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

About 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. We partner with tens of thousands of companies across France, Spain, Belgium, and Canada, serving over a million members. Our mission is to help people live in good health to 100 while helping employers treat health benefits as an investment.

How We Work – 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.

Opportunity

Technology is Alan’s core engine. Every product, every country launch, every member interaction runs on what our more than 150 engineers build across several countries. This role works directly with the VP Engineering and tech‑leadership on the operational and strategic layer that makes everything possible.

Scope

Strategic Projects & Partnerships – 40%

• 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 other initiatives.
• Strategic projects (AI training program, tech due diligence) have a single owner driving them from brief to delivery.

Community Operations – 40%

• Community events continually improve – better feedback, smoother execution, lower cost each time.
• Staffing moves and coaching reshuffles are managed from announcement to completion by a single owner.
• 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 productivity: build tools, create playbooks, teach engineers how to integrate AI into daily workflows.
• Engineering productivity improves measurably – you make that happen, not just track it.
• Operational work shrinks over time as you build tooling to replace manual processes.
• You ship internal tools that the community actually uses.

What This Role Is NOT

• A TPM for product crews – crews own their delivery.
• A personal assistant – you own outcomes, not logistics.

What You’ll Gain

• Deep understanding of a 150+ person, 4‑country engineering organization.
• Relationships across engineering, product, finance, and external partners.
• A portfolio of shipped projects – events, tools, dashboards, content.
• Personal coaching and weekly check‑ins with the VP Engineering and tech‑leadership group.

Is It You We’re Looking For?

• You own things end‑to‑end – research, draft, execute, follow up, and improve.
• You learn fast in unfamiliar territory – research new topics, write briefings, prepare meetings quickly.
• You switch contexts without losing quality – shift between conversations and projects seamlessly.
• You communicate clearly – improve writing and represent Alan’s perspective.
• You’re a natural teacher – help people adopt new tools or ways of working.
• Low ego, high agency – ask for direction, not permission.

Requirements

• At least one meaningful experience in operations, consulting, project management, or an associate role. • Native‑level fluency in French and English. • Proven ability to use and teach AI tools – not just use ChatGPT or Claude, but help others unlock their potential. • Track record of owning projects end‑to‑end.

Perks & Benefits

• Fair rewards – generous equity packages complement your base salary (permanent contracts only).
• Flexible office – HQ space, sponsored co‑working hubs or full‑remote experience with home‑office equipment sponsorship.
• All the tools you need – MacBook Pro, keyboard, laptop stand, monitor, Bose headphones.
• Flexible vacation policy and flexible working hours.
• Delightful healthcare insurance – 100% contribution covered by Alan for you and your family (permanent contracts only).
• Transport – country‑specific commuter benefits.
• Learning & training opportunities – flexible training policy, free books, conference budget.
• Parental leave – extended parental leave for all new parents (permanent contracts only).

Important Note

We hire people, not roles. If you feel you don’t have all the necessary prerequisites but this matches where you are or want to grow, we encourage you to apply. All are welcome to apply.