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.
Popular Podcasts
Las Culturistas with Matt Rogers and Bowen Yang
Ding dong! Join your culture consultants, Matt Rogers and Bowen Yang, on an unforgettable journey into the beating heart of CULTURE. Alongside sizzling special guests, they GET INTO the hottest pop-culture moments of the day and the formative cultural experiences that turned them into Culturistas. Produced by the Big Money Players Network and iHeartRadio.
Crime Junkie
Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by Audiochuck Media Company.
The Brothers Ortiz
The Brothers Ortiz is the story of two brothers–both successful, but in very different ways. Gabe Ortiz becomes a third-highest ranking officer in all of Texas while his younger brother Larry climbs the ranks in Puro Tango Blast, a notorious Texas Prison gang. Gabe doesn’t know all the details of his brother’s nefarious dealings, and he’s made a point not to ask, to protect their relationship. But when Larry is murdered during a home invasion in a rented beach house, Gabe has no choice but to look into what happened that night. To solve Larry’s murder, Gabe, and the whole Ortiz family, must ask each other tough questions.