Episode Summary

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.

—————

Open Source CXO is proudly presented by Active Logic - https://activelogic.com/

Check us out online: https://oscxo.com/ \_\_

Check us out on LinkedIn - https://www.linkedin.com/company/oscxopodcast

Follow us on Instagram! - https://www.instagram.com/oscxopodcast/?hl=en

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
• Don and Rob 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 -
• Ad Astra's Client Base and Development Team
• Overview of Ad Astra's client base and the size of their development team. Geoff explains the composition and roles within his team.
• 04:23 -
• Quality Assurance and Testing
• Discussion on the ratio of QA testers to developers. Geoff's philosophy on small cross-functional teams and the role of testers.
• 06:08 -
• Vision and Objectives
• How Ad Astra sets and communicates objectives. Challenges in aligning team efforts with business goals.
• 09:25 -
• Developer Engagement and Client Understanding
• Efforts to ensure developers understand client needs. Role of the CEO in communicating the company's vision.
• 11:07 -
• Team Structure, Product Management, and Technical Stack
• Structuring development work across small teams. Managing legacy and cloud-native products. Overview of Ad Astra's technical stack. Geoff's management style and approach to team organization.
• 15:27 -
• Transition to Milo and Holacracy
• Geoff's transition from Lexmark to Milo and the adoption of holacracy. Experiences and lessons learned from using holacracy.
• 20:05 -
• Principles of Holacracy and Application at Ad Astra
• Explanation of holacracy principles and their application. Role distribution and team self-management.
• 24:55 -
• Adoption and Perception of Holacracy
• Discussion on the adoption of holacracy at Zappos and other companies. Employee perceptions and the self-selection mechanism.
• 26:29 -
• AI and Future Trends
• Geoff's thoughts on AI and its potential impact. Current state of AI adoption in higher education.
• 28:25 -
• Closing Remarks

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.