The Content Cocktail Hour

“AI is reshaping the way agencies operate, but human creativity and strategic thinking will always be essential to differentiate and add true value,” says Clay Ostrom, Founder and Brand Strategist of Map & Fire and SmokeLadder.In this episode of The Content Cocktail Hour, Jonathan Gandolf sits down with Clay to discuss how the evolving landscape of AI is impacting the marketing industry, particularly for agency leaders navigating the challenge of maintaining human-driven creativity amidst the rise of automation tools. Clay talks about his work with SmokeLadder, which helps businesses analyze brand positioning and messaging using AI. He also explores how agencies are shifting from execution to strategic partnership roles in response to AI-driven changes.In this episode, you’ll learn:The importance of balancing human creativity with AI-driven efficiency in marketingWhy agencies are evolving from executional roles to becoming more strategic partnersHow AI is reshaping the way agencies work and what that means for the futureResources:Connect with Jonathan on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/Explore AudiencePlus: https://audienceplus.comConnect with Clay on LinkedIn: https://www.linkedin.com/in/clayostrom/ Explore Map & Fire: https://mapandfire.com/ Explore SmokeLadder: https://smokeladder.com/ Timestamps:(00:00) Intro(01:29) Clay’s background and SmokeLadder(03:14) AI’s impact on marketing and agencies(04:39) Exploring SmokeLadder(07:52) Challenges and opportunities with AI(16:44) Entrepreneurial insights and productization(25:02) Keeping humanity in marketing

“If you think AI is just for automating content, you're missing the point,” says Dr. Amy Cook, Co-Founder and Chief Marketing Officer at Fullcast.In this episode of The Content Cocktail Hour, host Jonathan Gandolf is joined by Amy Cook to discuss the evolving role of AI in marketing and sales. As a seasoned veteran in both marketing and tech, Amy shares her journey of integrating Fullcast’s platform into the broader sales performance management landscape.In this episode, you’ll learn:Why AI needs human verification to be truly effectiveHow to shift from a point solution to a platform solution in sales techWhy “personalization at scale” is an oxymoronResources:Connect with Jonathan on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/Explore AudiencePlus: https://audienceplus.com/Connect with Dr. Amy Cook on LinkedIn: https://www.linkedin.com/in/amyosmondcook/ Explore Fullcast: https://www.fullcast.com/ Explore Sellers’ Compass: https://www.compass.com/newsroom/press-releases/7GTGPrZsN0vVh15XkhDnWo/ Timestamps:(00:00) Intro(01:34) Dr. Amy's background and career journey(03:20) Exciting acquisition announcement(06:16) The importance of platform solutions(10:04) Understanding the buyer's journey(12:27) Branding and product naming decisions(19:58) Challenges with AI in marketing(24:14) “Personalization at scale is an oxymoron”

“Your content shouldn’t be benchmarked against your competitors,” says Alexander Bleeker, Content Marketing Consultant for Goldcast and Head of Operations at AI Marketing Alliance.In this episode of The Content Cocktail Hour, Jonathan Gandolf sits down with Alexander Bleeker to discuss what modern B2B content strategy looks like in a world reshaped by AI, YouTube, and shrinking blog traffic. With hands-on experience leading content strategy at Goldcast and co-running the AI Marketing Alliance, Alexander brings a pragmatic but future-focused POV to today’s shifting landscape.They talk about why blogs are losing ground to large language models, how to get started with video, and why marketers should rethink how they define SEO. Alexander shares how Goldcast’s team uses first-party data to drive better strategy and how consistency on YouTube can finally break through the noise.In this episode, you’ll learn:Why B2B brands should bet on video-first content and how to get startedWhy SEO is evolving and how to prepare for discoverability in the age of LLMsWhat makes a repurposing strategy scalable and ROI-positiveResources:Connect with Jonathan on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/Explore AudiencePlus: https://audienceplus.comConnect with Alexander on LinkedIn: https://www.linkedin.com/in/alexander-bleeker/ Explore Goldcast: https://www.goldcast.io/ Explore AI Marketing Alliance: https://www.aimarketingalliance.com/ Timestamps:(00:00) Intro(03:40) The power of video in B2B marketing(05:26) Consistency in video content(08:17) The impact of AI on video production(11:33) SEO and the shift to LLM search(15:18) First party data and webinar strategies(20:34) Why benchmarking may not matter in marketing

"Marketing isn't always about measurable metrics, sometimes it's about creating a vibe that connects with your audience," says Kristi Gamboni, Senior Integrated Marketing Manager at TrustRadius.In this episode of The Content Cocktail Hour, Jonathan Gandolf sits down with Kristi Gamboni to discuss the power of face-to-face marketing events, especially when it comes to dinner series. Kristi shares her experience organizing a successful series of executive dinners and the surprising ROI they generated. She explains how selecting the right venues and creating a relaxed, yet strategic atmosphere can lead to meaningful conversations and solid business outcomes. She emphasizes the importance of building relationships with both prospects and current customers, and why the “vibe” of an event can be just as crucial as the content. In this episode, you’ll learn:How to make executive dinners a key part of your marketing strategyWhy the right venue can be the secret to successful B2B eventsWhat makes a great event invite process that drives urgency and resultsResources:Connect with Jonathan on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/Explore AudiencePlus: https://audienceplus.comConnect with Kristi on LinkedIn: https://www.linkedin.com/in/kristigamboni/ Explore TrustRadius: https://trustradius.com/ Timestamps:(00:00) Intro(00:40) Kristi Gamboni’s journey(04:50) Choosing the right markets(06:09) Importance of venue and cuisine(08:50) Effective invite process(10:46) Results from the dinner series(11:18) Strategic partner selection(15:00) Maximizing executive time(16:27) Building a business case for dinners(18:22) Handling invitations and attendees(21:17) Unpopular opinions

"MarketingOps isn't just marketing—it's a product function," says Mike Rizzo, Community-led Founder & CEO at MarketingOps.comIn this episode of The Content Cocktail Hour, host Jonathan Gandolf is joined by Mike Rizzo for a deep dive into the rising influence—and expanding responsibilities—of MarketingOps. From building community-led ecosystems to redefining what it means to "do more with less," Mike shares how MarketingOps professionals are uniquely positioned to own the go-to-market tech stack in today’s AI-driven landscape. They explore why MarketingOps can’t be reduced to just CRMs or automation platforms, how practitioners can move from order-takers to strategic leaders, and why learning to align with business goals is the real unlock for long-term growth.In this episode, you’ll learn:Why MarketingOps is evolving into a strategic functionHow AI is changing the expectations (and tools) in go-to-market rolesWhat it takes to lead with clarity, alignment, and communityResources:Connect with Jonathan on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/Explore AudiencePlus: https://audienceplus.comConnect with Mike on LinkedIn: https://www.linkedin.com/in/mikedrizzo/Explore MarketingOps: https://www.MarketingOps.comCheck out MOps-Apalooza: https://mopsapalooza.com/Timestamps:(00:00) Intro (02:00) Building community-led growth(04:38) Starting from a team of one(07:00) MarketingOps in the age of AI(13:00) From order-taker to strategic leader(19:00) The GTM tech stack as a product(24:00) Unpopular opinion: MarketingOps isn’t marketing

“If you think content is a marketing thing, you're already doing it wrong,” says Selma Chauvin, Chief Revenue Officer at AgorapulseIn this episode of The Content Cocktail Hour, host Jonathan Gandolf welcomes Selma Chauvin to discuss how content must evolve from random acts of marketing into a critical tool for revenue growth. As a former marketer turned CRO, Selma unpacks how she flipped Agorapulse’s content strategy—starting at the bottom of the funnel and scaling upward—driven by sales insights and real customer conversations. Selma and Jonathan dive into how to bridge the gap between content creation and sales usage, why marketers should stop obsessing over attribution, and how aligning revenue teams can unlock smarter content strategies.In this episode, you’ll learn:Why the biggest content mistake is prioritizing production over promotionHow to reverse-engineer content from real sales conversationsWhat a CRO can do to finally unite marketing and salesResources:Connect with Jonathan on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/Explore AudiencePlus: https://www.agorapulse.com/Connect with Selma on LinkedIn: https://www.linkedin.com/in/selma-chauvin/Explore Agorapulse: https://www.agorapulse.com/Timestamps:(00:00) Intro(02:00) Content’s two halves: production vs. promotion(05:00) Why most content never gets used by sales(08:45) Sales as the customer of content(11:30) Flipping the funnel: starting with bottom-of-funnel insights(15:15) Building content with fewer assumptions(20:00) Why CROs should not come from sales(23:45) How Selma leads revenue at Agorapulse(25:30) “Let’s stop marketing ourselves and just do business”

“Out-of-home marketing might be the most underrated B2B channel right now,” says Charlie Riley, Head of Marketing at OneScreen.ai In this episode of The Content Cocktail Hour, host Jonathan Gandolf sits down with Charlie Riley to explore the creative resurgence of out-of-home (OOH) advertising—and why it’s becoming a powerful tool for modern marketers. From billboards and digital signage to guerrilla tactics and experiential stunts, Charlie shares real-world examples of brands breaking through the noise with memorable, measurable campaigns.They dive into how OOH has evolved from guesswork to data-driven precision, what B2B marketers can learn from D2C, and why internal storytelling is just as critical as external messaging. Plus, Charlie offers sharp insights on the limits of marketing titles, the value of partners over vendors, and how small teams can make a big impact.In this episode, you’ll learn:How out-of-home fits into modern marketing, and what makes it measurableWhy internal marketing is often more critical than external campaignsHow to use data and instinct to find your ideal customerResources:Connect with Jonathan on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/Explore AudiencePlus: https://audienceplus.comConnect with Charlie on LinkedIn: https://www.linkedin.com/in/charlieriley/Explore OneScreen.ai: https://www.onescreen.aiTimestamps:(00:00) Intro(01:27) Charlie’s path to marketing leadership(03:15) Why out-of-home is more than just billboards(05:30) Creative case studies and real-world OOH impact(07:10) How OneScreen uses data to eliminate the guesswork(10:45) The B2B vs D2C mindset shift(14:15) Using out-of-home for ABM(16:40) Storytelling with data(19:00) Why marketing titles are often misleading(21:10) Internal marketing is your hidden superpower(23:30) Snorkeling vs. deep diving as a modern marketer(25:00) How to partner with OneScreen

“Favor fit over fame for influencer marketing success,” says Vivien Garnès, co-CEO at UpfluenceIn this episode of The Content Cocktail Hour, Vivien Garnès, co-founder and co-CEO of Upfluence, joins Jonathan Gandolf to unpack influencer marketing in the B2B and B2B2C space. Vivien shares why aligning your influencer’s audience with your brand matters more than follower counts, how influencer marketing has matured beyond vanity metrics to focus on real business impact, and why brands should give influencers creative freedom to unlock authentic engagement. She also opens up about her entrepreneurial journey launching Upfluence, how the co-CEO model works for her company, and an unpopular marketing opinion that changed their approach to ad spend.In this episode, you’ll learn:Why fit matters more than fame when choosing influencersHow to measure influencer marketing success beyond impressions and likesThe benefits and challenges of sharing creative control with influencersResources:Connect with Jonathan on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/Explore AudiencePlus: https://audienceplus.comConnect with Vivien on LinkedIn: https://www.linkedin.com/in/vgarnes/?locale=en_USExplore Upfluence: https://www.upfluence.com/Timestamps:(00:00) Intro(00:06) Two schools of thought on B2B influencer marketing(06:20) Favoring fit over fame in influencer partnerships(09:00) Balancing editorial control and influencer freedom(12:15) Tracking meaningful ROI in influencer marketing(14:30) Vivien’s entrepreneurial beginnings and launching Upfluence(18:00) How the co-CEO model works for Upfluence(19:50) Branded ad campaigns and marketing assumptions

“Focus beats frenzy every time,” says Jason Hubbard, founder & CEO of DemandMagicIn this episode of The Content Cocktail Hour, Jason Hubbard, founder & CEO of DemandMagic, joins Jonathan Gandolf to explore the evolving world of growth marketing for B2B SaaS companies. Jason shares why narrowing your target market is critical to scaling from series A to B, how AI is transforming go-to-market strategies when applied thoughtfully, and why entrepreneurs need more grit than glamour. He also opens up about his journey as a serial founder and offers practical advice on using AI not as a gimmick but as a problem-solving tool.In this episode, you’ll learn:Why tight focus is vital for early-stage startup successHow to approach AI as a tool for solving specific business problemsThe realities and mindset needed to thrive as a serial entrepreneurResources:Connect with Jonathan on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/Explore AudiencePlus: https://audienceplus.comConnect with Jason on LinkedIn: https://www.linkedin.com/in/hubbardjason/Explore DemandMagic: https://demandmagic.ai/Timestamps:(00:00) Intro(03:00) Jason’s growth marketing origins and bootstrapped startup mindset(04:30) The rise of services as software and AI’s role(08:20) Why focus beats chasing a wide TAM(11:10) Using AI to solve real business problems, not just for show(14:30) Feeding go-to-market data into AI for actionable insights(16:00) Personal uses of AI and digital nomad lifestyle plans(17:30) The entrepreneurial mindset: why most won’t do it twice

“You don’t need to dumb down your message—you need to lift it up,” says Zach Messler, messaging strategistIn this episode of The Content Cocktail Hour, Jonathan Gandolf sits down with Zach Messler to unpack what clarity actually means in product marketing, and why so many companies get it wrong.Zach shares the three deceptively simple questions every founder and marketer should be able to answer: “What is it? What does it do? Why does it matter?” He further discusses how to translate product complexity into compelling messaging, and why features don’t matter unless they’re tied to a deeper narrative. Zach also explains how to test your message in the wild, how to avoid the “everything, everywhere, all at once” trap, and the unlikely branding power of a Friday bourbon toast.In this episode, you’ll learn:Why product marketing starts with positioning, and not performance tacticsHow to talk about your product without actually talking about your productWhat message clarity really means Resources:Connect with Jonathan on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/Explore AudiencePlus: https://audienceplus.comConnect with Zach on LinkedIn: https://www.linkedin.com/in/zachmessler/Get Zach’s workbook: https://www.clarityrules.com Check out Zach’s newsletter: https://boomshockalocka.kit.com/e247950337 Explore zachmessler.com: https://zachmessler.com/ Timestamps:(00:00) Intro(02:18) The bourbon journey begins(05:37) The art of sipping whiskey(07:35) Bourbon collections and their value(13:24) The shift to messaging(14:49) The essence of product marketing(16:40) Defining your product(17:25) The importance of clarity in messaging(17:38) Understanding the power of messaging(18:08) The importance of positioning statements(20:17) Balancing product and problem messaging(25:24) Testing and refining your message(28:45) Connecting features to value(30:28) Creating a messaging guide