Software Defined Interviews

Bryan Ross is a Field CTO at GitLab, a role he describes as straddling sales, customer success, and solution architecture - or, as one of his customers renamed it, chief therapy officer, which he has since turned into a Substack. Whitney and Coté talk with him about what the job actually looks like: getting catapulted into an account by the sales team, asking a lot of questions, and finding out about four minutes in that the tech problem is a human one. He makes the case that changing job titles - sysadmin, DevOps engineer, platform engineer, now context engineer - is mostly an organization trying to change its culture without knowing how, and that the real difference is mindset: keeping a box alive versus serving one team versus building a product. There’s a long stretch on metrics, including Goodhart’s law, why every metric needs a balancing one, and why he cared more about how many VMs were being decommissioned than how many were being provisioned. Also: whether anyone actually needs to ship faster (Coté’s pharmacy doesn’t), the UK Postal Service discovering that a friendly postman beat a modernized delivery fleet on customer satisfaction, and why copying Google is usually the wrong move. On AI, Bryan’s argument is that it will end up like spreadsheets - a few experts building the macros, everyone else using and lightly tinkering with what they made - and that which model you use should be a finance and data governance decision, not a developer one. Plus the hazard of a nicely formatted report: the pastel-shading trick for spreadsheets nobody will check, and why an AI scoring something 6 out of 10 gets the same unearned benefit of the doubt.

Also, ordering pizza in Amsterdam.

You can watch the video version of this episode as well, if you prefer that kind of thing.

Mentions:

Bryan Ross’s home page on the World Wide Web, which links to everything else.

Chief Therapy Officer, Bryan’s Substack.

Bryan on LinkedIn.

Coté's list of "laws," anecdotes, and common shit people say. See also Hacker Laws.

Special Guest: Bryan Ross.

W. Edwards Deming was a physicist, statistician, and quality theorist who taught post-war Japanese manufacturers what eventually became the Toyota Production System - and, decades later, DevOps. John Willis, one of the founders of the DevOps movement and the author of a book on Deming, walks Whitney and Coté through that lineage: Deming's system of profound knowledge (theory of knowledge, variation, psychology, and systems thinking), how it landed at Toyota, and how it threads through Lean software development into modern delivery practice. From there, the conversation turns to what the industry is getting wrong about AI: bragging about K-LOC and token counts instead of value, treating probabilistic systems with old deterministic notions of risk, and forgetting the social-technical lessons we already paid for. Along the way: VC moats and the buy-versus-build conversation inside large organizations, David Foster Wallace's "This is Water" and the ladder of inference, Jevons Paradox and whether AI gets us a three-day work week or a six-day one, and what CS students should be learning besides how to code. Also a brief detour into why John would want fifteen minutes with Bill Clinton.

You can watch the video version of this episode as well, if you prefer that kind of thing.

Mentions:

John on LinkedIn - the entry point to his author portal and writing.

John's book on Deming, Deming's Journey to Profound Knowledge.

John's book on AI, Rebels of Reason.

The DevOps Handbook, which John co-authored with Gene Kim, Jez Humble, and Patrick Debois.

Donella Meadows, Thinking in Systems.

Steven Spear, The High-Velocity Edge.

Mary and Tom Poppendieck, Lean Software Development.

David Foster Wallace, "This is Water" commencement speech.

The 1980 NBC documentary If Japan Can, Why Can't We?.

Whitney and Coté talk with Emily Long, CEO and co-founder of Edera, about building a hardened container runtime that secures infrastructure foundations instead of chasing detect-and-respond alerts. Emily describes how Edera lets teams swap in a new container runtime without re-platforming or adopting yet another zero-trust migration, and why the "zero days as the new hotness" landscape makes that kind of structural change worth doing.

The conversation also covers her jump from COO to CEO - the ambiguity of the COO title, what actually changes when you're the one absorbing every decision - and what it's like raising a deep-tech Series A as an all-woman founding team, including the downside-vs.-upside question pattern VCs fall into and the now-classic "I just Googled Kubernetes and I know more than you do" pitch moment.

They open with a long detour on to-do lists, Claude Code, and whether AI tooling just keeps expanding the list of things you feel obligated to do.

You can watch the video version of this episode as well, if you prefer that kind of thing.

Edera.

Emily Long on LinkedIn.

Rachel Chalmers, an Edera investor, was on the show a few episodes back.

Special Guest: Emily Long.

Whitney and Coté discuss with Josh Berkus (Red Hat, Kubernetes contributor) how liberal and fine arts degrees (philosophy, photography, sculpture, pottery) apply to tech careers. Berkus details how early hardware experience influenced his database performance work, noting hardware's renewed relevance with AI and multi-arch computing. The conversation covers Sun Microsystems’ 1990s internet role, internal politics, and its MySQL/Postgres strategy. They examine open source's shift from end-user to vendor-driven models, foundations' roles, and contributor incentives. Berkus describes Kubernetes release processes, contributor-experience programs, and its resilience to low-quality AI contributions.

You can also watch the video recording of this episode if you prefer that kind of thing.

Josh's home page on the World Wide Web.

And, check out Josh's pottery store, Fuzzy Chef.
Special Guest: Josh Berkus.

Whitney and Coté talk with Heidi Waterhouse, co-author of the book Progressive Delivery.

You can watch the video of the recording as well, if you're into that kind of thing.

Heidi on the World Wide Web:

LinkedIn.

Her Website.

The book, Progressive Delivery.
Special Guest: Hedi Waterhouse.