Turning operational friction into automated leverage.
I help small teams identify repetitive work, design practical workflow assistants, and build the small tools that take recurring tasks off their plate. Eighteen years of software engineering, applied to whatever your business actually does.
How I work.
Every engagement runs the same three stages. Diagnostic comes first. The build only starts after I can describe your work back to you, and only when it’s clear which recurring task is worth automating.
Two weeks of watching the work and drawing the system as it actually runs. Output: an annotated diagram of the current process, a short list of frictions worth automating, and an honest read on which ones I think are worth building. Not a proposal.
A small AI assistant scoped to one recurring task. Shipped end-to-end. Measured against the time-saved number from the diagnostic. Code stays yours; I leave you the runbook.
Thirty- and ninety-day audits. Adjust thresholds, retire what isn’t useful, write down what I learned. If the build doesn’t hold up, I want to know first.
- — Strategy decks
- — “AI transformation” engagements
- — Multi-quarter retainers
- — Anything I haven’t watched run
Account managers were spending fourteen hours a week triaging inbound RFP emails.
I shadowed three account managers for a week and watched the inbox up close. Most RFPs were either out of region, missing dates, or duplicated from a job already won — patterns that an experienced manager can read in two seconds but that still cost the time to read.
Built a small classifier that handles seven recurring patterns and routes anything outside them back to a manager with the matched-pattern reasoning attached. Reviewed every borderline call for the first thirty days. Adjusted thresholds twice.
Three POS feeds disagreed by a few hundred units every morning. Nobody had time to chase it.
I sat with the operations lead through two close-out cycles. The discrepancies weren’t random — twelve recurring categories explained most of them. The root cause turned out to be a vendor SKU map that nobody owned.
Built an overnight reconciler that posts a short discrepancy report to Slack at six. It flags — it doesn’t auto-correct accounting. The bigger win was fixing the SKU map; the assistant just made the fix discoverable.
Three channels of estimate requests, no single queue, no read on which to chase first.
I read eighteen months of won jobs against the leads that produced them. Roughly four variables — service type, zip cluster, source channel, season — explained most of the closeable ones. The owner’s gut had been right about three of the four; the fourth was a real find.
Built a scored queue, not a filter. The human always sees every lead — the score just changes the order. The scoring model is one page of code and an audit trail. Easy to question, easy to retrain.
Short notes from the workshop.
Things I’m working out. Not essays, not thought leadership. Closer to the right margin of a page I’m in the middle of writing.
- 2026·05·02Read →Why I write the diagnostic before I quote the buildA quote written before I have watched the work is just a guess in a suit.
- 2026·04·19Read →Seven patterns that cover most email triageA recurring shape: a long tail of categories disguising a very short head.
- 2026·04·03Read →On not building a "smart inbox"A new tool that you have to remember to open is not a tool, it is another inbox.
- 2026·03·12Read →How I draw the system-as-foundOn paper first. Then a one-page svg. The drawing is the deliverable.
One email. I read everything that comes in.
Send a paragraph about what your team does and what’s chewing up time. I’ll write back with whether I think it’s worth a diagnostic and what mine would cost.
caleb@leverageworkshop.com