Carving out time for large-scale engineering chores

Bill Doerrfeld | January 31, 2025

The latest edition of DirectorPlus features Kent Wills, Director of Engineering, Yelp around how to prioritize the engineering laundry list.


No one has time for migrations. But ignoring them? That’s a recipe for disaster.


The thing is, development teams are pressed to deliver more with less right now. It's becoming harder to prioritize tasks like OS and language migrations, major dependency updates, and everything else that keeps software running smoothly.


I recently spoke with Kent Wills, Director of Engineering at Yelp, for DirectorPlus about how they tackle these unavoidable engineering chores. At Yelp, they’re prioritizing changes by setting yearly timelines, creating paved roads, and finding engineers who actually enjoy optimizing software (yes, they exist!).



The fact is global engineering improvements need leadership from the top down to get prioritized — especially at a large org. These efforts are critical for keeping the lights on, retaining agility, and avoiding vulnerabilities.


Check out the full post, now live on LeadDev today! It’s packed with actionable advice for staying on top of the backlog.


Also, if you want monthly on-the-ground insights from leading engineering directors, be sure to sign up for the DirectorPlus newsletter here.


Lastly, if you'd like to be featured in DirectorPlus, reach out to me! We’re planning interviews for 2025.


Featured image credit: Tim Johnson on Unsplash.


Read: Carving out time for large-scale engineering chores

Sign up to the DirectorPlus newsletter for a new story in your inbox each month featuring on-the-ground insights from some of the industry's top engineering leaders. Or, if you would like to be featured in the series, please read this.

A grey articulated figure kneeling, arranging small white objects in a clear plastic container. White background.
By Bill Doerrfeld September 11, 2025
MCP shines for indeterministic workflows, novel integrations, and giving AI coding agents context on the fly. But for more predictable automation it may be overengineeering.
Overhead view of construction site with workers in orange vests, metal beams, and dark concrete.
By Bill Doerrfeld August 30, 2025
For my latest DirectorPlus column with LeadDev, I synced with JB Brown, VP of engineering at Smartsheet, to learn about their multi-agent AI development strategy.
Pink and purple sunset sky with dark, fluffy clouds.
By Bill Doerrfeld August 25, 2025
Alternative clouds are having a moment. Nearly 75% of orgs are using two or more alt clouds beyond the hyperscalers, according to a HostingAdvice.com report.
Digital global CIOs digital sovereignty
By Bill Doerrfeld August 20, 2025
The cloud is no longer borderless. Rising regional data laws and sovereign cloud mandates are forcing CIOs to act.
A
By Bill Doerrfeld August 11, 2025
In a multi-agent coding workflow, an engineer leads a "team" of specialist AI agents to perform various SDLC tasks: scaffolding, coding, testing, log analysis, deployment, and more.
Open source software churn end of life
By Bill Doerrfeld August 8, 2025
Open-source software churn is accelerating. With more frequent version end-of-lives and even total project abandonments, it's harder than ever to keep up.
Hype drives most programming language igrationsigra
By Bill Doerrfeld July 30, 2025
I covered a report from HostingAdvice.com, which found that the majority of programming language migrations are driven by hype, instead of proven outcomes.
Cross-functional teams help Stack Overflow adapt LeadDev DirectorPlus 2025
By Bill Doerrfeld July 28, 2025
Facing an existential crisis, Stack Overflow has had to pivot quickly. I synced with a director to discover what team strategies are helping them adapt.
System Initiative feature InfoWorld doerrfeld
By Bill Doerrfeld July 14, 2025
System Initiative aims to replace the toil of maintaining config files with a data-based digital twin and visual modeling engine. An engine for DevOps, if you will.
CIOs describe why AI agents need APIs
By Bill Doerrfeld July 10, 2025
My latest feature on CIO.com explores why CIOs view APIs as a critical linchpin to realize success with agentic AI. Learn what it'll all take.