Ganesh Datta
HostCTO & Co-founder of Cortex
Randy Shoup
SVP of Engineering at Thrive Market
February 26, 2026
In This Episode
In this episode of Braintrust, Cortex co-founder and CTO Ganesh Datta sits down with Randy Shoup, SVP of Engineering at Thrive Market. Randy shares lessons from his leadership roles across multiple companies and explains how measurement and transparency can help teams build stronger engineering cultures.
Randy and Ganesh chat about how fear can block progress, why recovery speed matters more than trying to prevent every failure, and how teams improve through steady, incremental gains. They also discuss a few practical ways to build trust around metrics so organizations can use visibility for learning instead of punishment.
You’ll learn
Randy says teams are much more likely to care about reliability and delivery when they can clearly see their current state.
Randy argues that metrics like deployment frequency, change failure rate, and MTTR should never be used to stack rank individual engineers.
Leaders can reduce anxiety by being direct about why they're introducing metrics and by proving over time that the data is used to help teams improve.
Randy says that resilience depends on how fast teams recover when failures happen, not on the unrealistic goal of eliminating all failures.
Sustained improvement comes from celebrating progress, sharing what works, and raising standards over time.
Quotes
"The sole goal of the team is to mitigate the failure, whatever it is, and restore service as quickly and as fully as possible."
Randy Shoup
SVP of Engineering at Thrive Market
"As a service provider, I should prioritize recovering quickly when I do fail, as opposed to trying to prevent all failures."
Randy Shoup
SVP of Engineering at Thrive Market
"The unit of production of value is the team."
Randy Shoup
SVP of Engineering at Thrive Market
"A lot of times, incidents are unplanned investments."
Randy Shoup
SVP of Engineering at Thrive Market
"How do I get people to care about X? Measuring X and being transparent about X. That is the way to do it."
Randy Shoup
SVP of Engineering at Thrive Market
Timestamps
(02:45)
Three types of organizational culture and why fear blocks transparency.
(08:15)
Using DORA metrics to build trust and improve delivery at scale.
(11:24)
Why comparing a team to its past self works better than comparing teams to each other.
(18:03)
Treating incidents as unplanned investments and capturing the learning return.
(26:28)
Measurement and transparency as the first step toward a reliability culture.
(35:13)
Making MTTR visible and putting service owners on call.
Other episodes
Rob Zuber on quality, metrics, and what it means to move in the right direction at CircleCI
In this episode of Braintrust, Cortex co-founder and CTO Ganesh Datta sits down with Rob Zuber, CTO at CircleCI, who has spent over a decade at the center of how engineering teams build and ship software. Rob shares his thinking on two challenges that are becoming harder to ignore as AI accelerates output: the quiet erosion of software quality, and the pressure to move fast without a clear sense of direction.
They discuss what made the best QA engineers so effective and why that mindset largely disappeared, how LLMs could help bring it back, and why engineering leaders need to think about metrics very differently depending on whether their teams are scaling a mature system or exploring uncharted territory.
March 26, 2026
Randy Shoup
SVP of Engineering at Thrive Market
The platform engineering playbook for velocity, quality, and AI readiness at SIXT
In this episode of Braintrust, Cortex co-founder and CTO Ganesh Datta sits down with Boyan Dimitrov, CEO of SIXT, one of the world's largest mobility providers operating in over 100 countries. Boyan shares the story behind SIXT's engineering transformation, from shipping software once or twice a month to running nearly 10,000 deployments a month, and explains how extreme standardization became the engine driving both velocity and quality at the same time.
They discuss the pull-and-push model SIXT uses to drive platform adoption without mandating it from the top, how Boyan built a business case for platform investment by starting with specific problems rather than a platform-first vision, and how years of foundational standardization work is now paying significant dividends as SIXT accelerates its AI strategy.
March 12, 2026
Boyan Dimitrov
CTO of SIXT
