Operations

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Lessons from Stewart Butterfield

Stewart Butterfield, the Canadian entrepreneur behind Flickr and Slack, applies a background in philosophy to communication, collaboration, and software at scale, grounding his work in empathy, craftsmanship, and technology’s capacity to augment human potential.

Lessons from Drew Houston

Drew Houston, co-founder and CEO of Dropbox, turned a personal frustration into a global cloud-storage utility, pairing continuous learning and “healthy paranoia” with a practical framework for entrepreneurship, product design, personal growth, and life’s finite days.

Lessons from Melanie Perkins

Melanie Perkins, co-founder and CEO of Canva, moved from teaching design in Perth to building a global platform, demonstrating how persistence, visionary thinking, and sustained attention to meaningful problems can turn an ambitious idea into widely used technology.

Lessons from Andy Sparks

Andy Sparks, co-founder of Mattermark and Holloway and a coach to startup CEOs, translates operational experience into frameworks for leadership, sales, and self-management while asking how companies can combine high performance with genuine attention to people.

Lessons from Garrett Lord

Garrett Lord, co-founder and CEO of Handshake, built a career network around democratizing professional opportunity for students, confronting the role pedigree plays in hiring and widening access beyond the institutions traditionally favored by employers.

Lessons from Tony Xu

Tony Xu, co-founder and CEO of DoorDash, pairs long-range vision with close attention to the lowest operational detail, showing how immigrant grit and precision can address the messy physical-world logistics underlying the modern local economy.

Lessons from Brandon Sammut

Brandon Sammut, Zapier’s chief people and AI transformation officer, leads at the intersection of talent and technology in a remote company, pairing an AI-first philosophy with transparency, human-centered culture, and experience managing large-scale digital change.

Lessons from Allen Shim

Allen Shim, Slack’s first chief financial officer, helped guide a direct listing and Salesforce acquisition before becoming a strategic advisor in Singapore, drawing on experience scaling organizations to mentor a new generation of technology founders.

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