AI've Got Questions

In this episode of AI’ve Got Questions, Stacey sits down with Megan Eisenberg, CMO of Samsara, to unpack how she’s turned AI from a vague mandate into real momentum across a 230-person marketing organization.

Megan shares how she set clear expectations for AI usage, gave her team permission to experiment, and created the conditions for real innovation, without waiting for a perfect playbook. From internal hackathons and AI “power hours” to building in-house tools that track how Samsara shows up in LLMs, this conversation goes deep on what’s actually working.

You’ll hear how Samsara’s marketing team is:

• Driving productivity and speed with AI-native workflows
• Rethinking SEO and PR in a world dominated by LLMs
• Automating ABM campaigns that used to take weeks to build
• Creating a culture where experimentation, curiosity, and learning are rewarded

This episode is a must-listen for CMOs and marketing leaders who know they need to embrace AI but aren’t sure where to start, especially inside larger, more complex organizations.

In this episode, Datadog CMO Sara Varni breaks down what AI adoption really looks like inside a large, scaled marketing organization.

Sara shares how her team is experimenting with AI while also selling AI-driven products, and why Datadog now expects every headcount or budget request to be evaluated through an “AI productivity” lens. She talks through the real use cases that are working, and the ones that are still too early.

Sara also walks through Datadog’s bottoms-up AI Council, their cross-functional AI hackathon, and the 21 projects that surfaced from it. She offers a candid look at evaluating AI-native tools vs. AI add-ons from legacy vendors, and how she decides which innovations truly matter for a company at Datadog’s scale.

We also get into:
 • why she doesn’t over-index on “AI experience” when hiring
 • misconceptions about how fast big companies are moving
• how to pilot new AI tools inside smaller product lines
• why curiosity matters more than credentials in the AI era

It’s a grounded, practical look at what AI-enabled marketing actually looks like inside one of the industry’s most respected enterprise software companies.

Today I’m joined by someone very special to me, Abhishek GP. We worked together at Freshworks and have stayed close ever since. I’ve had the chance to mentor him over the years, and it has been incredible to watch him grow into a leader who is respected, thoughtful, and already driving major impact.

Now he is running growth at Atlan, one of the fastest rising and most AI native companies out there. This episode is a behind the scenes look at what it actually feels like to operate inside a company where AI is not an experiment but a core part of how marketing works.

We get into:
 • How Atlan connects Google Ads, HubSpot, and Gong to find real demand signals
 • The paid search insight that reshaped their strategy
 • The internal BDR intelligence system his team built without adding new tools
 • How Atlan’s AI task force partners with marketing to push what is possible
 • Why AI still needs human judgment and strategic thinking
 • What it looks like to grow your career inside a truly AI forward company

This is a killer episode with someone who is already doing big things and is only going to go further. Do not miss it.

In this episode of AI’ve Got Questions, I sit down with Sydney Sloan, CMO of G2 and one of the most thoughtful and dynamic marketing leaders I know.

Sydney has spent her career shaping categories, scaling powerhouse SaaS companies, and building marketing teams that know how to spot the signal through the noise. Now she’s at the center of one of the biggest shifts we’ve seen in years: the rise of AI-driven buyer behavior, agentic workflows, and AEO.

We get into all of it, from how CMOs should rethink signals, to why “weed and speed” is the new growth mindset, to the exploding world of AEO tools (67 and counting - 67!). Sydney shares what she’s seen on her global AI tour, the data G2 is surfacing on how buyers actually research today, and the simple steps every marketer should take right now to keep up.

If you’re a marketing leader trying to build smarter, faster workflows in an agentic world, this one is full of practical insight.

Tune in.

This week on AI’ve Got Questions, Stacey sits down with Sylvia LePoidevin, CMO of Iru (formerly Kandji), to talk about how she’s turning AI from a buzzword into a company-wide movement.

Sylvia shares how she built an “AI-first” marketing team, starting with a scrappy hackathon that produced a working content system in just four hours, to a company-wide “Marketing Shark Tank” where bold, AI-powered ideas compete for cash prizes.

They dig into:

• How to make AI adoption fun instead of intimidating
• The rise of “tastemakers” and “operators” on modern marketing teams
• Why every brand should build a human “anchor” for its content flywheel
• The surprising SEO “hack” that boosted Iru's AI discoverability

If you’ve been wondering how to bring your team along on the AI journey, and actually make it exciting, this episode is for you.

In this episode of AI’ve Got Questions, Stacey sits down with Ashley Stepien, CMO of Hex, to talk about how AI is transforming modern marketing. Ashley shares how her team uses tools like ChatGPT and Claude to automate tedious tasks, test messaging at scale, and even rethink the structure of a marketing org.

They dive into the balance between build vs. buy in the age of AI, what it means to create “AI-native” marketers, and why brand creativity is making a big comeback.

If you’re a marketing leader trying to figure out where to start, or how to go deeper, with AI, this one’s packed with practical inspiration.

Stacey sits down with longtime friend and colleague Liz Carter, CMO of Reputation, to explore the new playbook for brand and reputation management in the GenAI era. Liz shares why Reputation rebuilt its platform around a unified intelligence hub, how buyers’ generative searches are changing discovery, and why reputation data can’t live in marketing silos anymore. With examples from healthcare, auto, and property management—and a peek at “Voice of Brand,” which aligns review responses to brand guidelines—you’ll leave with practical ways to monitor how your brand shows up daily, uncover blind spots across the journey, and bring reputation intelligence into BI/RevOps.

In this episode, Stacey sits down with Tejas Manohar, co-founder and co-CEO of Hightouch, to talk about the evolution of customer data platforms (CDPs) and how Hightouch is changing the game. Tejas shares his journey from early engineer at Segment to building a “composable CDP” that sits directly on top of the data warehouse. They dive into real-world examples from companies like Grammarly, PetSmart, and DoorDash, and explore how AI is reshaping marketing by turning raw data into smarter, automated decisions.

In this episode, I’m joined by someone who knows me better than most—my big brother, Barry Epstein. Barry is the founder of Ovation Solutions, a company that's been transforming how B2B brands use video to sell for over two decades.

We talk about the evolution of corporate video, how AI is now supercharging video libraries into virtual sales engineers, and what it takes to deliver real go-to-market value in the age of content overload. Barry shares insights on how leading companies like Salesforce are leveraging video and AI to move buyers down the funnel faster—and smarter.

And here's something extra: we used Ovation's own AI capabilities to enhance this very episode. Check out the interactive, AI-enabled version of the video at ovationsolutions.com/pages/aive-got-questions.

Whether you're a marketer, a founder, or a video producer, this one’s packed with practical wisdom (and a few sibling moments too!)

In this episode, Stacey sits down with Yash Tekriwal, Head of Education at Clay, to dive deep into how AI is reshaping go-to-market teams, not by replacing people, but by empowering them. Yash shares Clay’s philosophy of “automating the inhumane” so sales and marketing teams can focus on what really matters: building relationships and driving impact. They talk data hygiene, AI adoption hurdles, and why clean, enriched data is the unsung hero behind every successful GTM strategy. Whether you're a CMO trying to modernize your stack or just wondering where to start with AI, Yash offers clarity, tactical advice, and a glimpse into Clay’s unique approach to AI-powered growth.