"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 the Lost Lifecycle," this is a playbook for injecting swagger back into marketing without sacrificing pipeline, rigor, or credibility.

Sponsor

Brought to you by Hightouch - the leading composable CDP and decisioning platform trusted by brands like Domino's, Chime, and Aritzia. 90% of customers have a real use case live within their first week, delivering world-class personalization at scale. Learn more at www.hightouch.com/msom.

Timestamps

00:25 – First Martech tools, Mixpanel obsession, and Jason's weekly grilled cheese ritual

06:30 – Shaping brand storytelling: experience at Dropbox, BetterCloud, Microsoft

11:43 – What made early Salesforce so magnetic and why Martech lost its spark

16:40 – Making Martech cool again: inside Customer.io's Bob Ross, Hot Ones, and Raiders of the Lost Lifecycle concepts and playful brand identity

20:00 – What modern marketers actually want from live experiences

25:55 – Can mascots, memes, and influencers bring consumer fandom dynamics to Martech?

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!

Questions: https://themartechweekly.com/podcast/question/

Confessions: https://themartechweekly.com/podcast/confession-corner/

Reddit: https://www.reddit.com/r/MSoMPodcast/comments/1morng8/office_hours_questions/

Production Credit: Edited and produced by @the32collective_ / https://www.the32collective.co/

"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 platform trusted by brands like Domino's, Chime, and Aritzia. 90% of customers have a real use case live within their first week, delivering world-class personalization at scale. Learn more at www.hightouch.com/msom.

Timestamps

00:04 – MWF NYC debrief and why this year felt like a turning point for Martech

05:10 – Stranger Things and what "good" co-marketing actually looks like

10:30 – Woo-Woo vs data: how much of marketing is still intuition dressed up in dashboards

16:20 – Adobe buys Semrush: GEO data, media consolidation, and why Adobe blinked on AI search

24:40 – Quarterly Martech earnings: mid-market outpaces the enterprise and AI narratives without ROI

33:30 – BFCM early numbers: mobile-plus-AI shopping, BNPL growth, and fewer margin-killing discounts

36:56 – ChatGPT's third anniversary: national rollbacks and the societal risks of AI

42:15 – Subscriber question: How to drive change inside organizations when tooling and incentives clash?

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!

https://theMartechweekly.com/podcast/question/ https://theMartechweekly.com/podcast/confession-corner/ https://www.reddit.com/r/MSoMPodcast/comments/1morng8/office_hours_questions/

"If you're not treating deliverability as revenue insurance, you're already losing money." — Matt

This Hot Seat episode puts Matt McFee, an email veteran and founder of Inbox Monster, under the microscope. Jacqueline digs into how he went from Wall Street and Yahoo to co-founding BriteVerify, acquired by Validity, and why he thinks most brands are still wildly underestimating deliverability. He unpacks why inbox placement is really a revenue insurance program, not just a technical hygiene task, and why the real customer "moment of value" usually happens months after the contract is signed.

Brought to you by Hightouch - the leading composable CDP and decisioning platform trusted by brands like Domino's, Chime, and Aritzia. 90% of customers have a real use case live within their first week, delivering world-class personalization at scale. Learn more at www.hightouch.com/msom.

Timestamps

01:03 – What would make Martech better?

05:22 – What 25 years in email have taught him about the inbox

07:32 – Lightbulb moment that led to found BriteVerify and Inbox Monster

11:58 – AI previews, creative rendering, and why annotations actually matter

15:48 – What marketers should be paying more attention to in deliverability

19:55 – Quantifying deliverability as a revenue insurance program for stakeholders

25:02 – Opinions on industry innovation and consolidation

28:23 – What vendors can do to better help marketers

Connect & Subscribe

Subscribe to Making Sense of Martech wherever you get your podcasts. Engage with the community on Reddit and follow us 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!

Questions: https://themartechweekly.com/podcast/question/

Confessions: https://www.themartechweekly.com/podcast/confession-corner/

Reddit: https://www.reddit.com/r/MSoMPodcast/comments/1morng8/office_hours_questions/

LinkedIn: https://www.linkedin.com/showcase/making-sense-of-martech

"Zero party data reflects what customers say they want; first party data reveals what they actually do." – David

In this Hot Seat episode, Jacqueline sits down with David Joosten, co-founder of GrowthLoop and coauthor of First-Party Data Activation, to unpack why so many brands are "doing" first-party data yet still serving generic experiences. They dig into the tension between what customers say versus how they behave, and why marketers need to reconcile that gap with experimentation, empathy, and better use of their own data. Discover why embracing AI decisioning and continuous experimentation are crucial, and learn how to navigate the ethical red lines of using first-party data and AI responsibly in marketing. A must-listen for marketers looking to future-proof their data strategy.

David goes deep on why composable should be the default (not a buzzword), how to think about clean rooms without creeping out your customers, and what AI decisioning actually changes about the marketer's job. From compound growth engines and agentic workflows to team structures and org politics, this is a roadmap for leaders who want first-party data to drive real, measurable growth — not just prettier dashboards.

This episode wouldn't have been possible without the help of our sponsor Hightouch. Looking for a smarter way to activate your customer data? Hightouch is the leading composable CDP and decisioning platform trusted by brands like Domino's, Chime, and Aritzia. 90% of customers have a real use case live within their first week, delivering world-class personalization at scale. Learn more at www.hightouch.com/msom.

Timestamps

01:03 - Rapid Fire: AI generated content (Yay or Nay) and the marketing buzzword that needs to go.

02:30 - Is there ever a time to use third-party data ethically?.

03:54 - The most underrated skill for marketers today.

07:06 - Reconciling the gap between zero-party data (aspiration) and first-party data (behavior).

09:16 - The evolving role of first-party data in the next 3-5 years.

11:50 - Can clean rooms truly scale without compromising trust, and what's the next evolution of ethical data collaboration?

17:18 - What a "future-ready" Martech stack looks like in practice.

21:30 - Ethical red lines for AI: ensuring innovation respects privacy.

33:53 - The three-part advice for CMOs looking to future-proof their data strategy.

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!

• https://theMartechweekly.com/podcast/question/
• https://theMartechweekly.com/podcast/confession-corner/
• https://www.reddit.com/r/MSoMPodcast/comments/1morng8/office_hours_questions/

"92% of enterprises say AI is a priority, and 78% also say they can't integrate it." — Juan

In this Office Hours episode, Jacqueline Freedman and Juan Mendoza unpack the biggest Martech realities of the season: record-breaking BFCM performance and the widening "AI hype gap." From $10.8 billion in U.S. online spending (69% on mobile) to reports revealing that 95% of marketers want AI personalization but only 2% have delivered it, the duo exposes where Martech optimism meets operational reality.

The episode wraps with a philosophical debate on attribution, why it's not a model but a mindset, and how every marketer needs a "margin for mystery" to keep creativity alive.

Don't miss the webinar "Has Martech Failed Marketers?" on November 13, featuring Scott Brinker and Adam Greco. Hightouch's latest survey found that nearly 75% of Martech struggles are rooted in data, not tools or strategy. Learn how to fix your data to unlock cleaner reporting and true personalization at scale.

RSVP at hightouch.com/has-martech-failed

Timestamps

00:15 — Martech World Forum NYC next week and the launch of Melbourne 2026

04:51 — Black Friday & Cyber Monday: "The Super Bowl of Martech" and the $74B global spend moment

09:30 — From stores to platforms: the mobile commerce shift and why eCommerce needs enterprise-level investment

16:11 — The AI Report Card: 92% say AI is a priority, 78% can't integrate it — reality check from Zapier, G2, Hightouch, and Wharton

20:39 — Hightouch findings: 95% want AI-driven personalization, but only 2% deliver — the hype gap exposed

41:30 — AI decisioning vs. contextual bandits: semantics, strategy, and the need for real discipline

46:32 — Why attribution sucks: brand, politics, and the "margin for mystery" behind measurement

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!

• https://themartechweekly.com/podcast/question/
• https://themartechweekly.com/podcast/confession-corner/
• https://www.reddit.com/r/MSoMPodcast/comments/1morng8/office_hours_questions/

"Curiosity is the number one trait I'm looking for when hiring." — Brian Minick

Jacqueline and Brian Minick, COO of ZeroBounce, get practical about AI's impact on hiring, email deliverability, and Martech operations. They unpack how AI is reshaping hiring, from candidates using copilots during interviews to the ethical implications of automation in recruitment. Brian shares how his gut helped him catch an AI-assisted candidate mid-interview, why curiosity and speed are the real differentiators in a digital-first world, and how he's balancing innovation with humanity at scale. Expect real talk on personalization trade-offs, customer data hygiene, leadership, and why curiosity still beats credentials. If you care about AI, Martech, leadership, and deliverability, this episode helps you cut noise and double down on what moves the needle.

Brought to you by Hightouch, On November 13, Hightouch is hosting Has Martech Failed Marketers? featuring Scott Brinker of chiefmartec and Adam Greco to unpack what's really behind the pain and how fixing your data unlocks cleaner reporting and true personalization at scale. RSVP at www.hightouch.com/has-martech-failed

Timestamps 00:28 — Early Martech Days: Google Ads, Analytics, and the hustle era. 03:12 — AI in Content: great for ideas, never for copy-paste. 04:07 — The New Deliverability: why engagement, not volume, wins. 06:25 — Curiosity-Driven Leadership: lessons from a selfless CEO. 09:37 — Using AI Internally: copilots, data storytelling, and guardrails. 18:35 — The Deliverability Gap: why no AI tool fully solves it—yet. 21:10 — The AI-Assisted Interview: red flags, silence tricks, and hiring truths. 38:23 — Leadership Without Ego: humility, speed, and follow-through. 43:28 — What's Next: AI-generated video and the future of short-form content.

Connect & Subscribe Subscribe to Making Sense of Martech wherever you get your podcasts. Leave a review, share with your team, and send us your questions and confessions. We may feature you in an upcoming episode!

Send them here: https://themartechweekly.com/podcast/question/ https://themartechweekly.com/podcast/confession-corner/ https://www.reddit.com/r/MSoMPodcast/comments/1morng8/office_hours_questions/

"You're supposed to be your customer relationship management platform of the era, and you're not listening to your very own customers." — Jacqueline Freedman

Jacqueline and Juan dissect Salesforce's Dreamforce rebranding of all major products to Agentforce, the erosion of its once-strong Ohana culture, and Benioff's billionaire behavior. They unpack the AWS outage, explore operational resilience, and talk about how to overcome analysis paralysis.

Brought to you by Hightouch

On November 13, Hightouch is hosting Has Martech Failed Marketers? featuring Scott Brinker of chiefmartec and Adam Greco to unpack what's really behind the pain and how fixing your data unlocks cleaner reporting and true personalization at scale. RSVP at www.hightouch.com/has-martech-failed

Timestamps

00:23 — Scott Brinker's "You Are the Change Agent" for Martech World Forum.

02:53 — Making QBRs (Quarterly Business Reviews) fun with a "meme wall".

06:41 — What happened to "Ohana" at Salesforce/Dreamforce?.

09:11 — Salesforce product renaming: The "Agent Force" trend.

19:26 — The massive AWS Outage felt by companies globally.

26:01 — Hot Take: Alan Trevor on using AI decisioning backwards.

34:49 — Office Hours Question: Overcoming analysis paralysis.

37:37 — The connection between analysis paralysis and a lack of courage/risk-taking.

40:07 — Confession Corner: Forgetting an elevator pitch in front of the CEO.

Connect & Subscribe

Subscribe to Making Sense of Martech wherever you get your podcasts. Leave a review, share with your team, and send us your questions and confessions — we may feature you in an upcoming episode!

Send them here:

• https://themartechweekly.com/podcast/question/
• https://themartechweekly.com/podcast/confession-corner/
• https://www.reddit.com/r/MSoMPodcast/comments/1morng8/office_hours_questions/

"Marketing engineers are the lovechild of marketers, product managers, and software engineers — they're the Avengers of your Martech stack." - Neha Dadbhawala

Join Jacqueline and Neha, Head of Martech at SEEK, to unpack how the role of the marketing engineer is reshaping the future of digital transformation.

Neha shares her insights on bridging strategy and execution, building operational readiness, and applying systems thinking to deliver scalable marketing outcomes. From the rise of AI to managing legacy tech, Neha reveals what it takes to drive meaningful innovation across marketing, technology, and customer experience.

Key Insights

• Discover the Rise of the Marketing Engineer
• Learn the 70-20-10 Rule for Operational Readiness
• Explore System-Level Thinking
• Bridge the Marketing–Tech Divide
• Navigate Legacy Systems with Agility
• Build the Future Martech Leader

Timestamps

00:30 — Rapid-Fire Intro: Neha's favorite Martech tool, the "build vs. buy" dilemma, and her least-favorite buzzword: "hyper-personalization."

3:30 — Defining the Marketing Engineer: The evolution from technologist to system architect and problem solver.

7:00 — Skills for the Future: Systems thinking, product mindset, and emotional intelligence as core leadership traits.

9:30 — Operational Readiness & the 70-20-10 Rule: How to plan for change and innovation simultaneously.

14:00 — Agility in Legacy Systems: Managing tech debt while maintaining scalability and speed.

18:30 — Breaking Silos: Why shared data definitions and transparent priorities unlock collaboration.

25:00 — The Future of Martech Careers: How marketing engineers can evolve into CMOs, Chief Growth Officers, and beyond.

Connect & Subscribe

Subscribe to Making Sense of Martech wherever you get your podcasts. Leave a review, share with your team, and send us your questions and confessions — we may feature you in an upcoming episode!

Brought to you by Hightouch - the leading composable CDP and decisioning platform trusted by brands like Domino's, Chime, and Aritzia. 90% of customers have a real use case live within their first week, delivering world-class personalization at scale. Learn more at www.hightouch.com/msom.

"Don't be the Taylor Swift of Martech." - Jacqueline Freedman

Jacqueline and Juan break down three of the latest Martech moments: Braze's all-in AI decisioning push, Zeta Global's acquisition of Marigold, and what Taylor Swift's marketing playbook reveals about loyalty and fandom.

Drawing from recent Martech World Forum events in London and San Francisco, they cut through the hype around AI, vendor economics, and what real enterprise teams are actually doing to make Martech work.

Highlights

Discover how Taylor Swift's variant strategy rewrites loyalty and first-party data engagement.

Learn why most AI decisioning pilots stall—and how to tell if your org is ready.

Understand what the Zeta–Marigold deal says about Martech consolidation and the future of loyalty tech.

Explore how enterprise teams turn "global rollouts" into many small, scalable wins.

Hear why authenticity and data discipline still beat automation and hype.

This episode wouldn't have been possible without the help of our sponsor Hightouch.

This episode wouldn't have been possible without the help of our sponsor Hightouch. Looking for a smarter way to activate your customer data? See what Hightouch can do for you at hightouch.com/msom.

Timestamps3:25 — Lessons from HSBC & Tailored Brands (Men's Wearhouse) on rolling out AI at scale. 7:12 — Braze's AI Decisioning: Analyzing the early use cases and the hard truth about ROI. 10:28 — Vendor rush: CDPs, decisioning, and the hidden cost of data operations. 14:04 — The Real Cost of AI: Why governance and data readiness are the biggest factors in Total Cost of Ownership (TCO). 16:34 — Zeta Global acquires Marigold: strategy, price, and implications. 21:01 — The Taylor Swift Effect: loyalty, data, fandom economics, and corporate greed. 28:37 — Office Hours Q&A: Do you think the real power of a show like this is in analyzing the companies—or in challenging how the industry itself thinks about using (or refusing) AI in daily work?

Connect & Subscribe:

Subscribe to Making Sense of Martech wherever you get your podcasts. Leave a review, share with your team, and send us your questions and confessions — we may feature you in an upcoming episode!

"There's a big difference between consent and attention — you still have to earn the attention." - Lauren Meyer

Lauren Meyer, CMO of SocketLabs, joins Jacqueline Freedman on The Hot Seat to discuss what marketers get wrong about email. She shares how to earn real engagement, why "inbox placement rate" is a lie, and how to prove email's value inside your org. A must-listen for anyone in marketing ops, lifecycle, or Martech leadership who wants to make smarter, data-backed email decisions.

This episode wouldn't have been possible without the help of our sponsor Hightouch.

Looking for a smarter way to activate your customer data? See what Hightouch can do for you at hightouch.com/msom.

Highlights

Learn why consent alone isn't enough and how to earn lasting attention.

Discover how to win internal buy-in with small, proof-of-concept projects.

Understand why marketers must accept churn and stay consistent.

Cut through noisy metrics and drop "inbox placement rate" from your reports.

Get smart about measuring engagement post-MPP using replies, site visits, and revenue.

Spot vendor red flags: no one can "guarantee" inbox placement.

Episode Breakdown

2:16 — Epic Fail Story: The migration mistake that led to 3,000 spam complaints and a deliverability meltdown.

8:15 — The Consent Myth: Why consent is just the handshake and attention is the real battle.

12:54 — Fighting for Email: How to advocate for email internally with small proof-of-concept wins.

15:08 — Data Hygiene: The B2B vs. B2C data gap and why you should offer personal email sign-ups.

17:52 — Data Overload: Why giving marketers too much data leads to paralysis and bad assumptions.

19:52 — The Metric to Ban: Why "Inbox Placement Rate" is unreliable and based on robot "seed testing."

22:06 — Vendor Red Flags: What to ask about human support and why no one can guarantee inbox placement.

25:02 — Post-APP World: How to measure engagement through conversions, replies, and site visits, not opens.

33:09 — AI Limits: The doctor vs. over-the-counter analogy for AI in deliverability.

Subscribe to Making Sense of Martech wherever you get your podcasts. Leave a review, share with your team, and send us your questions and confessions. We may feature you in an upcoming episode!