Team Enablement & AI Delivery Coaching
TL;DR
The founding team had a working prototype but zero confidence shipping AI features to production. I embedded with their five engineers, rebuilt their delivery rituals, and co-implemented the first three AI-powered workflows. By the time I rolled off, they were shipping without me.
Key Results
What Was Broken
The Problems
- The team shipped to staging only once every two weeks
- No one could explain how prompts were evaluated—QA literally eyeballed random outputs
- Webhooks failed silently because no one owned observability
- Knowledge was stuck in the CTO's head
The Playbook
1. Architecture Guardrails
Documented how data flows between Supabase, FastAPI, and OpenAI. Added sequence diagrams inside Notion so onboarding took hours, not weeks.
2. Evaluation Harnesses
Built a LangChain evaluation notebook + Supabase table to score prompts deterministically. Engineers finally had a red/green signal.
3. Pair Programming Sprints
Sat with each engineer to implement one AI workflow end to end (ingestion → vector store → API → UI).
4. Ops Hardening
Added retry/backoff policies, structured logging, and a "pager" rotation so production incidents weren't guesswork.
5. Playbooks
Captured seven SOPs (deploying embeddings, rotating keys, debugging prompts, etc.) so the team had references after I left.
The Architecture Flow
Data Enrichment Workflow
Outcome
Results
- Team ships twice a week with automated evaluation gates
- Founders have visibility through dashboards + alerts
- Engineers own the system; I'm on a lightweight advisory retainer only
The Lesson
Most AI teams don't need more models—they need better processes. Shipping AI reliably is 30% prompts, 70% engineering discipline.
Key Takeaways
- Documentation beats tribal knowledge: Write it down or it doesn't exist
- Evaluation is non-negotiable: You can't improve what you don't measure
- Pair programming transfers knowledge: Better than any workshop
- Observability prevents firefighting: See problems before users do
Need an embedded lead to unblock your internal team?
I can help your engineers ship AI features confidently through hands-on coaching, architecture reviews, and process improvements.
💳 No payment required to book • 📅 Free 15-min discovery call