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Lessons Learned: Two Years as Carta's CTO

2025-05-24

Reflecting on his two-year tenure as Carta's CTO, the author shares key learnings in engineering strategy, LLM adoption, and organizational management. He discusses refining his leadership style to delve deeper into details, writing a book on engineering strategy, successful LLM implementation at Carta for internal workflows and new product features, and the impactful 'Navigator' program for increased senior engineer involvement. He also details strategies for managing engineering costs and effectively communicating R&D investments to boards.

The AI Job Market Shift: Is 2025 a Career Winter?

2025-03-16

The rapid advancement of AI, especially large language models, has created a challenging job market for many software engineers, particularly those who entered senior roles between 2010 and 2020. Traditional management skills are less valued now, replaced by a demand for meticulous detail-orientation, rapid project execution, and adaptation to the AI transition. This leaves many senior leaders feeling overwhelmed, while potential leaders skilled in technical details and rapid iteration struggle for promotion. Simultaneously, rapid AI advancements challenge established company advantages, demanding product and development process redesign. This creates immense pressure on job seekers, with reduced hiring, promotions, and slower salary growth. In short, the current job market is highly competitive, demanding more from job seekers.