Head of Technology, Keyspire
Mar, 2026 - Present
Promoted to succeed the departing Head of Technology; sole technical decision-maker.
Built the Keyspire AI Assistant from prototype to paid launch in ~3.5 weeks: an LLM coaching agent (OpenAI Agents SDK, TypeScript, PostgreSQL) with RAG over a 337K-word course library, persistent conversation memory, live listing search, and deterministic deal-analysis tools, at under 1¢ per reply.
Made model behavior measurable: a ~130-check live-model eval suite runs on every behavior-changing PR. Used it to cut consistently failing knowledge checks from 24 of 92 to 0 by forcing retrieval and tuning a relevance cutoff from measured score distributions; added prompt-injection fencing, domain allow-listing, and per-user rate limits.
Built a review-gated agentic development workflow (parallel coding agents in isolated worktrees, automated review, CI tests, live-model evals) that lets one engineer run several production systems; set the architecture across 8 ADRs and review every merge.
Built and run a nightly Python pipeline managing the subscription lifecycle for ~1,000 subscriptions (~$40K MRR): ~975 automated updates over 67 production runs, Stripe reconciliation, and a nightly exceptions list for ops, replacing ~20 hours/week of manual work.
Audited 110+ CRM workflows end to end and fixed 65+ bugs.
Kept customer, billing, and operations running after three roles (two customer service, one operations support) were eliminated, through automation and process redesign; cut annualized software spend 67% ($286.9K → $93.2K CAD).
Built the Deal Analyzer, a full-stack investment-analysis app (React, Express, PostgreSQL) with Google OAuth and CRM-gated access, launch-ready for the ~1,000-member community; its calculation engine already powers the Assistant's deal analysis.