Were building the future of mobility.

At hlpy, were building much more than a company.

Were building the technology platform that is transforming how mobility services are delivered across Europe.

Every month, our platform orchestrates tens of thousands of real-world operations, connecting drivers, insurers, fleets, OEMs, service providers and business partners through technology.

As we continue to expand internationally, broaden our product offering and integrate new businesses, the complexity of what we do grows with us.

Scaling hlpy isnt simply about increasing revenues.

Its about building an organization capable of executing consistently across countries, products and teams.

To get there, strategy alone isnt enough.

Execution is what makes the difference.

Thats why were looking for our next Chief of Staff.

This isnt a support role.

Its one of the highest-impact positions inside hlpy.

Youll work directly with our CEO and Leadership Team, helping transform ambitious ideas into company-wide execution.

Youll have visibility across every function, every country and every strategic initiative.

Youll be in the room where the most important decisions are made.

And often, youll be the person making sure those decisions actually happen.

If you enjoy solving complex problems, connecting people, challenging assumptions and making organizations move faster, youll probably love this role.

What youll be working on

There is no typical week.

Depending on the companys priorities, you could be:

- Coordinating the execution of strategic initiatives across multiple countries.
- Leading cross-functional projects involving Operations, Product, Technology, Sales, Finance and HR.




- Supporting the integration of newly acquired companies.
- Preparing Board materials, executive presentations and strategic analyses.
- Helping define company priorities and tracking execution across the organization.
- Working alongside department leaders to remove execution bottlenecks.
- Improving internal processes to make the company more scalable.
- Supporting organizational projects and leadership initiatives.
- Representing the CEO in selected internal and external initiatives when appropriate.

If something is strategically important for hlpy, chances are youll be involved.

Who were looking for

Were not looking for someone with the perfect résumé.

Were looking for someone with exceptional judgment, curiosity and execution skills.

Someone who naturally brings order to complexity.

Someone who enjoys taking ownership before being asked.

You may come from consulting, investment banking, private equity, strategy, high-growth startups or another demanding environment.

More importantly, you:

- Learn incredibly fast.
- Think in a structured and analytical way.
- Communicate with clarity and influence.
- Are comfortable switching between strategy and execution.
- Thrive in ambiguity and fast-changing environments.
- Take ownership and make things happen.




- Have excellent interpersonal skills and know how to build trust across teams.
- Speak fluent Italian and English.

Why this role is different

Most Chief of Staff positions help companies operate.

This one helps build one.

Youll work side by side with the CEO during one of the most transformational phases in hlpys journey.

International expansion.

New products.

Strategic acquisitions.

Organizational scaling.

Technology evolution.

Very few roles offer this level of exposure, responsibility and learning.

If youre ambitious, curious and eager to make an impact, this role will accelerate your career faster than almost any traditional functional position.

What success looks like after 12 months

- Youve become one of the CEOs most trusted sparring partners.
- Strategic initiatives move faster because youre driving alignment and execution.
- Leadership meetings are more effective, focused and action-oriented.
- Cross-functional collaboration has significantly improved.
- Youve personally led projects that created measurable impact on hlpys growth and scalability.
- Youve helped build a stronger, faster and more effective organization.

Why hlpy

Because were building something meaningful.

Because we move fast.

Because responsibility grows faster than hierarchy.

Because we believe the best ideas can come from anyone.

Because we value ownership over politics and execution over bureaucracy.

And because if we do our job well, millions of people across Europe will experience mobility in a smarter, faster and more reliable way.

If building rather than maintaining excites you, wed love to meet you.

📌 Chief of Staff (Milano)
🏢 HLPY
📍 Milano