistent campaign — and how Matt's team asks it before anything gets made
•What it actually feels like to lead brand inside a 100-year-old institution — and what IBM's design sophistication taught a startup veteran who thought he'd seen everything

Your SEO traffic is up. Your pipeline is flat. Something broke, and it's not your team — it's the entire model most B2B marketers were trained on. The buyers who used to find you on Google are now getting their shortlists from ChatGPT, and if you're not in that conversation, you're invisible at the exact moment it matters most.In this episode, Josh and Ross sit down with Hadassah Pegado Dalisay, Head of Content Strategy, SEO, and AEO at Outreach — the agentic AI platform for revenue teams — who has spent over a decade watching the search game change and finally break. Hadassah makes a case that will sting a little: the old keyword-volume playbook didn't just stop working, it actively made you worse at the thing that actually matters — being the trusted answer when a buyer asks an AI what to buy. Her fix isn't to abandon SEO. It's to collapse the wall between SEO, content strategy, and revenue intelligence into something that actually earns attention.We also cover:
•Why mining your own sales transcripts is the most underrated content research method in B2B — and how Outreach does it at scale every quarter
•The difference between signal-driven and keyword-driven content strategy, and why the companies chasing volume right now are building a liability, not an asset
•How to make the case inside your org that AI visibility isn't a marketing metric — it's a pipeline metric

While B2B companies debate whether to "embrace AI," one of the fastest-growing HR platforms in the world is already asking its designers to ship production code, run their own research, and rethink what a UI is in the first place.

In this episode, Avi Ashkenazi — Senior Product Design Director at Deel, where 97 product designers work without a physical office, operate directly with the CEO, and are expected to unblock themselves — breaks down what actually separates designers who thrive in high-velocity environments from those who flame out. He makes the case that taste, devotion, and the willingness to stay opinionated are what AI can't automate, and explains why "vibe coding" will always hit a wall the moment a client asks for something exact.

We also cover:

• Why Deel built a "Delight" team — and what it tells you about the ROI of caring about the emotional texture of your product, not just its functionality
• The agentic design system Deel is actively building, where interfaces construct themselves on demand and no two users ever see the same page
• How to run a 120-person distributed design org with no office and quarterly themes that actually move everyone in the same direction

Most brand teams talk about blurring the line between brand and product. Jon Howell has spent a decade actually doing it — at Twitch, Lyft, Robinhood, Dropbox, and now Ramp. There's a reason that line keeps surviving: most companies aren't set up to erase it. In this episode, Josh and Ross sit down with Jon Howell, who leads brand experience design at Ramp — one of the fastest-moving fintechs building right now. Jon makes the case that brand and product design aren't two lanes on the same highway; they're an infinity loop that feeds itself. He breaks down what it takes to actually build the connective tissue between those two worlds — not as a philosophy, but as a daily practice of shipping fast, reading the room, and sweating the details before the PM moves on.

Also in this episode: • Why the "we'll polish it next cycle" myth is quietly degrading your product — and what to do before the engineer ships and moves on • How AI is making brand design more efficient and more generic at the same time, and the discipline required to use it without losing your point of view • The interpersonal moves that actually break down silos between brand and product teams — before you ever show up

B2B marketing keeps asking why it can't earn the same attention as consumer brands — then keeps writing copy that reads like a product spec sheet. The problem isn't the category. It's that most enterprise marketers confuse explanation with storytelling and call the result strategy.

Ryan Hammill, Creative Director at ServiceNow has built campaigns that ran post-Super Bowl and earned 99th-percentile creative effectiveness scores — not by chasing flash, but by getting ruthlessly clear on what a human being actually feels when they choose enterprise software. He makes the case that cutting the B2B bullshit isn't an aesthetic choice: it's a revenue strategy. From Idris Elba to Notorious B.I.G. to the moment Taylor Swift's kiss cut to his AWS spot, Ryan explains how humanizing invisible technology at scale actually works.

Bullet Points

• Why the Fernando Machado 6-to-1 multiplier argument should change how every CMO thinks about creative risk — and why most don't let it
• How ServiceNow's character-driven campaign structure borrows more from The Office than from enterprise SaaS playbooks
• The brand-vs-demand false binary: what Airbnb's ad spend restructure teaches B2B companies about search efficiency and brand gravity

Timestamps:
0:42 Introduction & Ryan's Background
1:31 From Agency to Tech: The Career Journey
5:50 ServiceNow's Bold Brand Identity
8:53 B2B Storytelling: Cutting Through the Jargon
18:24 Risk-Taking and the Two-Way Door Mentality
21:10 The AWS NFL Campaign: A Case Study
26:14 AI, Buzzwords & Authentic Messaging
31:39 Brand Building vs. Demand Generation
38:19 The Emotional Intelligence of B2B Buyers
41:18 Proudest Work & What's Next

Most B2B marketing teams are sprinting to adopt AI and landing in exactly the same place they started — more content, same forgettable results. The problem isn't the tools. It's that nobody stopped to ask what actually needed to change before reaching for them.

In this episode, we sit down with Asher Rumack — Column Five's VP of Creative Strategy — who has spent the last year dismantling the idea that AI is a shortcut and rebuilding it as a craft. Asher makes the case that creative, strategy, and marketing have never been three different jobs, and that the agencies still pretending otherwise are going to feel it. He also breaks down why AI search is the most underpriced channel in B2B right now — and why most brands are showing up in it completely wrong.

We also cover:

• Why 'catching up with AI' is a trap — and the mindset shift that actually makes the tools useful
• The specific reason your LLM search presence is probably lying to your buyers right now (and the low-effort fix)
• Why the wild idea in the pitch deck is about to become the default — and what that means for how agencies price creative risk

Everyone’s pumping out content at scale—but it all sounds like it came from the same intern with a chatbot. So here’s the real question: if AI is doing the writing, who’s actually steering the story?

In this episode, Column Five co-founder Jason Lankow breaks down the uncomfortable truth most B2B teams are avoiding: AI isn’t a content problem—it’s a brand system problem. While everyone else obsesses over speed and scale, Jason makes the case for something far less sexy (but far more critical): governance at the moment of creation. We dig into what it really takes to build a “brand operating system”—one that doesn’t just sit in a dusty PDF but actually shows up inside the tools your team is using every day. From eliminating brand drift across AI-generated content to making your messaging machine-readable (yes, really), this episode is a wake-up call for anyone still treating AI like a shortcut instead of infrastructure.

We also explore:

• Why “just use AI” is the most dangerous mandate in B2B right now
• The real reason your brand is becoming invisible in AI search (AEO)
• How to scale content without turning it into generic sludge
• Why taste—not tools—is your last unfair advantage

AI isn’t replacing your team. It’s exposing how replaceable your thinking is.
Everyone’s obsessed with speed—but no one’s talking about the real problem: mediocre work at scale. So what’s actually happening here… is AI making you better, or just faster at being average?

In this episode, Josh sits down with Julien Palliere, Business Development Lead at Column Five to unpack how we cut through the hype and get real about how AI is changing B2B—from strategy and content to client trust and sales. Josh and Julien break down why “what AI says about your brand” is the new SEO, how smart teams are winning before the first call, and where most companies are getting it completely wrong.

No fluff. Just what works—and what quietly kills your credibility.

We also explore:

• Why “what AI says about you” is the new SEO
• The hidden risk of over-automating your workflows
• AI etiquette—and why most teams are getting it wrong
• How AI is reshaping trust in B2B sales and marketing
• Why small, scrappy teams are about to outcompete everyone

In a world flooded with AI-generated noise, most B2B brands are still treating social like a billboard—when it’s actually the front page of their brand.

In this episode, Jacqui Morgan, breaks down why most content gets ignored and what it really takes to earn attention, build trust, and drive results. We get into why social is a business driver (not a support channel), why chasing the algorithm is a losing game, and how to shift from “posting to exist” to creating content people actually want. From B2B influencers to employee advocacy, this is a no-BS playbook for making social work. If your feed feels like a ghost town, this episode will tell you why and how to fix it.

We also explore:

• Why “likes” are a vanity metric—and what actually signals real impact
• The death of the follower and the rise of interest-based algorithms
• How to turn employees into brand advocates (without forcing cringe posts)
• Why most CEOs fail at personal branding—and how to not be one of them
• The shift from mass reach to small, high-value communities that actually convert.

Google used to be your gatekeeper. Now an AI can summarize your entire category… and forget your brand exists.

In this episode, Lexi Croisdale Director of Global Content Marketing at Varonis breaks down what happens when search stops being clicks and starts being answers. We talk about why the old SEO playbook is getting cooked by AI discovery (AEO/“AI search”), and how B2B teams need to shift from “more content” to more credibility—the kind that gets quoted, sourced, and repeated by LLMs.

We also explore:

• Why “being the right answer” beats “being #1” in an AI-first world
• How to write so LLMs understand your context (and stop mislabeling you)
• The new content stack: search + video + social distribution as one system
• Employee advocacy as the new influencer marketing B2B didn’t see coming

If your product isn’t in the protected AI budget line, you’re about to become an “optional tool” with a UI.

In this episode, Julien Sauvage CMO at Cordial delivers the reality check B2B teams don’t want—but need: the AI wave isn’t just changing how software gets built, it’s changing where money goes. And if you’re still running marketing like it’s an infinite-seat-count world, you’re basically trying to win Formula 1 with a tricycle.

AI spend is ballooning, everything else is fighting for scraps, and the CMO job is mutating from campaign conductor to capital allocator. We get into what it takes to stay relevant when “more pipeline” isn’t enough, how to prove brand impact with actual data (yes, he built a custom GPT for it), and why “do more with less” is a trap—unless you’re willing to do less, but better. 

We also explore: 

• Why AI gets you to “V1”… and the real work starts after
• The new CMO mandate: get closer to product, budgets, and workflows—or get ignored
• How to use AI for competitive intel + VoC mining without pretending it’s magic
• AI search visibility: why it’s Greenfield chaos, and how to measure without chasing ghosts
• POV that cuts through: pick a villain, or sound like everyone else

If your B2B “strategy” is still a funnel diagram and a stack of specialists, you’re not building growth — you’re maintaining a bureaucracy with a logo.

In this episode, Devin Bramhall, Fractional Chief Growth Officer delivers the uncomfortable truth most teams avoid: B2B companies don’t fail because marketing “needs to do more.” They fail because the funding model doesn’t fit the moment… and the math doesn’t math. And when budgets tighten, the classic response (more content, more tools, more “motions”) isn’t leadership — it’s denial with a weekly standup.

We unpack the real shift happening in modern go-to-market: the collapse of “marketing” as a fixed set of activities. The teams that win aren’t chasing the next SEO hack — they’re thinking from first principles: What are our assets? What are our constraints? What’s the fastest experiment that proves signal? Then repeat until growth shows up.

We also explore:

• Why VC-era expectations are still sabotaging “profitable growth” teams.
• The case for killing funnels, playbooks, and “marketing work” in favor of growth loops.
• Why community + IRL + bespoke experiences are the real post-SEO advantage.
• How to get executive buy-in without drowning leaders in tactics.
• Why the “creator-consultant” era is rising — and what it means for modern teams.

If your content marketing strategy still depends on gated PDFs and vanity metrics, you’re basically shouting into a void and calling it demand gen.

In this episode, Matt Hemsley, Marketing Operations Team Lead at Asana delivers the unsexy truth: the funnel isn’t “broken”—it’s been replaced. He breaks down what happens when AI becomes the new front door, web traffic gets weird, and attribution starts lying to your leadership team with a straight face.

We get into the real power shift happening inside modern B2B orgs: marketing ops moving from order-taker to architect, building guardrails and self-serve systems that let teams ship faster without turning the brand into a global game of telephone. Matt also calls out the silent killer of high-growth marketing: data overload that creates analysis paralysis—and how the best teams balance measurement with judgment.

We also explore:

• Why ungating content isn’t a “nice-to-have”—it’s survival in an AI-first buyer journey.
• The self-serve model that removes bottlenecks and protects brand consistency.
• Why attribution oversimplifies enterprise buying (and how it misleads execs).
• The difference between automating “work about work” vs automating decisions you’ll regret.
• Why retention is still the most ignored growth lever in B2B.

Search isn’t broken—it’s been replaced. Buyers are skipping funnels, ignoring gated PDFs and asking AI to decide who’s credible before they ever talk to sales. If your content still assumes attention is linear, you’re not behind—you’re irrelevant.In this episode, Amanda Verdino, Director of Content Marketing at Forma dismantles the comfortable lies B2B marketers tell themselves about storytelling. We talk about why differentiation without defensible substance collapses under AI scrutiny, how first-party data becomes your only real narrative advantage, and why most “thought leadership” is just recycled opinion dressed up as confidence. Amanda shares how Forma keeps humanity and joy alive inside HR tech, what actually earns trust in AI-mediated discovery, and why restraint—not volume—is the new power move.We also dig into:

• Why louder messaging accelerates brand decay instead of stopping it
• How original research outperforms hot takes in AI-driven buyer journeys
• The mistake teams make when they treat clicks as commitment
• Why LinkedIn credibility now matters beyond LinkedIn itself
• The uncomfortable shift marketers must make from persuasion to diagnosis
  
  

This episode is for B2B teams still polishing templates while the buyer rewrites the rules—and for the ones ready to build stories that survive contact with AI.

Search is decaying, attention is fragmented and AI is rewriting the rules faster than most teams can update their decks. If you’re still planning content like it’s 2019, you’re already invisible.

In this episode, Kyle Denhoff, Sr Director of Marketing at HubSpot, pulls the curtain back on what happens after the inbound era. We get brutally honest about why channel-first thinking is dead, how HubSpot rebuilt itself as a media company inside a SaaS giant, and why “always-on” isn’t a buzzword—it’s survival. Kyle also breaks down how AI is actually being used behind the scenes (no, not to replace marketers), and why taste, editorial judgment, and distribution matter more than ever in a world flooded with machine-made content.

We also explore:

• Why “more content” is the fastest way to lose relevance
• How audience-first strategy replaces blogs, funnels, and campaign calendars
• The real way HubSpot uses AI to drive conversion—without killing the brand
• Why creators and practitioners now beat brands in buyer trust
• The uncomfortable truth: nobody has the playbook, and pretending you do is the risk

This is a reality check for B2B teams still clinging to templates while the ground shifts under them.

AI proof isn’t “building trust.” It’s getting ignored—or worse, backfiring—because it’s generic, gated, and wildly irrelevant. In a world of risk-averse buying committees and AI-driven discovery, your “best case study” might be your biggest liability.In this episode, Jillian Hoefer (Head of Content at UserEvidence) delivers the reality check B2B teams keep dodging: buyers don’t need more claims—they need credible, searchable, situation-matched evidence that makes choosing you feel safe. Jillian breaks down why the classic “one giant ROI story for everyone” approach erodes trust, how AI search punishes gated proof, and why the winners in 2026 will treat customer evidence like a living system—not a dusty PDF trophy. If your strategy is “big stat → blast it everywhere,” this one’s going to sting (in a helpful way).We also explore:

• The trust-killer nobody tracks: irrelevant proof that makes buyers think you don’t get them
• Why evidence belongs at the top of the funnel, not just the “deal’s stalling” panic button
• The “no one gets fired for buying Salesforce” problem—and how proof reduces career-risk
• The content moat play: original research + human thought leadership in an age of AI slop

How to repurpose one report into a year of credibility (without turning into a content farm)

Your brand content isn’t “showing up.” It’s getting summarized, re-ranked, and sometimes straight-up misrepresented by AI—and your pipeline won’t tell you why. In a world where buyers ask ChatGPT first, the homepage isn’t your front door anymore. The chat box is.

In this episode, Kevin White (Head of Marketing at Scrunch) delivers a much-needed reality check on AI Search: there are no true “experts” yet, the platforms are a black box, and anyone selling guaranteed hacks is basically selling essential oils for your funnel. 

We also explore:

• The one metric that matters first: “brand presence” (aka: do explaining you?)
• Why AEO vs GEO is just acronym cosplay
• The long-tail play that converts 6–10x because the bot did the research for your buyer

Your brand content isn’t “scaling.” It’s getting cloned into beige mush by AI—and your buyers can smell it. In a world where everyone can publish 10x more, “more” doesn’t win. Better wins.

In this episode, Jessica Rosenberg (Head of Brand at AirOps) delivers the reality check B2B teams keep dodging: AI doesn’t make marketing magically faster—it makes mediocre faster. Jessica unpacks why AI search raises the stakes on quality, how “AI-first” brands build movements (not feature piles), and why the new moat isn’t content volume—it’s taste, narrative, and systems that actually improve over time. If your strategy is “prompt → post → pray,” this one’s going to sting (in a helpful way).

We also explore:

• The brand-building cheat code in 2026: education that changes behavior, not sales enablement in a trench coat
• The two-pizza team advantage: how a tiny crew shipped a six-week rebrand with speed and sanity

What a real AI workflow looks like (hint: it’s not a prompt with a fancy name)
And much more.

Your SEO traffic isn’t “dipping.” It’s getting mugged in broad daylight by AI Overviews and answer engine output.

In this episode, Artem Kubatkin of Attune lays out the uncomfortable new reality: AI assistants are becoming the first stop in the buyer journey—and they don’t “browse.” They decide. Artem breaks down what it really takes to show up inside high-intent AI conversations (and why most brands are accidentally training the models to ignore them).

We also explore:

• The 3 pillars of AI visibility: coverage, structure, authority—and how they map to modern content strategy
• Why AI answers are non-deterministic (and why measuring “one prompt” is fake confidence)
• How “first paragraph” becomes the new “first page” in a voice-first world
• The underrated power move: fixing brand misalignment across directories and third-party sources
• Why YouTube and timecodes may be the most practical AEO play hiding in plain sight
• And much more. 

Your brand isn’t losing to “faster” AI teams. It’s losing to the ones protecting their humanity. As generative tools flood feeds with beige, lookalike creative, the real threat isn’t robots—it’s your team quietly lowering the bar. Are you using AI to unlock better ideas…or to justify shipping forgettable work faster?

In this episode, Jeff Stark, Head of Creative at Suki AI, gets brutally honest about what AI can’t do: develop taste, earn trust, or build a point of view. He shares how Suki—an AI healthcare company—thinks about ambient clinical intelligence and why their creative approach starts with real clinicians, real stories, and craft that doesn’t feel like it came out of a content vending machine. 

We also get into:

• Rebrands as high-stakes bets: the real variable isn’t color—it’s courage.
• Art vs. design: why “beautiful but useless” is the most expensive mistake in B2B.
• Jazz-room leadership: running creative teams like improv, not assembly lines.
• AI as assist, not author: a “bookend” model that keeps humans in the creative core.
• Living an integrated life and how one’s faith and beliefs should show up in every aspect of their lives. 
• And much more. 

Your brand isn’t losing to competitors, it’s getting flattened by “good enough.”
In a world where AI can generate passable B2B content in seconds, bland isn’t safe. It’s fatal.

In this episode, Dan Schwer of Rippling breaks down what brand actually looks like inside a 6.000-person SaaS company with a creative team of 15. We go straight at the uncomfortable stuff: why “brand vs. demand” is a lazy (and expensive) debate, how a brand refresh becomes a business lever (not a design hobby), and what it takes to keep quality high when the org is moving at startup speed and the pipeline still wants receipts.

If you’re still treating brand as the “pretty layer” on top of performance, this one’s going to sting — in a useful way.

We also cover:

• Brand ROI without the fantasy math: Measuring impact through speed, scale, and craft.
• The “brand vs. demand” trap: Why the fight is fake — and what actually drives pipeline.
• Video as the new moat: Product launches, customer stories, and earning attention in B2B.
• AI won’t fix bad taste: Where AI helps, where it slows you down, and why judgment still wins.

Your brand isn’t losing to competitors, it’s drowning in “helpful” content no one remembers. In an AI-everywhere world, bland is broken and volume is just a faster way to disappear.

If LLMs can write what you ship in 10 seconds, why would a buyer choose you?This week, Sylvia LePoidevin delivers the reality check B2B marketers have been dodging: content volume is a commodity, brand is the moat. We dig into how AI-native teams actually work (tastemakers and operators), why “helpful” guides are table stakes, and how human stories, conviction, and point of view become the only defensible edge in a world where production is free.

 We also get into:

• Content brands > corporate blogs: Building something people follow, not just something you publish.
• Helpful is dead: Why every piece needs a person, a story, and a spine—or it’s AI fodder.
• Anchors and distribution: Human-made “anchor” content, AI-powered repurposing, zero soul lost.
• Manifestos, not messaging decks: Founder-fueled conviction as the real brand operating system.
• Brand as last moat: Community, ecosystem marketing, and taste as the next-gen B2B unfair advantage.

Your brand isn’t losing to competitors, it’s getting ghosted by the algorithm. As AI eats search, the “spray and pray” content playbook turns invisible. Are you training the models…or training your team to burn cash?

This week, Jenna Hannon, Founder & CEO of Hatter, drops a State of the Union that B2B marketers need to hear: SEO isn’t dead, AEO (AI Engine Optimization) is here and lazy tactics are DOA. We unpack why LLMs reward actual marketing (crisp messaging, specific content, real PR) and punish AI-slop; how to merge SEO, AEO, and content into one motion instead of siloed teams; and why product marketing is the new growth core powering every channel.

We also get into:

• SEO → AEO: Same inputs, new outputs and the extra layers that matter now.
• Quality > quantity: Why “programmatic, no-human” content craters (and how Google/LLMs sniff it out).
• Metrics that matter: Beyond traffic to AI visibility, context, and link-back citations that convert.
• Org design for 2026: Product marketing as the engine; experts in the loop; PR that teaches LLMs.

Your funnel isn’t broken, but your nerve is. “Best practices” are just average practices with better PR. If every headline, homepage, and hot take sounds the same… what’s the one bold move that makes you unforgettable?

In this episode, Udi Ledergor, Chief Evangelist at Gong and author of Courageous Marketing, torches the safe playbook and helps us build a braver one: a sharp, differentiated POV that slices through “sea of sameness” B2B. We get brutally practical on how to stop shipping beige content, why the CEO (not marketing) owns the brand, and how psychological safety unlocks the kind of creative risks that actually move pipeline. 

We also cover:

• Why “best practices” guarantee mediocrity and how to replace them with courageous bets.
• How to punch above your weight at tentpole events without buying the $500K booth.
• The 3-part brand promise test (and how most orgs break it in customer support).
• How to interview your CEO and Sales for risk tolerance before you take the job.
• Using AI to kill drudgery, not taste so your POV stays unmistakably human.

Marketing is drowning in AI sludge, vanity dashboards, and “spray and pray” content. Your brand is getting lost, not because your product is weak, but because your taste is.

In this episode, we sit down with Andrew Lee, Partner Marketing Leader at Microsoft, to torch the illusion that more content equals more impact. Together, we unpack why “brand vs. performance” is a fake fight, why taste is the last unfair advantage, and how to build owned distribution that survives algorithm mood swings. Your CMO will either thank you or feel attacked.

We also cover:

• Annual planning as a power move: kill random acts of marketing.
  Turning founder POV into a scalable channel (without turning them into a dancing bear).
• How to benchmark “taste” (with simple, brutal quality bars your team can actually use).
• Converting narrative into numbers: story→search→sales enablement→SQLs.
• The “No Rented Moats” playbook: email + podcast + events > social roulette.

LLMs are already “deciding” your brand for buyers. Are you shaping that story or letting the machine write it? If your marketing still sounds like everybody else’s, congratulations: you’ve trained the models to ignore you.

This week we rip into the hottest B2B reality: AI Engine Optimization (AEO) meets human-only brand. Ari Yablok, head of brand at Island, shows how to beat sameness by sending clear “this is new” signals, building experiential brands that people feel (not just read), and using unreasonable hospitality to make products and events feel theirs, not “yours.”

We also cover:

• AEO is the new SEO: how to show up inside LLM answers and make people prefer you before they ever ask a bot.
• Signals over slogans: designing booths, visuals, and copy that telegraph “category shift” without a single bullet point.
• Unreasonable hospitality in B2B: turning product nuance and in-person moments into retention (and reputation) machines.
• The “feeling of knowing”: why brand confidence shortens deals—even when buyers can’t explain why.
• Human as the counter-trend: embracing curated flaws and analog touchpoints to stand out as AI perfects the average.

Budgets are shrinking, patience is thinner and the CMO seat is a revolving door. Keep playing the old playbook and you’re next.

What if the path forward isn’t “more content, faster”, but a hard reset on power, process and what we even call “brand”?

In this episode, Drew Neisser, Founder of CMO Huddles, drops a reality check on B2B: CMOs are operating in Antarctica—hostile, short-term, and PE-pressured and it’s still the most exciting moment in marketing. We get blunt about the “do more with less” lie, why “brand” is a budget-killing word (start saying “reputation”), and how AI should first nuke your workflows and org chart before you let it ghostwrite your strategy.). This is the insider’s guide to surviving the freeze and shipping work that closes.

We also cover:

• CMO power plays: why owning Partnerships/Rev levers earns a real seat at the table.
• Short-termism judo: aligning with CFOs on “metrics that matter” and fixing attribution theater.
• What actually converts now: late-stage, face-to-face moments (small dinners > giant trade shows).
• Direct mail’s comeback: high-impact, targeted sends that unblock stalled deals.

Everyone’s racing to “do more with less,” then wondering why everything sounds the same. Budgets shrink, headcount drops, and the AI mandate lands like a memo from Mount Olympus: use it, ship faster, cut costs. Here’s the plot twist: AI isn’t your edge but your point of view is. If your story’s bland, the tech just scales blandness.

In this episode, Julien Palliere, AI Strategist at Column Five joins Jason and Josh to deliver a necessary reality check.

We unpack why “just add AI” is a lazy brief, how AEO is quietly disintermediating brands, and why volume is the enemy of results. The verdict: bad marketing makes you generic, not AI. 

We also cover:

• The Wedge System: Turning a sharp POV into a repeatable AI-powered content engine.
• Personalization That Actually Personalizes: Using CRM, 6sense, and LinkedIn signals to change copy by persona in real time.
• Where AI Belongs (and Doesn’t): Map the workflow, target structured/repeatable steps, avoid breaking fragile creative processes.

Marketers are hooked on attribution perfection. Meanwhile, your buyers are ghosting and your “AI-powered” campaigns sound like everyone else’s. What if the edge isn’t more dashboards but it’s better judgment?

In this episode, Nicole Gates, VP Growth Marketing at Varonis tears up the playbook B2B keeps clinging to. She shows how a “process person” builds a launch machine that actually ships, why tiering by customer impact (not internal hype) changes everything, and how moving SDRs under marketing with real SLAs turns MQL theater into pipeline. We dig into the noisy AI arms race (robots fighting robots), shifting budget from paid-to-play to earned trust via thought leadership, and using AI where it improves outcomes (routing, enrichment, speed-to-lead), not where it creates slop.

We also cover:

• How to tier your launches by what matters to customers, not your org chart.
• Why the best growth marketers think more like editors than analysts.
• What happens when you replace data obsession with decision confidence.

When everyone’s chasing quick wins, it’s easy to forget the one lever that compounds everything: brand clarity. But cramming “agentic AI” into your homepage won’t save you, it just makes you sound like the chorus.

In this episode, we sit down with Jess Ellis, Head of Brand, Content, Creative & Comms at Attentive, to talk about what it really takes to build a brand that drives pipeline in a crowded B2B market. Jess gets candid about bringing a hypergrowth org back to its foundation-mission, values, and a point of view people can actually feel. We dig into consent-based personalization that respects customers, why brand and demand aren’t enemies, and how to use AI as a speed-up.

We Also Explore

• Why slapping “AI” on your homepage isn’t a strategy
• How to make personalization feel human, not creepy
• Brand vs. demand is a fake fight (and how to prove it)
• The metric that earns budget: brand health with teeth

If your marketing feels harder than it should, you’re not imagining it. So what’s the smarter way forward?

In this episode, Adam Greco, Product Evangelist at Hightouch argues for a simpler model: composable CDP. Instead of locking yourself into a monolithic suite, you keep data where it already lives and activate it directly. That means days instead of quarters to get value, and less money wasted on campaigns that annoy customers instead of delighting them. Adam pulls from decades in analytics to show how organizations can finally stop tripping over their own tech, build trust between data and marketing, and focus on the few initiatives that really move the needle.

The question: are you doing more, but achieving less?

We also explore:

• Why annual planning done right can be a superpower, not a slog.
• How to kill the “brand vs. performance” tug-of-war with shared goals.
• The messy reality of category creation and how not to get steamrolled.
• Why short-form video is quietly replacing SEO as the new credibility engine.

Everyone’s talking about AI, but let’s be honest, most B2B brands still sound like copy-paste corporate speak. The scary part? While you’re stuck writing “safe” content, your competitors are out there building cult followings.

On this episode, Jason and Josh talk with Sandy Mangat, Head of Marketing at Pocus, about what it really takes to make people care. Sandy has worked in product, growth, and brand teams, so she’s here to share the lessons you won’t find in a playbook. From building a community people actually want to be part of, to cutting through the AI hype without sounding like a bot, this conversation is all about marketing that feels alive.

Here’s what we dig into:

• Why so many startups crash when product, growth, and brand don’t align.
• The real secret to category creation (spoiler: it’s not just slapping “2.0” on a slide).
• How to turn a community from “nice idea” into a genuine growth engine.
• The fine line between brand personality and just being unclear.
• Sandy’s one-line marketing philosophy: everything is easier when you’re famous.

Marketers are under constant pressure to prove impact. Often with smaller teams and tighter budgets. The challenge? Balancing brand building with demand generation while keeping content fresh and effective.

In this episode, Jess Cook, Head of Marketing at Vector, shares how she’s tackling that balance in real time. Jess talks through practical ways to get more value from every piece you create, without burning out your team. She explains why “minimum viable content” can help you move faster, how repurposing can multiply your reach, and why even unexpected moments (like a CEO going rogue on LinkedIn) can become brand building opportunities.

We also cover:

• How to establish authority in a new category.
• Why repurposing can be your most effective growth strategy.
• The benefits of testing fast instead of chasing perfection.
• How to turn unpredictable moments into authentic brand stories.
• The evolving relationship between brand and demand.

When AI can spin up a logo in seconds and templates are everywhere, it’s fair to wonder: why hire a designer at all? Because people don’t connect with “good enough.” They connect with taste, the kind that feels intentional, lived-in, and real.

In this episode, Andrew Chen, Head of Brand Design at Hive, makes a simple case: tools help, but taste wins. He talks about how skating and the hardcore scene taught him to make things people actually want, why trust (not slide decks) gets bold ideas approved, and how the next wave favors curators who know what to keep and what to cut. Andrew’s path is a reminder that great work isn’t about pedigree; it’s about context, craft, and caring enough to sweat the details.

We also get into:

• How building trust gets buy-in faster than any moodboard.
• Using “yes, and” to turn rigid briefs into better ideas.
• Why juniors shouldn’t wait for permission to pitch the risky thing.
• How food (seriously) can sharpen your storytelling instincts.

When everyone’s shouting that they’re “#1 in AI,” how do you actually stand out? Sometimes, the move isn’t a flashy campaign—it’s just saying what you mean, clearly and confidently.

This week, we sit down with Scott Smith, VP of Brand at Intercom and the creative mind behind Fin, their new AI agent. Scott speaks about how they built a brand that breaks the rules—ditching rigid style guides for something more like a magazine: expressive, evolving, and full of soul. We talk about what it takes to launch a new brand inside a legacy company, how “boring” billboards became their secret weapon, and why AI isn’t here to steal creative jobs—it’s here to level up the whole game.

We also get into:
- Why great art direction matters more than ever in an AI-first world
- How Intercom reimagined branding as a living, breathing system
- Letting go of the “creative genius” myth and building with your team
- What it looks like when in-house creative teams run like agencies

With everyone talking about AI, it’s easy to feel like your brand has to shout just to be heard. But sounding like everyone else isn’t the answer, it’s a missed opportunity to connect in a meaningful way.

In this episode, we sit down with Steph Bowker, Head of Marketing at Metaview, to talk about what it really takes to stand out in today’s crowded B2B landscape. Steph shares her honest perspective on building brands that feel human, specific, and rooted in real value. We explore what makes people care, how to create a brand that feels lived-in and why thoughtful storytelling (inside and outside your company) might just be your strongest asset.

If you’re looking for practical ways to cut through the noise without losing your voice, you’ll want to hear this one.

We Also Explore:

• Why slapping “AI” on your homepage isn’t a strategy
• How to turn customers into your most powerful marketing channel
• What makes a real community (hint: it’s not just a Slack group)
• How smaller teams can punch way above their weight with sharp storytelling

Maybe it’s not a content problem. Maybe it’s a clarity problem.

With AI-generated posts flooding every channel and SEO playbooks changing by the week, B2B marketers are creating more content than ever—yet somehow, it’s hitting with less impact. So what actually sets a brand apart today? It might come down to something deceptively simple: better storytelling.

In this episode, Roman, Head of Marketing at Sifflet, shares his thoughtful take on why “90% of marketing is content”—and why we need to rethink how we approach it.

We also discuss:

• Why founder content is peaking—and what comes next
• The quiet return of PR, direct mail, and other "dead" tactics
• The one field in your contact form that tells you what your dashboard never will

Everyone’s chasing AI—but what if the real magic in B2B is a rap video, a meme, and two actors with a camera?

While most brands stick to safe, polished playbooks, Chris Cunningham is building ClickUp’s marketing like it’s a full-blown media company—and it’s working. In this episode, he takes us behind the scenes of how their small but mighty team racked up 200 million+ impressions by leaning into creativity, comedy, and community.

Chris, one of ClickUp’s original team members and now Head of Brand, shares the real (and often hilarious) story of how they went from startup scrappiness to building an in-house content engine that moves the needle. From hiring actors full-time, to turning their content meetings into writers’ rooms, to making rap albums that actually convert.

We talk about:

• The content framework that helps their team test and scale what really works
• Why they bet on humor at the top of the funnel—and what makes it land
• How they avoid burnout while making videos every week
• The limits of AI content (and why originality still matters most)
• What most B2B teams get wrong when they try to “act like media companies”

Let’s be real: most B2B brands are stuck on repeat. Same buzzwords, same bland websites, same tired playbooks. And in a sea of sameness, nobody stands out. So how do you make people actually care?

In this episode, we sit down with Bill Macaitis, founder at SaaS CMO Pro. Bill pulls back the curtain on what’s broken in B2B marketing and how to fix it. Spoiler: it’s not another lead-gen campaign or cranking out more content. It’s about building a brand people actually remember.If you’re tired of playing it safe, this one’s for you.

We Also Get Into:

• The secret behind customer marketing that actually drives growth
• How to create bold, consistent brand moments without becoming a robot
• Why most marketing teams lose trust—and how to win it back

We’re creating more content than ever—but at what cost to meaning and connection?

In this episode, Kelly Phillips—VP of Brand Marketing at Faire, and former brand leader at Airbnb, YouTube, and Google—shares what it really takes to build a brand that people trust and feel connected to.

We talk about what makes brand matter in the age of AI, how to build trust on both sides of a marketplace, and what it looks like when your brand actually helps people succeed—not just sells to them.

We also discuss:

• Why Faire wants to be a partner, not just a platform, for small retailers
• The “Fair Forecast” and the power of data-driven, non-boring trend reports
• Why early brand investment is no longer optional for AI-first companies

If your brand doesn’t spark a feeling, it’s already forgettable. In a world where every product looks the same, the only thing that truly sells is vibe.

B2B marketing is broken. Everyone’s selling the same tools with the same bland copy—and in the AI era, product parity is only getting worse. So how do you stand out when sameness is the default? You build a brand people actually feel something about. In this episode, Kevin Branscum, VP of Brand Marketing at Typeform, breaks down how to inject personality, culture, and staying power into your B2B brand.

We also discuss:

• Why most B2B brands sound like AI wrote them—and how to sound human again
• How to borrow from the playbooks of fashion and luxury to build worlds, not just marketing campaigns
• How to think beyond spreadsheets and bring real people—your customers and their customers—into the heart of your marketing
  
  

Too often, B2B brands chase clicks that don’t lead to real results. The fix? It’s not more ad spend—it’s aligning your systems and strategy.

In this episode, Deanna Adams, Senior Director of Integrated Campaign Marketing at Dropbox, reveals how to actually make your brand show up across the entire customer journey—not just in a 15-second pre-roll.

Deanna shares how her team re-engineered Dropbox’s content engine for agility, built emotional resonance through integrated campaigns, and created a structure that lets the brand promise echo from awareness to advocacy. It’s not theory—it’s game film from the frontlines of modern B2B marketing.

We also cover:

• Why the “brand vs. performance” debate is holding your team back
• How AI is shifting from shiny feature to workflow essential
• What a truly integrated customer journey looks like in practice
• How to structure agile teams that actually collaborate