How I scaled an engineering team to a 400m exit and why I am using AI to do it again.

Ben Gracewood is one of those rare tech leaders who’s done the whole arc—starting in low-level code, scaling product and engineering teams at Vend through to a $400 million exit, and now leading in a world where AI is rewriting the playbook. With a deep background in software development and executive leadership, Ben has built teams, shaped product strategy, and helped grow one of New Zealand’s most successful SaaS companies. But he’s not stuck in nostalgia. Today, he’s laser-focused on what comes next—and he’s convinced that we can now do more with fewer people. Ben’s current work explores how artificial intelligence can augment product and engineering teams—not to replace humans, but to strip away busywork and let great people focus on what matters. He’s open in questioning the bloat that’s crept into many tech orgs, and he’s even willing to say what others won’t: maybe Elon wasn’t entirely wrong when he gutted Twitter’s headcount. Brutal? Maybe. But Ben thinks it opened up an uncomfortable truth—most tech teams are overstaffed and under-focused. Whether it’s scaling with soul, building leaner, smarter teams, or staying close to the craft as a leader, Ben brings a no-BS, high-empathy perspective to what modern product leadership looks like. He’s still a builder at heart—and now he’s building with AI at his side. This podcast was brought to you by our amazing sponsor in Vanta 🙌🏻 Get USD $1000 off Vanta using the link https://www.vanta.com/startuptheatre.