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 ...

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 cros...

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 com...

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 ...

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 intimidatin...