Living Interfaces, OpenAI Collabs, & Enterprise AI with Josh Payne, CEO of Coframe
Release Date: 09/10/2025
Confessions of an Email Provocateur with Dela Quist
Making Sense of Martech
Why impressions — not clicks — reveal email’s real power, and who’s quietly profiting from your inbox. Email is still treated like a messaging channel, and that mistake is quietly destroying value. In this episode, Jacqueline sits down with Dela to challenge the default rules of email marketing and reframe the inbox as what it actually is: owned media and intent infrastructure. Nearly every sacred KPI is put on trial, including opens, clicks, suppression, and frequency caps, and replaced with a media-first lens focused on reach, impressions, and long-term behavior. Dela...
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Pilots to Proof: AI Agents in the Enterprise with Keanu Taylor
Making Sense of Martech
Pilots to Proof: AI Agents in the Enterprise with Keanu Taylor AI agents are being positioned as the answer to shrinking budgets and rising expectations, but most enterprise teams are still stuck in pilot mode. In this Office Hours episode, Jacqueline is joined by guest host and industry analyst Keanu Taylor to examine what’s actually working inside large organizations. Drawing on insights from his research, the conversation explores why many “AI strategies” amount to fragmented experiments, and what it really takes to move from internal pilots to external...
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Sweet, Suite Relief with Adam Greco
Making Sense of Martech
“Suite Fatigue is the moment you realize you’re paying more every year for less flexibility and less value.” — Adam Marketing was supposed to get simpler. Instead, it got more expensive, harder to operate, and increasingly rigid. Jacqueline sits down with Adam Greco (previously at Salesforce, Adobe, and Amplitude) to unpack the rise of “Suite Fatigue,” the growing frustration with all-in-one marketing technology platforms that promised the world but delivered fragments. They get into why this moment feels different, how renewal pressure and slow innovation are turning...
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The 6 Pain Points Martech Leaders Face
Making Sense of Martech
"We’ve seen companies locked into vendors for a decade with no way out." – Juan Jacqueline and Juan kick off 2026 with a quick reality check: stepping away from screens feels great, but the Martech stack doesn’t magically get simpler while you’re gone. They get brutally practical, drawing on conversations with 300+ brand-side marketers to map the six biggest pain points emerging across enterprise teams right now. They dig into why “Customer 360” is still mostly a fantasy, how integration complexity turns stacks into brittle Jenga towers, and why AI pressure is...
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Battle of the Bots with Mariska Calabrese, beehiiv & Jakub Alexa, Omnivery
Making Sense of Martech
Email feels free, but the economics are brutal: zero-cost sending makes abuse infinitely scalable. In this episode, Jacqueline sits down with Mariska and Jakub to unpack the “bot layer” that’s quietly wrecking modern email: security scanners, crawlers, and malicious automation that inflate clicks, poison dashboards, and trigger the wrong automations. They get specific about why bad actors iterate faster than platforms, why “heuristic guesswork” leads to painful false positives, and how beehiiv opted for radical transparency by showing verified clicks alongside raw data....
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The Renaissance
Making Sense of Martech
Farewell, 2025 — what a year. It marked the revival of Making Sense of Martech, and we owe it all to you and the incredible guests who took a chance on us. Here are a few standout moments. Wishing you happy holidays and a brilliant new year! Connect & Subscribe Subscribe to Making Sense of Martech wherever you get your podcasts. Engage with the community on Reddit and follow Making Sense of Martech on LinkedIn, and don't forget to like and subscribe on YouTube. Leave a review, share with your team, and send us your questions and confessions. We may feature you...
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The Blooper Reel
Making Sense of Martech
Merry everything and more. Here’s your very own present from us to you! Connect & Subscribe Subscribe to Making Sense of Martech wherever you get your podcasts. Engage with the community on Reddit and follow Making Sense of Martech on LinkedIn, and don't forget to like and subscribe on YouTube. Leave a review, share with your team, and send us your questions and confessions. We may feature you in an upcoming episode!
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2026 Predictions: Agents, AI Decisioning, & The Techstack
Making Sense of Martech
As 2025 closes out, Juan and Jacqueline team up with Keanu Taylor, The Martech Weekly’s Head of Research, to read the tea leaves on what 2026 has in store for marketing technology. Their forecast is a “make or break” year in which the winners won’t be the loudest early adopters, but the teams whose data and operating habits are clean enough for AI actually to stick. Keanu predicts a sharper split between the AI “haves” and “have-nots,” with organizational readiness acting like gravity on every agent, model, and workflow. The bet: 2026 will expose which stacks are...
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Make Martech Cool Again: A Conversation with Jason Lyman, Customer.io’s CMO
Making Sense of Martech
“Marketing to marketers is the dream job, but it makes everything that much more high stakes.” – Jacqueline In this Hot Seat episode, Jacqueline sits down with Jason, CMO at Customer.io, to ask a simple question: what would it actually take to make martech cool again? Drawing on stints at Dropbox, BetterCloud, and Microsoft, he unpacks how brand storytelling, design, and experience can turn forgettable software into something people genuinely want to be around — and why so many teams lost that plot after the early cloud-era glory days. From Bob Ross livestreams to “Raiders of...
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Adobe’s Semrush Gamble, BFCM Enters the Upside Down, & AI-Washed Earnings
Making Sense of Martech
"Adobe didn’t just buy an SEO tool – it bought a negotiating position with the AI overlords of discovery." – Juan Jacqueline and Juan unpack what “more human” marketing actually looks like when AI is mediating everything from search to Black Friday deals. They break down Adobe’s acquisition of Semrush, quarterly Martech earnings, the Black Friday/Cyber Monday shift toward mobile-plus-AI shopping, BNPL’s surge, and ChatGPT’s three-year impact on how people search, think, and buy. Brought to you by Hightouch — the leading composable CDP and decisioning...
info_outline“We see the future of digital experiences as living — personalized and self-improving 24/7.” - Josh Payne
In this episode, Jacqueline Freedman puts Josh Payne in The Hot Seat to unpack “living interfaces,” AI-driven experimentation, and what agentic marketing really looks like in practice.
Josh shares lessons from collaborating with OpenAI, why most CRO tests fail, and where generative engine optimization (GEO) is headed next.
We delve into enterprise realities, including privacy and governance, avoiding spaghetti code, and what a “living interface” entails.
Highlights
- Discover how “living interfaces” adapt websites in real time to lift conversion and usability.
- Learn a practical framework for automating ~90% of the CRO workflow with agents.
- Understand when to start with global experiments vs. personalization to reduce data-privacy friction.
- Explore the rise of generative engine optimization (GEO) and why it will rival SEO in influence.
- Adopt guardrails: define measurable evals, keep specs specific, and stay model-agnostic for compliance.
- Hear what enterprises actually need from vendors: context, integration, and disciplined measurement.
Timestamps
03:50 - What “living interfaces” are and how they create real-time, self-improving digital experiences
04:57 - Partnering with OpenAI: visual grounding, UI generation, and early access to models
11:25 - Why most CRO tests fail—and how AI agents flip the economics of experimentation
14:50 - What “agent marketing” means: automating workflows and scaling high-leverage loops
17:45 - Common AI pitfalls and why clear goals, specs, and evals matter
24:20 - Navigating privacy concerns and model choices in enterprise AI
27:30 - How Josh filters the AI noise and stays sharp
Subscribe to Making Sense of Martech wherever you get your podcasts. Leave a review, share with your team, and send us your questions. We may feature you in an upcoming episode.