Senior Backend Engineer (FDE · Embedded Technical Lead)
Checkmate · Full-time · Remote
All-in-one platform for restaurant brands — digital ordering, admin panel, loyalty, and delivery orchestration.
Jul 2023 — Present
- Embedded technical lead across 35+ enterprise clients — scoped per-client requirements, coordinated 10+ engineers on features and integrations, and owned incident response end-to-end on a multi-tenant platform.
- Established AI-native engineering standards adopted org-wide: built do-ai-context — a shared Claude Code context layer with domain files, PII/secrets safety hooks, and LLM-orchestrated release workflows — cutting triage costs ~$4,600/yr.
- Built PageIndex, a codebase navigation index reducing AI triage steps by ~75%; automated release workflow cross-referencing Asana, GitHub, and cherry-pick history via LLM orchestration.
- Built Slack-triggered AI debug agent (Claude SDK + Celery) with brand-scope isolation and PII guardrails.
- Drove 99% reduction in menu sync latency (40m → 3s) via distributed Redis caching across 35+ restaurant brands.
- Led multi-provider delivery orchestration (DoorDash, Uber Eats, Relay) with unified abstraction layer for quoting, dispatching, and tracking; designed real-time failover mechanism reducing order cancellations.
- Hardened inbound webhooks with HMAC signature verification, timestamp checks, replay protection; owned OAuth2/JWT auth for internal and external APIs.
- Owned security hardening — reduced audit cycles from 30+ hrs to 6 hrs via AI-assisted tooling; shipped admin 2FA, per-brand password rotation, login audit trail, and breach incident response.
- Led Flask 1.x → Flask 3 + Connexion 3 (ASGI/uvicorn) migration and shipped ML-powered recommendations v2.
Stack: Python Flask · Redis · React · Docker · JWT · Datadog · Claude SDK · NMI · FreedomPay · Celery