David Laing

Principled Context Engineer

Summary

Collaborative engineering leader who thrives in high-trust environments with fast feedback loops and authentic direction-setting. Passionate about learning loops, structured decision-making, and data-informed leadership - built Decision Copilot to help teams make better choices together. Excels at leading initiatives I believe in and have helped shape, bringing genuine conviction rather than organizational theater. Values long-term thinking over quarterly theater and fixing root causes over chasing new shiny objects. Specializes in data reliability engineering, platform SRE, cross-functional team leadership, and pioneering work as Principled Context Engineer for AI agent orchestration.

Experience

Mechanical Orchard

September 2023 - Present

Staff Software Engineer - AI Context Engineering Lead

Platform Engineering team member who evolved into pioneering role orchestrating AI agents for DevOps automation. Built cloud infrastructure and established practices for AI-assisted development workflows. Collaborative IP agreement enables continued Decision Copilot development.

  • Pioneered AI agent orchestration for Kubernetes/Terraform automation - creating environments where AI agents collaborate and self-correct
  • Continued Decision Copilot development through collaborative IP sharing agreement
  • Built and maintained cloud infrastructure on GCP and AWS for Imogen modernization platform
  • Applied behavior-driven transformation methodology to legacy system modernization

Make Time Together Ltd

August 2023 - Present

Co-founder

Co-founded investment company focused on decision-making tools and small business finance applications. Built Decision Copilot from initial concept to open-source platform for structured team decision-making.

  • Built Decision Copilot - open-source tool for structured team decision-making (started 2023-08)
  • Developed full-stack applications using NextJS, React, and TypeScript for decision-making tools
  • Established IP sharing agreement with Mechanical Orchard enabling collaborative development while retaining ownership
  • Applied data-driven decision frameworks to business development and product strategy

Shopify Ltd

May 2022 - July 2023

Senior Staff Reliability Engineer

Established Data Reliability Practice for Shopify's platform, then transitioned to core SRE role maintaining commerce systems for 3 million merchants during peak traffic periods.

  • Maintained platform reliability during $3.5M/minute peak traffic (BFCM) through data-driven monitoring
  • Pioneered data reliability engineering practices for large-scale data lake infrastructure
  • Applied long-term reliability thinking to commerce platform serving millions of merchants

VMware Ltd

May 2020 - April 2022

Staff 2 Software Engineer (Data)

R&D Portfolio Insights team member who established data engineering practices and provided data-driven insights to business leadership across VMware's product portfolio.

  • Built and maintained dagster.io data pipelines for cross-portfolio analytics
  • Established telemetry gathering and data curation practices for R&D insights
  • Created data-driven feedback loops for business unit strategic decisions

Pivotal Software Ltd

December 2015 - April 2020

Director of Engineering/SRE

Engineering Lead orchestrating initiatives across 80+ R&D teams in 6 global offices. Built SRE team and established company-wide practices for reducing customer deployment friction.

  • Orchestrated balanced leadership team driving shared outcomes across ~80 R&D teams globally
  • Built SRE team from scratch to operate Cloud Foundry and Kubernetes platforms
  • Established reliability practices for pivotaltracker.com (1M users) and UK charity donation platforms (£1B+ donations)
  • Created data-driven understanding of enterprise customer upgrade challenges
  • Collaborated with Google SRE engineers on SLI/SLO design and error budget implementation

StayUp.io Ltd

March 2015 - December 2015

Co-founder

Co-founded company creating log search solutions. Successfully acquired by Pivotal to form basis of PCF Log Search product.

  • Created open-source ELK distribution for Cloud Foundry ecosystem
  • Built product from concept to acquisition in 7 months

City Index Ltd

December 2008 - March 2015

R&D Team Leader

Led R&D transformation at financial spread-betting company, establishing modern engineering practices and cloud adoption strategies.

  • Established TDD & Agile practices across development teams
  • Led organizational transition to open-source software adoption
  • Pioneered migration to public cloud infrastructure

BBC Worldwide

May 2008 - October 2008

Agile Developer

Early career exposure to collaborative development practices on BBC's digital media platform.

  • Learned foundational XP, TDD, and pair programming practices
  • Contributed to Kangaroo digital media platform development

Open Source Projects

AI Agent Orchestration for DevOps

January 2023 - January 2025

Pioneering work in creating environments where AI coding agents can collaborate, self-detect mistakes, and work together on complex automation tasks

AI Agent Orchestration
Context Engineering
DevOps Automation
Collaborative AI
  • Developed frameworks for AI agent collaboration and error detection
  • Created context engineering practices for AI-assisted development
  • Applied learning loop principles to AI agent improvement

Decision Copilot Development

January 2023 - January 2025

Open-source tool for structured team decision-making, addressing the gap between individual expertise and collective decision quality. Developed under Make Time Together Ltd with collaborative IP sharing enabling continued development at Mechanical Orchard.

Decision Making
Team Collaboration
Open Source
Learning Loops
IP Strategy
  • Built framework for transparent, repeatable decision processes
  • Created learning loops for decision quality improvement
  • Established sustainable development model through strategic IP sharing agreement
  • Growing community around structured decision-making practices

Upgrades & Extended Support Portfolio

January 2018 - January 2020

Engineering Lead orchestrating shared outcomes across ~80 R&D teams in Pivotal's first 'programme balanced leadership team'

Team Orchestration
Data-driven Strategy
Enterprise Systems
Long-term Planning
  • Established data-driven understanding of enterprise customer challenges
  • Created cross-office collaboration framework spanning 6 R&D locations
  • Applied long-term thinking to customer upgrade friction problems

Education

University of Cape Town

January 1997 - December 2000

Bachelor of Business Science (Honours) Information Systems

  • Information Systems
  • Statistics

Publications

Staying up-to-date with Kubernetes

Web Publication

Explorable model for understanding enterprise software upgrade challenges and long-term maintenance practices

SRE & the Vulnerability Budget

March 2019
SRECon AMER

Using Error Budget model to balance security patching with feature development - applying structured decision-making to operational priorities

Tracker's Journey Through the Cloud

January 2017

Documentation of pivotaltracker.com migration to GCP with Google SRE collaboration on reliability practices