How to Use Humor in B2B Marketing (Without Being Cringe)

Brand Marketing Expert: How to make B2B brands stand out

Chelsea Castle is a content and brand marketing leader who most recently led content and brand at Close, the small business CRM. She joins the show to share what she's learned from building and inheriting content programs at startups including Chili Piper, Lavender, and Emma/Campaign Monitor, and why marketing is closer to renovating a house than following a playbook. Chelsea opens up on building memory structures through repetition, finding spiky points of view that compound over time, and why protecting human judgment matters more than ever in an AI-driven landscape. Tune in to this episode as we explore: * (00:54) Chelsea's path from journalism and agency life into content marketing in tech * (02:32) Balancing strategy and tactics: what working at Lavender taught her * (06:57) The differences between reviving a brand, scaling one, and building from scratch * (13:30) Why marketers should still absorb context the old-school way before reaching for AI * (20:35) Brands as memory structures and why everything in content compounds * (24:51) Red threads and brand associations at Chili Piper, Notion, Asana, and Vector * (30:31) Getting company-wide buy-in for brand, and why it has to start at the top * (35:38) What makes a spiky point of view different from a hot take or rage bait * (42:42) Staying consistent with your message without sounding like a broken record * (47:30) Quickfire: connecting MCP to a CRM for content IP, and a skydiving road show Links: * Chelsea Castle's LinkedIn: https://www.linkedin.com/in/chelseacastle/  [https://www.linkedin.com/in/chelseacastle/%20] * Close [https://close.com/%20] * Lavender [https://www.lavender.ai/%20] * Chili Piper [https://www.chilipiper.com/%20] * Peep Laja (Wynter) [https://wynter.com/author/peep-laja%20] * Jess Cook (Vector) LinkedIn [https://www.linkedin.com/in/jesscook-contentmarketing/%20] * Dave Gerhardt (Exit Five) [https://www.linkedin.com/in/davegerhardt/] * Andy Raskin [https://andyraskin.com/%20] * Chris Walker [https://www.refinelabs.com/chris-walker%20] * Adam Robinson (RB2B) [https://www.linkedin.com/in/retentionadam/]

Minisode - Compliance Content & AI Search

Sarah Cameron, Head of Content & PR at ComplyAdvantage, cuts through the AEO hype to share what's actually moving the needle - and what your exec team is probably already asking you about. From vendor comparison content to tracking AI citations, she brings the receipts on a strategy that's delivering higher demo conversion rates than organic search. Tune into this episode, as we explore: * (00:03) AEO vs. SEO  * (03:04) The vendor comparison bet that paid off big (and why they almost didn't take it) * (04:41) How to build your first prompt tracking list when you're starting from scratch * (05:50) Why AI search converts better than organic - and what that tells you about buyer intent * (07:02) Keeping your exec team and board informed on AI search without losing your mind Listen to the full episode here: https://open.spotify.com/episode/1mVJj6o7TokSHljPFlpZU0 [https://open.spotify.com/episode/1mVJj6o7TokSHljPFlpZU0]

Growth lessons from Darren Chait (beehiiv CMO /ex-Calendly)

Darren Chait is the CMO at beehiiv and ex-Head of Growth at Calendly. He joins the show to share how an Australian corporate lawyer ended up co-founding Hugo, leading growth at Calendly, and now shaping the playbook at one of the fastest-growing creator platforms. Along the way, he explains why the best CMOs think like CFOs, how the role of a marketer has shifted in 2026, and what actually makes a newsletter worth subscribing to. Tune in to this episode as we explore: * (00:34) The beehiiv philosophy: why creators should own their audience, not rent it * (06:35) From corporate lawyer in Australia to co-founding Hugo and joining Calendly * (08:26) What four years at Calendly taught Darren about growth at real volume * (11:23) Why there's no traditional marketer archetype left in 2026 * (15:41) The best CMOs are actually CFOs: understanding every lever in your business * (19:33) A three-step playbook for the first weeks in a new marketing leadership role * (22:12) Calendly vs beehiiv: incremental experiments vs big swings * (28:35) How AI changes the job of a marketer without replacing judgment * (34:25) What makes a newsletter genuinely work: trust, consistency, and multi-channel reach * (45:53) Newsletter vs email marketing: the two-way relationship that changes everything * (49:28) Darren's dream campaign: dominating cities with out-of-home advertising * (53:17) Final recommendation: Growth Daily by Marketing Max Links: * Darren Chait's LinkedIn: https://www.linkedin.com/in/darrenchait/  [https://www.linkedin.com/in/darrenchait/] * beehiiv: https://www.beehiiv.com/  [https://www.beehiiv.com/] * Calendly: https://calendly.com/  [https://calendly.com/] * Kyle Poyar: https://www.growthunhinged.com/  [https://www.growthunhinged.com/] * Growth Daily by Marketing Max: https://www.marketingmax.com/ [https://www.marketingmax.com/]

How to Use Humor in B2B Marketing (Without Being Cringe)

Esther Dawson, Global Brand & Content Lead at Breadcrumb, tackles one of B2B marketing's trickiest challenges: how to build a genuinely funny brand without making everyone cringe. She gets into the culture, the craft, and the calculated risks behind making humour work in industries where no one expects it. Tune into this episode, as we explore: * (00:24) Culture first: why humour has to exist inside the company before it ever hits the feed * (02:31) The cringe problem and why you can't just hire someone and tell them to "be funny" * (04:32) Gallows humour in cybersecurity and why the best campaigns meet your audience where they actually are * (06:18) Where humour earns its place: brand awareness, pain points, and the printer you've formed an unhealthy relationship with * (09:20) Scaling a humour-led brand: how to keep the confidence (and the buy-in) as the stakes get higher * (11:36) Witty vs. jokester - the distinction that keeps your brand from becoming one person's version of funny Listen to the full episode here: https://open.spotify.com/episode/1DpkFKoGo7i7Po30ux8WOZ

BTS @ Brighton SEO with Top 50 PPC Expert & BrightonSEO/HeroConf organiser

Sophie Logan is one of the Top 50 Most Influential PPC Experts of 2026 and Community and Editorial Manager at Rough Agenda, the company behind Brighton SEO and HeroConf. She joins the show to pull back the curtain on what it actually takes to programme a large-scale marketing conference: managing 180 speakers, keeping content off the sales pitch, and building communities that outlast the event itself. As a longtime PPC practitioner and international conference speaker herself, Sophie brings a rare dual perspective on what makes events genuinely valuable for the people in the room. Tune in to this episode as we explore: (00:37) Sophie's background  (02:23) What goes into managing 180 speakers across a two-day event (06:45) How Rough Agenda filters out salesy content through the deck review process (10:57) Using post-event surveys and live room observation to sharpen the agenda (15:54) How COVID changed the events industry and why in-person is bouncing back (21:13) Why relatable content beats big names - and how events create community (27:30) Catering for generalist marketers across specialist conference tracks (33:24) Practical advice for running a great event on any budget (44:42) How AI has helped Sophie as a dyslexic writer - and an honest career screw-up Links mentioned in this episode: Sophie Logan on LinkedIn: https://www.linkedin.com/in/sophielogan/  https://marketingsoph.com/  Rough Agenda: https://roughagenda.com/  Brighton SEO: https://brightonseo.com/  HeroConf: https://ppchero.com/hero-conf/  The AI-Amplified Marketer by Frederik Boysen: https://www.barnesandnoble.com/w/the-ai-amplified-marketer-frederick-vallaeys/1149791057