Senior AI Engineer

About us

In Italy, managing the finances of an SME or an accounting firm means dealing with tools that don't talk to each other, chasing invoices and bank statements, and struggling with deadlines.

The result? Wasted time, decisions made too late, zero growth.

Sibill changes all of this: invoicing, payments, treasury and accounting for SMEs and accountants, all in a single platform powered by artificial intelligence.

Today more than 5,000 companies and over 300 firms work with Sibill. In 2025 we closed a €12 million round led by Creandum, the fund that believed in Spotify, Klarna and Trade Republic.

Our values are ambition, pragmatism, efficiency and integrity. In practice: never settle, cut useless meetings, alert the client immediately when there is a problem, and give honest feedback even to your own manager.

To grow, we look for people who are curious, able to simplify complexity and to challenge the status quo, in other words the "cazzimma".

If what you have read has sparked even a little interest, apply: a team of over 130 talented people awaits you.

What you will do

You will report directly to the Head of AI. Together with them you will build the AI products that help our clients manage their business better. It will not be a solitary job: you will collaborate every day with the data, engineering, infrastructure, product and design teams.

We work on the most critical data of a company: cash flows, bank transactions, invoices, receipts, receivables and payables, general ledger entries. We are the operating system for finance and accounting for our clients. Your task will be to leverage this information asset to solve concrete problems for clients.

Your responsibilities will include:

• Discovery, domain understanding and experimentation

• Design and development of AI systems in production

• Definition and management of evals: metrics, test datasets, monitoring of quality, costs and latency

• Continuous iteration on existing AI products, choosing the most suitable approach each time. The work is not "done" when the model is in prod, but when clients use it every day and depend on it

Some examples of projects you could work on from the first month:

• Introducing re-ranking into our automatic reconciliation algorithm.

• Building a new system for knowledge management, retrieval, memory and tool use for Sibill's AI agents.

• Following training and evals of a language model for Italian bank transactions.

You are the right person if

• You hold a master's degree or a PhD in Computer Science, Data Science, Engineering, Mathematics or another STEM discipline. Solid foundations in mathematics, statistics, probability and machine learning will make the difference.

• You have concrete experience and successful cases in building and bringing into production AI-based applications used by thousands of users.

• You have not taken shortcuts: you know the fundamentals (linear models, linear algebra, neural networks, backprop) and you master the "low level".

• You master modern Python and software development tools (git, Docker, CI/CD, unit testing, evals). We do not run data pipelines on Jupyter Notebook in production.

• You know the APIs of the main model providers and the ecosystem frameworks, but you also know when to do without them.

• You have an end-to-end ownership mindset, especially at the beginning. It will not happen every day, but if needed you may have to build a data pipeline from scratch, write a batch ETL, write code in Elixir or TypeScript, or support colleagues with an ad hoc empirical analysis.

• You speak Italian and English fluently.

• Bonus point: at least 7-8 years of experience in software or ML, part of it on AI systems in production. You have already coached and mentored junior colleagues.

Mindset

You are probably a great fit if:

• You are passionate about technology, artificial intelligence and business. All three

• You do not feel "arrived", you are a builder and want to stay hands-on

• You are excited to work in a flat, political-free environment at high speed

• You have excellent analytical skills and great attention to detail

• You have high ownership and high agency

• You identify with the values we share at Sibill: ambition, pragmatism, efficiency, integrity

Salary and benefits

• Gross annual salary: €80K - €100K depending on experience

• Meal vouchers (€8/day)

• Welfare budget

• Fully remote (with residence in Italy). We will only ask you to come to Milan for a few weeks during onboarding. If you are in Milan, you are more than welcome to come to the office!

• You will work in a team of brilliant, passionate people who work hard and are also great fun. At Sibill people tend to be very happy. Happiness is an underrated benefit :)

Selection process

1. Interview with Gaia, HR Manager (30')

2. Interview with Dario, CDTO, and Elisa, Head of AI (30')

3. Technical interview (45')

4. You will meet some of the key people you will work with (engineering, data, product - together in an introductory session)

5. Final interview with Mattia, CEO, and Lorenzo, CPO (45')

6. Offer

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