Episode Summary

Ad Astra’s very own Geoff Vandegrift is back for our 20th episode of Open Source CXO. Geoff shares his journey from being a developer to leading Ad Astra’s technology initiatives and then shifts gears to stir the “WFH” pot. He dives into the evolving dynamics of work environments, emphasizing the data-backed benefits and challenges of working from home versus in-office collaboration.

Geoff highlights the importance of a flat organizational structure, small cross-functional teams, and the need for high-bandwidth communication facilitated by in-office collaboration. He also discusses the challenges and benefits of maintaining a Kansas City-based development team, emphasizing the value of social cohesion and spontaneous communication in producing better software.

Tune in to gain valuable insights on navigating the complexities of integrating innovative management practices, fostering a collaborative engineering culture, and maintaining a mission-driven approach in the fast-paced tech industry!

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About Our Guest

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.

Episode Chapters

00:00 - Introduction and Overview of Ad Astra

• Hosts introduce Geoff Vandegrift, CTO at Ad Astra, and provide a brief overview of the company, its mission, and its role in higher education.

02:25 - Career Path to Leadership

• Discussion on Geoff's career path to becoming an executive. His initial interest in physics, transition to software development, and eventual move into management roles.

05:51 - Management Philosophy and Continuous Integration

• Geoff's initial reluctance towards management and how his perception evolved over time. Introduction to continuous integration and its impact on his career.

08:20 - Transition to Ad Astra and Holacracy

• Geoff's move to Ad Astra and his experience with Holacracy. How this experience transformed his understanding of management and organizational structure.

11:07 - Importance of Co-location and Team Productivity

• Geoff discusses the benefits of having the development team based in Kansas City and the importance of co-location for team productivity and communication.

15:27 - Challenges of Hybrid and Remote Work

• Insights into the challenges and benefits of hybrid work models. Discussion on team synchronization, productivity, and social cohesion in a hybrid work environment.

19:27 - Personal Preferences in Productivity & Closing Remarks

• Geoff's personal preference for in-office work and the impact of open office plans on productivity. Balancing deep work needs with team communication.

Resources:

• "Culture Code" by Daniel Coyle
• -
• Amazon Link
• Explores the secrets behind highly successful groups and teams, revealing how they cultivate trust, cooperation, and innovation. Daniel Coyle examines the culture of various organizations, offering practical advice on how to create a thriving, cohesive group.
• "Team Topologies" by Matthew Skelton and Manuel Pais -
• Amazon Link
• A practical guide to organizational design and team interaction patterns that enhance software delivery performance. The authors explain how to structure teams for effective collaboration and improved system architecture through clear, adaptable team models.
• Concept: Holacracy -
• Holacracy Book by Brian J. Robertson
• Holacracy is a decentralized management system that distributes authority and decision-making through self-organizing teams. Developed by Brian J. Robertson, it aims to increase agility, transparency, and accountability within organizations by replacing traditional management hierarchies.
• "Radical Candor" by Kim Scott -
• Amazon Link
• A framework for providing feedback that is both caring and direct, fostering open communication and strong relationships in the workplace. Kim Scott draws on her extensive management experience to guide leaders in building a culture of trust and respect.