We are hiring a Junior AI Support Specialist to assist an Italian financial services firm as they implement new data processing technologies. You will support the technical side of their digital shift while ensuring the financial logic remains sound and accurate.

About Blue Oak Consulting Blue Oak Consulting provides independent advisory on pricing, portfolio economics, capital allocation, and acquisition assumptions. We are not a traditional consulting firm focused on broad transformation programs or high level strategy decks.

Instead, we interrogate specific commercial decisions where the financial stakes are high and the existing narrative is not sufficient. Our team looks past corporate language and P&L; complexity to identify where value is leaking or capital is trapped. We work across sectors like software, manufacturing, and healthcare to test whether the assumptions behind a growth plan or an acquisition actually hold under pressure.

We are a small, principal led firm where the people who do the work are the ones accountable for the results. We do not take transaction contingent fees, which allows us to be completely honest about whether the economics of a decision make sense. Our goal is to provide clarity through financial discipline and a healthy amount of skepticism.

We stay through the execution phase because decisions that look sound in theory often fail when they meet real world friction.

The Role Working at Blue Oak Consulting means looking for the friction in every financial model. In this fully remote role, you will help our team and our client, an Italian financial services firm, use AI tools to sift through large datasets more effectively.

You will not just be technical support:



you will be an active part of our skepticism process, checking to see if technology is clarifying the truth or obscuring it. Since we are a small, principal led firm, you will see exactly how your work impacts the final advice we give. This is a tempo pieno position where you will gain experience at the intersection of finance and artificial intelligence.

What You Will Be Doing

- Setting up AI tools to help analysts review large sets of financial contracts and documents.
- Verifying that AI generated data matches the source material to prevent errors in reporting.
- Helping senior advisors refine their prompts to get more specific financial insights from unstructured data.
- Maintaining organized logs of how AI tools are used during specific client audits for transparency.
- Identifying where AI tools are failing to grasp complex pricing nuances in the financial services sector.
- Assisting with basic data cleanup so that models can process information accurately and consistently.
- Researching new AI functionalities that can save time during the capital allocation process.
- Communicating technical hurdles to the rest of the team in plain English without using jargon.
- Monitoring the output of automated systems to ensure they align with the firm's rigorous standards.

What You Bring

- A degree or equivalent background in finance, economics,



or information systems.
- Curiosity about how AI can be applied to business logic and data analysis.
- Competency with standard spreadsheet software and a willingness to learn more advanced functions.
- A detail oriented approach that catches small discrepancies in numbers or text.
- Strong problem solving skills and the ability to figure out why a tool is not working as expected.
- Excellent communication skills to help non-technical team members use new tools effectively.
- Reliability in a fully remote environment with the discipline to meet deadlines independently.
- A skeptical mindset that does not take automated results at face value.

What We Offer

- Competitive pay that is attractive for an entry level professional in this sector.
- A 100 percent remote workplace where you have autonomy over your environment.
- Mentorship from senior principals who have deep experience in financial advisory.
- A work culture that avoids corporate buzzwords in favor of clear, honest results.
- Continuous learning as you work with the latest AI tools in a practical, real world setting.
- Participation in high level projects where your technical input directly aids decision making.

At Blue Oak, we value the ability to be wrong as much as the ability to be right. We want a team member who is willing to question a machine output and dig into the files to find the real answer. This position offers a chance to see how high level financial decisions are made and how technology is changing that process for the better. We focus on results and logic rather than optics, and we expect our team to approach every challenge with that same level of rigor.

📌 Junior AI Support Specialist (Milano)
🏢 Blue Oak Consulting
📍 Milano