This week, David Wright is joined by Darlene Reina, Head of IT & Business Systems at Calendly, to discuss the evolving role of IT leadership and strategic alignment within fast-growing tech companies.

Key Takeaways:

(02:58) Darlene shares a piece of career advice and its significance to her career.

(04:00) From working at Apple and higher education to leading IT at Calendly.

(05:50 Communicate and engage with different audiences: The importance of storytelling in IT.

(09:00) Learning from failures and the critical role of alignment and stakeholder buy-in for successful IT management.

(16:00) Exploring the broader responsibilities and vision for IT within Calendly, including improving internal operations and system integrations.

(19:55) The impact of strategic IT management on company-wide alignment and operational efficiency during scale-up phases.

(27:01) Integration of large language models and AI within Calendly to streamline operations and enhance internal efficiencies.

(34:00) Reflections on the future of work and the role of AI in transforming organizational tasks and responsibilities.

Resources Mentioned:

“Amp It Up” by Frank Slootman 

“Radical Candor” by Kim Scott 

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