David Laing

Principled Context Engineer

Summary

Collaborative engineering leader who thrives in high-trust environments with fast feedback loops, authentic direction-setting, and clear accountability structures. 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. Requires supportive leadership and clear decision frameworks to enable bottom-up innovation. 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 AI agent orchestration role. 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 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. Brings unique combination of platform engineering expertise and financial systems knowledge.

  • 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
  • Applied platform engineering principles to financial systems architecture and data reconciliation
  • Established IP sharing agreement with Mechanical Orchard enabling collaborative development while retaining ownership

Shopify Ltd

May 2022 - July 2023

Senior Staff Reliability Engineer

Established Data Reliability Practice for Shopify's 100PB data warehouse, then transitioned to core SRE maintaining commerce systems for 3 million merchants during peak traffic. Role ended due to 2023 tech industry layoffs.

  • Maintained platform reliability during $3.5M/minute peak traffic (BFCM) through data-driven monitoring
  • Pioneered data reliability engineering practices for 100PB 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 active 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 to commercialize LogSearch open source project from City Index. Acquired by Pivotal after 7 months to form basis of PCF Log Search product.

  • Created open-source ELK distribution handling 2TB daily log ingest 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 company, establishing modern engineering practices and cloud adoption. During tenure, children were born and led LogSearch open source project that became foundation for StayUp.io.

  • Led LogSearch open source project for Cloud Foundry ecosystem log aggregation
  • 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

Lucid Communications Ltd

August 2003 - April 2007

Senior Developer

Senior development role in communications technology company.

Vardus Internet Solutions

January 2001 - August 2002

Developer

Early career development role.

Open Source Projects

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

Education

University of Cape Town

January 1997 - December 2000

Bachelor of Business Science (Honours) Information Systems

  • Information Systems
  • Statistics

Publications

From Values to Velocity: Building Momentum Through Aligned Systems

February 2024
Unpublished Thoughts

Exploration of how shared values create alignment frameworks that enable sustainable team momentum - with practical examples from engineering leadership

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