Executive Assistant to the CEO

📍 Milan (in-person, founder-side) · Full-time · Start: immediately

The short version

Pillar just closed a €12M seed, reaching €2M ARR in less than 10 months, serves ~600 construction companies, and scaled from 6 to 60 people this year.
The CEO's days are a moving target: board prep, investor calls in three languages, hiring, International expansion, offsites, last-minute flights, fundraising and decks that need to look good by tomorrow morning.

This role exists to own all of it so nothing falls through the cracks and the CEO's hours go to the things only they can do.

This is not a "help out sometimes" job. It's the operational backbone of how the CEO runs the week. If you're the kind of person who feels physical discomfort when a calendar has a conflict, an email goes 24 hours unanswered, or a trip has a gap with no hotel booked keep reading.

What you'll own

The calendar. Defend it, optimize it, protect deep-work blocks, resolve conflicts before they escalate. Time zones across Europe and LatAm are a daily reality.

The inbox. Triage, flag what's urgent, draft replies when needed, chase the threads that go quiet, make sure nothing important dies in the noise. Italian, English, and Spanish all show up here.

Travel. Flights, trains, hotels, transfers, the whole chain domestic and international, often planned fast and changed faster. You make it seamless and you have a plan B ready before anyone asks.

Offsites & retreats. We do real ones (ask about Ibiza). Venues, logistics, budgets, vendors, the 100 details that make a team trip feel effortless to everyone except the person organizing it.

Slides & docs. Pulling together decks, cleaning up formatting, prepping board and investor materials so they're sharp and on-brand. You don't need to be a designer, but you need taste and speed.

Everything else. Expenses, reminders, follow-ups, errands, vendor coordination, the random new thing that appears at 6pm and needs to be solved by morning. The job is the unexpected. No two weeks look the same.

Who you are

- You're organized to a level that other people find slightly intimidating. Nothing gets lost. Ever.

- You're proactive, not reactive. You see what's coming and handle it before it's a problem.

- You're trustworthy with sensitive information comp, investor relations, personal logistics. Total discretion is non-negotiable.

- You operate in Italian and English fluently. Spanish is a strong plus (we're expanding into Spain and active across LatAm).

- You're fast, low-ego, and resourceful. You'd rather figure it out than wait to be told.

- You're comfortable in a startup that moves fast and changes its mind. Ambiguity doesn't rattle you.
- You do not get annoyed by the massive context switching and do not mind burocracy

- You can start right away.

Nice to have

- Previous experience supporting a founder, executive, or in a high-tempo environment.

- Comfort with modern tools (Notion, Slack, claude, AI tools we use them heavily here).

- A good eye for slides and written communication.

Why this role

You'll sit closer to how a fast-growing company actually gets. You'll see board prep, fundraising, hiring, strategy and you'll be trusted with it. For the right person this is a launchpad, not a dead end.

If you read this and thought "that's me", apply and tell us one thing you organized that you're proud of, and why you can start now.