+00:00 GMT

Adaptability in engineering orgs: how management systems, executive priorities & career transitions evolve

with Cosmin Nicolaescu

April 9, 2024


Cosmin (@getCos) leads engineering at Brex, building financial technology to accelerate entrepreneurs. Prior to Brex, he was at Stripe, leading financial infrastructure teams, building Stripe Terminal, and establishing engineering teams globally. His career started at Microsoft, launching Azure and Office365.

"How are you actually changing the trajectory of something. If the person wasn't there, would things have come out differently? If the person jumped in on something, did that meaningfully change the trajectory of that particular project? The answer should be yes and I think that is a good proxy for, as a manager, are you actually leading teams, people, projects, initiatives, and moving the company forward or are you just operating the machinery?”

- Cosmin Nicolaescu   

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  • How Cosmin's transition to the U.S. set the foundation for his approach to adaptability (2:40)
  • Learn to accept what you can & cannot control as an eng leader (5:00)
  • Frameworks for identifying / understanding what execs spend their time on (7:13)
  • Navigating the transition from Microsoft to Stripe (9:12)
  • Building out a successful & impactful management organization (12:08)
  • In-demand qualities of managers during the shift to flatters orgs (15:00)
  • Prioritizing which fires to focus on & willingness to delegate (16:39)
  • Cosmin’s approach to triaging fires @ Brex (18:31)
  • Restructure meetings for output rather than review (21:52)
  • Approaches for adapting to the current macroeconomic environment (25:36)
  • Roles that contributed to successful distributed hiring (29:09)
  • Necessary elements that need to exist for an unconventional transition (31:28)
  • Recommendations for developing & executing a succession plan (34:44)
  • Rapid fire questions (37:30)


  • Outlive: The Science and Art of Longevity - Wouldn’t you like to live longer? And better? In this operating manual for longevity, Dr. Peter Attia draws on the latest science to deliver innovative nutritional interventions, techniques for optimizing exercise and sleep, and tools for addressing emotional and mental health.
  • Zero to One: Notes on Startups, or How to Build the Future - If you want to build a better future, you must believe in secrets. The great secret of our time is that there are still uncharted frontiers to explore and new inventions to create. In Zero to One, legendary entrepreneur and investor Peter Thiel shows how we can find singular ways to create those new things.
  • Hit Refresh: The Quest to Rediscover Microsoft's Soul and Imagine a Better Future for Everyone - As told by Microsoft CEO Satya Nadella, Hit Refresh is the story of corporate change and reinvention as well as the story of Nadella’s personal journey, one that is taking place today inside a storied technology company, and one that is coming in all of our lives as intelligent machines become more ambient and more ubiquitous.
  • Generations: The Real Differences Between Gen Z, Millennials, Gen X, Boomers, and Silents―and What They Mean for America's Future - Professor of psychology Jean Twenge does a deep dive into a treasure trove of long-running, government-funded surveys and databases to answer these questions. Are we truly defined by major historical events, such as the Great Depression for the Silents and September 11 for Millennials? Or, as Twenge argues, is it the rapid evolution of technology that differentiates the generations?

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

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