Episode 51: Matt Mochary

In this episode, BigID CEO Dimitri Sirota discusses the company’s journey, capitalizing on GDPR’s emergence to become a leader in data and AI security, compliance, and governance. He shares how an early pivot to target Chief Privacy Officers, strategic channel partnerships, and a focus on solving one critical problem fueled rapid growth. Dimitri also explores how AI is transforming BigID’s operations, product capabilities, and customer use cases, while stressing the need for realistic expectations and nuanced understanding of AI’s potential.

In this episode, Jake Stein (co-founder of Common Paper, Stitch, and RJMetrics) joins Grant Miller to talk through the evolution of B2B contracts and how software—particularly AI—is transforming the sales process. Jake shares the origin story of Common Paper, lessons learned from previous startups, and how he’s leveraging AI with their new product "Jerry" to streamline contract negotiations and redlines. The two dive into the importance of standardization, what’s “market” in enterprise contracts, and why faster sales cycles are a major growth lever. A must-watch for SaaS founders, sales leaders, and legal ops pros.

In this special crossover episode of EnterpriseReady and The Kubelist Podcast, Replicated co-founders Grant Miller and Mark Campbell join Benji DeGroote to unveil SecureBuild—a new open source initiative delivering zero-CVE container images with commercial-grade SLAs. They trace Replicated’s 10-year journey from pioneering on-prem software delivery to redefining modern software distribution with Helm, Kubernetes, and air-gapped environments. The conversation covers lessons learned from scaling, shifting product-market fit, and building sustainable open source monetization. Plus, they dive deep into how AI tools like Cursor and Devvin are transforming software development at Replicated—from leadership to engineering. Don’t miss this episode packed with history, humor, and hard-won insights on enterprise software and open source sustainability.

In this podcast conversation, Grant Miller, CEO of Replicated, interviews Ev Kontsevoy, co-founder of Teleport (formerly Gravitational), reflecting on their past competition and the evolution of their respective companies. They discuss how their perspectives on competition have matured, evolving from emotional reactions to seeing competitors as allies who share a similar vision. Ev shares the origin story of Gravity, initially aimed at creating an operating system for the cloud, and how Teleport spun out as a more successful identity management solution. They dive into the challenges of enterprise sales, emphasizing the need to align product design and go-to-market strategy around minimizing the number of stakeholders involved in purchasing decisions. Ev also explains the concept of "trusted computing" and why decoupling infrastructure access from human behavior is crucial for robust security. They touch on the role of AI in modern systems, advocating for identity models that treat AI agents as first-class citizens, integrated into the same security and identity frameworks as humans and machines. The episode is a candid, philosophical, and tactical exchange about product evolution, security, enterprise sales, and the future of infrastructure.

In this relaunch episode of the EnterpriseReady Podcast, host Grant Miller, CEO of Replicated, sits down with Tristan Handy, founder and CEO of dbt Labs. They dive into the evolution of dbt from a consulting project to an open source CLI tool with a thriving enterprise product and ecosystem. The conversation explores the strategic nuances of commercializing open source software, scaling developer-focused tools, introducing AI-powered copilots, and navigating modern enterprise sales. Handy shares hard-earned lessons on product-market fit, technical re-architecture, M&A, and building opinionated platforms. Whether you're a SaaS founder, data engineer, or enterprise operator, this episode delivers tactical insights on building and scaling enterprise software in today’s AI-infused landscape.

In episode 51 of EnterpriseReady, Grant Miller speaks with leadership coach, investor, and filmmaker Matt Mochary. Together they explore themes on executive coaching, building trust, scaling businesses, conflict resolution, and customer retention. Additionally, Matt unpacks the characteristics of CEOs that drive the most success.

In episode 50 of EnterpriseReady, Grant speaks with Matias Woloski of Auth0. This talk contains unparalleled lessons on utilizing authentication and authorization services, landing your first enterprise customer, making smarter hiring decisions, and understanding the complexity of the CTO role. About the Guest Matias Woloski is an engineer with a passion for building frictionless products. He is the Co-Founder & CTO of Auth0 and an angel investor.

In episode 49 of EnterpriseReady, Grant speaks with Omri Gazitt of Aserto. They began with a dive into Omri’s early beginnings in enterprise software, including his time at Microsoft working on the .NET framework and XML team at Microsoft, and the lessons learned that would lead to the creation of Azure. Finally, Omri unpacks what led him to found Aserto, a solution to enterprise-grade access control. About the Guest Omri Gazitt is CEO and Co-Founder of Aserto. His expansive enterprise career journey includes 13 years overseeing product at Microsoft, founding the Seattle startup BuiltSteady, working in cloud at Hewlett Packard Enterprise, and leading product at Puppet as CPO.

In episode 48 of EnterpriseReady, Grant Miller is joined by Sanjay Poonen. This expansive conversation draws on Sanjay’s long and storied career in software, from the early engineering days at Apple and Microsoft to his executive and entrepreneurial experience building and scaling multi-billion dollar businesses like VMware. Together, Grant and Sanjay unpack invaluable lessons on engineering, product management, marketing, sales, work-life balance, and much more. About the Guest Sanjay Poonen’s software career journey began in the early 1990s, when he pursued software engineering at Microsoft, and then Apple. In 1997 he founded AlphaBlox. In the years to follow, Sanjay held executive roles at Informatica, Symantec, and SAP. From 2013 - 2021, he was COO of VMware, where he led the company’s growth from $6B to $12B in revenue. He is currently on the Board of Directors at Snyk.

In episode 47 of EnterpriseReady, Grant speaks with Mark Lorion of Tempo. They discuss Mark’s programming background and early enterprise software roles, the importance of seeking customer data at the source, and deep insights on enterprise marketing. About the Guest Mark Lorion is an entrepreneurial and analytical software executive currently serving as CEO of Tempo Software, Board Director of Mass Technology Leadership Council, and Co-Founder of Boston TechJam.