Braintrust by Cortex

Why DevOps transformations fail in regulated industries, with Merge Ready's Matt Bailey

37 min · 21. maj 2026
episode Why DevOps transformations fail in regulated industries, with Merge Ready's Matt Bailey cover

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Cortex co-founder and CTO Ganesh Datta sits down with Matt Bailey, DevOps consultant and founder of Merge Ready. Matt shares lessons from helping large regulated organizations in finance, healthcare, and government transform their DevOps practices, and explains why DevOps is an outcome rather than a toolchain. Matt and Ganesh discuss why compliance can be mostly automated rather than a mandatory bottleneck, how to turn 30-day approval processes into continuous audit readiness through controls as code, and why treating platform teams as product teams drives natural adoption. They also explore decision latency as a core organizational problem, the importance of stakeholder management as a DevOps skill, and how AI agents may shift infrastructure drift management from prevention to embrace.

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Alle episoder

15 episoder

episode Why DevOps transformations fail in regulated industries, with Merge Ready's Matt Bailey cover

Why DevOps transformations fail in regulated industries, with Merge Ready's Matt Bailey

Cortex co-founder and CTO Ganesh Datta sits down with Matt Bailey, DevOps consultant and founder of Merge Ready. Matt shares lessons from helping large regulated organizations in finance, healthcare, and government transform their DevOps practices, and explains why DevOps is an outcome rather than a toolchain. Matt and Ganesh discuss why compliance can be mostly automated rather than a mandatory bottleneck, how to turn 30-day approval processes into continuous audit readiness through controls as code, and why treating platform teams as product teams drives natural adoption. They also explore decision latency as a core organizational problem, the importance of stakeholder management as a DevOps skill, and how AI agents may shift infrastructure drift management from prevention to embrace.

21. maj 202637 min
episode Building a developer platform like a product: Inside The New York Times with Sneha Rao and Ahmed Bebars cover

Building a developer platform like a product: Inside The New York Times with Sneha Rao and Ahmed Bebars

Cortex co-founder and CTO Ganesh Datta sits down with Sneha Rao, VP of Product, and Ahmed Bebars, Principal Engineer, both from The New York Times Developer Platforms team, to discuss what it means to build and operate a developer platform at scale across a complex media organization. Sneha and Ahmed explain why developer platforms need a product mindset alongside engineering, how renaming their team from Delivery Engineering opened a broader strategic mandate, and why SRE and reliability belong inside the platform rather than a separate function. They also share how to think about build vs. buy, when to start a platform function, and why AI is another evolution in the platform story rather than a revolution.

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episode Rootly's Dan Sadler on why AI coding tools are driving more incidents and why reliability is the product cover

Rootly's Dan Sadler on why AI coding tools are driving more incidents and why reliability is the product

Cortex co-founder and CTO Ganesh Datta sits down with Dan Sadler, VP of Engineering at Rootly. Dan explains how Rootly treats reliability as a product feature rather than just a technical metric, and why culture might be the most impactful element of building reliable systems. Dan and Ganesh discuss weekly operational reviews that tie technical metrics back to user experience, how load testing and chaos engineering help Series A companies mature faster, and why dogfooding their own on-call product creates better engineering decisions. They also explore a concerning trend in Rootly's customer data showing that AI coding assistants are driving more incidents, and why reliability practices become even more critical as code generation speeds up.

23. apr. 202638 min
episode From IC to VP: Engineering Leadership at Every Level, with Box's Tamar Bercovici cover

From IC to VP: Engineering Leadership at Every Level, with Box's Tamar Bercovici

Cortex co-founder and CTO Ganesh Datta sits down with Tamar Bercovici, VP of Engineering at Box, who spent 15 years at the company growing from senior IC to leading its core platform organization, to talk about what engineering leadership looks like at each level of the org. Tamar walks through how the job fundamentally changes as you move from manager to director to VP, including a key shift at director level where you stop working within constraints and start reshaping them. She and Ganesh dig into how AI is less a new challenge than a pressure test on existing engineering practices, and why teams with strong CI/CD and observability will move faster while undisciplined teams will struggle. Tamar also shares a mentorship pairing program where engineers already effective with AI coach those still learning, sometimes reversing the usual seniority dynamic. And she explains how Box's platform team connects internal standardization directly to external customer value through security, access control, and product cohesion.

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