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David Cockson

Hope is not a strategy.

Systems thinker with a focus on identifying constraints and designing robust controls within complex environments. With 8 years of experience analyzing high-stakes regulatory systems (AML gambling and data protection), I bring a T-shaped generalist perspective to technical problem-solving. I am now applying this analytical rigor to hands-on engineering, building observable and resilient infrastructure across cloud and AI systems.
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Technical Projects

Monitoring & Observability

  • Full stack: Telegraf → Prometheus → Grafana across homelab and Contabo VPS
  • Diagnosed silent cAdvisor failure (cgroup v2+ non-standard Docker root), pivoted to Telegraf Docker socket API
  • Published Grafana community dashboard (ID 25012)
  • Grafana Cloud setup (free tier, eu-west-2)
  • Multi-cloud monitoring: Prometheus + Node Exporter + Grafana deployed to Contabo VPS (Ubuntu 24.04, Germany)

maps to → monitoring, observability, Prometheus, Grafana, incident diagnosis, multi-cloud

Linux & Containerisation

  • Proxmox hypervisor running Ubuntu VM with 20+ Docker containers
  • Services: Plex, Immich, Gitea, SearXNG, Nginx Proxy Manager, Portainer, Syncthing
  • Multi-stage Docker builds (Node/Vite → nginx:alpine) for project deployments
  • systemd service authoring (Tailscale metrics proxy — Python HTTP proxy exposing client metrics to Prometheus)
  • Linux Mint as primary dev environment

maps to → Linux, Docker, containerisation, virtualisation, systemd, process management

Cloud Infrastructure

  • AWS: self-taught runbook methodology through 23 reps — click-ops → CLI → scripted automation → self-healing fleet (3 EC2 instances)
  • LCCP Regulation Filter deployed to EC2 (multi-stage Docker build: Node/Vite → nginx:alpine)
  • Contabo VPS: self-hosted AI stack (Ollama Qwen2.5 14B, Prometheus, Grafana, Syncthing) on Ubuntu 24.04, accessible via Tailscale mesh
  • Multi-provider experience: AWS, Contabo, Cloudflare, GCP Skills Boost

maps to → AWS, EC2, CLI, multi-cloud, VPS management, cloud infrastructure

Python Development

  • Code kata system: self-designed, multi-domain reps (AWS, Linux, networking) — same 7 concepts applied across 3 contexts per rep
  • ARN decoder script — committed to public repo
  • Discord server with 3 webhooks configured as alerting channel for monitoring stack
  • Scripting across homelab and cloud automation tasks
  • Google ADK (Agent Development Kit) crash course completed — AI agent framework

maps to → Python, scripting, automation, webhooks, ChatOps, AI agents

Terraform & IaC

  • Runbook self-learning methodology: 4 reps completed, committed to pinned infra-practice repo
  • Progression: single EC2 → User Data + IAM + CloudWatch → ALB + HTTPS → full production stack (ASG + Launch Template) in a single terraform apply
  • GCP Skills Boost badges (Terraform, Kubernetes, Google Cloud Network)

maps to → Terraform, IaC, HCL, ALB, ASG, GCP exposure

Networking & Access Control

  • Tailscale mesh networking across homelab, laptop, phone, and Contabo VPS
  • Nginx Proxy Manager as reverse proxy for all services
  • DNS management across multiple custom domains (Cloudflare)
  • Labelled physical network infrastructure with structured cabling and surge protection
  • Tailscale metrics proxy: custom Python service exposing network metrics to Prometheus

maps to → networking, DNS, reverse proxy, VPN/zero-trust, infrastructure documentation

Volunteer — Geeks for Social Change (GFSC)

  • Drafted initial observability strategy (Uptime Kuma → Node Exporter → Grafana Cloud) collaboratively in HedgeDoc
  • Iterated infrastructure review based on community maintainer feedback
  • First external contribution: committed final technical proposals and system documentation to the organisation's public GitHub repo

maps to → infrastructure mapping, Git collaboration, technical documentation, systems discovery, open-source community

Professional Experience

Compliance Manager — Gambling Commission of Great Britain

July 2024 – Present

  • Assessment of regulated gambling companies including casinos, betting shops, bingo, AGCs (in-person) and remote casinos, sportsbooks, bingo and B2B software development companies (online)
  • Led all 2025 Software Development Licence assessments, including ISO 27001 reviews, Change Management evaluations, policy and procedure assessments, and governance interviews with C-level executives (CTO/CEO), Heads of Departments and SMEs
  • Managed end-to-end incident response—from real-time triage to root-cause investigation—for complex software failures. Evaluated active incident reports and sensitive disclosures, gathered critical system context, and escalated high-severity findings to executive committees to enforce necessary technical remediations.
  • Supported cross-functional technical initiatives and unplanned operational workstreams, managing highly sensitive data escalations and critical internal risk disclosures.
  • Utilise Microsoft Copilot, SharePoint and proprietary software to streamline regulatory reporting and maintain audit trails for complex assessment workflows

Regulatory Compliance Assurance Manager — William Hill (888 Holdings)

May 2023 – December 2023

  • Recruited, trained and directed an Assurance team across Marketing Compliance, Technical Compliance and VIP/HVC schemes for 3 business units (UK & Ireland, International, US) spanning 22 regulated markets
  • Established procedural frameworks and authored the Risk Matrix for the Group Assurance department; planned and executed all non-AML and SG assurance testing for 2023
  • Coordinated operations for a 5-person international data and monitoring team and a 19-person testing team (Manila), providing task allocation and performance feedback
  • Integrated Assurance into group regulatory and controls mapping with external entities including KPMG; authored the framework and supported delivery of RTS testing framework automation and the GB annual assurance statement
  • Developed and delivered specialist training (Assurance Testing, GB Regulatory Actions, 3rd Party Risk Analysis, Marketing Compliance)

Compliance Officer — Allwyn UK (National Lottery)

September 2022 – March 2023

  • Authored technical Business Requirement Documents (BRDs) and facilitated critical operational handover workshops with legacy service providers.
  • Architected and deployed the foundational system monitoring frameworks and operational control registers for the platform transition.
  • Advised Marketing, Retail and Product Development teams on technical implementation and regulatory alignment as a Subject Matter Expert
  • Managed tier-one technology vendor relationships (Scientific Games) and coordinated international infrastructure efficiency (Net Zero) initiatives.
  • Directed a joint Machine Learning development project with Oxford University, bridging the gap between academic AI models and commercial product deployment.

Previous Roles