Technical Challenges and Scale

Code can be written faster than ever. But getting that code safely into production is where many engineering teams lose time.

As organizations grow, CI failures, flaky tests, and conflicting pull requests start to compound.

In this episode of High Bit, Initialized managing partner Brett Gibson sits down with Eli Schleifer, founder and CEO of Trunk, to talk about the systems that keep CI green and allow engineering teams to land code reliably as organizations grow.

Before starting Trunk, Eli built developer infrastructure at Microsoft, started a company that was acquired by Google, and later worked with hundreds of engineers at Uber ATG. At Google he saw how powerful internal developer tooling could be. At Uber he saw engineers spend days trying to land code because those systems did not exist. That gap led him to start Trunk.

Eli explains why engineering productivity slows once dozens or hundreds of engineers share the same repository, how flaky tests quietly waste engineering time, and how merge queues prevent broken builds and conflicting pull requests.

Topics include:

• Why CI becomes the bottleneck as engineering teams grow
• How merge queues keep builds reliable
• Why flaky tests waste engineering time
• The build vs buy decision for developer tooling
• How coding tools are increasing pull request volume
• How engineering workflows are changing

(00:00) AI fixing flaky tests

(00:40) What Trunk builds

(02:13) When CI becomes the bottleneck

(02:33) Eli’s background: Microsoft, Google, Uber

(04:29) Why dev tools must solve real pain

(05:09) The merge queue problem

(09:25) Build vs buy for developer tooling

(14:22) How merge queues handle large codebases

(18:58) How coding tools increase PR volume

(21:53) Flaky tests and engineering productivity

(25:24) Using CI and test history to debug failures

(27:37) How engineers prune the search space

(33:23) Engineers as conductors of automated systems

(37:49) What’s next for Trunk

Follow Eli and Trunk:

Eli Schleifer

X: https://x.com/elischleifer

LinkedIn: https://www.linkedin.com/in/elischleifer/

Trunk

Website: [https://trunk.io](https://trunk.io/)

X: https://x.com/trunkio

LinkedIn: https://www.linkedin.com/company/trunk-io/

High Bit

Hosted by Brett Gibson, managing partner, Initialized

https://open.spotify.com/show/36gTYrH1wlYzTZwLQywbIf