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Ep. 019: What the Holacracy? The Basics & Benefits of Flat Organizations in Development

Join Geoff Vandegrift, Chief Technology Officer at Ad Astra, on this week's episode of Open Source CXO. We’re examining the evolving landscape of technology leadership as Geoff shares his journey and experiences from different companies, culminating in his current role at Ad Astra. With Ad Astra's mission being ‘to graduate more students faster,’ Geoff and his team provide higher education institutions with solutions to offer the right courses in the right format at the right place. Highlighting the transition to a cloud-native, serverless architecture, Geoff acknowledges the benefits and challenges of holacracy. He emphasizes how it allows for greater flexibility and empowerment among team members, fostering a self-managed and collaborative work environment. Tune in to gain valuable insights into managing a self-managed organization, integrating innovative practices like holacracy, and maintaining a mission-driven approach in the fast-paced tech industry. Geoff's story offers a unique perspective on fostering an agile, customer-focused engineering culture while navigating the complexities of the higher education sector. ————— 00:00 - Introduction and Overview of Ad Astra 02:25 - Ad Astra's Client Base and Development Team 04:23 - Quality Assurance and Testing 06:08 - Vision and Objectives 09:25 - Developer Engagement and Client Understanding 11:07 - Team Structure, Product Management, and Technical Stack 15:27 - Transition to Milo and Holacracy 20:05 - Principles of Holacracy and Application at Ad Astra 24:55 - Adoption and Perception of Holacracy 26:29 - Future Trends of AI/Closing Remarks ————— Geoff Vandegrift is an accomplished technology leader with a proven track record in driving innovation and performance in software engineering teams. Currently serving as the Chief Technology Officer at Ad Astra, Geoff oversees product engineering, including product management, testing, user experience, and software development. With a focus on higher education, he leads efforts to create solutions that help institutions optimize course offerings and improve student graduation rates. Previously, Geoff held significant roles at Perceptive Software and Lexmark, where he managed large, globally distributed teams and implemented continuous integration practices. His experience with Holacracy at Milo has shaped his leadership approach, emphasizing flat organizational structures and flexible team roles. Known for his strategic vision and ability to foster collaborative, mission-driven cultures, Geoff is dedicated to advancing educational technology and operational efficiency.