The CISO Playbook for AI Agents | Datadog

a16z’s Katie Kirsch sits down with Harvey VP of Talent Maggie Landers to discuss what happens inside a company growing at AI speed, and how you preserve culture while adding more than 1,000 employees in a year. Maggie explains why Harvey prioritizes progress over perfection, how its values of simplicity, decisiveness, and “job’s not finished” shape the way people work, and why moving quickly requires giving employees significant trust and autonomy. For people accustomed to being the “A student,” that can mean learning to experiment, make mistakes, and course-correct quickly. They also get into how Harvey identifies people who can thrive in that environment, what changes when most of your company is relatively new, the role its founders play in maintaining culture, and why judgment becomes increasingly important when employees are given the freedom to move fast.

Erik Torenberg sits down with Box CEO Aaron Levie, and a16z’s Martin Casado, and Steven Sinofsky to debate how the AI industry should think about safety, security, and regulation as increasingly capable agents move into the real world. They argue that much of today’s conversation is happening before we have clearly defined the risks we’re trying to regulate. Drawing on earlier waves of computing, from computer viruses and the early internet to aviation and automobiles, they ask what AI can learn from industries that developed safety standards only after understanding how their technologies actually failed. The conversation then gets concrete: agents don’t get tired, can operate at enormous scale, and can probe systems in ways human employees never could. That could require rethinking permissions, authentication, operating systems, and the security stack itself. They also discuss why AI innovation may increasingly move beyond the frontier labs and into the software built around the models.

a16z’s Erik Torenberg sits down with Josh Elman, Olivia Moore, and David Booth to introduce Cosign, a new product built around professional reputation and the people, companies, and products you’re willing to put your name behind. They unpack a simple idea at the heart of Silicon Valley: some of the most valuable professional signals aren’t credentials, but who believes in you. From the mentor who shaped your career to the colleague you’d work with anywhere or the young builder you think everyone should be watching, Cosign is an attempt to make those signals more visible and durable. They also discuss why human endorsements may become more valuable as AI makes outreach and information abundant, what existing professional networks get right and miss, and how making reputation more legible could help talented people get discovered earlier, find collaborators, and carry the work they’ve done behind the scenes into whatever they do next.

a16z crypto General Partner Eddy Lazzarin joins Theo Jaffee on MTS to debate the increasingly prominent calls to slow AI development and whether the current safety conversation is conflating very different kinds of risk. Eddy argues that the debate puts too much emphasis on speculative superintelligence and not enough on the costs of delaying useful technology. Rather than treating every AI failure as evidence of an alignment problem, he makes the case for familiar tools like cybersecurity, accountability, liability, market incentives, and stronger technical controls. They also discuss whether AI models can develop reputations for trustworthiness, the risks of concentrating oversight among a small group of evaluators, and why Eddy thinks the collision between Silicon Valley’s AI debates and broader politics could fundamentally reshape the conversation over the next year.

Erik Torenberg sits down with Replit founder and CEO Amjad Masad and Horowitz and Andreessen Academy co-founder and CEO Gagan Biyani to ask what education should look like for a generation growing up with AI. Amjad argues that one of the most valuable things young people bring to society is their willingness to question deeply held assumptions. They discuss how education could create more room for that instinct through project-based learning, intellectual side quests, and giving students the freedom to follow an idea deeply rather than optimizing around grades and credentials. They also explore whether young founders are being pushed to professionalize too early, why Amjad thinks starting a company can sometimes be a form of “premature optimization,” and how curiosity led him from learning chess to experimenting with AI that can conduct machine-learning research. Finally, they discuss trust, judgment, and what it means to develop as a person, not just a builder, including why being contrarian and ambitious still needs to be balanced with the ability to work with other people.