# Andrew Stevens - Long-Form Profile > Strategy and execution at the intersection of cloud, data, AI, and security. Operator, board member, and investor. ## Identity - Name: Andrew Stevens - Locations: Amsterdam, Netherlands; San Francisco, USA - Website: https://www.andrewjstevens.com - Email: andrew@andrewjstevens.com - LinkedIn: https://www.linkedin.com/in/andrewjstevens - Mastodon: https://mastodon.online/@andrewjstevens - PGP Fingerprint: F9B3 CECE F5D4 9ABD 682B 388B 17F8 4E48 609C 3BBB ## Summary Andrew Stevens is an executive operator, board member, and investor working at the intersection of cloud, data, AI, and security. He has worked across multiple cycles of growth, transformation, and exit, operating at the intersection of technology strategy, commercial execution, and long-term value creation. His experience spans fintech, media, gaming, and AI - with a track record across product development, scale-ups, and M&A. He brings technical depth in cloud architecture, data, machine learning, and cybersecurity, together with a commercial lens on growth, resilience, investor alignment, and strategic outcomes. He is drawn to opportunities where technology, capital, and timing align - and where the right strategy, operating discipline, and market positioning can create durable advantage. ## Current Focus - Enterprise AI strategy and governance - Trustworthy agentic AI - the architecture, controls, and human-in-the-loop patterns required for safe autonomy - Cloud and data platform modernisation in regulated industries - Board and advisory engagements with founders building durable companies - Where AI regulation meets the runtime - closing the gap between policy and engineering ## Roles Open To - Board director and non-executive director seats - Advisory engagements with founders, executive teams, and investors - Selective operating roles where strategy, capital, and timing align - Pro-bono and volunteer work in human rights, privacy, and social action ## Sectors Fintech, media, gaming, AI, cloud infrastructure, cybersecurity, wealthtech, blockchain, regulated digital platforms. ## Geographies North America, EMEA, APAC. Currently based in Amsterdam with continuing San Francisco presence. ## Publications ### The Executive AI Playbook (2025) Strategy, governance, and execution - a working guide for leadership teams operationalising AI across regulated and high-growth businesses. URL: https://whitepaper.download/aiplaybook/ ### The Governed Agent Trust Environment - GATE (2026) A cloud reference framework of controls for enterprise-grade trustworthy AI agents. GATE closes the gap between agent capability and operational accountability, providing the missing infrastructure layer for agentic AI. URL: https://github.com/deterministic-agents ### The Trustworthy Agentic AI Blueprint (2025) Design principles, missing primitives, and the human-in-the-loop patterns required to deploy autonomous agents responsibly inside the enterprise. URL: https://whitepaper.download/trustworthyagenticai/ ### The Autonomous Horizon (2026) A strategic white paper for the executive team - the operating model, the architecture, and the leadership decisions that will define the next decade of autonomous enterprise. URL: https://www.sakurasky.com/white-papers/autonomous-horizon/ ### Signal-to-Noise (2026) A practical checklist for evaluating AI security tools - built around the four-stage funnel from finding to actionable vulnerability. URL: https://sakurasky.com/white-papers/signal-to-noise-checklist/ ### Still Dangerous (Forthcoming 2026) A Practitioner's Guide to Strength, Composure, and Capability for Executives Over Forty. A book on martial arts - discipline, practice, and the long road. ## Selected Essays and Series - The Regulatory Stack, Parts 1-6 (May 2026): Where AI regulation meets the runtime, and what boards and engineers have to build to close the gap. https://www.sakurasky.com/blog/regulatory-stack-part-1/ - The Mythos Ledger, Parts 1-5 (April 2026): The Firefox Watershed and the new baseline of vulnerability. https://www.sakurasky.com/blog/mythos-ledger-part-1/ - The Autonomous Horizon, Parts 1-6 (April 2026): Beyond digital transformation - the architecture of trust and governed execution at machine speed. https://www.sakurasky.com/blog/autonomous-horizon-part-1/ - GATE: The Missing Infrastructure Layer for Agentic AI (Apr 23, 2026). https://www.sakurasky.com/blog/gate-launch/ - Engineering the Trustworthy Autonomous Enterprise (Dec 01, 2025). https://www.sakurasky.com/blog/engineering-the-trustworthy-autonomous-enterprise/ - The Missing Primitives for Trustworthy AI Agents, Parts 0-17 (October 2025): Long-form series on the missing primitives required for trustworthy agentic AI. https://www.sakurasky.com/blog/missing-primitives-for-trustworthy-ai/ - Reflections on the 2024 DORA Report (Dec 11, 2024). https://www.sakurasky.com/blog/dora-report-2024-reflections/ - EU AI Act: Implications for Data and Cloud in Banking, Ecommerce, and Gaming (Nov 28, 2024). https://www.sakurasky.com/blog/eu-ai-act/ Full archive: https://www.sakurasky.com/author/andrew-stevens/ ## Experience ### Board Member - Distinct Star (2026 - Present) Founder-first platform for high-quality services businesses. Long-term strategy, member-company alignment, and operating perspective across cloud, data, security, and AI. ### Co-Founder - Sakura Sky (2013 - Present) Global consultancy focused on cloud, data, and AI. Growth strategy, hyperscaler partnerships, repeatable delivery systems, and enterprise AI and platform programmes across NA, EMEA, and APAC. ### Chief Technology Officer - Orbx (2024 - 2026) Modernised commerce and platform systems across simulation, ecommerce, and digital content. Cloud-native architecture, DevOps and SRE maturity, and the foundations for AI-first systems. ### Co-Founder / CISO - HereToday (2020 - 2025) Blockchain venture for digital legacy and asset succession. Zero-trust architecture, ML-assisted threat modelling, and compliance readiness across GDPR, CCPA, ISO 27001, and emerging digital asset regulation. ### Head of Data Security - Canopy (2015 - 2016) Built cloud security, governance, and AI lifecycle controls for a regulated wealthtech platform. Reported to executive and board stakeholders on risk, resilience, and security strategy. ### Co-Founder - Jiku.io (2014 - 2016) Cross-platform content and commerce for publishers and retailers - Channel Nine, Pacific Magazines, and others. Product direction, customer delivery, and early-stage growth. ### Chief Information Officer - APC Global Systems (2014) Digital transformation across global mining operations - telemetry, edge computing, early ML and computer vision, and IT/OT integration into executive dashboards. ### Chief Mobile Officer - HotelsCombined (2012 - 2013) Owned the mobile roadmap and growth across iOS and Android. Helped position the business for acquisition by Booking Holdings. ### CTO / Head of Product - CarAdvice / Nine (2011 - 2012) CTO and Head of Product for CarAdvice, acquired by Nine Entertainment Co. (ASX:NEC). ## Technical Depth - Cloud architecture: AWS, GCP, Azure, multi-cloud, hybrid, sovereign cloud - Data platforms: data warehouses, lakehouses, streaming, MLOps - AI/ML: enterprise AI strategy, agentic systems, model governance, RAG, vector stores, LLM operations - Security: zero-trust, cloud security posture, AI security, regulated industry compliance (GDPR, CCPA, ISO 27001, EU AI Act) - DevOps and SRE: platform engineering, DORA metrics, reliability engineering ## Themes Andrew writes and speaks about the systems that make autonomous AI trustworthy, the governance gap in agentic systems, and the operating models that let leadership teams move from AI experimentation to durable enterprise advantage. Recurring themes include verification, trust infrastructure, controls for autonomy, the regulatory stack at runtime, and the human-in-the-loop patterns required at machine speed. ## Contact For board, advisory, or investment conversations: andrew@andrewjstevens.com