Chief of Staff to VP Engineering (x/f/m)

You. Better. With Alan. Alan is building a vertically integrated health partner that unites insurance and smart healthcare delivery into one seamless system. Our vision is to make prevention the new norm of care for all. Our mission: Help people live in good health to 100 while helping employers feel proud, turning health benefits from a cost centre into their most valuable investment. By connecting all aspects of care (private, public, and direct to consumer) we create the most member-centric healthcare experience, reducing claims costs while generating new monetization opportunities. We partner with tens of thousands of companies across France 🇫🇷, Spain 🇪🇸, Belgium 🇧🇪, and Canada 🇨🇦, serving over a million members. How we work: our Leadership Principles Mission is the Boss — We think long-term and are methodical optimists who take risks, seeking our mission's success above all else. Distributed Ownership — Accountable enlightened despots: everyone owns their decisions and results. Radical Transparency — All information is accessible and written-first, so everyone can make the best decisions asynchronously. Always Growing — Direct, positive, and caring feedback, combined with self-growth ownership. ⭐️ The Opportunity ⭐️ Technology is Alan's core engine. Every product, every country launch, every member interaction runs on what our 150+ engineers build across several countries. We move fast, with a lot of ownership, and are proud to tackle big problems. But as we scale we need someone to work directly with our VP Engineering and tech-leadership on the operational and strategic layer that makes this all possible. Some weeks you're in a room with AWS negotiating cloud infrastructure for a new country. Other weeks you're coordinating a GenAI Circle lunch or running a 150-person offsite. The common thread: you own things end-to-end, and your work directly shapes how engineering operates at Alan. ⭐️ Scope ⭐️ Strategic projects & partnerships — 40% High-impact initiatives owned end-to-end alongside the VP Engineering and tech-leadership group. Outcomes: Country expansions are researched, coordinated with partners and GMs, and delivered on schedule Strategic vendor relationships (AWS, Anthropic) are well-prepared Alan's tech brand grows externally — through the blog, the GenAI Circle, podcast episodes, and whatever comes next. Engineers want to join; companies want to partner. Strategic projects (AI training program, Acquisitions Due Dilligence) have a single owner who drives them from brief to delivery Community operations — 40% 150 engineers across 4 countries (soon more) need rhythm, connection, and well-run processes. You own that. Outcomes: Community events keep improving — better feedback, smoother execution, lower cost each time Staffing moves and coaching reshuffles have a single owner from announcement to completion Engineering reporting (MBR inputs, budget, vendor coordination with Finance) becomes self-serve for tech-leadership Building & productivity — 20% Accelerate AI adoption across the engineering community to multiply engineering productivity. Build tools, create playbooks, and teach engineers how to integrate AI into their daily workflows. What takes hours today takes minutes tomorrow. Outcomes: Engineering productivity improves measurably — you're the person who makes that happen, not just tracks it Operational work shrinks over time as you build tooling to replace manual processes You ship internal tools the community actually uses What this role is NOT Not a TPM for product crews — crews own their delivery Not a personal assistant — you own outcomes, not logistics What you'll gain Deep understanding of how a 150+-person, 4-country engineering organization actually works — strategy, operations, people, vendors, budget Relationships across engineering, product, finance, and external partners A portfolio of shipped projects — events, tools, dashboards, content — that you built and owned Personal coaching from day one and weekly check-ins with the VP Engineering and the tech-leadership group ⭐️ Is it you we’re looking for? ⭐️ You would be a good fit at Alan if most of this sounds like you: You own things end-to-end. You don't wait for the next instruction. You research, draft, execute, follow up, and improve. You learn fast in unfamiliar territory. You don't need to know what AWS Outposts is on day one, but you can research it, write a clear briefing, and prep the meeting within days. You switch contexts without losing quality. Monday you're drafting talking points for a partner meeting, Wednesday you're chasing 10 team leads for content, Friday you're building a staffing dashboard. You communicate clearly. You improve everything you write, and people trust you to represent Alan's perspective. You're a natural teacher. You've helped people adopt new tools or ways of working, and you get energy from watching others level up. Low ego, high agency. You ask for direction, not permission. Requirements: