Ken thinks about the build vs. buy decision differently than most engineering leaders. At Scripta Insights, a healthcare IT platform helping self-insured employers reduce pharmacy benefit costs, documentation isn't just a nice-to-have. It's a compliance requirement.
"We have to do docs and control management. We're subject to HIPAA and SOC2 Type 2."
That changes the calculus entirely. When documentation has regulatory weight, leaving it as ad hoc isn't a productivity problem. It's a liability.
Code shipped daily. Documentation didn't keep pace.
Before Doc Holiday, Scripta's release process had its limitations when it came to documentation. The 20-person engineering team worked in a microservices environment, pushing code daily, but documentation wasn't keeping pace. The team held a weekly meeting to work through the previous week's releases.
"It was ad hoc. We'd go through the past week of releases and cobble together release notes and documentation for posterity."
The cost was time, and time is expensive.
Not build vs. buy. A human allocation question.
Ken frames the decision to bring in Doc Holiday less as a productivity win and more of a human allocation question. In the AI era, he argues, every engineering leader has to make a version of this choice, but most ask the wrong question.
A lot of engineering leaders look at the buy vs. build decision. But it's different; it's a human automation decision. Do I want engineers writing docs or writing code?
Ken Pickering · Scripta InsightsFor a company operating under HIPAA and SOC2, that question answers itself. If documentation is mandatory and automation can handle it, putting humans on it is a choice, not a necessity. "If I can find something to help me with that and not put humans on it, I'm directly incentivized to do so. Why build in this day and age if you don't have to?"
The value isn't the notes. It's what happens downstream.
What Ken values most about Doc Holiday isn't the release notes themselves. It's what happens to that information downstream.
Scripta uses Glean as their internal knowledge tool. Release notes from Doc Holiday feed directly into Glean, which pushes summaries into Slack. The result is that every part of the organization, not just engineering, stays current on what's changing in the product.
It's information democratization. Release notes feed Glean, which does summaries into Slack. Glean is also reading Slack, builds more complete context on the dev lifecycle — even for non-dev stakeholders — and helps with complete transparency of tech ops.
Ken Pickering · Scripta InsightsIn a regulated environment where multiple teams need to understand what changed and when, that kind of automated information flow isn't a convenience. It's infrastructure.
High value. Low lift.
Ken's take on the implementation cuts to something most vendor case studies won't say plainly: the value of a tool is only as good as the lift required to get there.
It's a good use case of what LLMs are capable of. High value from a compliance perspective and a low lift. It was easy to integrate into the pipeline and we got value with super minor tweaks. That's the definition of a good SaaS solution.
Ken Pickering · Scripta Insights
