The practitioner
Jason O'Donnell
Thirty-plus years in enterprise software and semiconductor, all of it in and around customer success — twenty-plus in the knowledge management discipline, ten-plus running KCS programs and the transformations behind them. Contextkeeping is what that experience became when the methodology's two founding assumptions expired.
I'm a practitioner, not a vendor. Everything on this site exists because I needed it first: the operating model came out of running knowledge programs whose economics I had to defend, the maturity model out of watching AI projects fail for placement reasons nobody had named, and the measurement doctrine out of budget meetings where deflection numbers couldn't answer the question being asked.
The vantage point matters: I come out of customer success organizations, not the content team. Knowledge was never the deliverable — retained, successful customers were, and the knowledge program was the machinery behind that number. It's why Contextkeeping measures in cost per answer and coverage against real ticket demand rather than article counts: a knowledge program only matters where it touches a person with a question.
It's also why the maturity model here is a transformation instrument, not a scorecard. Three decades of enterprise transformations — methodology rollouts, platform migrations, org redesigns, and now the AI turn — taught me that programs rarely fail on intent; they fail on sequencing. Strategy, as practiced here, means placing your program honestly, then executing the shortest defensible path to the next level — sequencing first, tooling when the level can hold it.
The Governed Knowledge Loop isn't a slideware framework. I build and run its reference implementation — a git-backed system of record with a validation gate, metadata-aware retrieval, and a candidate queue — and the Contextkeeping Toolkit ships the same templates, gates, and workbook I use. The toolkit's own source repository follows the toolkit's own rules; I sell the thing by being the thing.
Everything here is designed to be run without me. The operating model is the executive view — the roles, the gates, the cadence, and the number the program answers to. If you take one page to your leadership, take that one; evidence over opinion, and an honest list of what not to build yet — that last part is usually where the money is.
If you want to talk shop: LinkedIn, or hello@contextkeeping.com.