Ganesh Datta
HostCTO & Co-founder of Cortex
Randy Shoup
SVP of Engineering
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
"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
"The unit of production of value is the team."
Randy Shoup
SVP of Engineering
"A lot of times, incidents are unplanned investments."
Randy Shoup
SVP of Engineering
"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
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
July 9, 2026Your Ops Review is Theater, and That's the Point: Aleks Rudzitis on Turning Reliability into a Shared Value
Aleks Rudzitis
Principal Engineer
July 9, 2026Operational Excellence (OpEx) Reviews: The Weekly Meeting That Actually Changes Behavior
Shawn Burke
Distinguished Engineer
July 9, 2026Okta's Dinesh Sukhija on Meeting AI with AI, and the Convergence of Platform, SRE, and Security
Dinesh Sukhija
Director of Engineering
