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.