AI've Got Questions

120 AI Use Cases Later: How Meagen Eisenberg Scaled Samsara’s Marketing with AI

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.

Inside Datadog: How Sara Varni Scales AI Across a Global Team

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.

Becoming AI-Native: Inside Atlan’s Growth Engine with Abhishek GP

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.

Signals, AEO, and the New Buyer Journey with Sydney Sloan, CMO of G2

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.

From Hackathons to an AI Content Engine: Sylvia LePoidevin on Iru’s Marketing Transformation

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.