Backend Engineer · San Diego, CA

I'm Ross MacDonald.

I ship backend systems end-to-end.

I take features from design doc through data model, API, and rollout — and I like modernizing the systems underneath them along the way. Right now I'm a Backend Engineer III at ChowNow, building products that help local restaurants thrive, and using AI to move faster while I do it.

Download résumé See highlights

01

About

I'm a backend engineer who ships. Over the last few years at ChowNow I've owned initiatives end-to-end — writing the design doc, driving cross-functional sign-off, then building the data model, APIs, payments logic, and rollout to land them. I care as much about modernizing the systems underneath a feature as about the feature itself.

Lately a big part of that work is AI. I built an AI phone agent that answers restaurant calls and places orders, and I've built my own Claude-powered developer tooling — custom agents and skills that take a ticket from spec to a tested, self-reviewed pull request — to move faster on everything else.

Before tech, I spent five years as a 911 emergency dispatcher — where I learned to stay calm, own the problem in front of me, and achieve positive outcomes under pressure. Habits that still shape how I engineer.

02

Selected work

A few things I've built and led at ChowNow — from AI to core platform modernization.

AI

Heard — AI phone agent for restaurants

Built an AI voice agent (Twilio ConversationRelay + Claude, ~9 tools over our existing endpoints) that answers restaurant calls and submits pickup orders through our real ordering pipeline — call-event persistence, per-restaurant AI settings, and a transcript dashboard. Solo, in two days. Won ChowNow's internal Innovation Day.

  • Claude API
  • Twilio
  • Tool use
AI

Custom AI developer tooling

Authored my own Claude Code skills to move faster — including ship-ticket, which takes a Jira ticket from spec to a tested, self-reviewed draft PR — plus per-repo agent-guidance configs and a Claude-powered automated PR-review action now running across multiple team repos.

  • Claude Code
  • Agents
  • Automation

Catering product, end-to-end

Led the backend build-out of ChowNow's catering product across 15+ epics (~40 PRs): data model, admin APIs, commission and fee calculation, catering menus, ordering rules, delivery dispatch, and merchant notifications. Authored the design doc and drove sign-off across frontend, QA, and eng leadership.

  • Python
  • API design
  • Payments

Self-serve reporting service

Authored the Reporting Service RFC and built the proof of concept — a Cube Cloud analytics layer over Snowflake with JWT row-level security — giving restaurant partners self-serve reporting.

  • Snowflake
  • Cube
  • dbt

Python 3.11 modernization

Owned our monolith's Python 3.11 upgrade: migrated a large legacy codebase and four internal libraries, upgraded marshmallow (v2→v3), redis, alembic, and pytest, and removed the legacy future dependency — diagnosing and re-landing a production serializer regression along the way.

  • Python
  • Migration
  • Legacy systems

Auth & security

Built passwordless OTP login via Twilio Verify — 1M+ users now have a verified phone or email. Designed JWT refresh-token auth, hardened Cuboh SSO, and added HMAC verification for inbound Uber webhooks.

  • OTP / JWT
  • SSO
  • HMAC

03

Experience

  1. Backend Engineer II → III

    ChowNow · 2023 – Present
    • Led the end-to-end backend build-out of the catering product — data model, admin APIs, commission and fee calculation, menus, ordering rules, and notifications — and drove cross-functional sign-off.
    • Authored the Reporting Service RFC and built the Cube-over-Snowflake proof of concept with JWT row-level security, passing security review.
    • Owned the Python 3.11 upgrade across a large legacy codebase and four internal libraries, modernizing core dependencies.
    • Built an AI phone agent (Twilio + Claude) that takes real pickup orders — won internal Innovation Day — and authored custom Claude Code tooling to speed up the whole team.
    • Shipped passwordless OTP auth (1M+ verified users), JWT refresh tokens, SSO hardening, and webhook HMAC verification; removed 36k+ lines of legacy menu code ahead of the menu-service cutover.

  2. Software QA Engineer I / II

    ChowNow · 2022 – 2023
    • Owned QA for the Managed Delivery Service (multi-provider dispatch, Uber integration) and authored its release and regression runbooks.
    • Wrote automated coverage in Python/Selenium across web and mobile.

  3. QA Engineer · Business & Technology Analyst

    Axos Bank · 2021 – 2022
    • Built an internal API (Node.js, Elasticsearch, Kibana) to export and visualize test results.
    • Led automation coverage reviews with offshore staff.

Technical skills

Languages
  • Python
  • JavaScript / Node.js
  • SQL
Frameworks
  • Bottle
  • Django
  • Pydantic
  • React
  • SQLAlchemy / Alembic
Data
  • MySQL
  • Redis
  • Snowflake
  • Cube
  • dbt
Infra
  • AWS
  • Terraform
  • Docker
  • LaunchDarkly
  • Datadog
  • GitHub Actions
AI & other
  • Claude API (tool use, streaming, caching)
  • Claude Code agents & skills
  • REST / OpenAPI design

04

Get in touch

Always happy to talk backend, platform work, or building with AI.

rmac2289@gmail.com